Dehydronorketamine

Dehydronorketamine
Clinical data
ATC code	None;
Identifiers
	IUPAC name 6-Amino-6-(2-chlorophenyl)cyclohex-2-en-1-one;
CAS Number	57683-62-2;
PubChem CID	162835;
ChemSpider	142954;
UNII	J5442FVV58;
CompTox Dashboard (EPA)	DTXSID80973283 ;
Chemical and physical data
Formula	C12H12ClNO
Molar mass	221.68 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC(C(=O)C=C1)(C2=CC=CC=C2Cl)N;
	InChI InChI=1S/C12H12ClNO/c13-10-6-2-1-5-9(10)12(14)8-4-3-7-11(12)15/h1-3,5-7H,4,8,14H2; Key:BXBPJMHHWPXBJL-UHFFFAOYSA-N;

Dehydronorketamine (DHNK), or 5,6-dehydronorketamine, is a minor metabolite of ketamine which is formed by dehydrogenation of its metabolite norketamine.^[1]^[2] Though originally considered to be inactive,^[1]^[2]^[3] DHNK has been found to act as a potent and selective negative allosteric modulator of the α₇-nicotinic acetylcholine receptor (IC₅₀ = 55 nM).^[4]^[5] For this reason, similarly to hydroxynorketamine (HNK), it has been hypothesized that DHNK may have the capacity to produce rapid antidepressant effects.^[6] However, unlike ketamine, norketamine, and HNK, DHNK has been found to be inactive in the forced swim test (FST) in mice at doses up to 50 mg/kg.^[7] DHNK is inactive at the α₃β₄-nicotinic acetylcholine receptor (IC₅₀ > 100 μM) and is only very weakly active at the NMDA receptor (K_i = 38.95 μM for (S)-(+)-DHNK).^[4] It can be detected 7–10 days after a modest dose of ketamine, and because of this, is useful in drug detection assays.^[8]

References

^ ^a ^b Booker PD, Chadderton N (14 May 2014). "Intravenous Agents". In Bissonnette B (ed.). Pediatric Anesthesia. PMPH-USA. pp. 366–. ISBN 978-1-60795-213-8.
^ ^a ^b Lapidus KA, Mathew SJ (9 May 2013). "Ketamine in treatment-resistant depression". In Mann JJ, McGrath PJ, Roose SP (eds.). Clinical Handbook for the Management of Mood Disorders. Cambridge University Press. pp. 345–357 (347). doi:10.1017/CBO9781139175869.027. ISBN 978-1-107-06744-8.
^ Bearn J, O'Brien M (2015). Taba P, Lees A, Sikk K (eds.). ""Addicted to Euphoria": The History, Clinical Presentation, and Management of Party Drug Misuse". International Review of Neurobiology. 120. Elsevier Science: 205–233 (225). doi:10.1016/bs.irn.2015.02.005. ISBN 978-0-12-803003-5. PMID 26070759.
^ ^a ^b Moaddel R, Abdrakhmanova G, Kozak J, Jozwiak K, Toll L, Jimenez L, et al. (January 2013). "Sub-anesthetic concentrations of (R,S)-ketamine metabolites inhibit acetylcholine-evoked currents in α7 nicotinic acetylcholine receptors". European Journal of Pharmacology. 698 (1–3): 228–234. doi:10.1016/j.ejphar.2012.11.023. PMC 3534778. PMID 23183107.
^ Lester RA (11 November 2014). Nicotinic Receptors. Springer. pp. 445–. ISBN 978-1-4939-1167-7.
^ Paul RK, Singh NS, Khadeer M, Moaddel R, Sanghvi M, Green CE, et al. (July 2014). "(R,S)-Ketamine metabolites (R,S)-norketamine and (2S,6S)-hydroxynorketamine increase the mammalian target of rapamycin function". Anesthesiology. 121 (1): 149–159. doi:10.1097/ALN.0000000000000285. PMC 4061505. PMID 24936922.
^ Sałat K, Siwek A, Starowicz G, Librowski T, Nowak G, Drabik U, et al. (December 2015). "Antidepressant-like effects of ketamine, norketamine and dehydronorketamine in forced swim test: Role of activity at NMDA receptor". Neuropharmacology. 99: 301–307. doi:10.1016/j.neuropharm.2015.07.037. PMID 26240948. S2CID 19880543.
^ Xu QA (1 April 2013). Ultra-High Performance Liquid Chromatography and Its Applications. John Wiley & Sons. pp. 1–. ISBN 978-1-118-53398-7.

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[Bissonnette2014-1] Booker PD, Chadderton N (14 May 2014). "Intravenous Agents". In Bissonnette B (ed.). Pediatric Anesthesia. PMPH-USA. pp. 366–. ISBN 978-1-60795-213-8.

[Mann2013-2] Lapidus KA, Mathew SJ (9 May 2013). "Ketamine in treatment-resistant depression". In Mann JJ, McGrath PJ, Roose SP (eds.). Clinical Handbook for the Management of Mood Disorders. Cambridge University Press. pp. 345–357 (347). doi:10.1017/CBO9781139175869.027. ISBN 978-1-107-06744-8.

[pmid26070759-3] Bearn J, O'Brien M (2015). Taba P, Lees A, Sikk K (eds.). ""Addicted to Euphoria": The History, Clinical Presentation, and Management of Party Drug Misuse". International Review of Neurobiology. 120. Elsevier Science: 205–233 (225). doi:10.1016/bs.irn.2015.02.005. ISBN 978-0-12-803003-5. PMID 26070759.

[MoaddelAbdrakhmanova2013-4] Moaddel R, Abdrakhmanova G, Kozak J, Jozwiak K, Toll L, Jimenez L, et al. (January 2013). "Sub-anesthetic concentrations of (R,S)-ketamine metabolites inhibit acetylcholine-evoked currents in α7 nicotinic acetylcholine receptors". European Journal of Pharmacology. 698 (1–3): 228–234. doi:10.1016/j.ejphar.2012.11.023. PMC 3534778. PMID 23183107.

[Lester2014-5] Lester RA (11 November 2014). Nicotinic Receptors. Springer. pp. 445–. ISBN 978-1-4939-1167-7.

[PaulSingh2014-6] Paul RK, Singh NS, Khadeer M, Moaddel R, Sanghvi M, Green CE, et al. (July 2014). "(R,S)-Ketamine metabolites (R,S)-norketamine and (2S,6S)-hydroxynorketamine increase the mammalian target of rapamycin function". Anesthesiology. 121 (1): 149–159. doi:10.1097/ALN.0000000000000285. PMC 4061505. PMID 24936922.

[pmid26240948-7] Sałat K, Siwek A, Starowicz G, Librowski T, Nowak G, Drabik U, et al. (December 2015). "Antidepressant-like effects of ketamine, norketamine and dehydronorketamine in forced swim test: Role of activity at NMDA receptor". Neuropharmacology. 99: 301–307. doi:10.1016/j.neuropharm.2015.07.037. PMID 26240948. S2CID 19880543.

[Xu2013-8] Xu QA (1 April 2013). Ultra-High Performance Liquid Chromatography and Its Applications. John Wiley & Sons. pp. 1–. ISBN 978-1-118-53398-7.

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See also

References