Compound: theobromine
SMILES: O=c1n(c2ncn(c2c([nH]1)=O)C)C
InChIKey: YAPQBXQYLJRXSA-UHFFFAOYSA-N
Synonyms: theobromine, 83-67-0, 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, 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione, FEMA No. 3591, Theobrominum, 1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-, SC 15090, DTXSID9026132, 3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione, NSC-5039, OBD445WZ5P, SC-15090, CHEBI:28946, DTXCID506132, RefChem:6504, 201-494-2, Thesodate, Theobromin, Xanthine, 3,7-dimethyl-, 2,6-Dihydroxy-3,7-dimethylpurine, MFCD00022830, NSC 5039, 519-41-5, 2,6-Dihydroxy-3,7-dimethyl-purine, BRN 0016464, CHEMBL1114, NSC5039, Theobromine (3,7-Dimethylxanthine), CAS-83-67-0, NCGC00016023-11, 3,7-Dimethyl-1H-purine-2,6(3H,7H)-dione, 3,7-dimethyl-1,3,7-trihydropurine-2,6-dione, Theobromine (natural), 7-Dimethylxanthine, CCRIS 2350, HSDB 7332, Caffeine EP impurity D, SR-01000000069, EINECS 201-494-2, UNII-OBD445WZ5P, Theobromine [INN:BAN:NF], 37T, 3,7-dimethyl-1H-purine-2,6-dione, Prestwick_1054, Theobromine(20%), 3,7-dimethylxanthin, Spectrum_000053, Theobromine (Standard), 3,7-Dimethyl-xanthine, THEOBROMINE [MI], Prestwick0_000874, Prestwick1_000874, Prestwick2_000874, Prestwick3_000874, Spectrum2_000985, Spectrum3_000279, Spectrum4_000403, Spectrum5_001387, Lopac-T-4500, Aminophylline EP ImpurityG, THEOBROMINE [FHFI], THEOBROMINE [HSDB], THEOBROMINE [IARC], Epitope ID:613459, THEOBROMINE [VANDF], THEOBROMINUM [HPUS], SCHEMBL3184, Theobromine, >=98.0%, THEOBROMINE [MART.], Lopac0_001187, BSPBio_000947, BSPBio_001758, KBioGR_000666, KBioSS_000433, THEOBROMINE [WHO-DD], 5-26-13-00553 (Beilstein Handbook Reference), MLS000028407, DivK1c_000611, SPECTRUM1500649, SPBio_001049, SPBio_002868, BPBio1_001043, orb1310438, orb3140211, SCHEMBL2136936, SCHEMBL7587207, Theobromine, analytical standard, SCHEMBL10582332, SCHEMBL27344668, HMS501O13, HY-N0138R, KBio1_000611, KBio2_000433, KBio2_003001, KBio2_005569, KBio3_001258, YAPQBXQYLJRXSA-UHFFFAOYSA-, MSK7920, THEOBROMINE [EP IMPURITY], NINDS_000611, HMS1570P09, HMS1921O13, HMS2092G04, HMS2097P09, HMS3263N15, HMS3714P09, Pharmakon1600-01500649, HY-N0138, Theobromine 0.1 mg/ml in Methanol, Theobromine, >=98.0% (HPLC), Tox21_110284, Tox21_300016, Tox21_501187, BBL034679, BDBM50014260, CCG-40078, EBC-13222, NSC757407, PDSP1_001017, PDSP2_001001, s2368, SBB012378, STL419465, AKOS000121558, Tox21_110284_1, 5-26-13-00553 (Beilstein), CS-7972, DB01412, FT33795, LP01187, NSC-757407, SDCCGMLS-0002875.P003, SDCCGSBI-0051154.P004, IDI1_000611, NCGC00016023-01, NCGC00016023-02, NCGC00016023-03, NCGC00016023-04, NCGC00016023-05, NCGC00016023-06, NCGC00016023-07, NCGC00016023-08, NCGC00016023-09, NCGC00016023-10, NCGC00016023-12, NCGC00016023-13, NCGC00016023-14, NCGC00016023-15, NCGC00016023-17, NCGC00016023-18, NCGC00016023-26, NCGC00024123-03, NCGC00024123-04, NCGC00024123-05, NCGC00024123-06, NCGC00024123-07, NCGC00024123-08, NCGC00179030-01, NCGC00179030-02, NCGC00253943-01, NCGC00261872-01, WLN: T56 BN DN FNVMVJ B1 F1, AC-11381, AC-34381, AS-13904, DA-68137, SMR000058357, ST069337, SY048379, SBI-0051154.P003, 1H-Purine-2, 3,7-dihydro-3,7-dimethyl-, AB00052141, EU-0101187, NS00009946, EN300-16609, purine-2,6(1H,3H)-dione, 3,7-dimethyl-, C07480, D71206, PENTOXIFYLLINE IMPURITY A [EP IMPURITY], T 4500, AB00052141_12, F787637, Q206844, 3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione #, SR-01000000069-2, SR-01000000069-4, SR-01000000069-7, SR-01000000069-8, SR-01000000069-9, BRD-K34888156-001-08-8, BRD-K34888156-001-11-2, BRD-K34888156-213-01-4, CAFFEINE MONOHYDRATE IMPURITY D [EP IMPURITY], CEC63CCA-3B4B-4F4F-92C1-1789DF3C880A, SR-01000000069-10, Z56347209, 1H-purine-2,6-dione,3,7-dihydro-3,7- dimethyl- (9CI), Theobromine, European Pharmacopoeia (EP) Reference Standard, 3,7-DIMETHYLXANTHINE; 3,7-DIMETHYLPURINE-2,6-DIONE, Caffeine EP Impurity D; Pentoxifylline EP Impurity A; Theobromine, Theobromine, Pharmaceutical Secondary Standard; Certified Reference Material, InChI=1/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
Theoretical properties:
molecular_formula: C7H8N4O2
molecular_weight: 180.16 g/mol
exact_mass: 180.06472551 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 13
topological_polar_surface_area: 67.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Monoclinic needles (/crystalline structure is/ lamellar twining on 001 /axis/) from water
color: Monoclinic needles (/crystalline structure is/ lamellar twining on 001 /axis/) from water
boiling_point: Sublimes at 554-563 °F (NTP, 1992)
melting_point: 675 °F (NTP, 1992)
density: 1.522 g/cu cm at 20 °C; relative density: 1.522 at 20 °C
solubility: less than 1 mg/mL at 64 °F (NTP, 1992)
Descriptions:
pubchem: Theobromine is a dimethylxanthine having the two methyl groups located at positions 3 and 7. A purine alkaloid derived from the cacao plant, it is found in chocolate, as well as in a number of other foods, and is a vasodilator, diuretic and heart stimulator. It has a role as a bronchodilator agent, a vasodilator agent, an adenosine receptor antagonist, a mouse metabolite, a plant metabolite, a food component and a human blood serum metabolite.
chebi: A dimethylxanthine having the two methyl groups located at positions 3 and 7. A purine alkaloid derived from the cacao plant, it is found in chocolate, as well as in a number of other foods, and is a vasodilator, diuretic and heart stimulator.
chembl: THEOBROMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: 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.
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.