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

• ChemBase ID: 175681
• Molecular Formular: C14H19NO
• Molecular Mass: 217.30676
• Monoisotopic Mass: 217.14666423
• SMILES: c12c(ccc(c1)O)C[C@@H]1NCC[C@]2(C1C)C
• Canonical SMILES: Oc1ccc2c(c1)[C@@]1(C)CCN[C@@H](C2)C1C
• InChI: InChI=1S/C14H19NO/c1-9-13-7-10-3-4-11(16)8-12(10)14(9,2)5-6-15-13/h3-4,8-9,13,15-16H,5-7H2,1-2H3/t9?,13?,14-/m0/s1
• InChIKey: DXESFJJJWBHLJX-FQXIOZCDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9S)-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol
• IUPAC Traditional name: (1S,9S)-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol
• Synonyms: (2R,6R,11R)-rel-1,2,3,4,5,6-Hexahydro-6,11-dimethyl-2,6-methano-3-benzazocin-8-ol; (+/-)-2'-Hydroxy-5,9-dimethyl-6,7-benzomorphan; (+/-)-Normetazocine; Norpentazocine; dl-Normetazocine

Database IDs

• CAS Number: 25144-78-9
• PubChem SID: 164231591
• PubChem CID: 91295

CALCULATED PROPERTIES

• Acid pKa: 9.882097
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.686872
• LogD (pH = 7.4): -0.10931383
• Log P: 1.9431611
• Molar Refractivity: 65.3864 cm^3
• Polarizability: 25.587225 Å^3
• Polar Surface Area: 32.26 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N721910

Antagonistic and analgetic activities. Precursor for the preparation of (+/-)-Pentazocine, (+/-)-Cyclazocine etc.

REFERENCES

• May, E., et al.: J. Med. Chem., 43, 5030 (2000)
• Ghosh, S., et al.: J. Biol. Chem., 276, 42108 (2001).