benzyl(2-chloroethyl)[(2S)-1-phenoxypropan-2-yl]amine hydrochloride

• ChemBase ID: 176284
• Molecular Formular: C18H23Cl2NO
• Molecular Mass: 340.28732
• Monoisotopic Mass: 339.11566972
• SMILES: c1(OC[C@@H](N(Cc2ccccc2)CCCl)C)ccccc1.Cl
• Canonical SMILES: ClCCN([C@H](COc1ccccc1)C)Cc1ccccc1.Cl
• InChI: InChI=1S/C18H22ClNO.ClH/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17;/h2-11,16H,12-15H2,1H3;1H/t16-;/m0./s1
• InChIKey: VBCPVIWPDJVHAN-NTISSMGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl(2-chloroethyl)[(2S)-1-phenoxypropan-2-yl]amine hydrochloride
• IUPAC Traditional name: phenoxybenzamine hydrochloride hydrochloride
• Synonyms: (S)-N-(2-Chloroethyl)-N-(1-methyl-2-phenoxyethyl)benzenemethanamine Hydrochloride; (-)-N-Benzyl-N-(2-chloroethyl)-1-phenoxyisopropylamine Hydrochloride; (-)-Phenoxybenzamine Hydrochloride; l-Phenoxybenzamine Hydrochloride; (S)-Phenoxybenzamine Hydrochloride

Database IDs

• CAS Number: 32378-29-3
• PubChem SID: 164232194
• PubChem CID: 71751496

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.206733
• LogD (pH = 7.4): 3.966591
• Log P: 4.639757
• Molar Refractivity: 88.915 cm^3
• Polarizability: 35.003498 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P228000

An irreversible α-antagonist. Used in the treatment of hypertension, it has a relatively slow onset and prolonged effect when compared to alternative α-blockers.

REFERENCES

• Portoghese, P., et al.: J. Med. Chem., 14, 561 (1971)
• Berry, D., et al.: Eur., J. Pharmacol., 28, 164 (1971)