3262. N,N-Dimethyltryptamine

Nomenclature

CAS number: 61-50-7
N,N-Dimethyl-1H-indole-3-ethanamine; 3-[2-(dimethylamino)ethyl]indole; DMT.
C12H16N2; mol wt 188.27.
C 76.55%, H 8.57%, N 14.88%.

Description and references

Occurs naturally in plants with hallucinogenic properties. Isoln from the leaves of Prestonia amazonica (Benth.) Macbride (Haemadictyon amazonicum Spruce & Benth.), Apocynaceae: Hockstein, Paradies, J. Am. Chem. Soc. 79, 5735 (1957). Metabolism: St. Szára, Experientia 12, 441 (1956); B. R. Sitaram et al., Biochem. Pharmacol. 36, 1509 (1987). Relationship between hallucinogenic activity and electronic configuration: Snyder, Merril, Proc. Natl. Acad. Sci. USA 54, 258 (1965). Synthesis: I. Fleming, M. Woolias, J. Chem. Soc. Perkin Trans. 1 1979, 829. Differential interaction with serotonin receptor subtypes: A. V. Deliganis et al., Biochem. Pharmacol. 41, 1739 (1991). Fluorometric detection: O. Jules et al., Anal. Chim. Acta 169, 355 (1985). Review of biosynthesis, metabolism and bioactivity: S. A. Barker et al., Int. Rev. Neurobiol. 22, 83-110 (1981).

Chemical structure

Properties

Crystals, mp 44.6-46.8°; also reported as plates from ethanol and light petroleum, mp 46° (Fleming, Woolias). bp 60-80°. pKa 8.68 (ethanol-water). Freely sol in dil acetic and dil mineral acids.

Derivative

Methiodide.

Properties

mp 216-217°.

Note

This is a controlled substance (hallucinogen): 21 CFR, 1308.11.