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TiHKAL#18 4-H2PO4-DMT
5058
Variant: N N+ R1 R4 all
Analogues: 3 1 2 9 15

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, 5.680

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.

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

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

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

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

Three N analogues:
5057
Analogue 1: Substituting Diethyl for Dimethyl at N

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.

5123
Analogue 2: Substituting Methyl for Dimethyl at N

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

5124
Analogue 3: Removing Dimethyl at N

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

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

One N+ analogue:
5373
Analogue 1: Adding Methyl at N+

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

Macor, JE; Blake, J; Fox, CB; Johnson, C; Koe, BK; 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

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

Two R1 analogues:
5233
Analogue 1: Adding Methyl at R1

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

5235
Analogue 2: Adding Butyl at R1

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

Nine R4 analogues:
5006
Analogue 1: Removing Phosphoryloxy 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

Fenderson5555. DMT from tryptophan? 23 Mar 2011. Wanted! Please contact me if you find this video.

Fenderson5555. Mechanisms in DMT synthesis. 3 Jan 2011. 2609 kB.

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.

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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

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

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

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

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

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

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

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

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.

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

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.

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

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

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

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

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; 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

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

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

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

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

5018
Analogue 2: Substituting Hydroxy for Phosphoryloxy 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, 5.680

See also Pharmacology notes II: p. 292, Psilocin

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.

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

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

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

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

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

5153
Analogue 3: Substituting Methoxy for Phosphoryloxy at R4

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

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

5171
Analogue 4: Substituting Methylthio for Phosphoryloxy 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 Phosphoryloxy 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 Phosphoryloxy 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 Phosphoryloxy 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

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

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.

5483
Analogue 8: Substituting Chloro for Phosphoryloxy 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 Phosphoryloxy 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

Show all 15 analogues and isomers Show only the three N analogues Show only the one N+ analogues Show only the two R1 analogues Show only the nine R4 analogues
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