alpha-Chloralose

Title: a-Chloralose
CAS Registry Number: 15879-93-3
CAS Name: 1,2-O-[(1R)-2,2,2-Trichloroethylidene]-a-D-glucofuranose
Additional Names: a-D-glucochloralose; glucochloral; anhydroglucochloral; chloralosane
Trademarks: Alphakil (Rentokil); Dorcalm (Frere); Somio
Molecular Formula: C8H11Cl3O6
Molecular Weight: 309.53
Percent Composition: C 31.04%, H 3.58%, Cl 34.36%, O 31.01%
Literature References: Prepd from anhydr glucose and trichloroacetaldehyde (anhydr chloral); b-chloralose is also formed. Prepn: M. Hanroit, C. Richet, C.R. Hebd. Seances Acad. Sci. 116, 63 (1893); and structure: Pictet, Reichel, Helv. Chim. Acta 6, 621 (1923); Freudenberg, Vajda, J. Am. Chem. Soc. 59, 1955 (1937); cf. Coles et al., ibid. 51, 519 (1929); White, Hixon, ibid. 55, 2438 (1933). Crystal structure: T. Taga et al., Acta Crystallogr. B38, 1874 (1982). Immobilizing agent in control of depredating birds: Redpath et al., Ann. Appl. Biol. 49, 77 (1961). Anesthetic for dogs in experimental work: B. G. Bass, N. M. Buckley, Am. J. Physiol. 210, 854 (1966); R. H. Cox, ibid. 223, 660 (1972). CNS depressant activity: J. L. Barker, Nature 252, 52 (1974). GLC determn in rodenticides: J. Theobald, J. Chromatogr. 129, 444 (1976); in tissue: E. Odam et al., Analyst 109, 1335 (1984). Acute toxicity: E. W. Schafer, Toxicol. Appl. Pharmacol. 21, 315 (1972). Review of pharmacology: G. U. Balis, R. R. Monroe, Psychopharmacologia 6, 1-30 (1964); and toxicology: P. Lees, Vet. Rec. 91, 330-333 (1972). Review as canine anesthetic: H. Holzgrefe et al., Lab. Anim. Sci. 37, 587-595 (1987).
Properties: Needles from alcohol or ether, mp 187°. [a]D22 +19° (c = 5 in 98% alc). One gram dissolves in 225 ml water at 15°, in 120 ml at 37°, in 15 ml alc at 25°. Sol in ether, glacial acetic acid; slightly in chloroform. Almost insol in petr ether. LD50 orally in mice: 400 mg/kg (Schafer).
Melting point: mp 187°
Optical Rotation: [a]D22 +19° (c = 5 in 98% alc)
Toxicity data: LD50 orally in mice: 400 mg/kg (Schafer)
Derivative Type: b-Chloralose
Properties: mp 227-230°, is much less sol in water, alcohol, and ether.
Melting point: mp 227-230°
Use: Rodenticide. Control of avian pests.
Therap-Cat: Sedative, hypnotic.
Therap-Cat-Vet: Surgical anesthetic for laboratory animals.
Keywords: Sedative/Hypnotic.
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