9282. Theobromine

Nomenclature

CAS number: 83-67-0
3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione; 3,7-dimethylxanthine.
C7H8N4O2; mol wt 180.16.
C 46.67%, H 4.48%, N 31.10%, O 17.76%.

Description and 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).

Chemical structure

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.

Derivative

Calcium salicylate.

Nomenclature

CAS number: 8065-51-8
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

Sodium acetate.

Nomenclature

CAS number: 8002-88-8
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

Sodium salicylate.

Nomenclature

CAS number: 8048-31-5
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.

Therapeutic Category

Diuretic, bronchodilator, cardiotonic.

Therapeutic Category (Veterinary)

Diuretic, myocardial stimulant, vasodilator.

Keywords

Bronchodilator; Xanthine Derivatives; Cardiotonic; Diuretic; Purines