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DMT Chemistry
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NAME :N,N-Dimethyltryptamine
CHEMICAL NAME :N,N-Dimethyl-1H-indole-3-ethanamine
ALTERNATE CHEMICAL NAMES : 3-[2-(dimethylamino)ethyl]indole, DMT
CHEMICAL FORMULAC12H16N2
MOLECULAR WEIGHT188.27
MELTING POINT44.6-46.8°C (116°F) (crystals) see below
BOILING POINT60-80°C (crystals) see below
From the Merck Index 12th Edition


DMT Molecule


MELTING POINT
"As to melting points, some in the literature are of plant isolates and other are of synthetic samples. A brief and incomplete survey has revealed the following numbers, all in C: 44, 44.6-46.8, 46, 47, 48-49, 49-50, 56-57, 57-59, 58-60, 64-67, 67 and 67-68. The 58-60 and 64-67 values are from the Aldrich Chemical Company, for samples bearing the purity claims of "puriss" and 99+% "Gold Label" resp. The Merck Index gives the very early, very low values of 46 C and 44.6-46.8 C and claimes that the bp is 60-80 C with atmospheric pressure being implied. It is clearly in error on both matters. No evidence has been published suggesting polymorphism. The published mp values for the trimethyl quaternary iodide span the range from 188 C to 233 C, including in-between values of 197 C and 216-217 C. This physical property is of limited value." --Alexander Shulgin from (DMT TiHKAL entry)




MERCK INDEX 12th Ed ENTRY
3251. N,N-Dimethyltryptamine.
N,N-Dimethyl-1H-indole-3-ethanamine.
3-[2-(dimethylamino)ethyl]indole.
DMT.

C12H16N2 - mol wt 188.26; C 76.55%, H 8.57%, N 14.88%

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). Synthesis: Szara, Experimentia 12,441(1956) using the method of Specter, Anthony J. J.Am.Chem.Soc. 76,6209(1954). Relationship between hallucinogenic activity and electronic configuration: Snyder, Merril, Proc.Nat.Acad.Sci. USA 54,258(1965).


                                H
                         /\     N
                       //   \ /   \
                      |      ||    ||
                      |      ||__ ||
                       \\   /       \ 
                         \/           CH2CH2N(CH3)2
Crystals, mp 44.6-46.8. pKa 8.68 (ethanol-water). 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.

Picrate, mp 169.5-170
Methiodide, mp 216-217
Caution: This is a controlled substance (hallucinogen) listed in the U.S. Code of Federal Regulations, Title 21 Part 1308.11 (1985).