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11 R5 analogues:

5006

Analogue 1: Removing Sulfoxy at R5

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-dimethylethanamine

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 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

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

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

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

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

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

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.

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

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

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

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

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; Young, R; Jacyno, JM. Indolealkylamine and phenalkylamine hallucinogens: Effect of &alpha-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

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

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

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

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

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

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

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

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. J. Psychedelic Drugs, 1 Jan 1976, 8 (2), 167–168. 1208 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

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.

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

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

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

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

Strassman, RJ. Human psychopharmacology of N,N,-dimethyltryptamine. Behav. Brain Res., 15 Dec 1995, 73 (1–2), 121–224. 396 kB. doi:10.1016/0166-4328(96)00081-2

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

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

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

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

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.

Fenderson5555. DMT from tryptophan?. 23 Mar 2011.

Fenderson5555. Mechanisms in DMT synthesis. 3 Jan 2011.

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

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

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., 0000, 20 (2), 149–153. 131 kB. doi:10.1002/pca.1110

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

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., . 685 kB. doi:10.1016/j.microc.2012.03.033

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

5-HO-DMT

5019

Analogue 2: Substituting Hydroxy for Sulfoxy at R5

5-HO-DMT
N,N-Dimethylserotonin
Bufotenine
Mappine
Tryptamine, N,N-dimethyl-5-hydroxy
Indol-5-ol, 3-[2-(dimethylamino)ethyl]
N,N-Dimethyl-5-hydroxytryptamine
3-(2-Dimethylaminoethyl)indol-5-ol

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

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

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

PubChem CID: 10257; ChemSpider: 9839; Erowid: Bufotenin; Wikipedia: Bufotenin

See also TiHKAL:	#3 DET #5 α,O-DMS	#6 DMT #35 Melatonin	#38 5-MeO-DMT

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

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

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

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

Lyttle, T; Goldstein, D; Gartz, J. Bufo toads and bufotenine: Fact and fiction surrounding an alleged psychedelic. J. Psychoactive Drugs, 1 Sep 1996, 28 (3), 267–290. 24650 kB. doi:10.1080/02791072.1996.10472488

Urban, JD; Clarke, WP; Zastrow, M; Nichols, DE; Kobilka, B; Weinstein, H; Javitch, JA; Roth, BL; Christopoulos, A; Sexton, PM; Miller, KJ; . Functional selectivity and classical concepts of quantitative pharmacology. J. Pharmacol. Exp. Ther., 1 Jan 2007, 320 (1), 1–13. 506 kB. doi:10.1124/jpet.106.104463

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.

Shulgin, AT. Profiles of psychedelic drugs. 11. Bufotenine. J. Psychoactive Drugs, 1 Jan 1981, 13 (4), 389. 848 kB.

McBride, MC. Bufotenine: Toward an understanding of possible psychoactive mechanisms. J. Psychoactive Drugs, 1 Jan 2000, 32 (3), 321–331. 959 kB.

Ott, J. Pharmanopo-psychonautics: human intranasal, sublingual, intrarectal, pulmonary and oral pharmacology of bufotenine. J. Psychoactive Drugs, 1 Sep 2001, 33 (3), 273–281. 145 kB.

5-MeO-DMT

5038

Analogue 3: Substituting Methoxy for Sulfoxy at R5

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-dimethylethanamine

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 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

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

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

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

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

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

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

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; 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

Glennon, RA; Lee, M; Rangisetty, JB; Dukat, M; Roth, BL; Savage, JE; McBridge, A; Rauser, L; Hufeisen, S; 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

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

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

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.

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

5-MeS-DMT

5046

Analogue 4: Substituting Methylthio for Sulfoxy at R5

5-MeS-DMT
Tryptamine, N,N-dimethyl-5-methylthio
Indole, 3-[2-(dimethylamino)ethyl]-5-methylthio
N,N-Dimethyl-5-methylthiotryptamine
3-[2-(Dimethylamino)ethyl]-5-methylthioindole

IUPAC: N,N-Dimethyl-2-[5-(methylsulfanyl)-1H-indol-3-yl]ethanamine

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

InChI=1S/C13H18N2S/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: 21180; ChemSpider: 19917; Wikipedia: 5-MeS-DMT

5-Br-DMT

5113

Analogue 5: Substituting Bromo for Sulfoxy at R5

5-Br-DMT
5-Bromo-N,N-dimethyltryptamine

IUPAC: 2-(5-Bromo-1H-indol-3-yl)-N,N-dimethylethanamine

Formula: C12H15BrN2 Molecular weight: 267.1649 g/mol InChI Key: ATEYZYQLBQUZJE-UHFFFAOYSA-N

InChI=1S/C12H15BrN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3

PubChem CID: 360252; ChemSpider: 319812; Wikipedia: 5-Bromo-DMT

See also TiHKAL:	#6 DMT

Morris, H; Wallach, J. Sea DMT: God Molecule or Barnacle Repellent?. Vice, 26 Mar 2013.

5-EtO-DMT

5130

Analogue 6: Substituting Ethoxy for Sulfoxy at R5

5-EtO-DMT
5-Ethoxy-N,N-dimethyltryptamine

IUPAC: 2-(5-Ethoxy-1H-indol-3-yl)-N,N-dimethylethanamine

Formula: C14H20N2O Molecular weight: 232.3214 g/mol InChI Key: OSUDCFCSUHGWJF-UHFFFAOYSA-N

InChI=1S/C14H20N2O/c1-4-17-12-5-6-14-13(9-12)11(10-15-14)7-8-16(2)3/h5-6,9-10,15H,4,7-8H2,1-3H3

PubChem CID: 57468316; ChemSpider: 26286732; Wikipedia: 5-Ethoxy-DMT

See also TiHKAL:	#19 5-HO-DMT

Tearavarich, R; Hahnvajanawong, V; Dempster, N; Daley, PF; Cozzi, NV; Brandt, SD. Microwave-accelerated preparation and analytical characterization of 5-ethoxy-N,N-dialkyl-[α,α,β,β-H4]- and [α,α,β,β-D4]-tryptamines. Drug Test. Anal., 1 Sep 2011, 3 (9), 597–608. 253 kB. doi:10.1002/dta.223

5-AcO-DMT

5132

Analogue 7: Substituting Acetoxy for Sulfoxy at R5

5-AcO-DMT
5-Acetoxy-N,N-dimethyltryptamine

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl acetate

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

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

PubChem CID: 15480709; ChemSpider: 23194786

See also TiHKAL:	#19 5-HO-DMT

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

5,N,N-TMT

5374

Analogue 8: Substituting Methyl for Sulfoxy at R5

5,N,N-TMT
5,N,N-Trimethyltryptamine
N,N,5-Trimethyltryptamine

IUPAC: N,N-Dimethyl-2-(5-methyl-1H-indol-3-yl)ethanamine

Formula: C13H18N2 Molecular weight: 202.29542 g/mol InChI Key: NCGJLYBZSJSCIC-UHFFFAOYSA-N

InChI=1S/C13H18N2/c1-10-4-5-13-12(8-10)11(9-14-13)6-7-15(2)3/h4-5,8-9,14H,6-7H2,1-3H3

PubChem CID: 1837; ChemSpider: 1771; Wikipedia: 5,N,N-TMT

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

Shulgin, AT. 5-Me-DMT or 5,N,N-TMT (5,N,N-trimethyltryptamine). Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 18 Nov 2002.

Sumatriptan

5085

Analogue 9: Substituting Methylaminosulfonylmethyl for Sulfoxy at R5

Sumatriptan

IUPAC: 1-{3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide

Formula: C14H21N3O2S Molecular weight: 295.40044 g/mol InChI Key: KQKPFRSPSRPDEB-UHFFFAOYSA-N

InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3

PubChem CID: 5358; ChemSpider: 5165

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

5-F-DMT

5227

Analogue 10: Substituting Fluoro for Sulfoxy at R5

5-F-DMT

IUPAC: 2-(5-Fluoro-1H-indol-3-yl)-N,N-dimethylethanamine

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

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

PubChem CID: 2762738; ChemSpider: 2043436

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.

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

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

5-Et-DMT

5708

Analogue 11: Substituting Ethyl for Sulfoxy at R5

5-Et-DMT

IUPAC: 2-(5-Ethyl-1H-indol-3-yl)-N,N-dimethylethanamine

Formula: C14H20N2 Molecular weight: 216.322 g/mol InChI Key: ZEHXYLDGQMEYAX-UHFFFAOYSA-N

InChI=1S/C14H20N2/c1-4-11-5-6-14-13(9-11)12(10-15-14)7-8-16(2)3/h5-6,9-10,15H,4,7-8H2,1-3H3

PubChem CID: 10775128; ChemSpider: 8950441