3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 1221
• Molecular Formular: C7H8N4O2
• Molecular Mass: 180.16402
• Monoisotopic Mass: 180.06472552
• SMILES: O=c1[nH]c(=O)n(c2ncn(c12)C)C
• Canonical SMILES: Cn1cnc2c1c(=O)[nH]c(=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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: theobromine
• Synonyms: Theobromine; 3,7-Dimethylxanthine; 2,6-Dihydroxy-3,7-dimethylpurine; 3; 7-Dimethylxanthine; Diurobromine; Santheose; Teobromin; Theosalvose; Theostene; Theobromine; 3,7-Dihydro-3,7-dimethyl-1H-purine-2,6-dione; 3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione; NSC 5039; SC 15090; Thesal; Theophylline-Ethylenediamine Imp. G (EP); 可可碱

Database IDs

• CAS Number: 83-67-0
• EC Number: 201-494-2
• MDL Number: MFCD00022830
• Beilstein Number: 16464
• Merck Index: 149282
• PubChem SID: 46508574; 24277679; 160964681
• PubChem CID: 5429

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.280305
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.769393
• LogD (pH = 7.4): -0.7749402
• Log P: -0.7693217
• Molar Refractivity: 44.9345 cm^3
• Polarizability: 16.05493 Å^3
• Polar Surface Area: 67.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.46
• LOG S: -1.27
• Solubility (Water): 9.74e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.33 mg/mL at 25 oC [YALKOWSKY,SH & HE,Y (2003)]; aqueous base: moderately soluble; DMSO; ethanol: slightly soluble; H2O: slightly soluble; hot MeOH
• Apperance: white solid; White to Off-White Solid
• Melting Point: >300°C (dec.); 345-350 °C; 345-350°C; 357°C
• Density: 1.50
• Hydrophobicity(logP): -0.78 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: XH2275000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22; R:22
• Safety Statements: 36; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301; H302
• GHS Precautionary statements: P264-P270-P301+P310-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)rat ... Adora1(29290)

Product Information

• Purity: ≥98.0% (HPLC); ≥99.0%; 99%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C7H8N4O2

DETAILS

MP Biomedicals - 02103023

Crystalline

DrugBank - DB01412

• Drug Groups: approved
• Description: 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)
• 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.
• 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).
• References: Usmani OS, Belvisi MG, Patel HJ, Crispino N, Birrell MA, Korbonits M, Korbonits D, Barnes PJ: Theobromine inhibits sensory nerve activation and cough. FASEB J. 2005 Feb;19(2):231-3. Epub 2004 Nov 17. [Pubmed] ; Slattery ML, West DW: Smoking, alcohol, coffee, tea, caffeine, and theobromine: risk of prostate cancer in Utah (United States). Cancer Causes Control. 1993 Nov;4(6):559-63. [Pubmed]
• External Links: Wikipedia

Selleck Chemicals - S2368

Research Area: Cardiovascular Disease
Biological Activity:
Theobromine(3,7-Dimethylxanthine) is 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. [1]

Sigma Aldrich - T4500

Biochem/physiol Actions
Phosphosdiesterase inhibitor; weak adenosine receptor antagonist; diuretic; smooth muscle relaxant.

Sigma Aldrich - 88304

Biochem/physiol Actions
Phosphosdiesterase inhibitor; weak adenosine receptor antagonist; diuretic; smooth muscle relaxant.

Toronto Research Chemicals - T343800

A metabolite of Caffeine.

REFERENCES

• Usmani OS, Belvisi MG, Patel HJ, Crispino N, Birrell MA, Korbonits M, Korbonits D, Barnes PJ: Theobromine inhibits sensory nerve activation and cough. FASEB J. 2005 Feb;19(2):231-3. Epub 2004 Nov 17. Pubmed
• Slattery ML, West DW: Smoking, alcohol, coffee, tea, caffeine, and theobromine: risk of prostate cancer in Utah (United States). Cancer Causes Control. 1993 Nov;4(6):559-63. Pubmed
• http://www.drugbank.ca/drugs/DB01412
• Suto, M., et al.: Anticancer Drug Des., 6, 107 (1991)
• Burkart, V., et al.: Nat. Med., 5, 314 (1991)
• Hassa, P., et al.: J. Biol. Chem., 278, 45145 2003), Veres, B., et al.: J. Pharmacol. Exp. Ther., 310, 247(1991)