[(2-bromophenyl)methyl](ethyl)dimethylazanium 4-methylbenzene-1-sulfonate

• ChemBase ID: 153511
• Molecular Formular: C18H24BrNO3S
• Molecular Mass: 414.35706
• Monoisotopic Mass: 413.06602663
• SMILES: CC[N+](C)(C)Cc1ccccc1Br.Cc1ccc(cc1)S(=O)(=O)[O-]
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)[O-].CC[N+](Cc1ccccc1Br)(C)C
• InChI: InChI=1S/C11H17BrN.C7H8O3S/c1-4-13(2,3)9-10-7-5-6-8-11(10)12;1-6-2-4-7(5-3-6)11(8,9)10/h5-8H,4,9H2,1-3H3;2-5H,1H3,(H,8,9,10)/q+1;/p-1
• InChIKey: KVWNWTZZBKCOPM-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2-bromophenyl)methyl](ethyl)dimethylazanium 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: bretylium tosylate
• Synonyms: 2-Bromo-N-ethyl-N,N-dimethylbenzenemethanaminium 4-Methylbenzenesulfonate; ASL 603; Bretylan; Bretylate; Bretylium p-Toluenesulfonate; Bretylium Tosilate; Bretylol; Darenthin; N-Ethyl-N-(o-bromobenzyl)-N,N-dimethylammonium Tosylate; NSC 62164; Ornid; Bretylium Tosylate; (o-Bromobenzyl)ethyldimethylammonium p-toluenesulfonate; Bretylium tosylate; N-(2-Bromobenzyl)-N,N-dimethylethanaminium 4-methylbenzenesulfonate

Database IDs

• CAS Number: 61-75-6
• EC Number: 200-516-8
• MDL Number: MFCD00038731
• PubChem SID: 162247650
• PubChem CID: 6100

CALCULATED PROPERTIES

• Acid pKa: 17.582369
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -1.1221335
• LogD (pH = 7.4): -1.1221335
• Log P: -1.1221335
• Molar Refractivity: 72.8857 cm^3
• Polarizability: 23.680477 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: white powder

Safety Information

• RTECS: BO9450000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36

Product Information

• Purity: >99% (TLC); 95+%
• Empirical Formula (Hill Notation): C18H24BrNO3S

DETAILS

Sigma Aldrich - B8406

Biochem/physiol Actions
Bretylium tosylate has a biphasic response, initially inducing norepinephrine release followed by sympathetic ganglionic blockade; class III antiarrhythmic agent; competitive inhibitor of acetylcholinesterase.

Toronto Research Chemicals - B677370

Bretylium tosylate has a biphasic response, initially inducing norepinephrine release followed by sympathetic ganglionic blockade. Bretylium tosylate is a class III antiarrhythmic agent and a competitive inhibitor of acetylcholinesterase.

REFERENCES

• Kuntzman, R., et al.: Clin. Pharmacol. Ther., 11, 829 (1970)
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1970)
• Carter, J.E., et al.: Anal. Profiles Drug Subs., 9, 71 (1970)