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Sub-anesthetic concentrations of (R, S)-ketamine metabolites inhibit acetylcholine-evoked currents in α7 nicotinic acetylcholine receptors
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The effect of the (R,S)-ketamine metabolites (R,S)-norketamine, (R,S)-dehydronorketamine, (2S,6S)-hydroxynorketamine and (2R,6R)-hydroxynorketamine on the activity of α7 and α3β4 neuronal nicotinic acetylcholine receptors was investigated using patch-clamp techniques. The data indicated that (R,S)-dehydronorketamine inhibited acetylcholine-evoked currents in α7-nicotinic acetylcholine receptor, IC(50) = 55 ± 6 nM, and that (2S,6S)-hydroxynorketamine, (2R,6R)-hydroxynorketamine and (R,S)-norketamine also inhibited α7-nicotinic acetylcholine receptor function at concentrations ≤ 1 μM, while (R,S)-ketamine was inactive at these concentrations. The inhibitory effect of (R,S)-dehydronorketamine was voltage-independent and the compound did not competitively displace selective α7-nicotinic acetylcholine receptor ligands [(125)I]-α-bungarotoxin and [(3)H]-epibatidine indicating that (R,S)-dehydronorketamine is a negative allosteric modulator of the α7-nicotinic acetylcholine receptor. (R,S)-Ketamine and (R,S)-norketamine inhibited (S)-nicotine-induced whole-cell currents in cells expressing α3β4-nicotinic acetylcholine receptor, IC(50) 3.1 and 9.1 μM, respectively, while (R,S)-dehydronorketamine, (2S,6S)-hydroxynorketamine and (2R,6R)-hydroxynorketamine were weak inhibitors, IC(50) >100 μM. The binding affinities of (R,S)-dehydronorketamine, (2S,6S)-hydroxynorketamine and (2R,6R)-hydroxynorketamine at the NMDA receptor were also determined using rat brain membranes and the selective NMDA receptor antagonist [(3)H]-MK-801. The calculated K(i) values were 38.95 μM for (S)-dehydronorketamine, 21.19 μM for (2S,6S)-hydroxynorketamine and>100 μM for (2R,6R)-hydroxynorketamine. The results suggest that the inhibitory activity of ketamine metabolites at the α7-nicotinic acetylcholine receptor may contribute to the clinical effect of the drug.
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“(2R,6R)-HNK has a binding affinity (Ki) and IC50 greater than 100 μM with 24% inhibition at 100 μM, and fails to impact NMDA-evoked currents in CA1 interneurons (Moaddel et al., 2013; Morris et al., 2017; Zanos et al., 2016).”
From Mechanisms of ketamine and its metabolites as antidepressants (2022) · cites this paper as Moaddel et al., 2013
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“its inability to displace MK-801 binding to NMDARs (10 μM).”
From Mechanisms of ketamine and its metabolites as antidepressants (2022) · cites this paper as Moaddel et al., 2013
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“Important for the mechanism of action of (2R,6R)-HNK as an antidepressant (and thus ketamine’s action) is the fact that at relevant concentrations (i.e., 10 mg/kg or brain Cmax = ~10 μmol/kg in mice), (2R,6R)-HNK does not appear to inhibit the NMDAR.”
From Mechanisms of ketamine action as an antidepressant (2018) · cites this paper as [112]
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“(S)-ketamine has ~4-fold greater affinity/potency at inhibiting the NMDAR compared to its (R)-ketamine enantiomer 13, 111–115.”
From Mechanisms of ketamine action as an antidepressant (2018) · cites this paper as [112]
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“[3H]-MK-801 binding displacement studies showed that the affinity of (2R,6R)-HNK to displace MK-801 from the NMDAR is >100 μM, and that of (2S,6S)-HNK is 7–20 μM 111, 112.”
From Mechanisms of ketamine action as an antidepressant (2018) · cites this paper as [112]
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Metadata
- Authors
- Moaddel, R., Abdrakhmanova, G., Kozak, J., Jozwiak, K., Toll, L., Jimenez, L., Rosenberg, A., Tran, T., Xiao, Y., Zarate, C. A., & Wainer, I. W.
- Affiliations
- National Institutes of Health (US)
- Virginia Commonwealth University (US)
- Medical University of Lublin (PL)
- Torrey Pines Institute For Molecular Studies (US)
- SRI International (US)
- Georgetown University (US)
- Corresponding author
- Wainer, Irving W.
- Venue
- European Journal of Pharmacology
- Publisher
- Elsevier BV
- Published
- 2013-01
- Volume
- 698
- Issue
- 1-3
- Pages
- 228-234
- ISSN
- 0014-2999 (ISSN-L)
- PMC
- PMC3534778
- OpenAlex
- W2068032560
- Cited by
- 176
- References
- 22
- Citations by year
- 2026: 6 · 2025: 9 · 2024: 11 · 2023: 14 · 2022: 14 · 2021: 15 · 2020: 23 · 2019: 11 · 2018: 15 · 2017: 16 · 2016: 15 · 2015: 14 · 2014: 9 · 2013: 4
- FWCI
- 3.47
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- European Journal of Pharmacology (publishedVersion)
- PubMed (publishedVersion)
- Europe PMC (PubMed Central) (acceptedVersion)
- PubMed Central (acceptedVersion)
- Funders
- Intramural Research Programs of the National Institute of Aging (IWW)
- National Institute of Mental Health (CAZ)
- Brain & Behavior Research Foundation Bipolar Disorders Award (CAZ), NIA (N01AG-3–1009 (GA,LT,LJ))
- Foundation for Polish Science (FOCUS and TEAM Programmes) (KJ).
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Nicotinic Acetylcholine Receptors Study
- Life Sciences › Neuroscience › Cellular and Molecular Neuroscience › Neuroscience and Neuropharmacology Research
- Health Sciences › Medicine › Anesthesiology and Pain Medicine › Anesthesia and Sedative Agents
- Keywords
- ketamine metabolites, norketamine, dehydronorketamine, hydroxynorketamine, alpha7 nicotinic acetylcholine receptor, α3β4 nicotinic acetylcholine receptor, negative allosteric modulation, NMDA receptor binding, nicotinic antagonists
- MeSH terms
- Acetylcholine, Anesthetics, Animals, Cell Line, Dose-Response Relationship, Drug, Ketamine, Receptors, Nicotinic, Receptors, N-Methyl-D-Aspartate, Nicotinic Agonists, Rats, Electrophysiological Phenomena, alpha7 Nicotinic Acetylcholine Receptor
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