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Names

5-HO-NMT
5-Hydroxy-N-methyltryptamine
N-Methylserotonin
NMe-5HT
Norbufotenine

IUPAC name

3-[2-(Methylamino)ethyl]-1H-indol-5-ol

ID 5131 · Formula C₁₁H₁₄N₂O · Molecular weight 190.242

Tags Tryptamine

InChI InChI=1S/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3

InChI Key ASUSBMNYRHGZIG-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES CNCCc1c[nH]c2c1cc(O)cc2

ChemSpider 132989
PubChem 150885
Wikidata Q855403
Wikipedia N-Methylserotonin
Trout’s Notes 5-Hydroxy-N-methyltryptamine. In Some Simple Tryptamines, 2nd ed., pp. 102–103

TiHKAL #19 5-HO-DMT

Wurst, M; Kysilka, R; Flieger, M. Psychoactive tryptamines from Basidiomycetes. Folia Microbiol., 1 Feb 2002, 47 (1), 3–27. 3.1 MB. https://doi.org/10.1007/BF02818560

Peroutka, SJ; McCarthy, BG; Guan, X. 5-Benzyloxytryptamine: a relatively selective 5-hydroxytryptamine_1D/1B agent. Life Sci., 1 Jan 1991, 49 (6), 409–418. 556 kB. https://doi.org/10.1016/0024-3205(91)90582-V

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., 1 Dec 2013, 27 (12), 1690-1700. 929 kB. https://doi.org/10.1002/bmc.2981

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. 1.5 MB. https://doi.org/10.1523/JNEUROSCI.1665-10.2010

Halberstadt, AL; Geyer, MA. Effect of hallucinogens on unconditioned behavior. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 159-199. 879 kB. https://doi.org/10.1007/7854_2016_466

Uthaug, MV; Lancelotta, R; van Oorsouw, K; Kuypers, KPC; Mason, N; Rak, J; Šuláková, A; Jurok, R; Maryška, M; Kuchař, M; Páleníček, T; Riba, J; Ramaekers, JG. A single inhalation of vapor from dried toad secretion containing 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) in a naturalistic setting is related to sustained enhancement of satisfaction with life, mindfulness-related capacities, and a decrement of psychopathological symptoms. Psychopharmacology, 13 Apr 2019, 236 (9), 2653-2666. 1.0 MB. https://doi.org/10.1007/s00213-019-05236-w #NMe-5HT

Mesley, RJ; Evans, WH. Infrared identification of some hallucinogenic derivatives of tryptamine and amphetamine. J. Pharm. Pharmacol., 1 May 1970, 22 (5), 321–332. 775 kB. https://doi.org/10.1111/j.2042-7158.1970.tb08533.x #5-Hydroxy-N-methyltryptamine IR

Gupta, SP; Singh, P; Bindal, MC. QSAR studies on hallucinogens. Chem. Rev., 1 Dec 1983, 83 (6), 633–649. 2.8 MB. https://doi.org/10.1021/cr00058a003 #111

N-HO-NMT · N-Hydroxy-N-methyltryptamine

2-HO-NMT · 2-Hydroxy-N-methyltryptamine

4-HO-NMT · 4-Hydroxy-N-methyltryptamine

5-MeO-T · 5-Methoxytryptamine · 5MT

4-HO-AMT · 4-Hydroxy-α-methyltryptamine

5-HO-AMT · 5-Hydroxy-α-methyltryptamine · α-Methyl-5-HT · αMS

1-Methyl-5-HO-T · 1-Methyl-5-hydroxytryptamine · 1-Methyl-5HT · 1-Methylserotonin

4-MeO-T · 4-Methoxytryptamine

5245

6-HO-AMT · 6-Hydroxy-α-methyltryptamine

2-Methyl-5-HO-T · 2-Methyl-5-hydroxytryptamine · 2-Methylseroronin

N-HO-AMT · N-Hydroxy-α-methyltryptamine

4,4′-DMAR · 4,4′-Dimethylaminorex

10073

10074

10075

4-EAR · 4-Ethylaminorex

4,N-DMAR · 4,N-Dimethylaminorex

3,4-DMAR

3′,4′-DMAR

N,N-DMAR · N,N-Dimethylaminorex

4,4-DMAR · 4,4-Dimethylaminorex

BNZP

7-MeO-T · 7-Methoxytryptamine

6-MeO-T · 6-Methoxytryptamine

β-Methyl-4-HO-T · β-Methyl-4-hydroxytryptamine

7994

7988

7 Dec 2019 · · Isomer Design