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Ketamine

For the functional group referred to as ketimine, see Imine.

Ketamine
(S)-Ketamine ball-and-stick model
Clinical data
Trade namesKetalar, others
Other namesCI-581; CL-369; CM-52372-2[1]
AHFS/Drugs.comMonograph
License data
Pregnancy
category
Addiction
liability		Moderate–high[3][4]
Routes of
administration		Any[5][6][7][8]
Drug classNMDA receptor antagonist; general anesthetic; dissociative hallucinogen; analgesic; antidepressant
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability
Protein binding23–47%[12]
MetabolismLiver, intestine (oral):
Metabolites
Onset of action
  • Intravenous: seconds[13]
  • Intramuscular: 1–5 min[13][14]
  • Subcutaneous: 15–30 min[14]
  • Insufflation: 5–10 min[13]
  • By mouth: 15–30 min[13][14]
Elimination half-life
  • Ketamine: 2.5–3 hours[13][7]
  • Norketamine: 12 hours[14]
Duration of action
  • Intramuscular: 0.5–2 hours[14]
  • Insufflation: 45–60 min[13]
  • By mouth: 1–6+ hours[13][14]
Excretion
Identifiers
  • (RS)-2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.027.095 Edit this at Wikidata
Chemical and physical data
FormulaC13H16ClNO
Molar mass237.73 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture:[13]
Melting point92[18] °C (198 °F)
  • Clc1ccccc1C2(NC)CCCCC2=O
  • 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 checkY
  • Key:YQEZLKZALYSWHR-UHFFFAOYSA-N checkY
  (verify)

Ketamine is a dissociative anesthetic used medically for induction and maintenance of anesthesia. It is also used as a treatment for depression and in pain management.[19] Ketamine is an NMDA receptor antagonist which accounts for most of its psychoactive effects.[20]

At anesthetic doses, ketamine induces a state of dissociative anesthesia, a trance-like state providing pain relief, sedation, and amnesia.[21] Its distinguishing features as an anesthestic are preserved breathing and airway reflexes, stimulated heart function with increased blood pressure, and moderate bronchodilation.[21] At lower, sub-anesthetic doses, it is a promising agent for treatment of pain and treatment-resistant depression.[22] As with many antidepressants, the results of a single administration wane with time.[23]

Ketamine is used as a recreational drug for its hallucinogenic and dissociative effects.[24] When used recreationally, it is found both in crystalline powder and liquid form, and is often referred to by users as "Special K" or simply "K". The long-term effects of repeated use are largely unknown, and are an area of active investigation.[25][26][27] Liver and urinary toxicity have been reported among regular users of high doses of ketamine for recreational purposes.[28]

Ketamine was first synthesized in 1962, derived from phencyclidine in pursuit of a safer anesthetic with fewer hallucinogenic effects.[29][30] It was approved for use in the United States in 1970.[19] It has been regularly used in veterinary medicine and was extensively used for surgical anesthesia in the Vietnam War.[31] It is on the World Health Organization's List of Essential Medicines[32] and is available as a generic medication.[33]

  1. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 159–. ISBN 978-94-011-4439-1. Archived from the original on 11 April 2017.
  2. ^ "Ketamine (Ketalar) Use During Pregnancy". Drugs.com. 22 November 2019. Archived from the original on 26 June 2020. Retrieved 18 May 2020.
  3. ^ "Drug Scheduling". US DEA. Archived from the original on 8 April 2024. Retrieved 29 December 2023. Ketamine is listed in Schedule III.
  4. ^ Huang, MC., Lin, SK. (2020). "Ketamine Abuse: Past and Present". In: Hashimoto, K., Ide, S., Ikeda, K. (eds.) Ketamine. Springer, Singapore. doi:10.1007/978-981-15-2902-3_1.
  5. ^ Bell RF, Eccleston C, Kalso EA (June 2017). "Ketamine as an adjuvant to opioids for cancer pain" (PDF). The Cochrane Database of Systematic Reviews. 6 (9): CD003351. doi:10.1002/14651858.CD003351.pub3. PMC 6481583. PMID 28657160. Archived (PDF) from the original on 12 January 2024. Retrieved 10 September 2018.
  6. ^ Moyse DW, Kaye AD, Diaz JH, Qadri MY, Lindsay D, Pyati S (March 2017). "Perioperative Ketamine Administration for Thoracotomy Pain". Pain Physician. 20 (3): 173–184. PMID 28339431.
  7. ^ a b c d e f g h Mathew SJ, Zarate Jr CA (25 November 2016). Ketamine for Treatment-Resistant Depression: The First Decade of Progress. Springer. pp. 8–10, 14–22. ISBN 978-3-319-42925-0. Archived from the original on 8 September 2017.
  8. ^ Brayfield A, ed. (9 January 2017). "Ketamine Hydrochloride: Martindale: The Complete Drug Reference". MedicinesComplete. London, UK: Pharmaceutical Press. Archived from the original on 28 August 2021. Retrieved 24 August 2017.
  9. ^ Kintz P (22 March 2014). Toxicological Aspects of Drug-Facilitated Crimes. Elsevier Science. pp. 87–. ISBN 978-0-12-416969-2. Archived from the original on 8 September 2017.
  10. ^ a b c Marland S, Ellerton J, Andolfatto G, Strapazzon G, Thomassen O, Brandner B, et al. (June 2013). "Ketamine: use in anesthesia". CNS Neurosci Ther. 19 (6): 381–9. doi:10.1111/cns.12072. PMC 6493613. PMID 23521979.
  11. ^ Hashimoto K (October 2019). "Rapid-acting antidepressant ketamine, its metabolites and other candidates: A historical overview and future perspective". Psychiatry and Clinical Neurosciences. 73 (10): 613–627. doi:10.1111/pcn.12902. PMC 6851782. PMID 31215725.
  12. ^ Dayton PG, Stiller RL, Cook DR, Perel JM (1983). "The binding of ketamine to plasma proteins: emphasis on human plasma". Eur J Clin Pharmacol. 24 (6): 825–31. doi:10.1007/BF00607095. PMID 6884418. S2CID 807011.
  13. ^ a b c d e f g h Sinner B, Graf BM (2008). "Ketamine". In Schüttler J, Schwilden H (eds.). Modern Anesthetics. Handbook of Experimental Pharmacology. Vol. 182. pp. 313–33. doi:10.1007/978-3-540-74806-9_15. ISBN 978-3-540-72813-9. PMID 18175098.
  14. ^ a b c d e f Cite error: The named reference Quibell2011 was invoked but never defined (see the help page).
  15. ^ a b Cite error: The named reference pmid4603048 was invoked but never defined (see the help page).
  16. ^ Hijazi Y, Boulieu R (July 2002). "Contribution of CYP3A4, CYP2B6, and CYP2C9 isoforms to N-demethylation of ketamine in human liver microsomes". Drug Metabolism and Disposition. 30 (7): 853–8. doi:10.1124/dmd.30.7.853. PMID 12065445. S2CID 15787750.
  17. ^ Cite error: The named reference pmid27763887 was invoked but never defined (see the help page).
  18. ^ Sass W, Fusari S (1977). "Ketamine". Analytical Profiles of Drug Substances. Vol. 6. Academic Press. pp. 297–322. doi:10.1016/S0099-5428(08)60347-0. ISBN 9780122608063.
  19. ^ a b Sachdeva B, Sachdeva P, Ghosh S, Ahmad F, Sinha JK (March 2023). "Ketamine as a therapeutic agent in major depressive disorder and posttraumatic stress disorder: Potential medicinal and deleterious effects". Ibrain. 9 (1): 90–101. doi:10.1002/ibra.12094. ISSN 2769-2795. PMC 10528797. PMID 37786516. S2CID 257117630.
  20. ^ Cite error: The named reference pmid29945898 was invoked but never defined (see the help page).
  21. ^ a b Green SM, Roback MG, Kennedy RM, Krauss B (May 2011). "Clinical practice guideline for emergency department ketamine dissociative sedation: 2011 update". Annals of Emergency Medicine. 57 (5): 449–461. doi:10.1016/j.annemergmed.2010.11.030. PMID 21256625.
  22. ^ Zhang K, Hashimoto K (January 2019). "An update on ketamine and its two enantiomers as rapid-acting antidepressants". Expert Review of Neurotherapeutics. 19 (1): 83–92. doi:10.1080/14737175.2019.1554434. PMID 30513009. S2CID 54628949.
  23. ^ Hibicke M, Landry AN, Kramer HM, Talman ZK, Nichols CD (March 2020). "Psychedelics, but Not Ketamine, Produce Persistent Antidepressant-like Effects in a Rodent Experimental System for the Study of Depression". ACS Chemical Neuroscience. 11 (6): 864–871. doi:10.1021/acschemneuro.9b00493. PMID 32133835. S2CID 212418003.
  24. ^ Morgan CJ, Curran HV (January 2012). "Ketamine use: a review". Addiction. 107 (1): 27–38. doi:10.1111/j.1360-0443.2011.03576.x. PMID 21777321. S2CID 11064759.
  25. ^ Cite error: The named reference pmid33065824 was invoked but never defined (see the help page).
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  27. ^ Cite error: The named reference pmid33162856 was invoked but never defined (see the help page).
  28. ^ Orhurhu VJ, Vashisht R, Claus LE, Cohen SP (April 2022). "Ketamine toxicity". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 31082131. Archived from the original on 16 May 2022. Retrieved 18 August 2022.
  29. ^ Peltoniemi MA, Hagelberg NM, Olkkola KT, Saari TI (September 2016). "Ketamine: A Review of Clinical Pharmacokinetics and Pharmacodynamics in Anesthesia and Pain Therapy". Clinical Pharmacokinetics. 55 (9): 1059–77. doi:10.1007/s40262-016-0383-6. PMID 27028535. S2CID 5078489.
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  32. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  33. ^ "Ketamine Injection". Drugs.com. Archived from the original on 10 December 2014. Retrieved 1 December 2014.

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