TiHKAL • info | explore | 7-MeO-DMT; 7-Methoxy-N,N-dimethyltryptamine

Five N analogues:

7-MeO-NCPT

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

7-MeO-MIPT

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

7-MeO-NIPT

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

7-MeO-NMT

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-methylethanamine

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

7-MeO-DIPT

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:

5,7-MeO-DMT

5473

Analogue 1: Adding Methoxy at R5

5,7-MeO-DMT

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

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:

DMT

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-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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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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Fenderson5555. Mechanisms in DMT synthesis. 3 Jan 2011.

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7-HO-DMT

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

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

N,N,7-TMT

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)ethanamine

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

7-Et-DMT

5715

Analogue 4: Substituting Ethyl for Methoxy at R7

7-Et-DMT

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

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

7-Br-DMT

5714

Analogue 5: Substituting Bromo for Methoxy at R7

7-Br-DMT

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

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

7-Br-DMT

5771

Analogue 6: Substituting Bromo for Methoxy at R7

7-Br-DMT

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

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

13 isomers:

4-HO-MET

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

5-MeO-DMT

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-dimethylethanamine

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

α,N,O-TMS

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

1-MeO-DMT; Lespedamine

5112

Isomer 4

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

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

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

CMY; 1-Methylpsilocin

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

5-MeO-α-ET

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

4-MeO-DMT

5153

Isomer 7

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

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

6-MeO-DMT

5154

Isomer 8

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

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

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

5-HTQ; Bufotenidine

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

5-MeO-NET

429

Isomer 10

5-MeO-NET

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

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

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

PubChem CID: 23009084; ChemSpider: 12955759

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

Glennon, RA; Dukat, M; El-Bermawy, M; Law, H; Angeles, JDL; 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

2-Methylpsilocin

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

α-Methylpsilocin

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

4-HO-DMHT

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

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