(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-(2-hydroxy-3,3-dimethylbutan-2-yl)-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-11-ol hydrochloride

• ChemBase ID: 163095
• Molecular Formular: C29H42ClNO4
• Molecular Mass: 504.10108
• Monoisotopic Mass: 503.28023651
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]45[C@@]3([C@H]([C@]([C@H](C4)C(C(C)(C)C)(C)O)(CC5)OC)O2)CCN1CC1CC1)O.Cl
• Canonical SMILES: CO[C@]12CC[C@]3(C[C@@H]1C(C(C)(C)C)(O)C)[C@@]14[C@H]2Oc2c4c(C[C@H]3N(CC1)CC1CC1)ccc2O.Cl
• InChI: InChI=1S/C29H41NO4.ClH/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28;/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3;1H/t20-,21-,24-,26?,27-,28+,29-;/m1./s1
• InChIKey: UAIXRPCCYXNJMQ-CYVYHKOSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-(2-hydroxy-3,3-dimethylbutan-2-yl)-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^2,^8.0^1,^6.0^6,^1^4.0^7,^1^2]icosa-7,9,11-trien-11-ol hydrochloride
• IUPAC Traditional name: (1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-(2-hydroxy-3,3-dimethylbutan-2-yl)-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^2,^8.0^1,^6.0^6,^1^4.0^7,^1^2]icosa-7,9,11-trien-11-ol hydrochloride
• Synonyms: [5α,7α(S)]-17-(Cyclopropylmethyl)-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-α-methyl-6,14-ethenomorphinan-7-methanol Hydrochloride; CL-112302; NIH-8805; UM-952; Buprenex; Lepetan; Subutex; Temgesic; Buprenorphine Hydrochloride

Database IDs

• CAS Number: 53152-21-9
• PubChem SID: 162257230
• PubChem CID: 5281091

CALCULATED PROPERTIES

• Acid pKa: 10.415402
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.58735055
• LogD (pH = 7.4): 1.6101108
• Log P: 3.5498807
• Molar Refractivity: 131.7623 cm^3
• Polarizability: 52.271748 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 260-262°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - B689570

Controllled substance (narcotic). Analgesic that demonstrates narcotic agonist-antagonist properties.

REFERENCES

• Martin, W.R., et al.: J. Pharmacol. Exp. Ther., 197, 517 (1976)
• Rance, M.J., Biochem. Pharmacol., 25, 735 (1976)
• Heel, R.C., et al.: Drugs, 17, 81 (1976)