Ketamine

Systematic (IUPAC) name
(RS)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone
Clinical data
AHFS/Drugs.com	Consumer Drug Information
Pregnancy cat.	B
Legal status	Controlled (S8) (AU) Schedule I (CA) CD (UK) Schedule III (US)
Dependence liability	Medium
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 Y
ATC code	N01AX03 N01AX14
PubChem	CID 3821
DrugBank	DB01221
ChemSpider	3689 Y
UNII	690G0D6V8H Y
KEGG	D08098 Y
ChEBI	CHEBI:6121 Y
ChEMBL	CHEMBL742 Y
Chemical data
Formula	C13H16ClNO
Mol. mass	237.725 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3 Y Key:YQEZLKZALYSWHR-UHFFFAOYSA-N Y
Physical data
Melt. point	262 °C (504 °F)
Y (what is this?)  (verify)

Ketamine is a drug used in human and veterinary medicine. Its hydrochloride salt is sold as Ketanest, Ketaset, and Ketalar. Pharmacologically, ketamine is classified as an NMDA receptor antagonist.^[2] At high, fully anesthetic level doses, ketamine has also been found to bind to opioid μ receptors type 2 in cultured human neuroblastoma cells – however, without agonist activity^[3] – and to sigma receptors in rats.^[4] Also, ketamine interacts with muscarinic receptors, descending monoaminergic pain pathways and voltage-gated calcium channels.^[5] Like other drugs of this class such as tiletamine and phencyclidine (PCP), it induces a state referred to as "dissociative anesthesia"^[6] and is used as a recreational drug.

Ketamine has a wide range of effects in humans, including analgesia, anesthesia, hallucinations, elevated blood pressure, and bronchodilation.^[7] Ketamine is primarily used 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. It has been shown to be effective in treating depression in patients with bipolar disorder who have not responded to other anti-depressants.^[8] In persons with major depressive disorder, it produces a rapid antidepressant effect, acting within two hours as opposed to the several weeks taken by typical antidepressants to work.^[9] It is also a popular anesthetic in veterinary medicine.

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

Ketamine is a core medicine in the World Health Organization's "Essential Drugs List", a list of minimum medical needs for a basic healthcare system.^[11]