(3S,4R)-1,3-dimethyl-4-phenylpiperidin-4-yl propanoate hydrochloride

• ChemBase ID: 176801
• Molecular Formular: C16H24ClNO2
• Molecular Mass: 297.82026
• Monoisotopic Mass: 297.14955669
• SMILES: Cl.[C@H]1([C@@](CCN(C1)C)(OC(=O)CC)c1ccccc1)C
• Canonical SMILES: CCC(=O)O[C@@]1(CCN(C[C@@H]1C)C)c1ccccc1.Cl
• InChI: InChI=1S/C16H23NO2.ClH/c1-4-15(18)19-16(14-8-6-5-7-9-14)10-11-17(3)12-13(16)2;/h5-9,13H,4,10-12H2,1-3H3;1H/t13-,16+;/m0./s1
• InChIKey: LFLUADVCIBEPQJ-MELYUZJYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-1,3-dimethyl-4-phenylpiperidin-4-yl propanoate hydrochloride
• IUPAC Traditional name: betaprodine hydrochloride
• Synonyms: (3R,4S)-rel-1,3-dimethyl-4-phenyl-4-piperidinol 4-Propanoate Hydrochloride; cis-(±)-1,3-Dimethyl-4-phenyl-4-piperidinol Propanoate Hydrochloride; (±)-Alphaprodine Hydrochloride; (±)-α-1,3-Dimethyl-4-phenyl-4-propionoxypiperidine Hydrochloride; Alphaprodine Hydrochloride; Nisentil; Nisintel; Nu 1196; Prisilidene; Prisilidene Hydrochloride; dl-1,3-Dimethyl-4-phenyl-4-piperidinol Propionate Hydrochloride; dl-Alphaprodine Hydrochloride; α-Prodine Hydrochloride

Database IDs

• CAS Number: 561-78-4
• PubChem SID: 164232711
• PubChem CID: 120737

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.36877137
• LogD (pH = 7.4): 1.2693775
• Log P: 2.7774558
• Molar Refractivity: 76.4094 cm^3
• Polarizability: 30.30668 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P755300

Analgesic (narcotic). Controlled substance (opiates).

REFERENCES

• Gruber, G.M., et al.: J. Pharmacol. Exp. Ther., 99, 312 (1950)
• Abdel-Monem, M.M., et al.: J. Med. Chem., 15, 494 (1950)