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Substance Name: Theobromine [INN:BAN:NF]
RN: 83-67-0
UNII: OBD445WZ5P
InChIKey: YAPQBXQYLJRXSA-UHFFFAOYSA-N

Note

  • 3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than THEOPHYLLINE and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9)

Molecular Formula

  • C7-H8-N4-O2

Molecular Weight

  • 180.1662
 

Classification Codes

Classification Codes

  • Anti-Asthmatic Agents
  • Autonomic Agents
  • Bronchodilator Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Respiratory System Agents
  • Tumor Data
  • Vasodilator Agents

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Theobromine
  • Theobromine [INN:BAN:NF]

MeSH Heading

  • Theobromine

Synonyms

  • 1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-
  • 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione
  • 3,7-Dimethylxanthine
  • 5-26-13-00553 (Beilstein Handbook Reference)
  • BRN 0016464
  • CCRIS 2350
  • Diurobromine
  • EINECS 201-494-2
  • FEMA No. 3591
  • HSDB 7332
  • NSC 5039
  • Santheose
  • SC 15090
  • Teobromin
  • Theobromine
  • Theobromine (natural)
  • Theosalvose
  • Theostene
  • Thesal
  • Thesodate
  • UNII-OBD445WZ5P
  • Xanthine, 3,7-dimethyl-

Systematic Names

  • 1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-
  • Theobromine

Superlist Name

  • Theobromine

Registry Numbers

CAS Registry Number

  • 83-67-0

FDA UNII

  • OBD445WZ5P

System Generated Number

  • 0000083670

Structure Descriptors

InChI

1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)

InChIKey

YAPQBXQYLJRXSA-UHFFFAOYSA-N

Smiles

Cn1cnc2c1c(=O)[nH]c(=O)n2C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 200mg/kg (200mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1372, 1986.
dog LD50 oral 300mg/kg (300mg/kg)   Toxicology and Applied Pharmacology. Vol. 53, Pg. 481, 1980.
human TDLo oral 26mg/kg (26mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

GASTROINTESTINAL: NAUSEA OR VOMITING		 Journal of Pharmacology and Experimental Therapeutics. Vol. 86, Pg. 113, 1946.
mouse LD50 intraperitoneal 552mg/kg (552mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Acta Pharmaceutica Vol. 46, Pg. 93, 1996.
mouse LD50 oral 837mg/kg (837mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(3), Pg. 59, 1982.
mouse LD50 subcutaneous 530mg/kg (530mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 6, Pg. 601, 1956.
rabbit LDLo subcutaneous 1gm/kg (1000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LD50 oral 1265mg/kg (1265mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(3), Pg. 59, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 357 deg C   EXP
pKa Dissociation Constant 9.9 (none)   EXP
log P (octanol-water) -0.78 (none)   EXP
Water Solubility 330 mg/L 25 EXP
Vapor Pressure 8.95E-10 mm Hg 25 EST
Henry's Law Constant 1.63E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.89E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.