Ketamine information

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	Moderate–high
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.^[18] It is a novel compound that was derived from phencyclidine in 1962 in pursuit of a safer anesthetic with fewer hallucinogenic effects.^[19]^[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 anesthesia 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 pain and treatment-resistant depression.^[22] As with many antidepressants, the results of a single administration wane with time.^[23] The long-term effects of repeated use are largely unknown, and are an area of active investigation.^[24]^[25]^[26]

Liver and urinary toxicity have been reported among regular users of high doses of ketamine for recreational purposes.^[27] Ketamine is an NMDA receptor antagonist, accounting for most of its psychoactive effects.^[28]

Ketamine was first synthesized in 1962 and approved for use in the United States in 1970.^[18] It has been regularly used in veterinary medicine and was extensively used for surgical anesthesia in the Vietnam War.^[29] Along with other psychotropic drugs, it is on the World Health Organization's List of Essential Medicines.^[30] It is available as a generic medication.^[31] 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.^[32]

^ 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.
^ "Ketamine (Ketalar) Use During Pregnancy". Drugs.com. 22 November 2019. Archived from the original on 26 June 2020. Retrieved 18 May 2020.
^ "Drug Scheduling". US DEA. Archived from the original on 8 April 2024. Retrieved 29 December 2023. Ketamine is listed in Schedule III.
^ 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.
^ 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.
^ ^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.
^ 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.
^ 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.
^ ^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.
^ 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.
^ 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.
^ ^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.
^ ^a ^b ^c ^d ^e ^f Cite error: The named reference Quibell2011 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference pmid4603048 was invoked but never defined (see the help page).
^ 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.
^ Cite error: The named reference pmid27763887 was invoked but never defined (see the help page).
^ 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.
^ ^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.
^ 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.
^ Cite error: The named reference pmid29870458 was invoked but never defined (see the help page).
^ ^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.
^ 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.
^ 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.
^ Cite error: The named reference pmid33065824 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid33174760 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid33162856 was invoked but never defined (see the help page).
^ 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.
^ Cite error: The named reference pmid29945898 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid20693870 was invoked but never defined (see the help page).
^ 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.
^ "Ketamine Injection". Drugs.com. Archived from the original on 10 December 2014. Retrieved 1 December 2014.
^ 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.

[MortonHall2012-1] 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.

[Drugs.com_pregnancy-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] 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.

[5] 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.

[MathewZarate2016-6] ^ ^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.

[MD-7] 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.

[Kintz2014-8] 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.

[pmid23521979-9] 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.

[Hashimoto2019-10] 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.

[pmid6884418-11] 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.

[sinner-12] ^ ^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.

[Quibell2011-13] ^ ^a ^b ^c ^d ^e ^f Cite error: The named reference Quibell2011 was invoked but never defined (see the help page).

[pmid4603048-14] Cite error: The named reference pmid4603048 was invoked but never defined (see the help page).

[15] 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.

[pmid27763887-16] Cite error: The named reference pmid27763887 was invoked but never defined (see the help page).

[17] 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.

[Sachdeva_2023-18] 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.

[19] 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.

[pmid29870458-20] Cite error: The named reference pmid29870458 was invoked but never defined (see the help page).

[GreenRoback2011-21] 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.

[Zhang2018-22] 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.

[acschemneuro.9b00493-23] 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.

[pmid33065824-24] Cite error: The named reference pmid33065824 was invoked but never defined (see the help page).

[pmid33174760-25] Cite error: The named reference pmid33174760 was invoked but never defined (see the help page).

[pmid33162856-26] Cite error: The named reference pmid33162856 was invoked but never defined (see the help page).

[Or-27] 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.

[pmid29945898-28] Cite error: The named reference pmid29945898 was invoked but never defined (see the help page).

[pmid20693870-29] Cite error: The named reference pmid20693870 was invoked but never defined (see the help page).

[WHO22nd-30] 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.

[KetPres2013-31] "Ketamine Injection". Drugs.com. Archived from the original on 10 December 2014. Retrieved 1 December 2014.

[morgan11-32] 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.

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