N,N-Dimethyltryptamine

1. Basics

From: Pharmacotheon - By: Johnathan Ott

Information	DIMETHYLTRYPTAMINE [Merck Index II: 3251; 12: 3311]
Synonyms	3-[2-(dimethylamino)ethyl]-indole; N,N-dimethyltryptamine; DMT; nigerina; nigerine; Dimethyltryptamin
Physical	C12 H16 N2 molecular weight 188.27; C 76.55% H 8.57% N 14.88%
Isolation	Fish, J. Am. Chem. Soc. 77:5892, 1955 (Anadenanthera peregrina); Agurell, Acta Chemica Scandinavica 23: 903, 1969 (Virola theidora)
Synthesis	Manske, Canadian Journal of Research 5: 592, 1931; Speeter & Anthony, Journal of American Chemical Society 76: 6208, 1954
Chemistry	Crystals from ethanol, mp 44.6 - 46.8°C, sol. in dilute acids; picrate, mp 169.5° - 170.5°C; methiodide, mp 216° - 217°C degrees; fumarate, mp 152° - 152.5°C
Pharmacology	psychoactive at 1mg/kg i.m. (Szara, Experientia 12: 441, 1956; Sai-Halasz, Psychiatria et Neurologia 135: 285, 1958)
Legal Status	DMT is explicitly named as a Schedule I drug in the Federal Controlled Substances Act; registry number 7435. (United States of America)

CAS Number	61-50-7
CID	6098
Unique ID	\|D004130
Molecular Weight	188.269g/mol
Molecular Formula	C12H16N2
XLogP	2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Topological Polar Surface Area	19
IUPAC Name	2-(1H-indol-3-yl)-N,N-dimethyl-ethanamine
Canonical SMILES	CN(C)CCC1=CNC2=CC=CC=C21
InChI	InChI=1/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