Naloxone
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 Lett. 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 (BMS); Narcan (Endo); Narcanti (BMS)
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.
Keywords: Narcotic Antagonist.

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