(3S,6S)-6-(methylamino)-4,4-diphenylheptan-3-yl acetate hydrochloride

• ChemBase ID: 175567
• Molecular Formular: C22H30ClNO2
• Molecular Mass: 375.9321
• Monoisotopic Mass: 375.19650689
• SMILES: C([C@@H](C(C[C@@H](NC)C)(c1ccccc1)c1ccccc1)OC(=O)C)C.Cl
• Canonical SMILES: CC[C@@H](C(c1ccccc1)(c1ccccc1)C[C@@H](NC)C)OC(=O)C.Cl
• InChI: InChI=1S/C22H29NO2.ClH/c1-5-21(25-18(3)24)22(16-17(2)23-4,19-12-8-6-9-13-19)20-14-10-7-11-15-20;/h6-15,17,21,23H,5,16H2,1-4H3;1H/t17-,21-;/m0./s1
• InChIKey: QOWPUUFVFLIYRR-PVMVIUQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S)-6-(methylamino)-4,4-diphenylheptan-3-yl acetate hydrochloride
• IUPAC Traditional name: L-α-acetyl-N-normethadol hydrochloride
• Synonyms: (αS)-α-Ethyl-β-[(2S)-2-(methylamino)propyl]-β-phenylbenzeneethanol Acetate (Ester) Hydrochloride; [S-(R*,R*)]-α-Ethyl-β-[2-(methylamino)propyl]-β-phenylbenzeneethanol Acetate (Ester) Hydrochloride; (-)-α-Noracetylmethadol Hydrochloride; L-α-Acetyl-N-normethadol Hydrochloride; l-α-Acetylnormethadol Hydrochloride; nor-LAAM Hydrochloride; α-l-Noracetylmethadol Hydrochloride; (-)-α-Noracetylmethadol Hydrochloride

Database IDs

• CAS Number: 55096-75-8
• PubChem SID: 164231477
• PubChem CID: 135259

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.2705826
• LogD (pH = 7.4): 1.7387435
• Log P: 4.5017214
• Molar Refractivity: 112.5629 cm^3
• Polarizability: 40.66775 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N660600

An active N-demethylated metabolite of the μ-opioid receptor agonist (-)-α-Acetylmethadol (A186325).

REFERENCES

• Borzelleca, J.F. et al.: J. Appl. Toxicol., 15, 339 (1995)
• McGivney, W.T. et al.: J. Phamacol. Exp. Therap., 216, 299 (1995)
• Holtzman, S.G. et al.: Pharmacol. Biochem. Behav., 10, 565 (1979)