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Dehydronorketamine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Dehydronorketamine
Clinical data
ATC code
  • None
Identifiers
  • 6-Amino-6-(2-chlorophenyl)cyclohex-2-en-1-one
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC12H12ClNO
Molar mass221.68 g·mol−1
3D model (JSmol)
  • C1CC(C(=O)C=C1)(C2=CC=CC=C2Cl)N
  • 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), or5,6-dehydronorketamine, is a minormetabolite ofketamine which is formed bydehydrogenation of its metabolitenorketamine.[1][2] Though originally considered to be inactive,[1][2][3] DHNK has been found to act as a potent and selectivenegative allosteric modulator of theα7-nicotinic acetylcholine receptor (IC50 = 55 nM).[4][5] For this reason, similarly tohydroxynorketamine (HNK), it has been hypothesized that DHNK may have the capacity to produce rapidantidepressant effects.[6] However, unlike ketamine, norketamine, and HNK, DHNK has been found to be inactive in theforced swim test (FST) in mice at doses up to 50 mg/kg.[7] DHNK is inactive at theα3β4-nicotinic acetylcholine receptor (IC50 > 100 μM) and is only very weakly active at theNMDA receptor (Ki = 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 indrug detection assays.[8]

See also

[edit]

References

[edit]
  1. ^abBooker PD, Chadderton N (14 May 2014)."Intravenous Agents". In Bissonnette B (ed.).Pediatric Anesthesia. PMPH-USA. pp. 366–.ISBN 978-1-60795-213-8.
  2. ^abLapidus 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.
  3. ^Bearn J, O'Brien M (2015).""Addicted to Euphoria"". In Taba P, Lees A, Sikk K (eds.).The Neuropsychiatric Complications of Stimulant Abuse. International Review of Neurobiology. Vol. 120. Elsevier Science. pp. 205–233 (225).doi:10.1016/bs.irn.2015.02.005.ISBN 978-0-12-803003-5.PMID 26070759.
  4. ^abMoaddel 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.
  5. ^Lester RA (11 November 2014).Nicotinic Receptors. Springer. pp. 445–.ISBN 978-1-4939-1167-7.
  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.
  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.
  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.
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(andPAMsTooltip positive allosteric modulators)
Antagonists
(andNAMsTooltip negative allosteric modulators)
Precursors
(andprodrugs)
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