Monograph Number: 1485
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). 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., Brit. J. Clin. Pharmacol. 13, 487 (1982). Clinical evaluation in treatment of opioid addiction: P. J. Fudala et al., Clin. Pharmacol. Ther. 47, 525 (1990). 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 & Colman); Lepetan (Otsuka); Subutex (Schering); Temgesic (Reckitt & Colman)
Molecular Formula: C29H41NO4.HCl
Molecular Weight: 504.11.
Percent Composition: C 69.10%, H 8.40%, N 2.78%, O 12.69%, Cl 7.03%
NOTE: This is a controlled substance (narcotic): 21 CFR, 1308.15.
Therap-Cat: Analgesic (narcotic).
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Monograph Number: 6388
Title: Naloxone
CAS Registry Number: 465-65-6
CAS Name: (5a)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)morphinan-6-one
Additional Names: 17-allyl-4,5a-epoxy-3,14-dihydroxymorphinan-6-one; (-)-N-allyl-14-hydroxynordihydromorphinone; N-allylnoroxymorphone
Molecular Formula: C19H21NO4
Molecular Weight: 327.37.
Percent Composition: C 69.71%, H 6.47%, N 4.28%, O 19.55%
Literature References: Specific opioid antagonist. Prepn: GB 939287 (1963 to Sankyo); M. J. Lewenstein, J. Fishman, US 3254088 (1966); R. A. Olofson et al., Tetrahedron Letters 1977, 1567. Clinical pharmacology and abuse potential: D. R. Jasinski et al., J. Pharmacol. Exp. Ther. 157, 420 (1967). Metabolism: J. M. Fujimoto, Proc. Soc. Exp. Biol. Med. 133, 317 (1970). Synthesis of (+)-form and stereospecific activity: I. Iijima et al., J. Med. Chem. 21, 398 (1978). Clinical trial in Alzheimer's disease: B. Reisberg et al., N. Engl. J. Med. 308, 721 (1983). Comprehensive description: M. M. A. Hasson et al., Anal. Profiles Drug Subs. 14, 453-489 (1985). Review of pharmacology and therapeutic uses: L. F. McNicholas, W. R. Martin, Drugs 27, 81-93 (1984); of clinical experience in Alzheimer's disease: C. Stowe, M. L. Gora, Ann. Pharmacother. 27, 447-448 (1993); in drug overdose: J. M. Chamberlain, B. L. Klein, Am. J. Emerg. Med. 12, 650-660 (1994).
Properties: Crystals from ethyl acetate, mp 184° (Lewenstein), 177-178° (Sankyo Co.). [a]D20 -194.5° (c = 0.93 in CHCl3). Sol in chloroform. Practically insol in petr ether.
Melting point: mp 184° (Lewenstein), 177-178° (Sankyo Co.)
Optical Rotation: [a]D20 -194.5° (c = 0.93 in CHCl3)
Derivative Type: Hydrochloride
CAS Registry Number: 357-08-4; 51481-60-8 (dihydrate)
Manufacturers' Codes: EN-15304
Trademarks: Nalone (Winthrop); Narcan (DuPont Pharma); Narcanti (DuPont Pharma)
Molecular Formula: C19H21NO4.HCl
Molecular Weight: 363.84.
Percent Composition: C 62.72%, H 6.09%, N 3.85%, O 17.59%, Cl 9.74%
Properties: Crystals from ethanol + ether, mp 200-205°. Sol in water, alcohol. Practically insol in ether.
Melting point: mp 200-205°
Therap-Cat: Narcotic antagonist.
Therap-Cat-Vet: Narcotic antagonist.
