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Dehydronorketamine

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Chemical compound Pharmaceutical compound
Dehydronorketamine
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 6-Amino-6-(2-chlorophenyl)cyclohex-2-en-1-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H12ClNO
Molar mass221.68 g·mol
3D model (JSmol)
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. Though originally considered to be inactive, DHNK has been found to act as a potent and selective negative allosteric modulator of the α7-nicotinic acetylcholine receptor (IC50 = 55 nM). For this reason, similarly to hydroxynorketamine (HNK), it has been hypothesized that DHNK may have the capacity to produce rapid antidepressant effects. 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. DHNK is inactive at the α3β4-nicotinic acetylcholine receptor (IC50 > 100 μM) and is only very weakly active at the NMDA receptor (Ki = 38.95 μM for (S)-(+)-DHNK). It can be detected 7–10 days after a modest dose of ketamine, and because of this, is useful in drug detection assays.

See also

References

  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.
  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.
  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.
  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.
  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.
Nicotinic acetylcholine receptor modulators
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(and PAMsTooltip positive allosteric modulators)
Antagonists
(and NAMsTooltip negative allosteric modulators)
Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators
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