theobromine

Also known as 3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione, 3,7-dimethylxanthine, theobromin, 3,7-dimethylpurine-2,6-dione, diurobromine, 3,7-dimethyl-xanthine, 2,6-dihydroxy-3,7-dimethyl-purine, 3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione

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.

OverviewAI-generated

Theobromine is a chemical compound with the formula C₇H₈N₄O₂. Its IUPAC name is 3,7-dimethylpurine-2,6-dione. The substance has a melting point of 351 and a defined daily dose of 4. Its mass is listed as 180.065, while its weight is recorded as 180.16.

Chemical properties include an xlogp value of -0.8 and a topological polar surface area of 67.2. The molecule features one hydrogen bond donor and three hydrogen bond acceptors, with a charge of 0. The canonical SMILES notation for theobromine is CN1C=NC2=C1C(=O)NC(=O)N2C.

In scientific literature, theobromine is the subject of 6,680 PubMed entries. It is referenced by 1,242 other encyclopedia articles.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 622941253
Drug.IUPAC_name: 3,7-dimethyl-1H-purine-2,6-dione
Drug.image: Theobromine.svg
Drug.image_class: skin-invert-image
Drug.width: 135
Drug.image2: Theobromine 3D ball.png
Drug.image_class2: bg-transparent
Drug.legal_status: In general: Unscheduled.
Drug.dependency_liability: None
Drug.routes_of_administration: Oral
Drug.metabolism: Hepatic demethylation and oxidation
Drug.elimination_half life: 6–8 hours
Drug.excretion: Renal (10% unchanged, rest as metabolites)
Drug.CAS_number: 83-67-0
Drug.ATC_prefix: C03
Drug.ATC_suffix: BD01
Drug.PubChem: 5429

via Wikipedia infobox

Chemical data

Formula: C7H8N4O2
Molecular weight: 180.16 g/mol
IUPAC name: 3,7-dimethylpurine-2,6-dione
SMILES: CN1C=NC2=C1C(=O)NC(=O)N2C
InChIKey: YAPQBXQYLJRXSA-UHFFFAOYSA-N
XLogP: -0.8
Polar surface area: 67.2 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

6,680 papers

Theobromine for treatment of uric acid stones and other diseases.Archivio italiano di urologia, andrologia : organo ufficiale [di] Societa italiana di ecografia urologica e nefrologica · 2024
Theobromine.IARC monographs on the evaluation of carcinogenic risks to humans · 1991
Theobromine and theophylline.Mutation research · 1975
Theobromine is associated with slower epigenetic ageing.Aging · 2025
Theobromine and the pharmacology of cocoa.Handbook of experimental pharmacology · 2011

via PubMed

~7 min read

Encyclopedic overview

12 sections

Contents

Structure
History
Etymology
Sources
Biosynthesis
Pharmacology
Effects
Humans
Toxicity
Animals
See also
References

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.

Excerpted from Wikipedia’s “theobromine” article, available under the CC BY-SA 4.0 licence.