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Chemistry

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Also known as: 83-67-0, 3,7-dimethylxanthine, Diurobromine, Theosalvose, Santheose, Teobromin
Molecular Formula
C7H8N4O2
Molecular Weight
180.16  g/mol
InChI Key
YAPQBXQYLJRXSA-UHFFFAOYSA-N
FDA UNII
OBD445WZ5P

Theobromine
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)
1 2D Structure

Theobromine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3,7-dimethylpurine-2,6-dione
2.1.2 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)
2.1.3 InChI Key
YAPQBXQYLJRXSA-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1C=NC2=C1C(=O)NC(=O)N2C
2.2 Other Identifiers
2.2.1 UNII
OBD445WZ5P
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 83-67-0

2. 3,7-dimethylxanthine

3. Diurobromine

4. Theosalvose

5. Santheose

6. Teobromin

7. Theostene

8. Thesodate

9. 3,7-dimethylpurine-2,6-dione

10. Thesal

11. 3,7-dimethyl-3,7-dihydro-1h-purine-2,6-dione

12. Theobromin

13. 3,7-dihydro-3,7-dimethyl-1h-purine-2,6-dione

14. Xantheose

15. Xanthine, 3,7-dimethyl-

16. 2,6-dihydroxy-3,7-dimethylpurine

17. Fema No. 3591

18. 1h-purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-

19. Sc 15090

20. Theobrominum

21. Nsc 5039

22. 2,6-dihydroxy-3,7-dimethyl-purine

23. Mfcd00022830

24. Brn 0016464

25. 519-41-5

26. 3,7-dimethyl-2,3,6,7-tetrahydro-1h-purine-2,6-dione

27. Nsc-5039

28. Chembl1114

29. Obd445wz5p

30. Chebi:28946

31. Nsc5039

32. 3,7-dimethyl-1h-purine-2,6-dione

33. Cas-83-67-0

34. Ncgc00016023-11

35. Sc-15090

36. Dsstox_cid_6132

37. 3,7-dimethyl-1h-purine-2,6(3h,7h)-dione

38. Dsstox_rid_78030

39. Dsstox_gsid_26132

40. Theobromine (natural)

41. 7-dimethylxanthine

42. Ccris 2350

43. Hsdb 7332

44. Sr-01000000069

45. Einecs 201-494-2

46. Unii-obd445wz5p

47. Theobromine [inn:ban:nf]

48. Theobromine;

49. Cocoa Theobromine

50. 37t

51. Theobromine (3,7-dimethylxanthine)

52. Prestwick_1054

53. Theobromine(20%)

54. 3,7-dimethylxanthin

55. Spectrum_000053

56. 3, 7-dimethylxanthine

57. Theobromine [mi]

58. Prestwick0_000874

59. Prestwick1_000874

60. Prestwick2_000874

61. Prestwick3_000874

62. Spectrum2_000985

63. Spectrum3_000279

64. Spectrum4_000403

65. Spectrum5_001387

66. Lopac-t-4500

67. Theobromine [fhfi]

68. Theobromine [hsdb]

69. Theobromine [iarc]

70. Theobromine [inci]

71. Theobromine [vandf]

72. Theobrominum [hpus]

73. Schembl3184

74. Theobromine, >=98.0%

75. 3,7-dimethyl-1,3,7-trihydropurine-2,6-dione

76. Theobromine [mart.]

77. Lopac0_001187

78. Bspbio_000947

79. Bspbio_001758

80. Kbiogr_000666

81. Kbioss_000433

82. Theobromine [who-dd]

83. 5-26-13-00553 (beilstein Handbook Reference)

84. Mls000028407

85. Divk1c_000611

86. Spectrum1500649

87. Spbio_001049

88. Spbio_002868

89. Bpbio1_001043

90. Zinc2151

91. Theobromine, Analytical Standard

92. Dtxsid9026132

93. Hms501o13

94. Kbio1_000611

95. Kbio2_000433

96. Kbio2_003001

97. Kbio2_005569

98. Kbio3_001258

99. Yapqbxqyljrxsa-uhfffaoysa-

100. Theobromine [ep Impurity]

101. Ninds_000611

102. Hms1570p09

103. Hms1921o13

104. Hms2092g04

105. Hms2097p09

106. Hms3263n15

107. Hms3714p09

108. Pharmakon1600-01500649

109. Hy-n0138

110. Theobromine 0.1 Mg/ml In Methanol

111. Theobromine, >=98.0% (hplc)

112. Tox21_110284

113. Tox21_300016

114. Tox21_501187

115. Bbl034679

116. Bdbm50014260

117. Ccg-40078

118. Nsc757407

119. Pdsp1_001017

120. Pdsp2_001001

121. S2368

122. Stl419465

123. Akos000121558

124. Tox21_110284_1

125. 5-26-13-00553 (beilstein)

126. Cs-7972

127. Db01412

128. Lp01187

129. Nsc-757407

130. Sdccgmls-0002875.p003

131. Sdccgsbi-0051154.p004

132. Idi1_000611

133. Ncgc00016023-01

134. Ncgc00016023-02

135. Ncgc00016023-03

136. Ncgc00016023-04

137. Ncgc00016023-05

138. Ncgc00016023-06

139. Ncgc00016023-07

140. Ncgc00016023-08

141. Ncgc00016023-09

142. Ncgc00016023-10

143. Ncgc00016023-12

144. Ncgc00016023-13

145. Ncgc00016023-14

146. Ncgc00016023-15

147. Ncgc00016023-17

148. Ncgc00016023-18

149. Ncgc00016023-26

150. Ncgc00024123-03

151. Ncgc00024123-04

152. Ncgc00024123-05

153. Ncgc00024123-06

154. Ncgc00024123-07

155. Ncgc00024123-08

156. Ncgc00179030-01

157. Ncgc00179030-02

158. Ncgc00253943-01

159. Ncgc00261872-01

160. Wln: T56 Bn Dn Fnvmvj B1 F1

161. Ac-11381

162. Ac-34381

163. As-13904

164. Smr000058357

165. Sy048379

166. Sbi-0051154.p003

167. 1h-purine-2, 3,7-dihydro-3,7-dimethyl-

168. Ab00052141

169. Eu-0101187

170. Ft-0660435

171. Ft-0675138

172. N1573

173. T0178

174. C07480

175. D71206

176. Pentoxifylline Impurity A [ep Impurity]

177. T 4500

178. Ab00052141_12

179. Q206844

180. 3,7-dimethyl-3,7-dihydro-1h-purine-2,6-dione #

181. Q-100848

182. Sr-01000000069-2

183. Sr-01000000069-4

184. Sr-01000000069-7

185. Sr-01000000069-8

186. Sr-01000000069-9

187. Brd-k34888156-001-08-8

188. Caffeine Monohydrate Impurity D [ep Impurity]

189. Cec63cca-3b4b-4f4f-92c1-1789df3c880a

190. Sr-01000000069-10

191. Z56347209

192. 1h-purine-2,6-dione,3,7-dihydro-3,7- Dimethyl- (9ci)

193. Theobromine, European Pharmacopoeia (ep) Reference Standard

194. 3,7-dimethylxanthine; 3,7-dimethylpurine-2,6-dione

195. Theobromine, Pharmaceutical Secondary Standard; Certified Reference Material

196. Theobromine Solution, 100 Mug/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 180.16 g/mol
Molecular Formula C7H8N4O2
XLogP3-0.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass180.06472551 g/mol
Monoisotopic Mass180.06472551 g/mol
Topological Polar Surface Area67.2 Ų
Heavy Atom Count13
Formal Charge0
Complexity267
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Diuretic, bronchodilator, cardiotonic. /Former use/

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1654


Formerly, theobromine and its derivatives were used in diuretics, myocardial stimulants, vasodilators and smooth muscle relaxants. Theobromine salts (calcium salicylate, sodium salicylate and sodium acetate) were used previously to dilate coronary arteries at doses of 300 to 600 mg per day. There is no current therapeutic use of theobromine. /Former use/

IARC. 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). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 422 (1991)


VET: Diuretic, myocardial stimulant, vasodilator. /Former use/

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1654


/EXPL THER/ Cough is a common and protective reflex, but persistent coughing is debilitating and impairs quality of life. Antitussive treatment using opioids is limited by unacceptable side effects, and there is a great need for more effective remedies. The present study demonstrates that theobromine, a methylxanthine derivative present in cocoa, effectively inhibits citric acid-induced cough in guinea-pigs in vivo. Furthermore, in a randomized, double-blind, placebo-controlled study in man, theobromine suppresses capsaicin-induced cough with no adverse effects. We also demonstrate that theobromine directly inhibits capsaicin-induced sensory nerve depolarization of guinea-pig and human vagus nerve suggestive of an inhibitory effect on afferent nerve activation. These data indicate the actions of theobromine appear to be peripherally mediated. We conclude theobromine is a novel and promising treatment, which may form the basis for a new class of antitussive drugs.

PMID:15548587 Usmani OS et al; FASEB J 19 (2): 231-3 (2005)


4.2 Drug Indication

theobromine is used as a vasodilator, a diuretic, and heart stimulant. And similar to caffeine, it may be useful in management of fatigue and orthostatic hypotension.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Theobromine, a xanthine derivative like caffeine and the bronchodilator theophylline, is used as a CNS stimulant, mild diuretic, and respiratory stimulant (in neonates with apnea of prematurity).


5.2 MeSH Pharmacological Classification

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


Bronchodilator Agents

Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)


5.3 ATC Code

C - Cardiovascular system

C03 - Diuretics

C03B - Low-ceiling diuretics, excl. thiazides

C03BD - Xanthine derivatives

C03BD01 - Theobromine


R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03D - Other systemic drugs for obstructive airway diseases

R03DA - Xanthines

R03DA07 - Theobromine


5.4 Absorption, Distribution and Excretion

The ratio of brain:blood theobromine concentrations decreased continuously from 0.96 at birth to 0.60 in 30-day-old rats. After 24 hr, no organ accumulation of theobromine or its metabolites could be seen in adult animals.

IARC. 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). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 425 (1991)


Theobromine is absorbed and distributed rapidly after oral administration to rats and equilibrates freely between plasma and testicular fluid.

IARC. 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). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 425 (1991)


Similar kinetic parameters were observed in male and female rabbits when theobromine was administered intravenously or orally at doses of 1 and 5 mg/kg bw, with complete gastrointestinal absorption. A reduction in the absorption rate constant was seen in rabbits when the dose was increased from 10 to 100 mg/kg bw. In spite of delayed gastrointestinal absorption at high doses, probably due to the low solubility of the compound, the absolute bioavailability of theobromine approached 100%. Labelled theobromine was almost completely absorbed after oral administration (1-6 mg/kg); the peak blood level tended to appear later with larger doses.

IARC. 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). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 425 (1991)


When theobromine was given as a single oral dose of 15-50 mg/kg bw to male dogs, peak plasma concentrations, with considerable individual variations, were observed within 3 hr. With a higher dose (150 mg/kg bw), the peak plasma concentrations were attained 14-16 hr later, showing delayed intestinal absorption. In rats, plasma protein binding was very low (8-17%) after oral administration of 1-100 mg/kg bw theobromine.

IARC. 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). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 425 (1991)


For more Absorption, Distribution and Excretion (Complete) data for 3,7-Dimethylxanthine (17 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Pregnancy and increased doses of theobromine were shown to modify theobromine metabolism. At a dose of 50 mg/kg bw, pregnant rabbits excreted more unchanged theobromine in the urine (51% versus 35%). Pregnant rats excreted a higher percentage of a 5 mg/kg dose as unchanged theobromine (53%) than non-pregnant rats (39%); this difference disappeared at the saturation dose (100 mg/kg), when unchanged theobromine corresponded to about 60% of the dose in the urine of both pregnant and non-pregnant animals. Rats given 100 mg/kg excreted more unchanged theobromine than those given 1 mg/kg (73% versus 51%), and showed a corresponding relative decrease in excretion of its uracil metabolite, 6-amino-5-(N-methylformylamino)-1-methyluracil (16% versus 28%).

IARC. 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). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 428 (1991)


The compounds identified in bile of phenobarbital-treated rats were 3,7-dimethyluric acid (64-76% of biliary radioactivity), dimethylallantoin (5-8%), 6-amino-5-(N-methylformylamino)- 1-methyluracil (10-17%) and theobromine (8-10%). In 3-methylcholanthrene-treated rats, urinary elimination of unchanged theobromine was reduced from 23-27% to only 2%, while excretion of 6-amino-5-(N-methylformylamino)-1- methyluracil was significantly increased. Only 3,7-dimethyluric acid was produced by liver microsomal incubation in control rats while phenobarbital and 3-methylcholanthrene pretreatment enhanced the biotransformation resulting in the production of all metabolites found in vivo as well as unknown polar compounds.

IARC. 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). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 426 (1991)


6-Amino-5-(N-methylformylamino)-1-methyluracil is quantitatively the most important theobromine metabolite in rats, accounting for 20-35% of urinary metabolites. The majority of theobromine-derived radioactivity in the feces of rats could be accounted for by 3,7-dimethyluric acid. The most extensive metabolism of theobromine was observed in rabbits and mice; male mice converted theobromine more extensively into this metabolite than did female mice. In contrast, oxidation of theobromine to 3,7-dimethyluric acid was significantly greater in female than in male rats. Rabbits and dogs metabolized theobromine primarily to 7-methylxanthine and 3-methylxanthine, respectively, and dogs excreted small quantities of an unidentified metabolite.

IARC. 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). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 426 (1991)


As a metabolite of caffeine, theobromine has been detected in variable amounts in plasma and urine of humans and different animal species.

IARC. 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). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 425 (1991)


For more Metabolism/Metabolites (Complete) data for 3,7-Dimethylxanthine (11 total), please visit the HSDB record page.


Theobromine has known human metabolites that include 3,7-Dimethyluric acid, 3-Methylxanthine, and 7-Methylxanthine.

Theobromine is a known human metabolite of caffeine.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.6 Biological Half-Life

The mean half-time of theobromine in human serum ranged from 6.1 to 10 hr.

IARC. 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). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 432 (1991)


The disposition half-life of theobromine averaged 7.1 +/- 2.1 hours ...

PMID:894424 Resman BH et al; J Pediatr 91 (3): 477-80 (1977)


In dogs, an average plasma half-time of 17.5 hr was reported after single oral doses of theobromine ranging from 15 to 150 mg/kg bw. In rabbits, the mean elimination half-time was 4.3-5.6 hr for doses ranging from 1 to 100 mg/kg bw.

IARC. 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). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 426 (1991)


5.7 Mechanism of Action

Theobromine stimulates medullary, vagal, vasomotor, and respiratory centers, promoting bradycardia, vasoconstriction, and increased respiratory rate. This action was previously believed to be due primarily to increased intracellular cyclic 3′,5′-adenosine monophosphate (cyclic AMP) following inhibition of phosphodiesterase, the enzyme that degrades cyclic AMP. It is now thought that xanthines such as caffeine and theobromine act as antagonist at adenosine-receptors within the plasma membrane of virtually every cell. As adenosine acts as an autocoid, inhibiting the release of neurotransmitters from presynaptic sites but augmenting the actions of norepinephrine or angiotensin, antagonism of adenosine receptors promotes neurotransmitter release. This explains the stimulatory effects of xanthine derivatives such as theobromine and caffeine. Blockade of the adenosine A1 receptor in the heart leads to the accelerated, pronounced "pounding" of the heart upon caffeine intake.


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