(1R,9R,10S)-17-(cyclobutylmethyl)(12,12,13,13,14,14-2H6)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol

• ChemBase ID: 163253
• Molecular Formular: C21H29NO2
• Molecular Mass: 327.46046
• Monoisotopic Mass: 327.21982917
• SMILES: c1(cc2c(cc1)C[C@@H]1[C@]3([C@@]2(CCCC3)CCN1CC1CCC1)O)O
• Canonical SMILES: Oc1ccc2c(c1)[C@]13CCCC[C@]3([C@@H](C2)N(CC1)CC1CCC1)O
• InChI: InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21-/m1/s1
• InChIKey: IFKLAQQSCNILHL-QHAWAJNXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10S)-17-(cyclobutylmethyl)(12,12,13,13,14,14-^2H₆)-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-triene-4,10-diol
• IUPAC Traditional name: (1R,9R,10S)-17-(cyclobutylmethyl)(12,12,13,13,14,14-^2H₆)-17-azatetracyclo[7.5.3.0^1,^1^0.0^2,^7]heptadeca-2(7),3,5-triene-4,10-diol
• Synonyms: 17-(Cyclobutylmethyl)morphinan-3,14-diol-d6; (-)-17-(Cyclobutylmethyl)-3,14β-dihydroxymorphinan-d6; (-)-Butorphanol-d6; BC 2627-d6; (-)-; Butorphanol-d6; Levo-BC 2627-d6; l-3,14-Dihydroxy-N-(cyclobutylmethyl)morphinan-d6; l-BC 2627-d6; (-)-Butorphanol-d6

Database IDs

• PubChem SID: 162257388
• PubChem CID: 71314360

CALCULATED PROPERTIES

• Acid pKa: 9.864343
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.16574237
• LogD (pH = 7.4): 0.8131535
• Log P: 2.8903294
• Molar Refractivity: 95.921 cm^3
• Polarizability: 37.630463 Å^3
• Polar Surface Area: 43.7 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 205-208°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B690552

Labelled Butorphanol (B690550). Mixed opioid agonist-antagonist. Analgesic (narcotic); antitussive. Controlled substance.

REFERENCES

• Vargas-Arreola, F., et al.: Curr. Ther. Res., 22, 186 (1977)
• Heel, R.C., et al.: Drugs, 16, 473 (1977)