Title: Buprenorphine
CAS Registry Number: 52485-79-7
CAS Name: [5a,7a(S)]-17-(Cyclopropylmethyl)-a-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-a-methyl-6,14-ethenomorphinan-7-methanol
Additional Names: 21-cyclopropyl-7a-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine; 21-cyclopropyl-7a-(2-hydroxy-3,3-dimethyl-2-butyl)-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine
Manufacturers' Codes: RX-6029-M
Molecular Formula: C29H41NO4
Molecular Weight: 467.64
Percent Composition: C 74.48%, H 8.84%, N 3.00%, O 13.69%
Literature References: Analgesic that demonstrates narcotic agonist-antagonist properties. Prepn: K. W. Bentley, GB 1136214; idem, US 3433791 (1968, 1969 to Reckitt & Sons). See also: K. W. Bentley, "The Morphine Alkaloids" in The Alkaloids vol. 13, R. F. Manske, Ed. (Academic Press, New York, 1971) pp 75-120. NMR and stereochemistry: B. C. Uff et al., Magn. Reson. Chem. 23, 454 (1985). Pharmacokinetics and HPLC determn in whole blood: S.-Y. Liu et al., J. Chromatogr. B 818, 233 (2005). Pharmacology: A. Cowan in Advan. Biochem. Psychopharmacol. vol. 8, M. C. Braude et al., Eds. (Raven Press, New York, 1974) pp 427-438; idem, J. Pharm. Pharmacol. 28, 177 (1976); W. R. Martin et al., J. Pharmacol. Exp. Ther. 197, 517 (1976). Metabolism: M. J. Rance, J. S. Shillingford, Biochem. Pharmacol. 25, 735 (1976). Clinical study in chronic pain: M. Kjaer et al., Br. J. Clin. Pharmacol. 13, 487 (1982). Clinical trial in treatment of opioid addiction: J. Kakko et al., Lancet 361, 662 (2003). Review: J. W. Lewis, "Ring C-Bridged Derivatives of Thebaine and Oripavine" in Advan. Biochem. Psychopharmacol. vol. 8, M. C. Braude et al., Eds. (Raven Press, New York, 1974) pp 123-137. Review of pharmacology and therapeutic efficacy: R. C. Heel et al., Drugs 17, 81-110 (1979).
Properties: Crystals, mp 209°.
Melting point: mp 209°
Derivative Type: Hydrochloride
CAS Registry Number: 53152-21-9
Manufacturers' Codes: CL-112302; NIH-8805; UM-952
Trademarks: Buprenex (Reckitt Benckiser); Lepetan (Otsuka); Subutex (Schering-Plough); Temgesic (Schering-Plough)
Molecular Formula: C29H41NO4.HCl
Molecular Weight: 504.10
Percent Composition: C 69.10%, H 8.40%, N 2.78%, O 12.70%, Cl 7.03%
Properties: White powder. Slightly acidic. Limited solubility in water.
NOTE: This is a controlled substance (narcotic): 21 CFR, 1308.13.
Therap-Cat: Analgesic (narcotic); in treatment of opioid dependence.
Keywords: Analgesic (Narcotic). |