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

• ChemBase ID: 162705
• Molecular Formular: C20H30ClNO2
• Molecular Mass: 351.9107
• Monoisotopic Mass: 351.19650689
• SMILES: c1(cc2c(cc1)CC1C([C@]2(CCN1CC1(CC1)O)CC)(C)C)O.Cl
• Canonical SMILES: CC[C@]12CCN(C(C2(C)C)Cc2c1cc(O)cc2)CC1(O)CC1.Cl
• InChI: InChI=1S/C20H29NO2.ClH/c1-4-20-9-10-21(13-19(23)7-8-19)17(18(20,2)3)11-14-5-6-15(22)12-16(14)20;/h5-6,12,17,22-23H,4,7-11,13H2,1-3H3;1H/t17?,20-;/m0./s1
• InChIKey: JNTDEEXUEKTYKU-FWCANSBWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-1-ethyl-10-[(1-hydroxycyclopropyl)methyl]-13,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol hydrochloride
• IUPAC Traditional name: (1S)-1-ethyl-10-[(1-hydroxycyclopropyl)methyl]-13,13-dimethyl-10-azatricyclo[7.3.1.0^2,^7]trideca-2(7),3,5-trien-4-ol hydrochloride
• Synonyms: (2R,6S)-6-Ethyl-1,2,3,4,5,6-hexahydro-3-[(1-hydroxycyclopropyl)methyl]-11,11-dimethyl-2,6-methano-3-benzazocin-8-ol Hydrochloride; Bremazocine Hydrochloride; (-)-Bremazocine Hydrochloride

Database IDs

• CAS Number: 74100-60-0
• PubChem SID: 162256840
• PubChem CID: 53299310

CALCULATED PROPERTIES

• Acid pKa: 10.469768
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.002796754
• LogD (pH = 7.4): 1.0046756
• Log P: 2.9841614
• Molar Refractivity: 93.0733 cm^3
• Polarizability: 36.52015 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B677350

A kappa-opioid receptor agonist for treatment of pain and inflammation.

REFERENCES

• George, S., et al.: J. Biol. Chem., 275, 26128 (2000)
• Chen, C., et al.: Eur. J. Pharmacol., 483, 175 (2000)
• Hasbi, A., et al.: Biochemistry, 46, 12997 (2000)