3D Mol Similar

8-BROMOTHEOPHYLLINE

Iupac Name：8-bromo-1,3-dimethyl-7H-purine-2,6-dione

CAS No.: 10381-75-6

Molecular Weight：259.063

Modify Date.: 2022-11-23 22:58

Introduction:

White Crystalline Powder

Bromotheophylline is the active moiety of pamabrom, a mixture of 2-amino-2-methyl-propanol and bromotheophylline. From this mixture, bromotheophylline acts as a weak diuretic that has been used along with some analgesics to relieve the symptoms of premenstrual syndrome. Bromotheophylline is categorized on the FDA as a drug substance with an inactive state since March, 1980. It is also approved by Health Canada to be used alone or in combination with [DB00316] in OTC products.

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1. Names and Identifiers

1.1 Name: 8-BROMOTHEOPHYLLINE
1.2 Synonyms: 1,3-Dimethyl-8-bromoxanthine 1H-Purine-2,6-dione, 8-bromo-3,7-dihydro-1,3-dimethyl- 1H-Purine-2,6-dione, 8-bromo-3,9-dihydro-1,3-dimethyl- 8-Bromo-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione 8-BROMO-1,3-DIMETHYL-3,7-DIHYDRO-PURINE-2,6-DIONE 8-BROMO-3,7-DIHYDRO-1,3-DIMETHYL-1H-PURINE-2,6-DIONE 8-bromo-3,7-dihydro-1,3-dimethyl-1h-purine-6-dione 8-Bromo-3,9-dihydro-1,3-dimethyl-1H-purine-2,6-dione 8-BROMOTHEOPHYLLINE AKOS NCG-0005 Bromotheaminum Bromotheophylline LABOTEST-BB LT00134545 NSC 164940 Theophylline, 8-bromo-

1.3 CAS No.: 10381-75-6

1.4 CID: 11808

1.5 EINECS(EC#): 233-846-6

1.6 Molecular Formula: C7H7BrN4O2 (isomer)

1.7 Inchi: InChI=1S/C7H7BrN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10)

1.8 InChkey: SKTFQHRVFFOHTQ-UHFFFAOYSA-N

1.9 Canonical Smiles: CN1C2=C(C(=O)N(C1=O)C)NC(=N2)Br

1.10 Isomers Smiles: CN1C2=C(C(=O)N(C1=O)C)NC(=N2)Br

2. Properties

2.1 Density: 1.862

2.1 Melting point: 295-297°C

2.1 Boiling point: 469.5 °C at 760 mmHg

2.1 Refractive index: 1.651

2.1 Flash Point: 237.7 °C

2.1 Precise Quality: 257.97500

2.1 PSA: 72.68000

2.1 logP: -0.27720

2.1 Appearance: White crystalline powder

2.2 Chemical Properties: White Crystalline Powder

2.3 pKa: pKa 5.45±0.1(H2O t=24) (Uncertain)

2.4 Water Solubility: H2O: soluble

3. Use and Manufacturing

3.1 Purification Methods: It is purified by dissolving in the minimum volume of dilute NaOH (charcoal), filtering and acidifying to pH ca 3.5-4. The solid that separates is collected, dried in vacuo at 100o and stored in a dark container. It has also been recrystallised from EtOH or AcOH. [Blitz & Beck J Prakt Chem [2] 118 158 1928, Fischer & Ach Chem Ber 28 3142 1895, Beilstein 26 H 476, 26 II 227, 26 III/IV 2447.] 8-BROMOTHEOPHYLLINE Preparation Products And Raw materials Raw materials

3.2 Usage: The active component in the diuretic Diurex.

4. Safety and Handling

4.1 Risk Statements: 20/21/22

4.1 Safety Statements: 24/25-36/37

4.1 Packing Group: III

4.1 Hazard Class: 6.1(b)

4.1 RIDADR: 2811

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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6. Synthesis Route

10381-75-6Total: 6 Synthesis Route

58-55-9 344 Suppliers

10381-75-6 29 Suppliers

Literatures:
Chemische Berichte, , vol. 28, p. 3139 Chemische Berichte, , vol. 39, p. 430
Yield: null

944-73-0 26 Suppliers

10381-75-6 29 Suppliers

Literatures:
Chemische Berichte, , vol. 28, p. 3139 Chemische Berichte, , vol. 39, p. 430
Yield: null

2099-73-2 1 Suppliers

10381-75-6 29 Suppliers

Literatures:
Annali di Chimica (Rome, Italy), , vol. 47, p. 362,364
Yield: null

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7. Precursor and Product

precursor:

2099-73-2

944-73-0

86468-95-3

10035-10-6

58-55-9

208577-20-2

product :

78740-20-2

944-73-0

961-48-8

78146-62-0

52943-89-2

10381-82-5

78960-64-2

111038-26-7

114431-60-6

111038-24-5

74808-90-5

30958-49-7

111038-27-8

19800-66-9

111038-28-9

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8. Other Information

8.0 BRN: 203069

8.1 Chemical Properties: White Crystalline Powder

8.2 Uses: The active component in the diuretic Diurex.

8.3 Purification Methods: It is purified by dissolving in the minimum volume of dilute NaOH (charcoal), filtering and acidifying to pH ca 3.5-4. The solid that separates is collected, dried in vacuo at 100o and stored in a dark container. It has also been recrystallised from EtOH or AcOH. [Blitz & Beck J Prakt Chem [2] 118 158 1928, Fischer & Ach Chem Ber 28 3142 1895, Beilstein 26 H 476, 26 II 227, 26 III/IV 2447.]

8.4 Absorption: When administered after one single oral dosage, bromotheophylline is rapidly absorbed and it reaches a maximal plasma concentration of 2.5 mg/L in 0.78 hours. The mean residence time is registered to be of 12 hours with an AUC in the first 8 hours of 27 mg.h/L.|This pharmacokinetic property has not been determined.

8.5 Metabolism: This pharmacokinetic property has not been determined.

8.6 Biological Half Life: The apparent elimination half-life is registered to be 21.35 hours.

8.7 Manufacturing Info: 1H-Purine-2,6-dione, 8-bromo-3,9-dihydro-1,3-dimethyl-: INACTIVE

9. Computational chemical data

Molecular Weight: 259.063g/mol
Molecular Formula: C₇H₇BrN₄O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 257.97524
Monoisotopic Mass: 257.97524
Complexity: 297
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 69.3
Heavy Atom Count: 14
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBjsAAAEAAAAAAAAAAAAAAAAWAAAAAsAAAAAAAAAFgBgAAAHgBQAAAAGAgBlgQDsBfJkACoAQdwdACAgC2HEKABEQGoVECASAhASCAUAIgIByJAAGAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==