Ketamine

Title: Ketamine
CAS Registry Number: 6740-88-1
CAS Name: 2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone
Molecular Formula: C13H16ClNO
Molecular Weight: 237.73
Percent Composition: C 65.68%, H 6.78%, Cl 14.91%, N 5.89%, O 6.73%
Literature 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).
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.
Melting point: mp 92-93°
pKa: pKa 7.5
Absorption maximum: uv max (0.01N NaOH in 95% methanol): 301, 276, 268, 261 nm (A1%1cm 5.0, 7.0, 9.8, 10.5)
Derivative Type: Hydrochloride
CAS Registry Number: 1867-66-9
Manufacturers' Codes: CI-581
Trademarks: Ketalar (Pfizer); Ketanest (Pfizer); Ketaset (Fort Dodge); Ketavet (Gellini); Vetalar (Bioniche)
Molecular Formula: C13H16ClNO.HCl
Molecular Weight: 274.19
Percent Composition: 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).
Melting point: mp 262-263°
Toxicity data: 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.
Therap-Cat: Anesthetic (intravenous).
Therap-Cat-Vet: Anesthetic (intravenous).
Keywords: Anesthetic (Intravenous).
Ketanserin Ketazolam Kethoxal Ketipic Acid Ketorolac

Ketamine
Ketamine.svg
Ketamine3Dan.gif
Systematic (IUPAC) name
(RS)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone
Clinical data
AHFS/Drugs.com Consumer Drug Information
Licence data US FDA:link
Pregnancy cat. B3 (AU) C (US)
Legal status Controlled (S8) (AU) Schedule I (CA) CD (UK) Schedule III (US)
Dependence liability Moderate
Routes IV, IM, Insufflated, oral, topical
Pharmacokinetic data
Metabolism Hepatic, primarily by CYP3A4[1]
Half-life 2.5–3 hours.
Excretion renal (>90%)
Identifiers
CAS number 6740-88-1 YesY
ATC code N01AX03
PubChem CID 3821
DrugBank DB01221
ChemSpider 3689 YesY
UNII 690G0D6V8H YesY
KEGG D08098 YesY
ChEBI CHEBI:6121 YesY
ChEMBL CHEMBL742 YesY
Chemical data
Formula C13H16ClNO 
Mol. mass 237.725 g/mol
Physical data
Melt. point 262 °C (504 °F)
 YesY (what is this?)  (verify)

Ketamine is a drug used in human and veterinary medicine, primarily for the induction and maintenance of general anesthesia, usually in combination with a sedative. Other uses include sedation in intensive care, analgesia (particularly in emergency medicine), and treatment of bronchospasm. Ketamine has a wide range of effects in humans, including analgesia, anesthesia, hallucinations, elevated blood pressure, and bronchodilation.[2] Like other drugs of its class, such as tiletamine and phencyclidine (PCP), ketamine induces a state referred to as "dissociative anesthesia"[3] and is used as a recreational drug.

Ketamine can be effective in treating depression in patients with depression and bipolar disorder who have not responded to antidepressants.[4] It produces a rapid antidepressant effect, acting within two hours as opposed to the several weeks taken by typical antidepressants to work.[5]

Its hydrochloride salt is sold as Ketanest, Ketaset, and Ketalar. Pharmacologically, ketamine is classified as an NMDA receptor antagonist.[6] At high, fully anesthetic level doses, ketamine has also been found to bind to μ-opioid receptors type 2 in cultured human neuroblastoma cells – however, without agonist activity[7] – and to sigma receptors in rats.[8] Also, ketamine interacts with muscarinic receptors, descending monoaminergic pain pathways and voltage-gated calcium channels.[9]

Ketamine is a chiral compound. Most pharmaceutical preparations of ketamine are racemic; however, some brands reportedly have (mostly undocumented) differences in their enantiomeric proportions. The more active enantiomer, (S)-ketamine, is also available for medical use under the brand name Ketanest S.[10]