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Chocolate Chemistry
by Erowid


Cocoa beans contain a variety of chemicals, with the primary psychoactive components being theobromine (about 1% of total weight) and caffeine (<.1%). Other chemicals include serotonin, histamine, salsolinol, methyltetrahydroisoquinoline, phenethylamine, telemethylhistamine, spermidine, p-tyramine,3-methyloxytyramine, tryptamine, and spermine. (from Biochemist, Apr/May 1993, p 15, as read from Chocolate, Melting the Myth)

NAME :Theobromine
CHEMICAL NAME :3,7-Dihydro-3,7-dimethyle-1H-prine-2,6-dione
ALTERNATE CHEMICAL NAMES :3,7-dimethylxanthine
CHEMICAL FORMULAC7H8N4O2
MOLECULAR WEIGHT180.17
From the Merck Index 12th Edition


Theobromine Molecule


Caffeine Molecule


MERCK INDEX ENTRY
9418. Theobromine. 3,7-Dihydro-3,7-dimethyle-1H-prine-2,6-dione; 3,7-dimethylxanthine C7H8N4O2; mol wt 180.17 C 46.67%, H 4.48%, N 31.10%, O 17.76%. The principal alkaloid of the cacao bean which which contains 1.5-3% of the base. Also present in cola nutes and in tea. Usually extracted from the hull of cacao beans which contains 0.7-1.2%.

Monoclinic needles (lamellar twinning on .001) from water, mp 357degrees. Sublimes 290-295deg. Kb at 18deg: 1.3x10-14; Ka 0.9x10-10. Absorption spectrum: Hartley, J Chem Soc 87, 1803, 1810 (1905). One gram dissolved in about 2000 ml of water, 150 ml boiling water, 2220 ml 95% alcohol; sol in the fixed alkali hydroxides, concd acids, in about 22 parts of 20% aq tribasic sodium phosphate soln; moderately sol in ammonia. Almost insol in benzene, ether, chloroform, carbon tetrachloride. Forms salts which are dec by water, and compounds with bases which are more stable.
Last Modified Tuesday, 24-Apr-2007 14:31:33 PDT Created by Erowid
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