Mr. Ibrahem/Ketamine

Clinical data
Trade names	Ketalar, others
Other names	CI-581; CL-369; CM-52372-2 [1]
AHFS/ Drugs.com	Monograph
License data	US  DailyMed:  Ketamine US  FDA:  Ketamine
Pregnancy category	AU: B3 [2]
Addiction liability	Low–moderate [3]
Routes of administration	Any [4] [5] [6] [7]
Drug class	NMDA receptor antagonists; General anesthetics; Dissociative hallucinogens; Analgesics; Antidepressants
Legal status
Legal status	AU: S8 (Controlled drug) CA: Schedule I UK: Class B US: Schedule III UN: Unscheduled In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Intravenous: 100% [6] Intramuscular: 93% [6] Subcutaneous: high [8] Epidural: 77% [9] Intranasal: 8–50% [6] [10] [11] Sublingual: 24–30% [6] [12] Rectal: 11–30% [13] [14] By mouth: 16–29% [9] [15] [14]
Protein binding	12–47% (low) [9] [11] [16]
Metabolism	Liver ( N-demethylation): [6] [19] Major: CYP3A4 Minor: CYP2B6, CYP2C9
Metabolites	Norketamine Dehydronorketamine Hydroxynorketamine Conjugates [17]
Onset of action	Intravenous: seconds [11] Intramuscular: 1–5 min [11] [18] Subcutaneous: 15–30 min [18] Insufflation: 5–10 min [11] By mouth: 15–30 min [11] [18]
Elimination half-life	Ketamine: 2.5–3 hours [11] [6] Norketamine: 12 hours [18]
Duration of action	Intramuscular: 0.5–2 hours [18] Insufflation: 45–60 min [11] By mouth: 1–6+ hours [11] [18]
Excretion	Urine: 91% [6] Feces: 1–3% [6]
Identifiers
IUPAC name (RS)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone
Chemical and physical data
Formula	C13H16ClNO
Molar mass	237.725 g·mol−1
3D model ( JSmol)	Interactive image
Chirality	Racemic mixture: [11] Esketamine (S(+)-isomer) Arketamine (R(−)-isomer)
Melting point	258 to 261 °C (496 to 502 °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 Y Key:YQEZLKZALYSWHR-UHFFFAOYSA-N Y
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Ketamine is a medication mainly used for starting and maintaining anesthesia. ^[22] It induces a trance-like state while providing pain relief, sedation, and memory loss. ^[23] Other uses include sedation in intensive care and treatment of pain and depression. ^{[24] [25] [14] [26] [27]} Heart function, breathing, and airway reflexes generally remain functional. ^[23] Effects typically begin within five minutes when given by injection, and last up to approximately 25 minutes. ^{[22] [28]}

Common side effects include agitation, confusion, or hallucinations as the medication wears off. ^{[22] [29] [30]} Elevated blood pressure and muscle tremors are relatively common. ^{[22] [30]} Spasms of the larynx may rarely occur. ^[22] Ketamine is an NMDA receptor antagonist, but it may also have other actions. ^[31]

Ketamine was discovered in 1962, first tested in humans in 1964, and approved for use in the United States in 1970. ^{[28] [32]} It was extensively used for surgical anesthesia in the Vietnam War due to its safety. ^[32] It is on the World Health Organization's List of Essential Medicines. ^[33] It is available as a generic medication. ^[22] The wholesale price in the developing world is between US$0.84 and US$3.22 per vial. ^[34] Ketamine is also used as a recreational drug for its hallucinogenic and dissociative effects. ^[35]

References