Ketamine

Ketamine
Clinical data
Trade names	Ketalar, others
Other names	CI-581; CL-369; CM-52372-2
AHFS/Drugs.com	Monograph
License data	US DailyMed: Ketamine; US FDA: Ketamine;
Pregnancy; category	AU: B3;
Addiction; liability	Low–moderate
Routes of; administration	Any
Drug class	NMDA receptor antagonists; General anesthetics; Dissociative hallucinogens; Analgesics; Antidepressants
ATC code	N01AX03 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class C1 (Other controlled substances); CA: Schedule I; DE: Unscheduled; UK: Class B; US: Schedule III; UN: Unscheduled; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Intravenous: 100%; Intramuscular: 93%; Epidural: 77%; Intranasal: 45–50%; Sublingual: 24–30%; Rectal: 25–30%; By mouth: 16–20%;
Protein binding	23 to 47%.
Metabolism	Liver, intestine (oral): Major: CYP3A4, CYP2B6;
Metabolites	Norketamine; Dehydronorketamine; Hydroxynorketamine;
Onset of action	Intravenous: seconds; Intramuscular: 1–5 min; Subcutaneous: 15–30 min; Insufflation: 5–10 min; By mouth: 15–30 min;
Elimination half-life	Ketamine: 2.5–3 hours; Norketamine: 12 hours;
Duration of action	Intramuscular: 0.5–2 hours; Insufflation: 45–60 min; By mouth: 1–6+ hours;
Excretion	Urine: 91%; Feces: 3%;
Identifiers
	IUPAC name (RS)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone;
CAS Number	6740-88-1 33643-46-8 (esketamine); 33643-49-1 (arketamine); ; HCl: 1867-66-9 ;
PubChem CID	3821;
IUPHAR/BPS	4233;
DrugBank	DB01221 ;
ChemSpider	3689 ;
UNII	690G0D6V8H;
KEGG	D08098 ; HCl: D00711 ;
ChEBI	CHEBI:6121 ;
ChEMBL	ChEMBL742 ;
CompTox Dashboard (EPA)	DTXSID8023187 ;
ECHA InfoCard	100.027.095
Chemical and physical data
Formula	C13H16ClNO
Molar mass	237.73 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture: Esketamine (S(+)-isomer); Arketamine (R(−)-isomer);
Melting point	92 °C (198 °F)
	SMILES Clc1ccccc1C2(NC)CCCCC2=O;
	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 ; Key:YQEZLKZALYSWHR-UHFFFAOYSA-N ;
	(verify)

Ketamine is a dissociative anesthetic used medically for induction and maintenance of anesthesia. It is also used as a treatment for depression and pain management. It is a novel compound that was derived from phencyclidine in 1962 in pursuit of a safer anesthetic with fewer hallucinogenic effects.

At anesthetic doses, ketamine induces a state of dissociative anesthesia, a trance-like state providing pain relief, sedation and amnesia. Its distinguishing features as anesthesia are preserved breathing and airway reflexes, stimulated heart function with increased blood pressure, and moderate bronchodilation. At lower, sub-anesthetic doses, it is a promising agent for pain and treatment-resistant depression. As with many antidepressants, the results of a single administration wane with time. The long-term effects of repeated use are largely unknown, and are an area of active investigation.

Liver and urinary toxicity have been reported among regular users of high doses of ketamine for recreational purposes. Ketamine is an NMDA receptor antagonist, accounting for most of its psychoactive effects.

Ketamine was first synthesized in 1962 and approved for use in the United States in 1970. It has been regularly used in veterinary medicine and was extensively used for surgical anesthesia in the Vietnam War. Along with other psychotropic drugs, it is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. When used as a recreational drug, it is found both in crystalline powder and liquid form, and is often referred to by recreational users as "Special K" or simply "K". It is used as a recreational drug for its hallucinogenic and dissociative effects.

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