(2S,3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate hydrochloride

• ChemBase ID: 177018
• Molecular Formular: C22H30ClNO2
• Molecular Mass: 375.9321
• Monoisotopic Mass: 375.19650689
• SMILES: c1cccc(c1)CC(OC(=O)CC)(c1ccccc1)[C@@H](CN(C)C)C.Cl
• Canonical SMILES: CCC(=O)OC(c1ccccc1)([C@@H](CN(C)C)C)Cc1ccccc1.Cl
• InChI: InChI=1S/C22H29NO2.ClH/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19;/h6-15,18H,5,16-17H2,1-4H3;1H/t18-,22+;/m1./s1
• InChIKey: QMQBBUPJKANITL-MYXGOWFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate hydrochloride
• IUPAC Traditional name: propoxyphene hydrochloride
• Synonyms: (αS)-α-[(1R)-2-(Dimethylamino)-1-methylethyl]-α-phenylbenzeneethanol Propanoate Hydrochloride; α-d-Propoxyphene Hydrochloride; α-(+)-Propoxyphene Hydrochloride; Dextropropoxyphene Hydrochloride; Algaphan; Antalvic; Darvon; Deprancol; Develin; Propoxyphene Hydrochloride Salt

Database IDs

• CAS Number: 1639-60-7
• PubChem SID: 164232928
• PubChem CID: 15424

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.5163397
• LogD (pH = 7.4): 2.7993603
• Log P: 4.9021554
• Molar Refractivity: 102.8806 cm^3
• Polarizability: 40.66616 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Ethanol; Water
• Apperance: White Solid
• Melting Point: 165-1670C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P831500

Dextropropoxyphene is a controlled substance (opiate). Analgesic (narcotic). The α-dl-and d-diastereoisomers possess marked analgesic activity in contrast to the β-diastereoisomers which are substantially inactive.

REFERENCES

• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• McEwan, B., et al.: Anal. Profiles Drug Subs., 1, 301 (1972)