(1S,9R)-1,13-dimethyl-10-(prop-2-en-1-yl)-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol hydrochloride

• ChemBase ID: 159692
• Molecular Formular: C17H24ClNO
• Molecular Mass: 293.83156
• Monoisotopic Mass: 293.15464207
• SMILES: N1([C@H]2C([C@](CC1)(c1c(C2)ccc(c1)O)C)C)CC=C.Cl
• Canonical SMILES: C=CCN1CC[C@]2(C([C@H]1Cc1c2cc(cc1)O)C)C.Cl
• InChI: InChI=1S/C17H23NO.ClH/c1-4-8-18-9-7-17(3)12(2)16(18)10-13-5-6-14(19)11-15(13)17;/h4-6,11-12,16,19H,1,7-10H2,2-3H3;1H/t12?,16-,17+;/m1./s1
• InChIKey: ZTGMHFIGNYXMJV-JSTMTBMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R)-1,13-dimethyl-10-(prop-2-en-1-yl)-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol hydrochloride
• IUPAC Traditional name: (1S,9R)-1,13-dimethyl-10-(prop-2-en-1-yl)-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol hydrochloride
• Synonyms: (2S,6S,11S)-1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(2-propen-1-yl)-2,6-methano-3-benzazocin-8-ol Hydrochloride; D-NANM; (+)-N-Allyl-N-normetazocine hydrochloride; (+)-N-Allyl Normetazocine Hydrochloride

Database IDs

• CAS Number: 133005-41-1
• PubChem SID: 162253827
• PubChem CID: 71313093

CALCULATED PROPERTIES

• Acid pKa: 10.346238
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.30034623
• LogD (pH = 7.4): 1.6692182
• Log P: 3.3593044
• Molar Refractivity: 79.8438 cm^3
• Polarizability: 30.888481 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A559000

Normetazocine analogue as opioid antagonist.

REFERENCES

• Martin, W., et al.: J. Pharmacol. Exp. Ther., 197, 517 (1976)
• Aceto, M., et al.: J. Pharm. Sci., 73, 1864 (1976)
• Bowen, W., et al.: Eur. J. Pharmacol., 279, R1 (1976)
• May, E., et al.: J. Med. Chem., 37, 3408 (1976)