1497. Buprenorphine

Nomenclature

CAS number: 52485-79-7
[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; 21-cyclopropyl-7α-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine; 21-cyclopropyl-7α-(2-hydroxy-3,3-dimethyl-2-butyl)-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine; RX-6029-M.
C29H41NO4; mol wt 467.64.
C 74.48%, H 8.84%, N 3.00%, O 13.69%.

Description and references

Semisynthetic derivative of thebaine, q.v. with mixed opioid 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. Review of synthesis and analgesic activity: 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. NMR and stereochemistry: B. C. Uff et al., Magn. Reson. Chem. 23, 454 (1985). LC/ESI-MS/MS determn in urine, blood and hair: D. Favretto et al., Rapid Commun. Mass Spectrom. 20, 1257 (2006). Review of pharmacology and therapeutic efficacy in cancer pain: M. P. Davis, Support. Care Cancer 13, 878-887 (2005); in opioid addiction: S. E. Robinson, CNS Drugs 20, 697-712 (2006).

Chemical structure

Properties

Crystals, mp 209°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 53152-21-9
CL-112302; NIH-8805; UM-952; Buprenex (Reckitt Benckiser); Lepetan (Otsuka); Subutex (Schering-Plough); Temgesic (Schering-Plough).
C29H41NO4.HCl; mol wt 504.10.
C 69.10%, H 8.40%, N 2.78%, O 12.70%, Cl 7.03%.

Properties

White powder. Highly lipophilic. Slightly acidic with limited solubility in water.

Note

This is a controlled substance (narcotic): 21 CFR, 1308.13.

Therapeutic Category

Analgesic; in treatment of opioid dependence.

Keywords

Analgesic; Opioids; Oripavine Derivatives