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7-MeO-DMT; 7-Methoxy-N,N-dimethyltryptamine
5155
Variant: N R5 R7 isomers all
Analogues: 5 1 6 17 29

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

Five N analogues:
5110
Analogue 1: Substituting Cyclopropyl for Dimethyl at N

7-MeO-NCPT
N-Cyclopropyl-7-methoxytryptamine

IUPAC: N-[2-(7-Methoxy-1H-indol-3-yl)ethyl]cyclopropanamine

Formula: C14H18N2O Molecular weight: 230.30552 g/mol InChI Key: NWCYUIAFBCJOPB-UHFFFAOYSA-N

InChI=1S/C14H18N2O/c1-17-13-4-2-3-12-10(9-16-14(12)13)7-8-15-11-5-6-11/h2-4,9,11,15-16H,5-8H2,1H3

PubChem CID: 41425; ChemSpider: 37798

See also TiHKAL: #6 DMT      
5158
Analogue 2: Substituting Isopropyl and Methyl for Dimethyl at N

7-MeO-MIPT
N-Isopropyl-7-methoxy-N-methyltryptamine

IUPAC: N-[2-(7-Methoxy-1H-indol-3-yl)ethyl]-N-methylpropan-2-amine

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

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

PubChem CID: 44382990; ChemSpider: 24683746

See also TiHKAL: #39 4-MeO-MIPT #40 5-MeO-MIPT    
See also Chemistry notes VIII: p. 127, 7-MeO-MIPT: GC-MS
p. 128, 7-MeO-MIPT: GC-MS

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

5159
Analogue 3: Substituting Isopropyl for Dimethyl at N

7-MeO-NIPT
N-Isopropyl-7-methoxytryptamine

IUPAC: N-[2-(7-Methoxy-1H-indol-3-yl)ethyl]propan-2-amine

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

InChI=1S/C14H20N2O/c1-10(2)15-8-7-11-9-16-14-12(11)5-4-6-13(14)17-3/h4-6,9-10,15-16H,7-8H2,1-3H3

ChemSpider: 27131552

See also TiHKAL: #40 5-MeO-MIPT      
5160
Analogue 4: Substituting Methyl for Dimethyl at N

7-MeO-NMT
7-Methoxy-N-methyltryptamine

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

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

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

ChemSpider: 27993389

See also TiHKAL: #40 5-MeO-MIPT      
5202
Analogue 5: Substituting Diisopropyl for Dimethyl at N

7-MeO-DIPT
N,N-Diisopropyl-7-methoxytryptamine

IUPAC: N-[2-(7-Methoxy-1H-indol-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine

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

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

One R5 analogue:
5473
Analogue 1: Adding Methoxy at R5

5,7-MeO-DMT

IUPAC: 2-(5,7-Dimethoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine

Formula: C14H20N2O2 Molecular weight: 248.3208 g/mol InChI Key: JHRIXTHEMSMGLN-UHFFFAOYSA-N

InChI=1S/C14H20N2O2/c1-16(2)6-5-10-9-15-14-12(10)7-11(17-3)8-13(14)18-4/h7-9,15H,5-6H2,1-4H3

PubChem CID: 12650291; ChemSpider: 10562576

See also Chemistry notes VIII: p. 155, 5-EtO-T: Synthesis; GC-MS
p. 156, 5-EtO-T: Synthesis
p. 157, 5-EtO-T: Synthesis
p. 158, 5-EtO-T: GC-MS
p. 159, 5-EtO-T: GC-MS
p. 160, 5-EtO-T: GC-MS

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

Six R7 analogues:
5006
Analogue 1: Removing Methoxy at R7

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

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

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5208
Analogue 2: Substituting Hydroxy for Methoxy at R7

7-HO-DMT

IUPAC: 3-[2-(Dimethylamino)ethyl]-1H-indol-7-ol

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

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

PubChem CID: 23757258

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

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; 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

5222
Analogue 3: Substituting Methyl for Methoxy at R7

N,N,7-TMT
N,N,7-Trimethyltryptamine

IUPAC: N,N-Dimethyl-2-(7-methyl-1H-indol-3-yl)ethan-1-amine

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

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

PubChem CID: 47747; ChemSpider: 43445

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

5714
Analogue 4: Substituting Bromo for Methoxy at R7

7-Br-DMT

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

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

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

PubChem CID: 12650285; ChemSpider: 23118496

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

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

5715
Analogue 5: Substituting Ethyl for Methoxy at R7

7-Et-DMT

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

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

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

PubChem CID: 12650284; ChemSpider: 23118849

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

5771
Analogue 6: Substituting Bromo for Methoxy at R7

7-Br-DMT

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

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

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

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      
5153
Isomer 7

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

5154
Isomer 8

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

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

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

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

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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