CAS No 83-67-0 , 3,7-dimethylpurine-2,6-dione

Title: Theobromine
CAS Registry Number: 83-67-0
CAS Name: 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione
Synonyms: 3,7-dimethylxanthine
Molecular Formula: C7H8N4O2
Molecular Weight: 180.16
Percent Composition: C 46.67%, H 4.48%, N 31.10%, O 17.76%
Literature References: The principal alkaloid of the cacao bean which contains 1.5-3% of the base. Also present in cola nuts and in tea. Usually extracted from the hull of cacao beans which contains 0.7-1.2%. Extraction process: Schwyzer, Die Fabrikation pharmazeutischer und chemisch-technischer Produkte (Berlin, 1931). Synthesis starting with 3-methyluric acid: Fischer, Ach, Ber. 31, 1980 (1898); cf. Gebner, Krebs, J. Gen. Chem. USSR 16, 179-186 (1946). Comparison with theophylline, q.v., of metabolism in humans: D. J. Birkett et al., Drug Metab. Dispos. 13, 725 (1985). Pharmacokinetics: A. Lelo et al., Br. J. Clin. Pharmacol. 22, 177 (1986). Bronchodilator effect in asthma: F. E. R. Simons et al., J. Allergy Clin. Immunol. 76, 703 (1985).
Properties: Monoclinic needles (lamellar twinning on 001) from water, mp 357°. Sublimes 290-295°. Kb at 18°: 1.3 ′ 10-14; Ka 0.9 ′ 10-10. Absorption spectrum: Hartley, J. Chem. Soc. 87, 1803, 1810 (1905). One gram dissolves in about 2000 ml 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 compds with bases which are more stable.
Melting point: mp 357°
 
Derivative Type: Calcium salicylate
CAS Registry Number: 8065-51-8
Trademarks: Theocalcin (Knoll); Calcium Diuretin
Properties: Double salt or mixture of calcium theobromine and calcium salicylate. Contains no less than 44% theobromine. White, amorphous powder. Slightly saline taste. Partly sol in water. Aq solns are alkaline to phenolphthalein.
 
Derivative Type: Sodium acetate
CAS Registry Number: 8002-88-8
Trademarks: Thesodate
Properties: Equimolar mixture of sodium theobromine and sodium acetate, containing 1H2O. Theobromine 59.6%, anhydr sodium acetate 27.1%. White, odorless or almost odorless, hygroscopic powder. Absorbs CO2 from the air becoming incompletely sol. Very sol in water, sparingly sol in cold alcohol; the solns are strongly alkaline. pH about 10. Keep tightly closed.
 
Derivative Type: Sodium salicylate
CAS Registry Number: 8048-31-5
Trademarks: Diuretin (Knoll)
Properties: Equimolar mixture of sodium theobromine and sodium salicylate, containing 1H2O. Theobromine 47.3%, sodium salicylate 42.1%. White, odorless or almost odorless, hygroscopic powder. Absorbs CO2 from the air and becomes incompletely soluble. Soluble in 1 part water; slightly sol in alcohol; the solns are strongly alkaline. pH about 10.
 
Therap-Cat: Diuretic, bronchodilator, cardiotonic.
Therap-Cat-Vet: Diuretic, myocardial stimulant, vasodilator.
Keywords: Bronchodilator; Xanthine Derivatives; Cardiotonic; Diuretic; Purines.