Exploring NMT. To explore a different substance…

TiHKAL#50 NMT
Names:
NMT · N-Methyltryptamine · 3-[2-(Methylamino)ethyl]indole · Indole, 3-[2-(methylamino)ethyl] · Tryptamine, N-methyl
IUPAC name:
2-(1H-Indol-3-yl)-N-methylethan-1-amine
ID: 5050 · Formula: C11H14N2 · Molecular weight: 174.242
InChI: InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3

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. http://dx.doi.org/10.1002/bmc.1551

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

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.

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.

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

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. http://dx.doi.org/10.1126/science.1166127

Khalil, EM; De Angelis, J; Cole, PA. Indoleamine analogs as probes of the substrate selectivity and catalytic mechanism of serotonin N-acetyltransferase. J. Biol. Chem., 13 Nov 1998, 273 (46), 30321–30327. 247 kB. http://dx.doi.org/10.1074/jbc.273.46.30321

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. http://dx.doi.org/10.1016/j.chroma.2009.10.088

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. http://dx.doi.org/10.1016/0024-3205(91)90582-V

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. http://dx.doi.org/10.1007/s00213-014-3557-7

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. http://dx.doi.org/10.1002/qsar.19860050404

Gartz, J. Biotransformation of tryptamine derivatives in mycelia cultures of Psilocybe. J. Basic. Microbiol., 1989, 29 (6), 347–352. 357 kB. http://dx.doi.org/10.1002/jobm.3620290608

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. http://dx.doi.org/10.1002/bmc.1657

Barker, SA; Borjigin, J; Lomnicka, I; Strassman, R. LCMS/MS analysis of the endogenous dimethyltryptamine hallucinogens, their precursors, and major metabolites in rat pineal gland microdialysate. Biomed. Chromatogr., 2013. 929 kB. http://dx.doi.org/10.1002/bmc.2981

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

DBT
TiHKAL#2 DBT
DET
TiHKAL#3 DET
DIPT
TiHKAL#4 DIPT
DMT
TiHKAL#6 DMT
DPT
TiHKAL#9 DPT
EIPT
TiHKAL#10 EIPT
MBT
TiHKAL#27 MBT
MIPT
TiHKAL#47 MIPT
NET
TiHKAL#49 NET
T
TiHKAL#53 T
NIPT
TiHKAL#49 NIPT
N-HO-NMT
N-HO-NMT; N-Hydroxy-N-methyltryptamine
NCPT
NCPT; N-Cyclopropyltryptamine
PIPT
PIPT; N-Isopropyl-N-propyltryptamine
BIPT
BIPT; N-Butyl-N-isopropyltryptamine
MET
MET; N-Ethyl-N-methyltryptamine
MPT
MPT; N-Methyl-N-propyltryptamine
NPT
NPT; N-Propyltryptamine
NBT
NBT; N-Butyltryptamine
NIBT
NIBT; N-Isobutyltryptamine
NSBT
NSBT; N-sec-Butyltryptamine
NTBT
NTBT; N-tert-Butyltryptamine
NAT
NAT; N-Pentyltryptamine
NHT
NHT; N-[2-(1H-Indol-3-yl)ethyl]hexan-1-amine
DALT
TiHKAL#57 DALT
5558
N-(2-Ethoxybenzyl)tryptamine
5559
N-(2-Methoxyphenylethan-2-yl)tryptamine
N-Benzyltryptamine
N-Benzyltryptamine
5565
N-(2-Hydroxybenzyl)tryptamine
5566
N-(2-Methoxybenzyl)tryptamine
DIBT
DIBT; N,N-Diisobutyltryptamine
EPT
EPT; N-Ethyl-N-propyltryptamine
MIBT
MIBT; N-[2-(1H-Indol-3-yl)ethyl]-N,2-dimethylpropan-1-amine
MSBT
MSBT; N-[2-(1H-Indol-3-yl)ethyl]-N-methylbutan-2-amine
DSBT
DSBT; N-(Butan-2-yl)-N-[2-(1H-indol-3-yl)ethyl]butan-2-amine
N-Formyltryptamine
N-Formyltryptamine
5601
N-Benzyl-2-(1H-indol-3-yl)-N-methylethan-1-amine
5602
N-(4-Bromobenzyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine
5603
2-(1H-Indol-3-yl)-N-methyl-N-(2-phenylethyl)ethan-1-amine
5604
2-(1H-Indol-3-yl)-N-methyl-N-[2-(2-methylphenyl)ethyl]ethan-1-amine
5605
2-(2-Fluorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5606
2-(2-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5607
2-(2,5-Dimethylphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5608
2-(1H-Indol-3-yl)-N-[2-(2-methoxyphenyl)ethyl]-N-methylethan-1-amine
5609
2-(2,5-Dimethoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5610
2-(2,6-Dichlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5611
2-(1H-Indol-3-yl)-N-methyl-N-[2-(3-methylphenyl)ethyl]ethan-1-amine
5612
3-(2-{[2-(1H-Indol-3-yl)ethyl](methyl)amino}ethyl)phenyl acetate
5613
2-(1H-Indol-3-yl)-N-[2-(3-methoxyphenyl)ethyl]-N-methylethan-1-amine
5614
2-(3-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5615
2-(3-Bromophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5616
2-(3,5-Dimethylphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5617
2-(3,4-Dimethoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5618
2-(3,4-Dichlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5619
2-(1H-Indol-3-yl)-N-methyl-N-[2-(4-methylphenyl)ethyl]ethan-1-amine
5620
2-(1H-Indol-3-yl)-N-[2-(4-methoxyphenyl)ethyl]-N-methylethan-1-amine
5621
2-(4-Fluorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5622
2-(4-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5623
2-(4-Bromophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5624
2-(1H-Indol-3-yl)-N-methyl-N-[2-(4-nitrophenyl)ethyl]ethan-1-amine
5625
2-(Biphenyl-4-yl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5626
2-(1H-Indol-3-yl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5627
2-(1H-Indol-3-yl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5628
2-(1H-Indol-3-yl)-N-methyl-N-[2-(naphthalen-1-yl)ethyl]ethan-1-amine
5629
2-(1H-Indol-3-yl)-N-methyl-N-[2-(naphthalen-2-yl)ethyl]ethan-1-amine
5630
N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-phenylpropan-1-amine
5631
N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-(3,4,5-trimethoxyphenyl)propan-1-amine
5632
N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-4-phenylbutan-1-amine
5633
N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-(phenylsulfanyl)propan-1-amine
5634
N-[2-(1H-Indol-3-yl)ethyl]-N-methylpentan-1-amine
5635
N-[2-(1H-Indol-3-yl)ethyl]-N-methylhexan-1-amine
5636
N-[2-(1H-Indol-3-yl)ethyl]-N-methylheptan-1-amine
5637
N-[2-(1H-Indol-3-yl)ethyl]-N-methyloctan-1-amine
5638
N-[2-(1H-Indol-3-yl)ethyl]-N-methyldodecan-1-amine
5639
N-[2-(1H-Indol-3-yl)ethyl]-N-methyltetradecan-1-amine
5640
N-[2-(1H-Indol-3-yl)ethyl]-N-methyloctadecan-1-amine
5641
N-(Cyclopropylmethyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine
5642
N-(Cyclopentylmethyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine
5643
N-(Cyclohexylmethyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine
5645
2-Ethyl-N-[2-(1H-indol-3-yl)ethyl]-N-methylbutan-1-amine
5646
N-[2-(1H-Indol-3-yl)ethyl]-N-methylprop-2-en-1-amine
5647
N-[2-(1H-Indol-3-yl)ethyl]-N-methylprop-2-yn-1-amine
5648
3-Cyclohexyl-N-[2-(1H-indol-3-yl)ethyl]-N-methylpropan-1-amine
5649
(2E)-N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-phenylprop-2-en-1-amine
5650
Methyl N-[2-(1H-indol-3-yl)ethyl]-N-methylglycinate
5651
tert-Butyl N-[2-(1H-indol-3-yl)ethyl]-N-methylglycinate
5652
N2-[2-(1H-Indol-3-yl)ethyl]-N2-methylglycinamide
5653
3-{[2-(1H-Indol-3-yl)ethyl](methyl)amino}propanenitrile
5654
2-{[2-(1H-Indol-3-yl)ethyl](methyl)amino}ethyl acetate
DAT
DAT; N-[2-(1H-Indol-3-yl)ethyl]-N-pentylpentan-1-amine
DHT
DHT; N-Hexyl-N-[2-(1H-indol-3-yl)ethyl]hexan-1-amine
HOT-T
HOT-T; N-Hydroxy-1-(1H-indol-3-yl)propan-2-amine
α,N-DMT
TiHKAL#8 ɑ,N-DMT
Abrine
Abrine
2-HO-NMT
2-HO-NMT; 2-Hydroxy-N-methyltryptamine
Baeocystin
Baeocystin
4-HO-NMT
4-HO-NMT; 4-Hydroxy-N-methyltryptamine
4-MeO-NMT
4-MeO-NMT; 4-Methoxy-N-methyltryptamine
5-MeO-NMT
TiHKAL#42 5-MeO-NMT
5-HO-NMT · Norbufotenine
5-HO-NMT; Norbufotenine
5860
N-Methyl-2-(5-propoxy-1H-indol-3-yl)ethan-1-amine
5891
3-[2-(Methylamino)ethyl]-1H-indole-5-carboxamide
5867
2-[5-(Benzyloxy)-1H-indol-3-yl]-N-methylethan-1-amine
5866
2-[5-(Cyclohexylmethoxy)-1H-indol-3-yl]-N-methylethan-1-amine
5865
2-[5-(Cyclopentylmethoxy)-1H-indol-3-yl]-N-methylethan-1-amine
5864
2-[5-(Cyclopentyloxy)-1H-indol-3-yl]-N-methylethan-1-amine
5863
2-[5-(Hexyloxy)-1H-indol-3-yl]-N-methylethan-1-amine
5862
N-Methyl-2-[5-(pentyloxy)-1H-indol-3-yl]ethan-1-amine
5861
N-Methyl-2-[5-(propan-2-yloxy)-1H-indol-3-yl]ethan-1-amine
5859
2-(5-Ethoxy-1H-indol-3-yl)-N-methylethan-1-amine
7-MeO-NMT
7-MeO-NMT; 7-Methoxy-N-methyltryptamine
pyr-T
TiHKAL#52 pyr-T
pip-T
pip-T; N,N-Pentamethylenetryptamine
mor-T
mor-T; 3-[2-(Morpholin-4-yl)ethyl]-1H-indole
5073
(1S,2R)-2-(1H-Indol-3-yl)cyclopropanamine
5074
(1R,2S)-2-(1H-Indol-3-yl)cyclopropanamine
Gramine
Gramine
dmpyrrol-T
dmpyrrol-T; 3-[2-(2,5-Dimethyl-1H-pyrrol-1-yl)ethyl]-1H-indole
mepipaz-T
mepipaz-T; 3-[2-(4-Methylpiperazin-1-yl)ethyl]-1H-indole
N-Methylhomotryptamine
N-Methylhomotryptamine
Homotryptamine
Homotryptamine
α-MT
TiHKAL#48 ɑ-MT
5-Me-T
5-Me-T; 5-Methyltryptamine
7-Me-T
7-Me-T; 7-Methyltryptamine
Homotryptamine
Homotryptamine
DBT
TiHKAL#2 DBT
DET
TiHKAL#3 DET
DIPT
TiHKAL#4 DIPT
DMT
TiHKAL#6 DMT
DPT
TiHKAL#9 DPT
EIPT
TiHKAL#10 EIPT
MBT
TiHKAL#27 MBT
MIPT
TiHKAL#47 MIPT
NET
TiHKAL#49 NET
T
TiHKAL#53 T
NIPT
TiHKAL#49 NIPT
N-HO-NMT
N-HO-NMT; N-Hydroxy-N-methyltryptamine
NCPT
NCPT; N-Cyclopropyltryptamine
PIPT
PIPT; N-Isopropyl-N-propyltryptamine
BIPT
BIPT; N-Butyl-N-isopropyltryptamine
MET
MET; N-Ethyl-N-methyltryptamine
MPT
MPT; N-Methyl-N-propyltryptamine
NPT
NPT; N-Propyltryptamine
NBT
NBT; N-Butyltryptamine
NIBT
NIBT; N-Isobutyltryptamine
NSBT
NSBT; N-sec-Butyltryptamine
NTBT
NTBT; N-tert-Butyltryptamine
NAT
NAT; N-Pentyltryptamine
NHT
NHT; N-[2-(1H-Indol-3-yl)ethyl]hexan-1-amine
DALT
TiHKAL#57 DALT
5558
N-(2-Ethoxybenzyl)tryptamine
5559
N-(2-Methoxyphenylethan-2-yl)tryptamine
N-Benzyltryptamine
N-Benzyltryptamine
5565
N-(2-Hydroxybenzyl)tryptamine
5566
N-(2-Methoxybenzyl)tryptamine
DIBT
DIBT; N,N-Diisobutyltryptamine
EPT
EPT; N-Ethyl-N-propyltryptamine
MIBT
MIBT; N-[2-(1H-Indol-3-yl)ethyl]-N,2-dimethylpropan-1-amine
MSBT
MSBT; N-[2-(1H-Indol-3-yl)ethyl]-N-methylbutan-2-amine
DSBT
DSBT; N-(Butan-2-yl)-N-[2-(1H-indol-3-yl)ethyl]butan-2-amine
N-Formyltryptamine
N-Formyltryptamine
5601
N-Benzyl-2-(1H-indol-3-yl)-N-methylethan-1-amine
5602
N-(4-Bromobenzyl)-2-(1H-indol-3-yl)-N-methylethan-1-amine
5603
2-(1H-Indol-3-yl)-N-methyl-N-(2-phenylethyl)ethan-1-amine
5604
2-(1H-Indol-3-yl)-N-methyl-N-[2-(2-methylphenyl)ethyl]ethan-1-amine
5605
2-(2-Fluorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5606
2-(2-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5607
2-(2,5-Dimethylphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5608
2-(1H-Indol-3-yl)-N-[2-(2-methoxyphenyl)ethyl]-N-methylethan-1-amine
5609
2-(2,5-Dimethoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5610
2-(2,6-Dichlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5611
2-(1H-Indol-3-yl)-N-methyl-N-[2-(3-methylphenyl)ethyl]ethan-1-amine
5612
3-(2-{[2-(1H-Indol-3-yl)ethyl](methyl)amino}ethyl)phenyl acetate
5613
2-(1H-Indol-3-yl)-N-[2-(3-methoxyphenyl)ethyl]-N-methylethan-1-amine
5614
2-(3-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5615
2-(3-Bromophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5616
2-(3,5-Dimethylphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5617
2-(3,4-Dimethoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5618
2-(3,4-Dichlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5619
2-(1H-Indol-3-yl)-N-methyl-N-[2-(4-methylphenyl)ethyl]ethan-1-amine
5620
2-(1H-Indol-3-yl)-N-[2-(4-methoxyphenyl)ethyl]-N-methylethan-1-amine
5621
2-(4-Fluorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5622
2-(4-Chlorophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5623
2-(4-Bromophenyl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5624
2-(1H-Indol-3-yl)-N-methyl-N-[2-(4-nitrophenyl)ethyl]ethan-1-amine
5625
2-(Biphenyl-4-yl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5626
2-(1H-Indol-3-yl)-N-[2-(1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5627
2-(1H-Indol-3-yl)-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-methylethan-1-amine
5628
2-(1H-Indol-3-yl)-N-methyl-N-[2-(naphthalen-1-yl)ethyl]ethan-1-amine
5629
2-(1H-Indol-3-yl)-N-methyl-N-[2-(naphthalen-2-yl)ethyl]ethan-1-amine
5630
N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-phenylpropan-1-amine
5631
N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-3-(3,4,5-trimethoxyphenyl)propan-1-amine
5632
N-[2-(1H-Indol-3-yl)ethyl]-N-methyl-4-phenylbutan-1-amine
5633