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Theobromine

Also called 3,7-Dimethylxanthine, Diurobromine, Theosalvose

Original Wikipedia articleen.wikipedia.org/wiki/Theobromine revision used (24 October 2026)

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Part of the metabolic pathway of Caffeine and Theobromine. See the timeline on the metabolic highway.

Common dose · Oral200–300 mg TS

Dosage

Oral

SourceThresholdLightCommonStrongHeavy
TripSit–100–200 mg TS200–300 mg TS300–600 mg TS600 mg+ TS

TripSit dose text

TripSit's factsheet also states its doses as text.

Light: 100-200mg Common: 200-300mg Strong: 300-600mg Heavy: 600mg+ TS

What dose are you on? (self-reported, unverified)
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Duration

TripSit factsheet

Onset
2-3 hours TS
Duration
30-40 hours TS

Mixing

Acute combinations: what happens when these are taken close together. Entries backed by a medical journal or agency are listed first.

Backed by medical journals

Awaiting sourcePeer-reviewed reports on acute combinations, from PubMed and the journals the harm reduction sites cite.

Risks and toxicity

Median lethal dose (LD50) in animals

Quoted from PubChem's Non-Human Toxicity Values, which come from the Hazardous Substances Data Bank (HSDB). PubChem describes them as: “Quantitative non-human toxicity values (e.g., lethal dose) for this compound. The data shown here are mostly for lab animals (e.g., rat, mouse, guinea pig, and rabbit).” and defines the “LD50 (median lethal dose, the estimated amount of a chemical expected to kill 50% of test animals in a single dose)”. PC

LD50 (as the source gives it)Reference
LD50 Dog oral 300 mg/kg bw PCIARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). (via HSDB record 7332)
LD50 Rat (acute) oral 950 mg/kg bw PCIARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). (via HSDB record 7332)
Awaiting sourceToxicity, overdose signs and dependence risk from harm reduction sites and journals.

Testing

Awaiting sourceReagent reactions and test kit guidance from a harm reduction testing service.

Effects

elevated heart ratevasodilationsweatingtremblingheadaches TS

Overview

Theobromine is the principal bitter alkaloid of the cacao bean. It has been used in various pharmaceutical products as vasodilator, diuretic and as heart stimulant. Theobromine is consumed in cocoa, chocolate and in various forms of chocolate-based foods. It is also present in small amounts in green coffee beans, tea, mate and the kola nut. TS

Theobromine, also known as xantheose, is the principal alkaloid of Theobroma cacao (cacao plant). Theobromine is slightly water-soluble (330 mg/L) with a bitter taste. In industry, theobromine is used as an additive and precursor to some cosmetics. It is found in chocolate and several other foods, including tea (Camellia sinensis), some American hollies (yaupon and guayusa) and the kola nut. It is a white or colourless solid, but commercial samples can appear yellowish.[1][2] WP

Theobromine, a metabolite of caffeine, is processed in the liver into xanthine and methyluric acid, peaks in the blood 2–3 hours after ingestion due to its fat solubility, and primarily acts by inhibiting adenosine receptors with minor phosphodiesterase inhibition. It is a mild heart stimulant and bronchodilator in humans with limited central nervous system effects. It can be toxic or fatal to animals like dogs and cats due to their slower metabolism of the compound. WP

History

History

Theobromine was discovered in 1841 in cacao beans by the chemist A. Woskresensky. Synthesis of theobromine from xanthine was first reported in 1882 by Hermann Emil Fischer.[3–7] WP

Pharmacology

Pharmacology

Even without dietary intake, theobromine may occur in the body as it is a product of the human metabolism of caffeine, which is metabolised in the liver into 12% theobromine, 4% theophylline, and 84% paraxanthine.[8] WP

In the liver, theobromine is metabolized into xanthine and subsequently into methyluric acid. Important enzymes include CYP1A2 and CYP2E1. The elimination half life of theobromine is between 6 and 8 hours.[9–12] WP

Unlike caffeine, which is highly water-soluble, theobromine is only slightly water-soluble and is more fat soluble, and thus peaks more slowly in the blood. While caffeine peaks after only 30 minutes, theobromine requires 2–3 hours to peak.[13] WP

The primary mechanism of action for theobromine inside the body is inhibition of adenosine receptors. Its effect as a phosphodiesterase inhibitor is thought to be small.[2][14] WP

Chemistry

Formula
C7H8N4O2 PC
CAS number
83-67-0 PC
Molar mass (g/mol)
180.16 PC
IUPAC name (computed by PubChem)
3,7-dimethylpurine-2,6-dione PC
SMILES
CN1C=NC2=C1C(=O)NC(=O)N2C PC
InChIKey
YAPQBXQYLJRXSA-UHFFFAOYSA-N PC
PubChem CID
5429

User reports

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Pop culture

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References

  1. Journal / agency Theobromine. 27 August 2022
  2. Journal / agency Smit HJ. Methylxanthines. 2011. doi:10.1007/978-3-642-13443-2_7 · PMID 20859797
  3. Other von Bibra E, Ott J. Plant Intoxicants: A Classic Text on the Use of Mind-Altering Plants. 1995
  4. Journal / agency Woskresensky A. Über das Theobromin. Liebigs Annalen der Chemie und Pharmacie. 1842. doi:10.1002/jlac.18420410117
  5. Other Thorpe TE. Essays in Historical Chemistry. 1902
  6. Journal / agency Fischer, Emil. Umwandlung des Xanthin in Theobromin und Caffein. Berichte der Deutschen Chemischen Gesellschaft. 1882. doi:10.1002/cber.18820150194
  7. Journal / agency Fischer E. Über Caffein, Theobromin, Xanthin und Guanin. Justus Liebigs Annalen der Chemie. 1882. doi:10.1002/jlac.18822150302
  8. Other Caffeine
  9. Journal / agency Cornish HH, Christman AA. A study of the metabolism of theobromine, theophylline, and caffeine in man. The Journal of Biological Chemistry. September 1957. doi:10.1016/S0021-9258(18)70714-X · PMID 13475320
  10. Journal / agency Gates S, Miners JO. Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism. British Journal of Clinical Pharmacology. March 1999. doi:10.1046/j.1365-2125.1999.00890.x · PMID 10215755 · PMC2014222
  11. Journal / agency Drouillard DD, Vesell ES, Dvorchik BH. Studies on theobromine disposition in normal subjects. Alterations induced by dietary abstention from or exposure to methylxanthines. Clinical Pharmacology and Therapeutics. March 1978. doi:10.1002/cpt1978233296 · PMID 627135
  12. Journal / agency Lelo A, Birkett DJ, Robson RA, Miners JO. Comparative pharmacokinetics of caffeine and its primary demethylated metabolites paraxanthine, theobromine and theophylline in man. British Journal of Clinical Pharmacology. August 1986. doi:10.1111/j.1365-2125.1986.tb05246.x · PMID 3756065 · PMC1401099
  13. Journal / agency Mumford GK, Benowitz NL, Evans SM, Kaminski BJ, Preston KL, Sannerud CA, Silverman K, Griffiths RR. Absorption rate of methylxanthines following capsules, cola and chocolate. European Journal of Clinical Pharmacology. 1 December 1996. doi:10.1007/s002280050205 · PMID 9010706
  14. Journal / agency Essayan DM. Cyclic nucleotide phosphodiesterases. The Journal of Allergy and Clinical Immunology. November 2001. doi:10.1067/mai.2001.119555 · PMID 11692087

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), TripSit factsheets, PubChem (public domain). Each value links to the exact revision it came from.