(1R,9S,10R)-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol

• ChemBase ID: 172288
• Molecular Formular: C17H23NO
• Molecular Mass: 257.37062
• Monoisotopic Mass: 257.17796436
• SMILES: c1(cc2c(cc1)C[C@H]1[C@H]3[C@@]2(CCCC3)CCN1C)O
• Canonical SMILES: Oc1ccc2c(c1)[C@]13CCCC[C@H]3[C@H](C2)N(CC1)C
• InChI: InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16-,17+/m0/s1
• InChIKey: JAQUASYNZVUNQP-BHYGNILZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9S,10R)-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-ol
• IUPAC Traditional name: (1R,9S,10R)-17-methyl-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-trien-4-ol
• Synonyms: 17-Methylmorphinan-3-ol (2R,3R)-2,3-Dihydroxybutanedioate Salt; 1,3,4,9,10,10a-Hexahydro-11-methyl- 2H-10,4a-imino-ethanophenanthren-6-ol Tartrate; Lemoran; (-)-N-Methylmorphinan-3-ol Tartrate; Aromarone Tartrate; D-(-)-Levorphan Tartrate; l-3-Hydroxy-N-methylmorphinan Tartrate; NSC 91012; Levorphanol Tartrate

Database IDs

• CAS Number: 125-72-4
• PubChem SID: 164228198
• PubChem CID: 6467

CALCULATED PROPERTIES

• Acid pKa: 10.461597
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.095644645
• LogD (pH = 7.4): 0.9349801
• Log P: 2.9030437
• Molar Refractivity: 78.0809 cm^3
• Polarizability: 30.3868 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L376500

Orally active synthetic morphine analog. Analgesic (narcotic). Controlled substance.

REFERENCES

• Randall, L.O., et al.: J. Pharmacol. Exp. Ther., 99, 163 (1950)
• Dajani, E., et al.: Eur. J. Pharmacol., 34, 105 (1950)
• Winpenny, J., et al.: Drugs, 8, 416 (1950)