CEY-19
4-H2PO4-DET
4-HO-DET phosphate ester
Ethocybin
Ethocybin
Tryptamine, N,N-diethyl-4-phosphoryloxy
4-Indolol, 3-[2-(diethylamino)ethyl], phosphate ester
N,N-Diethyl-4-phosphoryloxytryptamine
3-[2-(Diethylamino)ethyl]-4-indolol, phosphate ester

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

Formula: C14H21N2O4P Molecular weight: 312.301301 g/mol InChI Key: AAVKQQUBPHSCML-UHFFFAOYSA-N

InChI=1S/C14H21N2O4P/c1-3-16(4-2)9-8-11-10-15-12-6-5-7-13(14(11)12)20-21(17,18)19/h5-7,10,15H,3-4,8-9H2,1-2H3,(H2,17,18,19)

PubChem CID: 53633102; ChemSpider: 21106438; Wikipedia: Ethocybin

See also TiHKAL:	#18 4-HO-DMT

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

Baeocystin
N-Methyl-4-phosphoryloxytryptamine

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

Formula: C11H15N2O4P Molecular weight: 270.221561 g/mol InChI Key: WTPBXXCVZZZXKR-UHFFFAOYSA-N

InChI=1S/C11H15N2O4P/c1-12-6-5-8-7-13-9-3-2-4-10(11(8)9)17-18(14,15)16/h2-4,7,12-13H,5-6H2,1H3,(H2,14,15,16)

PubChem CID: 161359; ChemSpider: 141741; Wikipedia: Baeocystin

See also TiHKAL:	#18 4-HO-DMT	#39 4-MeO-MIPT

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

Leung, AY; Paul, AG. Baeocystin, a mono-methyl analog of psilocybin from Psilocybe baeocystis saprophytic culture. J. Pharm. Sci., 1 Jan 1966, 56 (1), 146. 101 kB. doi:10.1002/jps.2600560132

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

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

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

Norbaeocystin
4-Phosphoryloxytryptamine

IUPAC: 3-(2-Aminoethyl)-1H-indol-4-yl dihydrogen phosphate

Formula: C10H13N2O4P Molecular weight: 256.194981 g/mol InChI Key: IKQGYCWFBVEAKF-UHFFFAOYSA-N

InChI=1S/C10H13N2O4P/c11-5-4-7-6-12-8-2-1-3-9(10(7)8)16-17(13,14)15/h1-3,6,12H,4-5,11H2,(H2,13,14,15)

PubChem CID: 9795063; ChemSpider: 7970830; Wikipedia: Norbaeocystin

See also TiHKAL:	#18 4-HO-DMT	#39 4-MeO-MIPT

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

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

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

Aeruginascin
N,N,N-Trimethyl-4-phosphoryloxytryptamine

IUPAC: N,N,N-Trimethyl-2-[4-(phosphonooxy)-1H-indol-3-yl]ethanaminium

Formula: C13H19N2O4P Molecular weight: 298.274721 g/mol InChI Key: OIIPFLWAQQNCHA-UHFFFAOYSA-O

InChI=1S/C13H19N2O4P/c1-15(2,3)8-7-10-9-14-11-5-4-6-12(13(10)11)19-20(16,17)18/h4-6,9,14H,7-8H2,1-3H3,(H-,16,17,18)/p+1

PubChem CID: 60208480; ChemSpider: 26233970; Wikipedia: Aeruginascin

Shulgin, AT. Mushrooms and aeruginascin. Ask Dr. Shulgin Online, Center for Cognitive Liberty & Ethics, 21 Oct 2003.

Macor, JE; Blake, J; Fox, CB; Johnson, C; Koe, K; Lebel, LA; Morrone, JM; Ryan, K; Schmidt, AW; Schulz, DW; Zorn, SH. Synthesis and serotonergic pharmacology of the enantiomers of 3-[(N-methylpyrrolidin-2-yl)methyl]-5-methoxy-1H-indole: Discovery of stereogenic differentiation in the aminoethyl side chain of the neurotransmitter serotonin. J. Med. Chem., 1 Jan 1992, 35 (23), 4503–4505. 427 kB. doi:10.1039/jm00101a032

1-Methylpsilocybin

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

Formula: C13H19N2O4P Molecular weight: 298.274721 g/mol InChI Key: IXYYGDKANFIKTQ-UHFFFAOYSA-N

InChI=1S/C13H19N2O4P/c1-14(2)8-7-10-9-15(3)11-5-4-6-12(13(10)11)19-20(16,17)18/h4-6,9H,7-8H2,1-3H3,(H2,16,17,18)

PubChem CID: 29101; ChemSpider: 27071

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

1-Butylpsilocybin

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

Formula: C16H25N2O4P Molecular weight: 340.354461 g/mol InChI Key: NVAOXOUHEUIPDH-UHFFFAOYSA-N

InChI=1S/C16H25N2O4P/c1-4-5-10-18-12-13(9-11-17(2)3)16-14(18)7-6-8-15(16)22-23(19,20)21/h6-8,12H,4-5,9-11H2,1-3H3,(H2,19,20,21)

PubChem CID: 44404887; ChemSpider: 23263138

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

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

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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

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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.

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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

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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

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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

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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

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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

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 Pharmacology notes II:	p. 292, Psilocin

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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

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.

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.

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

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.

4-MeO-DMT
4-Methoxy-N,N-dimethyltryptamine

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

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

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

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

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

4-AcO-DMT
4-Acetoxy-DMT
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, S. 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.

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

4-F-DMT

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

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

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

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

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

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