5295. Ketamine

Nomenclature

CAS number: 6740-88-1
2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone.
C13H16ClNO; mol wt 237.73.
C 65.68%, H 6.78%, Cl 14.91%, N 5.89%, O 6.73%.

Description and references

Prepn: C. L. Stevens, BE 634208; idem, US 3254124 (1963, 1966 both to Parke, Davis). Isoln of optical isomers: T. W. Hudyma et al., DE 2062620 (1971 to Bristol-Myers), C.A. 75, 118119x (1971). Clinical pharmacology of racemate and enantiomers: P. F. White et al., Anesthesiology 52, 231 (1980). Toxicity: E. J. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Enantioselective HPLC determn in plasma: G. Geisslinger et al., J. Chromatogr. 568, 165 (1991). Comprehensive description: W. C. Sass, S. A. Fusari, Anal. Profiles Drug Subs. 6, 297-322 (1977). Review of pharmacology and use in veterinary medicine: M. Wright, J. Am. Vet. Med. Assoc. 180, 1462-1471 (1982). Review of pharmacology and clinical experience: D. L. Reich, G. Silvay, Can. J. Anaesth. 36, 186-197 (1989); in pediatric procedures: S. M. Green, N. E. Johnson, Ann. Emerg. Med. 19, 1033-1046 (1990).

Chemical structure

Properties

Crystals from pentane-ether, mp 92-93°. uv max (0.01N NaOH in 95% methanol): 301, 276, 268, 261 nm (A1%1cm 5.0, 7.0, 9.8, 10.5). pKa 7.5. pH of 10% aq soln 3.5.

Derivative

Hydrochloride.

Nomenclature

CAS number: 1867-66-9
CI-581; Ketalar (Pfizer); Ketanest (Pfizer); Ketaset (Fort Dodge); Ketavet (Gellini); Vetalar (Bioniche).
C13H16ClNO.HCl; mol wt 274.19.
C 56.95%, H 6.25%, Cl 25.86%, N 5.11%, O 5.84%.

Properties

White crystals, mp 262-263°. Soly in water: 20 g/100 ml. LD50 in adult mice, rats (mg/kg): 224 ±4, 229 ±5 i.p. (Goldenthal).

Note

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

Therapeutic Category

Anesthetic (intravenous).

Therapeutic Category (Veterinary)

Anesthetic (intravenous).

Keywords

Anesthetic (Intravenous)