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

• ChemBase ID: 126933
• Molecular Formular: C22H29NO2
• Molecular Mass: 339.47116
• Monoisotopic Mass: 339.21982917
• SMILES: O=C(OC(c1ccccc1)(Cc1ccccc1)[C@H](C)CN(C)C)CC
• Canonical SMILES: CCC(=O)OC(c1ccccc1)([C@@H](CN(C)C)C)Cc1ccccc1
• InChI: InChI=1S/C22H29NO2/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/t18-,22+/m1/s1
• InChIKey: XLMALTXPSGQGBX-GCJKJVERSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl propanoate
• IUPAC Traditional name: propoxyphene
• Brand Name: Darvon
• Synonyms: Dextropropoxyphene

Database IDs

• CAS Number: 469-62-5
• PubChem SID: 162221259
• PubChem CID: 10100
• CHEBI ID: 51173
• ATC CODE: N02AC04
• CHEMBL: 1213351
• Chemspider ID: 9696
• DrugBank ID: DB00647
• KEGG ID: D07809
• Unique Ingredient Identifier: S2F83W92TK
• Wikipedia Title: Dextropropoxyphene
• Medline Plus: a682325

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

• Melting Point: 75°C (167°F)

Pharmacology Properties

• Admin Routes: oral, IV, rectal
• Half Life: 3.6–6.5 hours
• Legal Status: S4 (Australia); Schedule II, Schedule IV (in dosage form) (US)
• Pregnancy Category: C, D for prolonged use (US)
• US Licence: Propoxyphene