Theobromine
Athanor · official
C7H8N4O2 · 180.16 g/mol
IUPAC name: 3,7-dimethylpurine-2,6-dione
Also called xantheose, cocoa alkaloid, chocolate
WarningHarmful if swallowed · Causes serious eye irritation · Suspected of causing cancerNames and identifiers
- IUPAC name
- 3,7-dimethylpurine-2,6-dione
- Synonyms
- xantheose, cocoa alkaloid, chocolate
+ 37 more
3,7-Dimethylxanthine, Diurobromine, Theosalvose, Santheose, Teobromin, Theostene, 3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione, Thesal, 3,7-dimethylpurine-2,6-dione, Xantheose, FEMA No. 3591, 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione, Theobrominum, 1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-, SC 15090, DTXSID9026132, OBD445WZ5P, 3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione, NSC-5039, SC-15090, CHEBI:28946, DTXCID506132, RefChem:6504, 201-494-2, Thesodate, Theobromin, Xanthine, 3,7-dimethyl-, 2,6-Dihydroxy-3,7-dimethylpurine, MFCD00022830, UNII-OBD445WZ5P, NSC 5039, 2,6-Dihydroxy-3,7-dimethyl-purine, BRN 0016464, Prestwick_1054, Prestwick1_000874, Spectrum4_000403, 3,7-dimethyl-1H-purine-2,6-dione
- Molecular formula
- C7H8N4O2
- Empirical formula
- C7H8N4O2
- Molecular weight
- 180.16 g/mol
- Exact mass
- 180.06473
- CAS number
- 83-67-0
- PubChem CID
- 5429
- Canonical SMILES
- CN1C=NC2=C1C(=O)NC(=O)N2C
- Isomeric SMILES
- CN1C=NC2=C1C(=O)NC(=O)N2C
- InChI
- 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
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Physical properties
- Appearance
- White powder or monoclinic needles[2]
2 values
From Hazardous Substances Data Bank (HSDB), the most authoritative source here.
Value As written Source – Theobromine is an odorless white crystalline powder. Bitter taste. pH (saturated solution in water): 5.5-7. (NTP, 1992) [1] CAMEO Chemicalscites National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. –shown White powder or monoclinic needles [2] Hazardous Substances Data Bank (HSDB)cites Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. V5: 4239 - Melting point
- 357 °C (675 °F, NTP 1992)[1]
- Boiling point
- Reported, but no value passed the checks.
The value and why
- Sublimes at 554-563 °F (NTP, 1992) (could not be read; source [1])
- Density
- 1.522 g/cu cm at 20 °C[2]
2 values
Only one source reports it.
Value As written Source 1.522 g/mLshown 1.522 g/cu cm at 20 °C [2] Hazardous Substances Data Bank (HSDB)cites ECHA; Search for Chemicals. Theobromine (83-67-0) Registered Substances Dossier. European Chemical Agency. Available from, as of Oct 21, 2016: https://echa.europa.eu/ – relative density: 1.522 at 20 °C [2] Hazardous Substances Data Bank (HSDB)cites ECHA; Search for Chemicals. Theobromine (83-67-0) Registered Substances Dossier. European Chemical Agency. Available from, as of Oct 21, 2016: https://echa.europa.eu/ - Solubility in water
- Slightly soluble in water[2]
5 values
From Hazardous Substances Data Bank (HSDB), the most authoritative source here.
Value As written Source – less than 1 mg/mL at 64 °F (NTP, 1992) [1] CAMEO Chemicalscites National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina. – In water, 330 mg/L at 25 °C [2] Hazardous Substances Data Bank (HSDB)cites Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 395 – In water, 500 mg/L, temp not specified [2] Hazardous Substances Data Bank (HSDB)cites ECHA; Search for Chemicals. Theobromine (83-67-0) Registered Substances Dossier. European Chemical Agency. Available from, as of Oct 21, 2016: https://echa.europa.eu/ –shown Slightly soluble in water [2] Hazardous Substances Data Bank (HSDB)cites Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V5: 4605 – For more Solubility (Complete) data for 3,7-Dimethylxanthine (7 total), please visit the HSDB record page. [2] Hazardous Substances Data Bank (HSDB) - log P
- log Kow = -0.78[2]
- pKa
- pKa = 9.90 (imide N)[2]
Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.
Calculated
- Heavy atoms
- 13
- Rings
- 2
- Aromatic rings
- 2
- Fraction sp³ carbons (Fsp3)
- 0.29
- H-bond donors
- 1
- H-bond acceptors
- 3
- Rotatable bonds
- 0
- TPSA (Ų)
- 72.7 computed here · PubChem 67.2
- Formal charge
- 0
- XLogP3
- -0.8 PubChem
- Complexity
- 267 PubChem
- Stereocenters
- None
- Double-bond geometry
- None specified
- Point group
- Cs of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C46.67%
- H4.48%
- N31.10%
- O17.76%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- -1.04 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -0.81 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 2.47 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 180.17
- log P ≤ 5 (Crippen): -1.04
- H-bond donors ≤ 5: 1
- H-bond acceptors ≤ 10: 3
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
Warning
Most widely reported: 277 company reports to ECHA. Source [3].
- Harmful or irritant
- Health hazard
- H302Harmful if swallowed (98.6% of reports)
- H319Causes serious eye irritation (47.7% of reports)
- H351Suspected of causing cancer (28.5% of reports)
Precautionary statements: P203, P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P318, P330, P337+P317, P405, P501
View all classifications (2)
- [3] European Chemicals Agency (ECHA) · 277 reports · WarningH302, H319, H351
- [2] Hazardous Substances Data Bank (HSDB) · WarningH302
First aid
- Eyes: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. Immediately transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. Skin: Immediately flood affected skin with water while removing and isolating all contaminated clothing.[1]
Storage
- Keep container tightly closed in a dry and well-ventilated place. Store under inert gas. Air sensitive.[2]
Incompatibilities
- Incompatible materials: Strong oxidizing agents[2]
Safety data sheets on the supplier’s page: J&H Chemical Co.,ltd, Accel Scientific, TCI (Tokyo Chemical Industry).
Always read the supplier’s safety data sheet before working with it.
Spectra
- NMRHazardous Substances Data Bank (HSDB) · NMRShiftDB
- 1H NMRHuman Metabolome Database (HMDB) (600 MHz · DMSO) · Human Metabolome Database (HMDB) (600 MHz · DMSO) · Human Metabolome Database (HMDB) (Bruker · 600 MHz · 100%_DMSO) · SpectraBase (Varian A-60D)
- 13C NMRSpectraBase
- 1H-13C NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · 100%_DMSO)
- GC-MSHuman Metabolome Database (HMDB) (EI-B · positive) · Human Metabolome Database (HMDB) (GC-MS) · MassBank of North America (MoNA) (Unknown · EI-B · positive) · MassBank of North America (MoNA) (GC-MS) · NIST Mass Spectrometry Data Center · NIST Mass Spectrometry Data Center
- MS-MSHuman Metabolome Database (HMDB) (Quattro_QQQ · Positive) · Human Metabolome Database (HMDB) (Quattro_QQQ · Positive) · Human Metabolome Database (HMDB) (Quattro_QQQ · Positive) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive)
- LC-MSMassBank Europe (Exploris 480 Orbitrap (Thermo Scientific) · LC-ESI-QFT · POSITIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (TripleTOF 5600 SCIEX · LC-ESI-QTOF · NEGATIVE)
- Other MSHazardous Substances Data Bank (HSDB) · MassBank Europe (Unknown · EI-B · POSITIVE) · MassBank of North America (MoNA) (Agilent 6550 iFunnel · Q-TOF · ESI) · MassBank of North America (MoNA) (Agilent 6550 iFunnel · Q-TOF · ESI) · MassBank of North America (MoNA) (Electron Impact (EI) · positive)
- UVHazardous Substances Data Bank (HSDB)
- UV-VISSpectraBase
- IRHazardous Substances Data Bank (HSDB)
- FTIRSpectraBase (KBr WAFER)
- ATR-IRSpectraBase (Bio-Rad FTS · ATR-Neat (DuraSamplIR II))
- RamanSpectraBase (FT-Raman)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]CAMEO Chemicals · Public domain (NOAA) · via PubChem · retrieved 2026-10-14
- [2]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
- [3]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [4]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
- [5]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [6]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [7]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- [8]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- [9]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.