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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
From the Merck Index 12th Edition

Theobromine Molecule

Caffeine Molecule

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.