Etorphine
Title: Etorphine
CAS Registry Number: 14521-96-1
CAS Name: [5a,7a(R)]-4,5-Epoxy-3-hydroxy-6-methoxy-a,17-dimethyl-a-propyl-6,14-ethenomorphinan-7-methanol
Additional Names: tetrahydro-7a-(1-hydroxy-1-methylbutyl)-6,14-endo-ethenooripavine; 7,8-dihydro-7a-[1(R)-hydroxy-1-methylbutyl]-O6-methyl-6,14-endo-ethenomorphine; 7a-[1(R)-hydroxy-1-methylbutyl]-6,14-endo-ethenotetrahydrooripavine; 19-propylorvinol; tetrahydro-7a-(2-hydroxy-2-pentyl)-6,14-endo-ethenooripavine
Molecular Formula: C25H33NO4
Molecular Weight: 411.53
Percent Composition: C 72.96%, H 8.08%, N 3.40%, O 15.55%
Literature References: Narcotic analgesic. Prepn: BE 618392; K. W. Bentley, GB 937214 (1962, 1963 both to J. F. MacFarlan); and structure: K. W. Bentley, D. G. Hardy, Proc. Chem. Soc. London 1963, 220. Improved prepn: W. R. Hydro, US 3763167 (1973 to U.S. Army). Determn by HPLC: I. Jane, A. McKinnon, J. Chromatogr. 323, 19 (1985). Analgesic activity: G. F. Blane, J. Pharm. Pharmacol. 19, 367 (1967). Pharmacology: Lister, ibid. 16, 364 (1964). Use as tranquilizer in dogs: J. L. Crooks et al., Vet. Rec. 87, 498 (1970); M. Grange et al., Rev. Med. Vet. 124, 899 (1973); in large animals: A. M. Harthoorn, J. Am. Vet. Med. Assoc. 149, 875 (1966); B. T. Alford et al., ibid. 164, 702 (1974).
Properties: White crystals from aqueous ethoxyethanol, mp 214-217°. (7b-isomer, melts at 280°).
Melting point: mp 214-217°; 7b-isomer, melts at 280°
 
Derivative Type: Hydrochloride
Manufacturers' Codes: M-99
Molecular Formula: C25H33NO4.HCl
Molecular Weight: 447.99
Percent Composition: C 67.03%, H 7.65%, N 3.13%, O 14.29%, Cl 7.91%
Properties: mp 266-267°. (7b-isomer hydrochloride, dec at 290)°.
Melting point: mp 266-267°
 
Derivative Type: Hydrochloride in combination with acepromazine
Trademarks: Immobilon (Reckitt & Colman)
 
Derivative Type: 3-Acetate
Additional Names: Acetorphine; O3-acetyl-7,8-dihydro-7a-[1(R)-hydroxy-1-methylbutyl]-O6-methyl-6,14-endo-ethenomorphine; 3-O-acetyl-7a-[1(R)-hydroxy-1-methylbutyl]-6,14-endo-ethenotetrahydrooripavine; 3-O-acetyl-17-propylorvinol
Molecular Formula: C27H35NO5
Molecular Weight: 453.57
Percent Composition: C 71.50%, H 7.78%, N 3.09%, O 17.64%
Properties: Crystals from methanol, mp 195°.
Melting point: mp 195°
 
Derivative Type: 3-Acetate hydrochloride
Manufacturers' Codes: M-183
Molecular Formula: C27H35NO5.HCl
Molecular Weight: 490.03
Percent Composition: C 66.18%, H 7.40%, N 2.86%, O 16.32%, Cl 7.23%
Properties: mp 206°.
Melting point: mp 206°
 
NOTE: Acetorphine and etorphine are controlled substances (opium derivatives): 21 CFR, 1308.11. Etorphine hydrochloride is a controlled substance (opiate): 21 CFR, 1308.12.
CAUTION: Use with extreme care; very small amounts may bring about respiratory paralysis and death: D. W. Upson, Upson's Handbook of Clinical Veterinary Pharmacology (VM Publishing, Bonner Springs, 1980) pp 380-381.
Therap-Cat-Vet: Used to immobilize large animals.

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