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4-MeO-DMT; 4-Methoxy-N,N-dimethyltryptamine
5153
Variant: N R1 R4 skeleton isomers all
Analogues: 6 18 9 5 17 55

IUPAC: 2-(4-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: HFYHBTWTJDAYGW-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-15(2)8-7-10-9-14-11-5-4-6-12(16-3)13(10)11/h4-6,9,14H,7-8H2,1-3H3

PubChem CID: 12017578; ChemSpider: 23126449; Drugs Forum: 4-MeO-DMT; Wikipedia: 4-MeO-DMT

See also TiHKAL: #39 4-MeO-MIPT #46 5-MeS-DMT    

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. doi:10.1021/jm00350a005

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Six N analogues:
5039
Analogue 1: Substituting Methyl and Isopropyl for Dimethyl at N

4-MeO-MIPT
Tryptamine, N-isopropyl-4-methoxy-N-methyl
Indole, 3-[2-(isopropylmethylamino)ethyl]-4-methoxy
N-Isopropyl-4-methoxy-N-methyltryptamine
3-[2-(Isopropylmethylamino)ethyl]-4-methoxyindole

IUPAC: N-[2-(4-Methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-2-amine

Formula: C15H22N2O Molecular weight: 246.34798 g/mol InChI Key: BJIWLHLNPTWSGD-UHFFFAOYSA-N

InChI=1S/C15H22N2O/c1-11(2)17(3)9-8-12-10-16-13-6-5-7-14(18-4)15(12)13/h5-7,10-11,16H,8-9H2,1-4H3

PubChem CID: 29935317; ChemSpider: 21106243; Wikipedia: 4-MeO-MiPT

See also TiHKAL: #40 5-MeO-MIPT      

Repke, DB; Grotjahn, DB; Shulgin, AT. Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents. J. Med. Chem., 1 Jan 1985, 28 (7), 892–896. 711 kB. doi:10.1021/jm00145a007

5156
Analogue 2: Substituting Diethyl for Dimethyl at N

4-MeO-DET
N,N-Diethyl-4-methoxytryptamine

IUPAC: N,N-Diethyl-2-(4-methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C15H22N2O Molecular weight: 246.34798 g/mol InChI Key: HIVMOHVUFLVCMM-UHFFFAOYSA-N

InChI=1S/C15H22N2O/c1-4-17(5-2)10-9-12-11-16-13-7-6-8-14(18-3)15(12)13/h6-8,11,16H,4-5,9-10H2,1-3H3

PubChem CID: 24802084; ChemSpider: 21436170; Drugs Forum: 4-MeO-DET

See also TiHKAL: #39 4-MeO-MIPT      

See also Transcripts: 4.462

5173
Analogue 3: Substituting Diisopropyl for Dimethyl at N

4-MeO-DIPT
N,N-Diisopropyl-4-methoxytryptamine

IUPAC: N-[2-(4-Methoxy-1H-indol-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine

Formula: C17H26N2O Molecular weight: 274.40114 g/mol InChI Key: WIVWUNUDMXNQJD-UHFFFAOYSA-N

InChI=1S/C17H26N2O/c1-12(2)19(13(3)4)10-9-14-11-18-15-7-6-8-16(20-5)17(14)15/h6-8,11-13,18H,9-10H2,1-5H3

PubChem CID: 24802108; ChemSpider: 21436143

See also TiHKAL: #46 5-MeS-DMT      
5533
Analogue 4: Substituting Diallyl for Dimethyl at N

4-MeO-DALT
N,N-Diallyl-4-methoxytryptamine

IUPAC: N-[2-(4-Methoxy-1H-indol-3-yl)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine

Formula: C17H22N2O Molecular weight: 270.36938 g/mol InChI Key: AOLUJOKBRLMQDR-UHFFFAOYSA-N

InChI=1S/C17H22N2O/c1-4-10-19(11-5-2)12-9-14-13-18-15-7-6-8-16(20-3)17(14)15/h4-8,13,18H,1-2,9-12H2,3H3

See also TiHKAL: #56 5-MeO-DALT      
5063
Analogue 5: Removing Dimethyl at N

4-MeO-T
4-Methoxytryptamine

IUPAC: 2-(4-Methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C11H14N2O Molecular weight: 190.24166 g/mol InChI Key: WMBARRJMPVVQEZ-UHFFFAOYSA-N

InChI=1S/C11H14N2O/c1-14-10-4-2-3-9-11(10)8(5-6-12)7-13-9/h2-4,7,13H,5-6,12H2,1H3

PubChem CID: 19219; ChemSpider: 18136

See also TiHKAL: #39 4-MeO-MIPT      
5064
Analogue 6: Substituting Methyl for Dimethyl at N

4-MeO-NMT
4-Methoxy-N-methyltryptamine

IUPAC: 2-(4-Methoxy-1H-indol-3-yl)-N-methylethan-1-amine

Formula: C12H16N2O Molecular weight: 204.26824 g/mol InChI Key: PLNZCXIDJPYSHZ-UHFFFAOYSA-N

InChI=1S/C12H16N2O/c1-13-7-6-9-8-14-10-4-3-5-11(15-2)12(9)10/h3-5,8,13-14H,6-7H2,1-2H3

ChemSpider: 23511915

See also TiHKAL: #39 4-MeO-MIPT      
18 R1 analogues:
5218
Analogue 1: Adding Cyclohexylsulfonyl at R1

IUPAC: 2-[1-(Cyclohexylsulfonyl)-4-methoxy-1H-indol-3-yl]-N,N-dimethylethan-1-amine

Formula: C19H28N2O3S Molecular weight: 364.50222 g/mol InChI Key: GXMGXAMGMUXSMF-UHFFFAOYSA-N

InChI=1S/C19H28N2O3S/c1-20(2)13-12-15-14-21(17-10-7-11-18(24-3)19(15)17)25(22,23)16-8-5-4-6-9-16/h7,10-11,14,16H,4-6,8-9,12-13H2,1-3H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5220
Analogue 2: Adding Phenylsulfonyl at R1

IUPAC: 2-[4-Methoxy-1-(phenylsulfonyl)-1H-indol-3-yl]-N,N-dimethylethan-1-amine

Formula: C19H22N2O3S Molecular weight: 358.45458 g/mol InChI Key: GEORPUVVXOBYHO-UHFFFAOYSA-N

InChI=1S/C19H22N2O3S/c1-20(2)13-12-15-14-21(17-10-7-11-18(24-3)19(15)17)25(22,23)16-8-5-4-6-9-16/h4-11,14H,12-13H2,1-3H3

PubChem CID: 44420491; ChemSpider: 23280393

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5231
Analogue 3: Adding 4-Methylphenylsulfonyl at R1

IUPAC: 2-{4-Methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}-N,N-dimethylethan-1-amine

Formula: C20H24N2O3S Molecular weight: 372.48116 g/mol InChI Key: CBWHWHGEDGRFQP-UHFFFAOYSA-N

InChI=1S/C20H24N2O3S/c1-15-8-10-17(11-9-15)26(23,24)22-14-16(12-13-21(2)3)20-18(22)6-5-7-19(20)25-4/h5-11,14H,12-13H2,1-4H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5234
Analogue 4: Adding 4-Aminophenylsulfonyl at R1

IUPAC: 4-({3-[2-(Dimethylamino)ethyl]-4-methoxy-1H-indol-1-yl}sulfonyl)aniline

Formula: C19H23N3O3S Molecular weight: 373.46922 g/mol InChI Key: ZVKYCQZJZJWLGG-UHFFFAOYSA-N

InChI=1S/C19H23N3O3S/c1-21(2)12-11-14-13-22(17-5-4-6-18(25-3)19(14)17)26(23,24)16-9-7-15(20)8-10-16/h4-10,13H,11-12,20H2,1-3H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5249
Analogue 5: Adding 4-Methylphenylthio at R1

IUPAC: 2-{4-Methoxy-1-[(4-methylphenyl)sulfanyl]-1H-indol-3-yl}-N,N-dimethylethan-1-amine

Formula: C20H24N2OS Molecular weight: 340.48236 g/mol InChI Key: DGXJOKXOQHWRRH-UHFFFAOYSA-N

InChI=1S/C20H24N2OS/c1-15-8-10-17(11-9-15)24-22-14-16(12-13-21(2)3)20-18(22)6-5-7-19(20)23-4/h5-11,14H,12-13H2,1-4H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5250
Analogue 6: Adding 4-Methoxyphenylthio at R1

IUPAC: 2-{4-Methoxy-1-[(4-methoxyphenyl)sulfanyl]-1H-indol-3-yl}-N,N-dimethylethan-1-amine

Formula: C20H24N2O2S Molecular weight: 356.48176 g/mol InChI Key: JTMGJGHWCCBPIU-UHFFFAOYSA-N

InChI=1S/C20H24N2O2S/c1-21(2)13-12-15-14-22(18-6-5-7-19(24-4)20(15)18)25-17-10-8-16(23-3)9-11-17/h5-11,14H,12-13H2,1-4H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5251
Analogue 7: Adding 4-Trifluoromethylphenylthio at R1

IUPAC: 2-(4-Methoxy-1-{[4-(trifluoromethyl)phenyl]sulfanyl}-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C20H21F3N2OS Molecular weight: 394.4537496 g/mol InChI Key: LTFWXBXBZZHKHC-UHFFFAOYSA-N

InChI=1S/C20H21F3N2OS/c1-24(2)12-11-14-13-25(17-5-4-6-18(26-3)19(14)17)27-16-9-7-15(8-10-16)20(21,22)23/h4-10,13H,11-12H2,1-3H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5252
Analogue 8: Adding 4-Chlorophenylthio at R1

IUPAC: 2-{1-[(4-Chlorophenyl)sulfanyl]-4-methoxy-1H-indol-3-yl}-N,N-dimethylethan-1-amine

Formula: C19H21ClN2OS Molecular weight: 360.90084 g/mol InChI Key: SCIRDVBTZVDVBW-UHFFFAOYSA-N

InChI=1S/C19H21ClN2OS/c1-21(2)12-11-14-13-22(24-16-9-7-15(20)8-10-16)17-5-4-6-18(23-3)19(14)17/h4-10,13H,11-12H2,1-3H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5253
Analogue 9: Adding 4-Aminophenylthio at R1

IUPAC: 4-({3-[2-(Dimethylamino)ethyl]-4-methoxy-1H-indol-1-yl}sulfanyl)aniline

Formula: C19H23N3OS Molecular weight: 341.47042 g/mol InChI Key: GNCDVBHEXVKQIO-UHFFFAOYSA-N

InChI=1S/C19H23N3OS/c1-21(2)12-11-14-13-22(24-16-9-7-15(20)8-10-16)17-5-4-6-18(23-3)19(14)17/h4-10,13H,11-12,20H2,1-3H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5497
Analogue 10: Adding Isopropylsulfonyl at R1

IUPAC: 2-[4-Methoxy-1-(propan-2-ylsulfonyl)-1H-indol-3-yl]-N,N-dimethylethan-1-amine

Formula: C16H24N2O3S Molecular weight: 324.43836 g/mol InChI Key: VLCGASXLCIZGJE-UHFFFAOYSA-N

InChI=1S/C16H24N2O3S/c1-12(2)22(19,20)18-11-13(9-10-17(3)4)16-14(18)7-6-8-15(16)21-5/h6-8,11-12H,9-10H2,1-5H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5498
Analogue 11: Adding Propylsulfonyl at R1

IUPAC: 2-[4-Methoxy-1-(propylsulfonyl)-1H-indol-3-yl]-N,N-dimethylethan-1-amine

Formula: C16H24N2O3S Molecular weight: 324.43836 g/mol InChI Key: DFTBKIHPVSOYOF-UHFFFAOYSA-N

InChI=1S/C16H24N2O3S/c1-5-11-22(19,20)18-12-13(9-10-17(2)3)16-14(18)7-6-8-15(16)21-4/h6-8,12H,5,9-11H2,1-4H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5499
Analogue 12: Adding Butylsulfonyl at R1

IUPAC: 2-[1-(Butylsulfonyl)-4-methoxy-1H-indol-3-yl]-N,N-dimethylethan-1-amine

Formula: C17H26N2O3S Molecular weight: 338.46494 g/mol InChI Key: GSCVMLPQPHOWJF-UHFFFAOYSA-N

InChI=1S/C17H26N2O3S/c1-5-6-12-23(20,21)19-13-14(10-11-18(2)3)17-15(19)8-7-9-16(17)22-4/h7-9,13H,5-6,10-12H2,1-4H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5598
Analogue 13: Adding Pentylsulfonyl at R1

IUPAC: 2-[4-Methoxy-1-(pentylsulfonyl)-1H-indol-3-yl]-N,N-dimethylethan-1-amine

Formula: C18H28N2O3S Molecular weight: 352.49152 g/mol InChI Key: WVILRQYSPXMXCE-UHFFFAOYSA-N

InChI=1S/C18H28N2O3S/c1-5-6-7-13-24(21,22)20-14-15(11-12-19(2)3)18-16(20)9-8-10-17(18)23-4/h8-10,14H,5-7,11-13H2,1-4H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5599
Analogue 14: Adding Octylsulfonyl at R1

IUPAC: 2-[1-(Heptylsulfonyl)-4-methoxy-1H-indol-3-yl]-N,N-dimethylethan-1-amine

Formula: C21H34N2O3S Molecular weight: 394.57126 g/mol InChI Key: ZORNQSZMSSOCJR-UHFFFAOYSA-N

InChI=1S/C21H34N2O3S/c1-5-6-7-8-9-10-16-27(24,25)23-17-18(14-15-22(2)3)21-19(23)12-11-13-20(21)26-4/h11-13,17H,5-10,14-16H2,1-4H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5780
Analogue 15: Adding (4-Methoxyphenyl)sulfonyl at R1

IUPAC: 2-{4-Methoxy-1-[(4-methoxyphenyl)sulfonyl]-1H-indol-3-yl}-N,N-dimethylethan-1-amine

Formula: C20H24N2O4S Molecular weight: 388.48056 g/mol InChI Key: WWFAOUCXCAJPIM-UHFFFAOYSA-N

InChI=1S/C20H24N2O4S/c1-21(2)13-12-15-14-22(18-6-5-7-19(26-4)20(15)18)27(23,24)17-10-8-16(25-3)9-11-17/h5-11,14H,12-13H2,1-4H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5781
Analogue 16: Adding [4-(Triflouromethyl)phenyl]sulfonyl at R1

IUPAC: 2-(4-Methoxy-1-{[4-(trifluoromethyl)phenyl]sulfonyl}-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C20H21F3N2O3S Molecular weight: 426.4525496 g/mol InChI Key: OGMAIWYTHJLCSP-UHFFFAOYSA-N

InChI=1S/C20H21F3N2O3S/c1-24(2)12-11-14-13-25(17-5-4-6-18(28-3)19(14)17)29(26,27)16-9-7-15(8-10-16)20(21,22)23/h4-10,13H,11-12H2,1-3H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5782
Analogue 17: Adding (4-Clorophenyl)sulfonyl at R1

IUPAC: 2-{1-[(4-Chlorophenyl)sulfonyl]-4-methoxy-1H-indol-3-yl}-N,N-dimethylethan-1-amine

Formula: C19H21ClN2O3S Molecular weight: 392.89964 g/mol InChI Key: AGWLOAWDFIZVCQ-UHFFFAOYSA-N

InChI=1S/C19H21ClN2O3S/c1-21(2)12-11-14-13-22(17-5-4-6-18(25-3)19(14)17)26(23,24)16-9-7-15(20)8-10-16/h4-10,13H,11-12H2,1-3H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

5783
Analogue 18: Adding Phenylthio at R1

IUPAC: 2-[4-Methoxy-1-(phenylsulfanyl)-1H-indol-3-yl]-N,N-dimethylethan-1-amine

Formula: C19H22N2OS Molecular weight: 326.45578 g/mol InChI Key: CHIIBHOOYYBXNW-UHFFFAOYSA-N

InChI=1S/C19H22N2OS/c1-20(2)13-12-15-14-21(23-16-8-5-4-6-9-16)17-10-7-11-18(22-3)19(15)17/h4-11,14H,12-13H2,1-3H3

Nyandege, A; Kolanos, R; Roth, BL; Glennon, RA. Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg. Med. Chem. Lett., 15 Mar 2007, 17 (6),. 151 kB. doi:10.1016/j.bmcl.2006.12.089

Nine R4 analogues:
5006
Analogue 1: Removing Methoxy at R4

DMT
Tryptamine, N,N-dimethyl
Indole, 3-[2-(dimethylamino)ethyl]
N,N-Dimethyltryptamine
Desoxybufotenine
3-[2-(Dimethylamino)ethyl]indole
Nigerine

IUPAC: 2-(1H-Indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H16N2 Molecular weight: 188.26884 g/mol InChI Key: DMULVCHRPCFFGV-UHFFFAOYSA-N

InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3

PubChem CID: 6089; ChemSpider: 5864; Drugs Forum: DMT; Erowid: DMT; Wikipedia: Dimethyltryptamine

See also TiHKAL: #2 DBT
#3 DET
#5 α,O-DMS
#7 2,α-DMT
#8 α,N-DMT
#9 DPT
#13 Harmaline
#14 Harmine
#16 4-HO-DET
#21 4-HO-MET
#27 MBT
#30 4,5-MDO-DMT
#31 5,6-MDO-DMT
#34 2-Me-DMT
#35 Melatonin
#38 5-MeO-DMT
#39 4-MeO-MIPT
#41 5,6-MeO-MIPT
#42 5-MeO-NMT
#43 5-MeO-pyr-T
#44 6-MeO-THH
#47 MIPT
#48 α-MT
#50 NMT
#52 pyr-T
#53 T
#54 Tetrahydroharmine
#55 α,N,O-TMS
#57 DALT

See also Transcripts: 1.137, 3.327

See also Pharmacology notes I: p. 137, DMT
See also Chemistry notes VIII: p. 66, DMT: Synthesis
p. 67, DMT: GC-MS
p. 68, DMT: GC-MS
p. 70, DMT: Synthesis
p. 71, DMT: GC-MS
p. 132, DMT: Synthesis

Brandt, SD; Moore, SA; Freeman, S; Kanu, AB. Characterization of the synthesis of N,N-dimethyltryptamine by reductive amination using gas chromatography ion trap mass spectrometry. Drug Test. Anal., 1 Jul 2010, 2 (7), 330–338. 192 kB. doi:10.1002/dta.142

McIlhenny, EH; Pipkin, KE; Standish, LJ; Wechkin, HA; Strassman, R; Barker, SA. Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry. J. Chromatogr. A, 18 Dec 2009, 1216 (51), 8960–8968. 450 kB. doi:10.1016/j.chroma.2009.10.088

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

Kalir, A; Szara, S. Synthesis and pharmacological activity of alkylated tryptamines. J. Med. Chem., 1 May 1966, 9 (3), 341–344. 482 kB. doi:10.1021/jm00321a017

Szara, S; Axelrod, J. Hydroxylation and N-demethylation of N,N-dimethyltryptamine. Experientia, 1 Jun 1959, 15 (6), 216–217. 304 kB. doi:10.1007/BF02158111

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Strassman, RJ. Human psychopharmacology of N,N,-dimethyltryptamine. Behav. Brain Res., 15 Dec 1995, 73 (1–2), 121–124. 396 kB. doi:10.1016/0166-4328(96)00081-2

Su, T; Hayashi, T; Vaupel, DB. When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor. Sci. Signal., 10 Mar 2009, 2 (61), 1–4. 392 kB. doi:10.1126/scisignal.261pe12

Martins, CPB; Freeman, S; Alder, JF; Brandt, SD. Characterisation of a proposed internet synthesis of N,N-dimethyltryptamine using liquid chromatography/electrospray ionisation tandem mass spectrometry. J. Chromatogr. A, 14 Aug 2009, 1216 (33), 6119–6123. 315 kB. doi:10.1016/j.chroma.2009.06.060

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Pires, APS; Oliveira, CDR; Moura, S; Dörr, FA; Silva, WAE; Yonamine, M. Gas chromatographic analysis of dimethyltryptamine and β-carboline alkaloids in ayahuasca, an Amazonian psychoactive plant beverage. Phytochem. Anal., 1 Mar 2009, 20 (2), 149–153. 131 kB. doi:10.1002/pca.1110

Brandt, SD; Martins, CPB; Freeman, S; Dempster, N; Riby, PG; Gartz, J; Alder, JF. Halogenated solvent interactions with N,N-dimethyltryptamine: Formation of quaternary ammonium salts and their artificially induced rearrangements during analysis. Forensic Sci. Int., 4 Jul 2008, 178 (2–3), 162–170. 785 kB. doi:10.1016/j.forsciint.2008.03.013

Gaujac, A; Martinez, ST; Gomes, AA; Andrade, SJ; Pinto, AC; David, JM; Navickiene, S; Andrade, JB. Application of analytical methods for the structural characterization and purity assessment of N,N-dimethyltryptamine, a potent psychedelic agent isolated from Mimosa tenuiflora inner barks. Microchem. J., Jul 2013. 685 kB. doi:10.1016/j.microc.2012.03.033

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Jacob, MS; Presti, DE. Endogenous psychoactive tryptamines reconsidered: an anxiolytic role for dimethyltryptamine. Med. Hypotheses, 2005, 64 (5), 930–937. 162 kB. doi:10.1016/j.mehy.2004.11.005

Gaujac, A; Ford, JL; Dempster, NM; Andrade, JB; Brandt, SD. Investigations into the polymorphic properties of N,N-dimethyltryptamine by X-ray diffraction and differential scanning calorimetry. Microchem. J., 1 Sep 2013, 110, 146–157. 1166 kB. doi:10.1016/j.microc.2013.03.009

Blackledge, RD; Taylor, CM. Psychotria viridis—A botanical source of dimethyltryptamine (DMT). Microgram J., 1 Jan 2003, 1 (1–2), 18–22. 429 kB.

Fasanello, JA; Placke, AD. The isolation, identification, and quantitation of dimethyltryptamine (DMT) in Mimosa Hostilis. Microgram J., 1 Jan 2007, 5 (1–4), 41–52. 168 kB.

Rodriguez-Cruz, SE. Analysis and characterization of designer tryptamines using electrospray ionization mass spectrometry (ESI-MS). Microgram J., 1 Jul 2005, 3 (3–4), 107–129. 1577 kB.

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomed. Chromatogr., 1 Mar 2012, 26 (3), 301–313. 557 kB. doi:10.1002/bmc.1657

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine. Biomed. Chromatogr., 1 Sep 2011, 25 (9), 970–984. 1030 kB. doi:10.1002/bmc.1551

Gambelunghe, C; Aroni, K; Rossi, R; Moretti, L; Bacci, M. Identification of N,N-dimethyltryptamine and β-carbolines in psychotropic ayahuasca beverage. Biomed. Chromatogr., 1 Oct 2008, 22 (10) 1056–1059. 140 kB. doi:10.1002/bmc.1023

Szára, S. The comparison of the psychotic effect of tryptamine derivatives with the effects of mescaline and LSD-25 in self-experiments. In Psychotropic Drugs [proceedings]; Garattini, S; Ghetti, V, Eds., Elsevier, 1957; pp 460–467. 480 kB.

Moura, S; Carvalho, FG; Oliveira, CDR; Pinto, E; Yonamine, M. qNMR: An applicable method for the determination of dimethyltryptamine in ayahuasca, a psychoactive plant preparation. Phytochem. Lett., 11 Jun 2010, 3 (2), 79–83. 227 kB. doi:10.1016/j.phytol.2009.12.004

Barker, SA; McIlhenny, EH; Strassman, R. A critical review of reports of endogenous psychedelic N,N-dimethyltryptamines in humans: 1955–2010. Drug Test. Anal., 2012. 270 kB. doi:10.1002/dta.422

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Fontanilla, D; Johannessen, M; Hajipour, AR; Cozzi, NV; Jackson, MB; Ruoho, AE. The hallucinogen N,N-dimethyltryptamine (DMT) is an endogenous sigma-1 receptor regulator. Science, 13 Feb 2009, 323 (5916):,934–937. 529 kB. doi:10.1126/science.1166127

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

Meyers-Riggs, B. N-Alkylated tryptamines. countyourculture: rational exploration of the underground, 10 Mar 2012.

Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture: rational exploration of the underground, 5 Dec 2011.

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Brandt, SD; Tearavarich, R; Dempster, N; Cozzi, NV; Daley, PF. Synthesis and characterization of 5-methoxy-2-methyl-N,N-dialkylated tryptamines. Drug Test. Anal., 1 Jan 2012, 4 (1), 24–32. 506 kB. doi:10.1002/dta.398

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

Cozzi, NV; Shulgin, AT; Daley, PF; Gopalakrishnan, A; Anderson, LL; Feih, JT; Ruoho, AE. Psychoactive N,N-dialkyltryptamines modulate serotonin transport by at least two mechanisms. Soc. Neurosci. Abs., 1 Jan 2008, 536.17. 52 kB.

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Cozzi, NV; Gopalakrishnan, A; Anderson, LL; Feih, JT; Shulgin, AT; Daley, PF; Ruoho, AE. Dimethyltryptamine and other hallucinogenic tryptamines exhibit substrate behavior at the serotonin uptake transporter and the vesicle monoamine transporter. J. Neural. Transm., 1 Dec 2009, 116 (12), 1591–1599. 420 kB. doi:10.1007/s00702-009-0308-8

Shulgin, AT. DMT and tryptophan. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 19 Sep 2002.

Szara, S; Hearst, E; Putney, F. Metabolism and behavioural action of psychotropic tryptamine homologues. Int. J. Neuropharmacol., 1 Nov 1962, 1 (1–3), 111–117. 1056 kB. doi:10.1016/0028-3908(62)90015-1

Szara, S. Dimethyltryptamin: Its metabolism in man; the relation to its psychotic effect to the serotonin metabolism. Experientia, 1 Jan 1956, 12 (11), 441–442. 333 kB. doi:10.1007/BF02157378

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3077 kB. doi:10.1007/BF02818560

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Böszörményi, Z; Szára, S. Dimethyltryptamine experiments with psychotics. Br. J. Psychiatry, 1 Apr 1958, 104 (435), 445–453. 1274 kB. doi:10.1192/bjp.104.435.445

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Ciprian-Ollivier, J; Cetkovich-Bakmas, MG. Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr. Res., 19 Dec 1997, 28 (2–3), 257–265. 722 kB. doi:10.1039/S0920-9964(97)00116-3

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. doi:10.1016/j.pbb.2007.06.001

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

Shulgin, AT. Profiles of psychedelic drugs. 1. DMT; 2. TMA-2. J. Psychedelic Drugs, 1 Jan 1976, 8 (2), 167–169. 2097 kB. doi:10.1080/02791072.1976.10471846

Kline, TB; Benington, F; Morin, RD; Beaton, JM; Glennon, RA; Domelsmith, LN; Houk, KN; Rozeboom, MD. Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives. J. Med. Chem., 1 Jan 1982, 25 (11), 1381–1383. 378 kB. doi:10.1021/jm00353a021

5018
Analogue 2: Substituting Hydroxy for Methoxy at R4

4-HO-DMT
CX-59
PSOH
Psilocin
Tryptamine, 4-hydroxy-N,N-dimethyl
4-Indolol, 3-[2-(dimethylamino)ethyl]
N,N-Dimethyl-4-hydroxytryptamine
3-[2-(Dimethylamino)ethyl]-4-indolol

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol

Formula: C12H16N2O Molecular weight: 204.26824 g/mol InChI Key: SPCIYGNTAMCTRO-UHFFFAOYSA-N

InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3

PubChem CID: 4980; ChemSpider: 4807; Drugs Forum: 4-HO-DMT; Erowid: Psilocybin & Psilocin; Wikipedia: Psilocin

See also TiHKAL: #16 4-HO-DET
#19 5-HO-DMT
#20 4-HO-DPT
#21 4-HO-MET
#22 4-HO-MIPT
#23 4-HO-MPT
#24 4-HO-pyr-T
#26 LSD
#31 5,6-MDO-DMT
#39 4-MeO-MIPT
#47 MIPT
#56 5-MeO-DALT

See also Transcripts: 2.292

See also Pharmacology notes II: p. 292, Psilocin

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

Gartz, J. Extraction and analysis of indole derivatives from fungal biomass. J. Basic. Microbiol., 1994, 34 (1), 17–22. 614 kB. doi:10.1002/jobm.3620340104

Meyers-Riggs, B. 4-Hydroxy tryptamines. countyourculture: rational exploration of the underground, 7 Jul 2012.

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Sarwar, M; McDonald, JL. A rapid extraction and GC/MS methodology for the identification of psilocyn in mushroom/chocolate concoctions. Microgram J., 1 Jul 2003, 1 (3–4), 177–183. 211 kB.

Sard, H; Kumaran, G; Morency, C; Roth, BL; Toth, BA; Hec, P; Shuster, L. SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist. Bioorg. Med. Chem. Lett., 1 Jan 2005, 15 (20), 4555–4599. 134 kB. doi:10.1016/j.bmcl.2005.06.104

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Hofmann, A; Heim, R; Brack, A; Kobel, H; Frey, A; Ott, H; Petrzilka, T; Troxler, F. Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen. Helv. Chim. Acta, 1959, 42 (5), 1557–1572. 1132 kB. doi:10.1002/hlca.19590420518

Troxler, F; Seemann, F; Hofmann, A. Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen. Helv. Chim. Acta, 1959, 42 (6), 2073–2103. 1589 kB. doi:10.1002/hlca.19590420638

Chilton, WS; Bigwood, J; Jensen, RE. Psilocin, Bufotenine and serotonin: Historical and biosynthetic observations. J. Psychoactive Drugs, 1 Jan 1979, 11 (1–2), 61–69. 9523 kB. doi:10.1080/02791072.1979.10472093

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. doi:10.1016/j.forsciint.2011.11.003

Migliaccio, GP; Shieh, TN; Byrn, SR; Hathaway, BA; Nichols, DE. Comparison of solution conformational preferences for the hallucinogens bufotenin and psilocin using 360-MHz proton NMR spectroscopy. J. Med. Chem., 1 Feb 1981, 24 (2), 206–209. 564 kB. doi:10.1021/jm00134a016

Morris, H. Blood Spore: Of Murder and Mushrooms. Harper’s Magazine, 1 Jul 2013, 41–56. 13834 kB.

Rodriguez-Cruz, SE. Analysis and characterization of psilocybin and psilocin using liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MS) with collision-induced-dissociation (CID) and source-induced-dissociation (SID). Microgram J., 1 Jul 2005, 3 (3–4), 175–182. 560 kB.

Wiseman-Distler, MH; Sourkes, TL. The effect of 4-hydroxyindoles on the metabolism of 5-hydroxytryptamine (serotonin). Ann. N.Y. Acad. Sci., 1 Jan 1962, 96, 142–151. 458 kB. doi:10.1111/j.1749-6632.1962.tb50109.x

Heim, R; Genest, K; Hughes, DW; Belec, G. Botanical and chemical characterisation of a forensic mushroom specimen of the genus psilocybe. J. Forensic Sci. Soc., 1 Jul 1966, 6 (4), 192–201. 2094 kB. doi:10.1016/S0015-7368(66)70336-3

Marona-Lewicka, D; Nichols, DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol. Biochem. Behav., 1 Jan 2007, 87 (4), 453–461. 266 kB. doi:10.1016/j.pbb.2007.06.001

Shulgin, AT. Drug testing for mushrooms. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 1 Dec 2004.

Shulgin, AT. Psilocybe mushroom extractions. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 5 Mar 2003.

Repke, DB; Ferguson, WJ; Bates, DK. Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols. J. Heterocycl. Chem., 1 Jan 1981, 18 (1), 175–179. 368 kB. doi:10.1002/jhet.5570180131

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Parker, MA; Kurrasch, DM; Nichols, DE. The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands. Bioorg. Med. Chem., 1 Jan 2008, 16 (8), 4661–4669. 296 kB. doi:10.1016/j.bmc.2008.02.033

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture: rational exploration of the underground, 5 Dec 2011.

Meyers-Riggs, B. Biosynthesis of 4-substituted tryptamine derivatives. countyourculture: rational exploration of the underground, 17 Feb 2012.

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3077 kB. doi:10.1007/BF02818560

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. doi:10.1016/0024-3205(91)90582-V

Gross, ST. Detecting psychoactive drugs in the developmental stages of mushrooms. J. Forensic Sci., 1 May 2000, 45 (3), 527–537. 6189 kB. doi:10.1520/JFS14725J

Gross, ST. Psychotropic drugs in developmental mushrooms: A case study review. J. Forensic Sci., 1 Nov 2002, 47 (6), 1–5. 369 kB. doi:10.1520/JFS15564J

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Pellegrini, M; Rotolo, MC; Marchei, E; Pacifici, R; Saggio, F; Pichini, S. Magic truffles or philosopher’s stones: a legal way to sell psilocybin? Drug Test. Anal., 1 Mar 2013, 5 (3), 182–185. 219 kB. doi:10.1002/dta.1400

5058
Analogue 3: Substituting Phosphoryloxy for Methoxy at R4

4-H2PO4-DMT
4-HO-DMT phosphate ester
CY-39
PSOP
Psilocybin
Psilocin, phosphate ester
Tryptamine, N,N-dimethyl-4-phosphoryloxy
4-Indolol, 3-[2-(dimethylamino)ethyl], phosphate ester
N,N-Dimethyl-4-phosphoryloxytryptamine
3-[2-(Dimethylamino)ethyl]-4-indolol, phosphate ester

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate

Formula: C12H17N2O4P Molecular weight: 284.248141 g/mol InChI Key: QVDSEJDULKLHCG-UHFFFAOYSA-N

InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)

PubChem CID: 10624; ChemSpider: 10178; Drugs Forum: 4-H2PO4-DMT; Erowid: Psilocybin & Psilocin; Wikipedia: Psilocybin

See also PiHKAL: #40 2C-T-2 #41 2C-T-4 #127 METHYL-DOB #132 MMDA
See also TiHKAL: #16 4-HO-DET
#19 5-HO-DMT
#22 4-HO-MIPT
#26 LSD
#30 4,5-MDO-DMT
#31 5,6-MDO-DMT
#46 5-MeS-DMT
#48 α-MT

See also Transcripts: 1.187, 2.323.4, 2.323.5, 3.400, 3.401, 3.402

See also Pharmacology notes I: p. 187, Psilocybin
See also Pharmacology notes II: app. 5, Untitled

Wark, C. A social and cultural history of the federal prohibition of psilocybin. Ph. D. Thesis, University of Missouri-Columbia, Columbia, MO, 1 Aug 2007. 2183 kB.

Sard, H; Kumaran, G; Morency, C; Roth, BL; Toth, BA; Hec, P; Shuster, L. SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist. Bioorg. Med. Chem. Lett., 1 Jan 2005, 15 (20), 4555–4599. 134 kB. doi:10.1016/j.bmcl.2005.06.104

Meyers-Riggs, B. 4-Hydroxy tryptamines. countyourculture: rational exploration of the underground, 7 Jul 2012.

Nichols, DE. Commentary on: Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance by Griffiths et al. Psychopharmacology, 1 Aug 2006, 187 (3), 284–286. 71 kB. doi:10.1007/s00213-006-0458-4

Gartz, J. Extraction and analysis of indole derivatives from fungal biomass. J. Basic. Microbiol., 1994, 34 (1), 17–22. 614 kB. doi:10.1002/jobm.3620340104

Hofmann, A; Heim, R; Brack, A; Kobel, H; Frey, A; Ott, H; Petrzilka, T; Troxler, F. Psilocybin und Psilocin, zwei psychotrope Wirkstoffe aus mexikanischen Rauschpilzen. Helv. Chim. Acta, 1959, 42 (5), 1557–1572. 1132 kB. doi:10.1002/hlca.19590420518

Troxler, F; Seemann, F; Hofmann, A. Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen. Helv. Chim. Acta, 1959, 42 (6), 2073–2103. 1589 kB. doi:10.1002/hlca.19590420638

Griffiths, RR; Richards, WA; McCann, U; Jesse, R. Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance. Psychopharmacology, 1 Aug 2006, 187 (3), 268–283. 342 kB. doi:10.1007/s00213-006-0457-5

Morris, H. Blood Spore: Of Murder and Mushrooms. Harper’s Magazine, 1 Jul 2013, 41–56. 13834 kB.

Rodriguez-Cruz, SE. Analysis and characterization of psilocybin and psilocin using liquid chromatography-electrospray ionization mass spectrometry (LC-ESI-MS) with collision-induced-dissociation (CID) and source-induced-dissociation (SID). Microgram J., 1 Jul 2005, 3 (3–4), 175–182. 560 kB.

Wiseman-Distler, MH; Sourkes, TL. The effect of 4-hydroxyindoles on the metabolism of 5-hydroxytryptamine (serotonin). Ann. N.Y. Acad. Sci., 1 Jan 1962, 96, 142–151. 458 kB. doi:10.1111/j.1749-6632.1962.tb50109.x

Pellegrini, M; Rotolo, MC; Marchei, E; Pacifici, R; Saggio, F; Pichini, S. Magic truffles or philosopher’s stones: a legal way to sell psilocybin? Drug Test. Anal., 1 Mar 2013, 5 (3), 182–185. 219 kB. doi:10.1002/dta.1400

Heim, R; Genest, K; Hughes, DW; Belec, G. Botanical and chemical characterisation of a forensic mushroom specimen of the genus psilocybe. J. Forensic Sci. Soc., 1 Jul 1966, 6 (4), 192–201. 2094 kB. doi:10.1016/S0015-7368(66)70336-3

Gouzoulis-Mayfrank, E. Differential actions of an entactogen compared to a stimulant and a hallucinogen in healthy humans. In Heffter Review; Nichols, DE, Ed., Heffter Research Institute, Santa Fe, NM, 2001; Vol. 2, pp 64–72. 261 kB.

Passie, T; Seifert, J; Schneider, U; Emrich, HM. The pharmacology of psilocybin. Addict. Biol., 1 Jan 2002, 7 (4), 357–364. 184 kB. doi:10.1080/135562102100000593

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Bunch, KS. Psilocybin and spiritual experience. Psy. D. Thesis, Alliant International University, San Francisco, CA, USA, 1 Aug 2009. 5715 kB.

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3077 kB. doi:10.1007/BF02818560

Shulgin, AT. Psilocybe mushroom extractions. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 5 Mar 2003.

Shulgin, AT. Drug testing for mushrooms. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 1 Dec 2004.

Leung, AY; Paul, AG. Baeocystin and norbaeocystin: New analogs of psilocybin from Psilocybe baeocystis. J. Pharm. Sci., 1 Jan 1968, 57 (10), 1667–1671. 399 kB. doi:10.1002/jps.2600571007

Nichols, DE; Frescas, SP. Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin. Synthesis, 1 Jan 1999, 1999, 935–938. 1481 kB. doi:10.1055/s-1999-3490

Blaazer, AR; Smid, P; Kruse, CG. Structure-activity relationships of phenylalkylamines as agonist ligands for 5-HT2A receptors. ChemMedChem, 15 Sep 2008, 3 (9), 1299–1309. 461 kB. doi:10.1002/cmdc.200800133

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Meyers-Riggs, B. Grid biosynthesis of psilocybin. countyourculture: rational exploration of the underground, 5 Dec 2011.

Vollenweider, FX; Kometer, M. The neurobiology of psychedelic drugs: implications for the treatment of mood disorders. Nat. Rev. Neurosci., 1 Sep 2010, 11 (9), 642–651. 588 kB. doi:10.1038/nrn2884

Agurell, S; Nilsson, JLG. Biosynthesis of psilocybin. Part II. Incorporation of labelled tryptamine derivatives. Acta Chem. Scand., 1 Jan 1968, 22 (4), 1210–1218. 805 kB. doi:10.3891/acta.chem.scand.22-1210

Shulgin, AT. Profiles of psychedelic drugs. 8. Psilocybin. J. Psychedelic Drugs, 1 Jan 1980, 12 (1), 79. 1595 kB. doi:10.1080/02791072.1980.10471557

Gross, ST. Detecting psychoactive drugs in the developmental stages of mushrooms. J. Forensic Sci., 1 May 2000, 45 (3), 527–537. 6189 kB. doi:10.1520/JFS14725J

Gross, ST. Psychotropic drugs in developmental mushrooms: A case study review. J. Forensic Sci., 1 Nov 2002, 47 (6), 1–5. 369 kB. doi:10.1520/JFS15564J

5171
Analogue 4: Substituting Methylthio for Methoxy at R4

4-MeS-DMT
N,N-Dimethyl-4-methylthiotryptamine

IUPAC: N,N-Dimethyl-2-[4-(methylsulfanyl)-1H-indol-3-yl]ethan-1-amine

Formula: C13H18N2S Molecular weight: 234.36042 g/mol InChI Key: YWCOPJQNWPEWQP-UHFFFAOYSA-N

InChI=1S/C13H18N2S/c1-15(2)8-7-10-9-14-11-5-4-6-12(16-3)13(10)11/h4-6,9,14H,7-8H2,1-3H3

PubChem CID: 21180; ChemSpider: 167880

See also TiHKAL: #46 5-MeS-DMT      

Kline, TB; Benington, F; Morin, RD; Beaton, JM; Glennon, RA; Domelsmith, LN; Houk, KN; Rozeboom, MD. Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives. J. Med. Chem., 1 Jan 1982, 25 (11), 1381–1383. 378 kB. doi:10.1021/jm00353a021

Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. doi:10.1021/jm00350a005

5370
Analogue 5: Substituting Acetoxy for Methoxy at R4

4-AcO-DMT
4-Acetoxy-DMT
PSOA
Psilacetin
4-Acetoxy-N,N-dimethyltryptamine

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl acetate

Formula: C14H18N2O2 Molecular weight: 246.30492 g/mol InChI Key: RTLRUOSYLFOFHV-UHFFFAOYSA-N

InChI=1S/C14H18N2O2/c1-10(17)18-13-6-4-5-12-14(13)11(9-15-12)7-8-16(2)3/h4-6,9,15H,7-8H2,1-3H3

PubChem CID: 15429212; ChemSpider: 21106357; Drugs Forum: 4-AcO-DMT; Erowid: 4-Acetoxy-DMT; Wikipedia: O-Acetylpsilocin

See also TiHKAL: #19 5-HO-DMT      

Nichols, DE; Frescas, SP. Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin. Synthesis, 1 Jan 1999, 1999, 935–938. 1481 kB. doi:10.1055/s-1999-3490

Meyers-Riggs, B. 4-Hydroxy tryptamines. countyourculture: rational exploration of the underground, 7 Jul 2012.

5223
Analogue 6: Substituting Amino for Methoxy at R4

4-Amino-DMT

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-amine

Formula: C12H17N3 Molecular weight: 203.28348 g/mol InChI Key: LRLDHGFFSHPWME-UHFFFAOYSA-N

InChI=1S/C12H17N3/c1-15(2)7-6-9-8-14-11-5-3-4-10(13)12(9)11/h3-5,8,14H,6-7,13H2,1-2H3

PubChem CID: 57438418

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Mckay, JB; Parkhursrt, RM; Silversteinax, M; Skinne, DWA. Analogues of psilocin and lysergic acid diethylamide. I. Chloro, nitro, and amino derivatives of 3-substituted indoles. Can. J. Chem., 1 Jan 1963, 41 (10), 2585–2590. 249 kB. doi:10.1139/v63-378

5226
Analogue 7: Substituting Fluoro for Methoxy at R4

4-F-DMT

IUPAC: 2-(4-Fluoro-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15FN2 Molecular weight: 206.2593032 g/mol InChI Key: ISJZKVWGUWBUFG-UHFFFAOYSA-N

InChI=1S/C12H15FN2/c1-15(2)7-6-9-8-14-11-5-3-4-10(13)12(9)11/h3-5,8,14H,6-7H2,1-2H3

PubChem CID: 11492162; ChemSpider: 9666968

Blair, JB. Synthesis and pharmacological evaluation of fluorinated hallucinogenic tryptamine analogs and thienopyrrole bioisosteres of N,N-dimethyltryptamine. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 1997. 3251 kB.

Sard, H; Kumaran, G; Morency, C; Roth, BL; Toth, BA; Hec, P; Shuster, L. SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist. Bioorg. Med. Chem. Lett., 1 Jan 2005, 15 (20), 4555–4599. 134 kB. doi:10.1016/j.bmcl.2005.06.104

Blair, JB; Kurrasch-Orbaugh, D; Marona-Lewicka, D; Cumbay, MG; Watts, VJ; Barker, EL; Nichols, DE. Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines. J. Med. Chem., 1 Jan 2000, 43 (24), 4701–4710. 494 kB. doi:10.1021/jm000339w

5483
Analogue 8: Substituting Chloro for Methoxy at R4

IUPAC: 2-(4-Chloro-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C12H15ClN2 Molecular weight: 222.7139 g/mol InChI Key: JLGAFYIPWQMGPG-UHFFFAOYSA-N

InChI=1S/C12H15ClN2/c1-15(2)7-6-9-8-14-11-5-3-4-10(13)12(9)11/h3-5,8,14H,6-7H2,1-2H3

PubChem CID: 23373080

Mckay, JB; Parkhursrt, RM; Silversteinax, M; Skinne, DWA. Analogues of psilocin and lysergic acid diethylamide. I. Chloro, nitro, and amino derivatives of 3-substituted indoles. Can. J. Chem., 1 Jan 1963, 41 (10), 2585–2590. 249 kB. doi:10.1139/v63-378

5484
Analogue 9: Substituting Nitro for Methoxy at R4

IUPAC: N,N-Dimethyl-2-(4-nitro-1H-indol-3-yl)ethan-1-amine

Formula: C12H15N3O2 Molecular weight: 233.2664 g/mol InChI Key: ZDIYDYYEQOZCGA-UHFFFAOYSA-N

InChI=1S/C12H15N3O2/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)15(16)17/h3-5,8,13H,6-7H2,1-2H3

Mckay, JB; Parkhursrt, RM; Silversteinax, M; Skinne, DWA. Analogues of psilocin and lysergic acid diethylamide. I. Chloro, nitro, and amino derivatives of 3-substituted indoles. Can. J. Chem., 1 Jan 1963, 41 (10), 2585–2590. 249 kB. doi:10.1139/v63-378

Five skeleton analogues:
5468
Analogue 1: With 2-(1H-Indol-3-yl)cyclopropanamine skeleton

4-MeO-ICPA

IUPAC: 2-(4-Methoxy-1H-indol-3-yl)cyclopropanamine

Formula: C12H14N2O Molecular weight: 202.25236 g/mol InChI Key: SVXXIYYEEVIKRL-UHFFFAOYSA-N

InChI=1S/C12H14N2O/c1-15-11-4-2-3-10-12(11)8(6-14-10)7-5-9(7)13/h2-4,6-7,9,14H,5,13H2,1H3

PubChem CID: 11820166; ChemSpider: 9994819

Vangveravong, S; Kanthasamy, A; Lucaites, VL; Nelson, DL; Nichols, DE. Synthesis and serotonin receptor affinities of a series of trans-2-(indol-3-yl)cyclopropylamine derivatives. J. Med. Chem., 1 Jan 1998, 41 (25), 4995–5001. 140 kB. doi:10.1021/jm980318q

5480
Analogue 2: With 2-(1-Benzothiophen-3-yl)ethanamine skeleton

IUPAC: 2-(4-Methoxy-1-benzothiophen-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H17NOS Molecular weight: 235.34518 g/mol InChI Key: VGRGPSBPNCBVLX-UHFFFAOYSA-N

InChI=1S/C13H17NOS/c1-14(2)8-7-10-9-16-12-6-4-5-11(15-3)13(10)12/h4-6,9H,7-8H2,1-3H3

PubChem CID: 21826572; ChemSpider: 10569659

Chapman, NB; Scrowston, RM; Sutton,, TM. Synthesis of the sulphur analogue of psilocin and some related compounds. J. Chem. Soc. Perkin Trans., 1 Jan 1972, 1, 3011. 731 kB. doi:10.1039/P19720003011

5481
Analogue 3: With 2-(1-Benzothiophen-3-yl)ethanamine skeleton

IUPAC: 2-(4-Methoxy-1-benzothiophen-3-yl)-N-methylethan-1-amine

Formula: C12H15NOS Molecular weight: 221.3186 g/mol InChI Key: ZFJMRPPGAVQVNH-UHFFFAOYSA-N

InChI=1S/C12H15NOS/c1-13-7-6-9-8-15-11-5-3-4-10(14-2)12(9)11/h3-5,8,13H,6-7H2,1-2H3

PubChem CID: 20144265

Chapman, NB; Scrowston, RM; Sutton,, TM. Synthesis of the sulphur analogue of psilocin and some related compounds. J. Chem. Soc. Perkin Trans., 1 Jan 1972, 1, 3011. 731 kB. doi:10.1039/P19720003011

5482
Analogue 4: With 2-(1-Benzothiophen-3-yl)ethanamine skeleton

IUPAC: 2-(4-Methoxy-1-benzothiophen-3-yl)ethan-1-amine

Formula: C11H13NOS Molecular weight: 207.29202 g/mol InChI Key: AAHOGLYCQZTPAG-UHFFFAOYSA-N

InChI=1S/C11H13NOS/c1-13-9-3-2-4-10-11(9)8(5-6-12)7-14-10/h2-4,7H,5-6,12H2,1H3

PubChem CID: 21826570; ChemSpider: 10569657

Chapman, NB; Scrowston, RM; Sutton,, TM. Synthesis of the sulphur analogue of psilocin and some related compounds. J. Chem. Soc. Perkin Trans., 1 Jan 1972, 1, 3011. 731 kB. doi:10.1039/P19720003011

5769
Analogue 5: With 1-(2,3,4,9-Tetrahydro-1H-carbazol-4-yl)methanamine skeleton

IUPAC: 6-Methoxy-4-(2-methylpropyl)-2,3,4,9-tetrahydro-1H-carbazole

Formula: C16H22N2O Molecular weight: 258.35868 g/mol InChI Key: MEUKAKNAKNCMKB-UHFFFAOYSA-N

InChI=1S/C16H22N2O/c1-18(2)10-11-5-4-6-15-16(11)13-9-12(19-3)7-8-14(13)17-15/h7-9,11,17H,4-6,10H2,1-3H3

Glennon, RA; Lee, M; Rangisetty, JB; Dukat, M; Roth, BL; Savage, JE; McBridge, A; Rauser, L; Hufeisen, SJ; Lee, DKH. 2-Substituted tryptamines: Agents with selectivity for 5-HT6 serotonin receptors. J. Med. Chem., 9 Mar 2000, 43 (5), 1011–1018. 137 kB. doi:10.1021/jm990550b

17 isomers:
5021
Isomer 1

4-HO-MET
Tryptamine, N-ethyl-4-hydroxy-N-methyl
4-Indolol, 3-[2-(ethylmethylamino)ethyl]
N-Ethyl-4-hydroxy-N-methyltryptamine
3-[2-(Ethylmethylamino)ethyl]-4-indolol

IUPAC: 3-{2-[Ethyl(methyl)amino]ethyl}-1H-indol-4-ol

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: ORWQBKPSGDRPPA-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-3-15(2)8-7-10-9-14-11-5-4-6-12(16)13(10)11/h4-6,9,14,16H,3,7-8H2,1-2H3

PubChem CID: 21786582; ChemSpider: 10513072; Drugs Forum: 4-HO-MET; Wikipedia: 4-HO-MET

Repke, DB; Ferguson, WJ; Bates, DK. Psilocin analogs II. Synthesis of 3-[2-(dialkylamino)ethyl]-, 3-[2-(N-methyl-N-alkylamino)ethyl]-, and 3-[2-(cycloalkylamino)ethyl]indol-4-ols. J. Heterocycl. Chem., 1 Jan 1981, 18 (1), 175–179. 368 kB. doi:10.1002/jhet.5570180131

Kjellgren, A; Soussan, C. Heaven and Hell—A phenomenological study of recreational use of 4-HO-MET in Sweden. J. Psychoactive Drugs, 1 Jul 2011, 43 (3), 211–219. 231 kB. doi:10.1080/02791072.2011.605699

5038
Isomer 2

5-MeO-DMT
N,N,O-TMS
OMB
Tryptamine, 5-methoxy-N,N-dimethyl
Indole, 5-methoxy-3-[2-(dimethylamino)ethyl]
5-Methoxy-N,N-dimethyltryptamine
5-Methoxy-3-[2-(dimethylamino)ethyl]indole
N,N,O-Trimethylserotonin
Bufotenine methyl ether
O-Methylbufotenine

IUPAC: 2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: ZSTKHSQDNIGFLM-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

PubChem CID: 1832; ChemSpider: 1766; Erowid: 5-MeO-DMT; Wikipedia: 5-MeO-DMT

See also TiHKAL: #6 DMT
#7 2,α-DMT
#10 EIPT
#13 Harmaline
#19 5-HO-DMT
#31 5,6-MDO-DMT
#35 Melatonin
#36 5-MeO-DET
#39 4-MeO-MIPT
#40 5-MeO-MIPT
#42 5-MeO-NMT
#43 5-MeO-pyr-T
#45 5-MeO-TMT
#46 5-MeS-DMT
#50 NMT

See also Transcripts: 1.194, 1.195, 2.298, 2.323.4

See also Pharmacology notes I: p. 194, 5-MeO-DMT
p. 195, 5-MeO-DMT
See also Pharmacology notes II: app. 4, Experiment for Death Valley
p. 298, 5-MeO-DMT

McIlhenny, EH; Pipkin, KE; Standish, LJ; Wechkin, HA; Strassman, R; Barker, SA. Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry. J. Chromatogr. A, 18 Dec 2009, 1216 (51), 8960–8968. 450 kB. doi:10.1016/j.chroma.2009.10.088

Jensen, N. Tryptamines as ligands and modulators of the serotonin 5-HT2A receptor and the isolation of aeruginascin from the hallucinogenic mushroom Inocybe aeruginascens. Ph. D. Thesis, Georg-August-Universität zu Göttingen, Göttingen, Germany, 4 Nov 2004. 2268 kB. Referent: Prof. Dr. H. Laatsch; Korreferent: Prof. D. E. Nichols.

McKenna, DJ; Repke, DB; Lo, L; Peroutka, SJ. Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes. Neuropharmacology, 1 Mar 1990, 29 (3), 191–198. 679 kB. doi:10.1016/0028-3908(90)90001-8

Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. doi:10.1021/jm00350a005

Glennon, RA; Hong, S; Bondarev, M; Law, H; Dukat, M; Rakhit, S; Power, P; Fan, E; Kinneau, D; Kamboj, R; Teitler, M; Herrick-Davis, K; Smith, C. Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors. J. Med. Chem., 5 Jan 1996, 39 (1), 314–322. 193 kB. doi:10.1021/jm950498t

Brandt, SD; Freeman, S; Fleet, IA; McGagh, P; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR. Analyst, 2005, 130 (3), 330–344. 403 kB. doi:10.1039/b413014f

Halberstadt, AL; Nichols, DE; Geyer, MA. Behavioral effects of α,α,β,β-tetradeutero-5-MeO-DMT in rats: comparison with 5-MeO-DMT administered in combination with a monoamine oxidase inhibitor. Psychopharmacology, 1 Jun 2012, 221 (4), 709–218. 296 kB. doi:10.1007/s00213-011-2616-6

Barker, SA; McIlhenny, EH; Strassman, R. A critical review of reports of endogenous psychedelic N,N-dimethyltryptamines in humans: 1955–2010. Drug Test. Anal., 2012. 270 kB. doi:10.1002/dta.422

Glennon, RA; Lee, M; Rangisetty, JB; Dukat, M; Roth, BL; Savage, JE; McBridge, A; Rauser, L; Hufeisen, SJ; Lee, DKH. 2-Substituted tryptamines: Agents with selectivity for 5-HT6 serotonin receptors. J. Med. Chem., 9 Mar 2000, 43 (5), 1011–1018. 137 kB. doi:10.1021/jm990550b

Takahashi, M; Nagashima, M; Suzuki, J; Seto, T; Yasuda, I; Yoshida, T. Analysis of phenethylamines and tryptamines in designer drugs using gas chromatography-mass spectrometry. J. Health Sci., 2008, 54 (1), 89–96. 1882 kB. doi:10.1248/jhs.54.89

Shen, H; Jiang, X; Winter, JC; Yu, A. Psychedelic 5-methoxy-N,N-dimethyltryptamine: Metabolism, pharmacokinetics, drug interactions, and pharmacological actions. Curr. Drug Metab., 1 Oct 2010, 11 (8), 659–666. 589 kB. doi:10.2174/138920010794233495

Schmid, CL; Bohn, LM. Serotonin, but not N-methyltryptamines, activates the serotonin 2A receptor via a β-arrestin2/Src/Akt signaling complex in vivo. J. Neurosci., 6 Oct 2010, 30 (40), 13513–13524. 1534 kB. doi:10.1523/JNEUROSCI.1665-10.2010

Glennon, RA; Rosecrans, JA; Young, R. Behavioral properties of psychoactive phenylisopropylamines in rats. Eur. J. Pharmacol., 17 Dec 1981, 76 (4), 353–360. 964 kB. doi:10.1016/0014-2999(81)90106-0

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

Benington, F; Morin, RD; Clark, LC. Synthesis of O- and N-methylated derivatives of 5-hydroxytryptamine. J. Org. Chem., 1 Dec 1958, 23 (12), 1977–1979. 401 kB. doi:10.1021/jo01106a046

Spratley, TK; Hays, PA; Geer, LC; Cooper, SD; McKibben, TD. Analytical profiles for five “designer” tryptamines. Microgram J., 1 Jan 2005, 3 (1–2), 54–68. 473 kB.

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LC/MS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. doi:10.1002/bmc.2981

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for determining major constituents of ayahuasca and their metabolites in blood. Biomed. Chromatogr., 1 Mar 2012, 26 (3), 301–313. 557 kB. doi:10.1002/bmc.1657

McIlhenny, EH; Riba, J; Barbanoj, MJ; Strassman, R; Barker, SA. Methodology for and the determination of the major constituents and metabolites of the Amazonian botanical medicine ayahuasca in human urine. Biomed. Chromatogr., 1 Sep 2011, 25 (9), 970–984. 1030 kB. doi:10.1002/bmc.1551

McKenna, DJ. Monoamine odixase inhibitors in Amazonian hallucinogenic plants: Ethnobotanical, phytochemical, and pharmacological investigations. Ph. D. Thesis, University of British Columbia, BC, Canada, 26 Apr 1984. 12211 kB.

Braden, MR; Nichols, DE. Assessment of the roles of serines 5.43(239) and 5.46(242) for binding and potency of agonist ligands at the human serotonin 5-HT2A receptor. Mol. Pharmacol., 1 Jan 2007, 72 (5), 1200–1209. 487 kB. doi:10.1124/mol.107.039255

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Brandt, SD; Tirunarayanapuram, SS; Freeman, S; Dempster, N; Barker, SA; Daley, PF; Cozzi, NV; Martins, CPB. Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines. J. Labelled Compd. Radiopharm., 1 Nov 2008, 51 (14), 423–429. 169 kB. doi:10.1002/jlcr.1557

Glennon, RA; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of α-methyl and N-methyl substituents on behavioral activity. Biochem. Pharmacol., 1 Apr 1983, 32 (7), 1267–1273. 591 kB. doi:10.1016/0006-2952(83)90281-2

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

Chen, B; Liu, J; Chen, W; Chen, H; Lin, C. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 15 Jan 2008, 74 (4), 512–517. 486 kB. doi:10.1016/j.talanta.2007.06.012

Halberstadt, AL; Geyer, MA. Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens. Neuropharmacology, 1 Sep 2011, 61 (3) 364–381. 817 kB. doi:10.1016/j.neuropharm.2011.01.017

Brandt, SD; Tearavarich, R; Dempster, N; Cozzi, NV; Daley, PF. Synthesis and characterization of 5-methoxy-2-methyl-N,N-dialkylated tryptamines. Drug Test. Anal., 1 Jan 2012, 4 (1), 24–32. 506 kB. doi:10.1002/dta.398

Ray, TS. Psychedelics and the human receptorome. PLOS ONE, 2 Feb 2010, 5 (2), e9019. 791 kB. doi:10.1371/journal.pone.0009019

Callaway, JC; Grob, CS; McKenna, DJ; Nichols, DE; Shulgin, AT; Tupper, KW; Sklerov, JH; Levine, B; Moore, KA. A demand for clarity regarding a case report on the ingestion of 5-methoxy-N, N-Dimethyltryptamine (5-MeO-DMT) in an Ayahuasca preparation. J. Anal. Toxicol., 1 Jul 2006, 30 (6), 406–407. 53 kB. doi:10.1093/jat/30.6.406

Braden, MR. Towards a biophysical understanding of hallucinogen action. Ph. D. Thesis, Purdue University, West Lafayette, IN, 1 Jan 2007. 8442 kB.

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. doi:10.1016/0024-3205(91)90582-V

Winter, JC; Filipink, RA; Timineri, D; Helsley, SE; Rabin, RA. The paradox of 5-methoxy-N,N-dimethyltryptamine: an indoleamine hallucinogen that induces stimulus control via 5-HT1A receptors. Pharmacol. Biochem. Behav., 1 Jan 2000, 65 (1), 75–82. 157 kB. doi:10.1016/S0091-3057(99)00178-1

Kline, TB; Benington, F; Morin, RD; Beaton, JM; Glennon, RA; Domelsmith, LN; Houk, KN; Rozeboom, MD. Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives. J. Med. Chem., 1 Jan 1982, 25 (11), 1381–1383. 378 kB. doi:10.1021/jm00353a021

Ciprian-Ollivier, J; Cetkovich-Bakmas, MG. Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr. Res., 19 Dec 1997, 28 (2–3), 257–265. 722 kB. doi:10.1039/S0920-9964(97)00116-3

Brandt, SD; Freeman, S; Fleet, IA; Alder, JF. Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS. Analyst, 1 Jan 2005, 130 (9), 1258–1262. 250 kB. doi:10.1039/b504001a

Glennon, RA; Titeler, M; Lyon, RA; Slusher, RM. N,N-Di-n-propylserotonin: Binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin. J. Med. Chem., 1 Jan 1988, 31 (4), 867–870. 600 kB. doi:10.1021/jm00399a031

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Macor, JE; Fox, CB; Johnson, C; Koe, BK; Lebel, LA; Zorn, SH. 1-(2-Aminoethyl)-3-methyl-8,9-dihydropyrano[3,2-e]indole: A rotationally restricted phenolic analog of the neurotransmitter serotonin and agonist selective for serotonin (5-HT2-type) receptors. J. Med. Chem., 1 Jan 1992, 35 (20), 3625–3632. 1944 kB. doi:10.1021/jm00098a005

5055
Isomer 3

α,N,O-TMS
α,N-Dimethyl-5-methoxytryptamine
Tryptamine, 5-methoxy-α,N-dimethyl
Indole, 5-methoxy-3-[2-(methylamino)propyl]
5-Methoxy-α,N-dimethyltryptamine
5-Methoxy-3-[2-(methylamino)propyl]indole
α,N,O-Trimethylserotonin
Serotonin, α,N,O-trimethyl

IUPAC: 1-(5-Methoxy-1H-indol-3-yl)-N-methylpropan-2-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: IYEMYZOLBLHKFE-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-9(14-2)6-10-8-15-13-5-4-11(16-3)7-12(10)13/h4-5,7-9,14-15H,6H2,1-3H3

PubChem CID: 20961; ChemSpider: 19718; Wikipedia: Alpha,N,O-TMS

See also TiHKAL: #8 α,N-DMT      
See also Chemistry notes VIII: p. 4, α,N,O-TMS: Synthesis
p. 5, α,N,O-TMS: Synthesis
p. 6, α,N,O-TMS: GC-MS
p. 7, α,N,O-TMS: GC-MS
5112
Isomer 4

1-MeO-DMT
Lespedamine
1-Methoxy-N,N-dimethyltryptamine

IUPAC: 2-(1-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: DXTZTYQDNUHCAB-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-14(2)9-8-11-10-15(16-3)13-7-5-4-6-12(11)13/h4-7,10H,8-9H2,1-3H3

PubChem CID: 11138594; ChemSpider: 9313707

See also TiHKAL: #6 DMT      
5127
Isomer 5

CMY
1-Methylpsilocin
4-Hydroxy-N,N,1-trimethyltryptamine

IUPAC: 3-[2-(Dimethylamino)ethyl]-1-methyl-1H-indol-4-ol

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: MZZRFEIDRWKTKJ-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-14(2)8-7-10-9-15(3)11-5-4-6-12(16)13(10)11/h4-6,9,16H,7-8H2,1-3H3

PubChem CID: 44404883; ChemSpider: 21686519

See also TiHKAL: #18 4-HO-DMT      

Sard, H; Kumaran, G; Morency, C; Roth, BL; Toth, BA; Hec, P; Shuster, L. SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist. Bioorg. Med. Chem. Lett., 1 Jan 2005, 15 (20), 4555–4599. 134 kB. doi:10.1016/j.bmcl.2005.06.104

5140
Isomer 6

5-MeO-α-ET
α-Ethyl-5-methoxytryptamine

IUPAC: 1-(5-Methoxy-1H-indol-3-yl)butan-2-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: JHTPCKWBFLMJMQ-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-3-10(14)6-9-8-15-13-5-4-11(16-2)7-12(9)13/h4-5,7-8,10,15H,3,6,14H2,1-2H3

PubChem CID: 13679707; ChemSpider: 21106244; Wikipedia: 5-MeO-AET

See also TiHKAL: #11 α-ET      
5154
Isomer 7

6-MeO-DMT
6-Methoxy-N,N-dimethyltryptamine

IUPAC: 2-(6-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: AWOWBKXVYZRYSP-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-8-11(16-3)4-5-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

PubChem CID: 12017579; ChemSpider: 23118889

See also TiHKAL: #39 4-MeO-MIPT #54 Tetrahydroharmine    

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Kline, TB; Benington, F; Morin, RD; Beaton, JM. Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety. J. Med. Chem., 1 Jan 1982, 25 (8), 908–913. 845 kB. doi:10.1021/jm00350a005

Schulze-Alexandru, M; Kovar, K; Vedani, A. Quasi-atomistic receptor surrogates for the 5-HT2A receptor: A 3D-QSAR study on hallucinogenic substances. Quant. Struct.-Act. Relat., 1 Dec 1999, 18 (6), 548–560. 312 kB. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B

5155
Isomer 8

7-MeO-DMT
7-Methoxy-N,N-dimethyltryptamine

IUPAC: 2-(7-Methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: GCEZYLSUTMYNRN-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-15(2)8-7-10-9-14-13-11(10)5-4-6-12(13)16-3/h4-6,9,14H,7-8H2,1-3H3

PubChem CID: 12017580; ChemSpider: 23183416

See also TiHKAL: #39 4-MeO-MIPT #40 5-MeO-MIPT    

Gessner, PK; Godse, DD; Krull, AH; McMullan, JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7 (5), 267–277. 362 kB. doi:10.1016/0024-3205(68)90200-2

Lyon, RA; Titeler, M; Seggel, MR; Glennon, RA. Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens. Eur. J. Pharmacol., 19 Jan 1988, 145 (3), 291–297. 533 kB. doi:10.1016/0014-2999(88)90432-3

Glennon, RA; Dukat, M; Grella, B; Hong, S; Costantino, L; Teitler, M; Smith, C; Egan, C; Davis, K; Mattson, MV. Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors. Drug Alcohol Depend., 1 Aug 2000, 60 (2), 121–132. 276 kB. doi:10.1016/S0376-8716(99)00148-9

Glennon, RA; Gessner, PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. 731 kB. doi:10.1021/jm00190a014

Gornez-Jeria, JS; Morales-Lagos, D; Cassels, BK; Saavedra-Aguilar, JC. Electronic structure and serotonin receptor binding affinity of 7-substituted tryptamines QSAR of 7-substituted tryptamines. Quant. Struct.-Act. Relat., 1986, 5 (4), 153–157. 577 kB. doi:10.1002/qsar.19860050404

5192
Isomer 9

5-HTQ
Bufotenidine
Cinobufagine
5-Hydroxy-N,N,N-trimethyltryptammonium

IUPAC: 3-[2-(Trimethylammonio)ethyl]-1H-indol-5-olate

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: HIYGARYIJIZXGW-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-15(2,3)7-6-10-9-14-13-5-4-11(16)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3

PubChem CID: 3083591; ChemSpider: 2340772

See also TiHKAL: #19 5-HO-DMT      
429
Isomer 10

5-MeO-NET

IUPAC: N-Ethyl-2-(5-methoxy-1H-indol-3-yl)ethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: UNPLGMNGAFLKSH-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-3-14-7-6-10-9-15-13-5-4-11(16-2)8-12(10)13/h4-5,8-9,14-15H,3,6-7H2,1-2H3

PubChem CID: 23009084; ChemSpider: 12955759

See also Chemistry notes VIII: p. 101, 5-MeO-NET: Synthesis

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; De Los Angeles, J; Teitler, M; King, A; Herrick-Davis, K. Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines. J. Med. Chem., 1 Jun 1994, 37 (13), 1929–1935. 1058 kB. doi:10.1021/jm00039a004

Blough, BE; Landavazo, A; Decker, AM; Partilla, JS; Baumann, MH; Rothman, RB. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes. Psychopharmacology, 298 kB. doi:10.1007/s00213-014-3557-7

5236
Isomer 11

2-Methylpsilocin

IUPAC: 3-[2-(Dimethylamino)ethyl]-2-methyl-1H-indol-4-ol

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: HXNGZUVNHQYMKL-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-9-10(7-8-15(2)3)13-11(14-9)5-4-6-12(13)16/h4-6,14,16H,7-8H2,1-3H3

PubChem CID: 44404892; ChemSpider: 23263143

Sard, H; Kumaran, G; Morency, C; Roth, BL; Toth, BA; Hec, P; Shuster, L. SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist. Bioorg. Med. Chem. Lett., 1 Jan 2005, 15 (20), 4555–4599. 134 kB. doi:10.1016/j.bmcl.2005.06.104

5237
Isomer 12

α-Methylpsilocin

IUPAC: 3-[2-(Dimethylamino)propyl]-1H-indol-4-ol

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: GRWDWEFPYLWISL-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-9(15(2)3)7-10-8-14-11-5-4-6-12(16)13(10)11/h4-6,8-9,14,16H,7H2,1-3H3

PubChem CID: 44404906; ChemSpider: 23263155

Sard, H; Kumaran, G; Morency, C; Roth, BL; Toth, BA; Hec, P; Shuster, L. SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist. Bioorg. Med. Chem. Lett., 1 Jan 2005, 15 (20), 4555–4599. 134 kB. doi:10.1016/j.bmcl.2005.06.104

5247
Isomer 13

4-HO-DMHT

IUPAC: 3-[3-(Dimethylamino)propyl]-1H-indol-4-ol

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: IBSZSSDQXMYZOZ-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-15(2)8-4-5-10-9-14-11-6-3-7-12(16)13(10)11/h3,6-7,9,14,16H,4-5,8H2,1-2H3

PubChem CID: 44404905; ChemSpider: 23263154

Sard, H; Kumaran, G; Morency, C; Roth, BL; Toth, BA; Hec, P; Shuster, L. SAR of psilocybin analogs: Discovery of a selective 5-HT2C agonist. Bioorg. Med. Chem. Lett., 1 Jan 2005, 15 (20), 4555–4599. 134 kB. doi:10.1016/j.bmcl.2005.06.104

5796
Isomer 14

1-Methylbufotenine

IUPAC: 3-[2-(Dimethylamino)ethyl]-1-methyl-1H-indol-5-ol

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: MRSBJIAZTHGJAP-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-14(2)7-6-10-9-15(3)13-5-4-11(16)8-12(10)13/h4-5,8-9,16H,6-7H2,1-3H3

Benington, F; Morin, RD; Clark, LC. Synthesis of O- and N-methylated derivatives of 5-hydroxytryptamine. J. Org. Chem., 1 Dec 1958, 23 (12), 1977–1979. 401 kB. doi:10.1021/jo01106a046

5859
Isomer 15

IUPAC: 2-(5-Ethoxy-1H-indol-3-yl)-N-methylethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: OJYLRVHEILMFSU-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-3-16-11-4-5-13-12(8-11)10(9-15-13)6-7-14-2/h4-5,8-9,14-15H,3,6-7H2,1-2H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5852
Isomer 16

IUPAC: 2-[5-(Propan-2-yloxy)-1H-indol-3-yl]ethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: IDOVDUDFEFJDPP-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-9(2)16-11-3-4-13-12(7-11)10(5-6-14)8-15-13/h3-4,7-9,15H,5-6,14H2,1-2H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

5851
Isomer 17

IUPAC: 2-(5-Propoxy-1H-indol-3-yl)ethan-1-amine

Formula: C13H18N2O Molecular weight: 218.29482 g/mol InChI Key: SXHSCDTUUHPMSY-UHFFFAOYSA-N

InChI=1S/C13H18N2O/c1-2-7-16-11-3-4-13-12(8-11)10(5-6-14)9-15-13/h3-4,8-9,15H,2,5-7,14H2,1H3

Prainer, B. Tryptamin-derivate als 5-HT4-rezeptorliganden: synthese und in-vitro-pharmakologie dissertation. Ph. D. Thesis, Universität Regensburg, Regensburg, Germany, 21 Jul 2008. 2220 kB. In German.

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