Norketamine (original) (raw)
Norketamine, or N-desmethylketamine, is the major active metabolite of ketamine, which is formed mainly by CYP3A4. Similarly to ketamine, norketamine acts as a noncompetitive NMDA receptor antagonist (Ki = 1.7 μM and 13 μM for (S)-(+)-norketamine and (R)-(–)-norketamine, respectively), but is about 3–5 times less potent as an anesthetic in comparison. Also, similarly again to ketamine, norketamine binds to the μ- and κ-opioid receptors. Relative to ketamine, norketamine is much more potent as an antagonist of the α7-nicotinic acetylcholine receptor, and produces rapid antidepressant effects in animal models which have been reported to correlate with its activity at this receptor. However, norketamine is about 1/5 as potent as ketamine as an antidepressant in mice as per the forced swim tes
| Property | Value |
|---|---|
| dbo:abstract | Norketamine, or N-desmethylketamine, is the major active metabolite of ketamine, which is formed mainly by CYP3A4. Similarly to ketamine, norketamine acts as a noncompetitive NMDA receptor antagonist (Ki = 1.7 μM and 13 μM for (S)-(+)-norketamine and (R)-(–)-norketamine, respectively), but is about 3–5 times less potent as an anesthetic in comparison. Also, similarly again to ketamine, norketamine binds to the μ- and κ-opioid receptors. Relative to ketamine, norketamine is much more potent as an antagonist of the α7-nicotinic acetylcholine receptor, and produces rapid antidepressant effects in animal models which have been reported to correlate with its activity at this receptor. However, norketamine is about 1/5 as potent as ketamine as an antidepressant in mice as per the forced swim test, and this seems also to be in accordance with its 3–5-fold reduced comparative potency in vivo as an NMDA receptor antagonist. Norketamine is metabolized into dehydronorketamine and hydroxynorketamine, which are far less or negligibly active as NMDA receptor antagonists in comparison, but retain activity as potent antagonists of the α7-nicotinic acetylcholine receptor. (en) |
| dbo:casNumber | 35211-10-0 79499-59-5 (HCl) |
| dbo:chEMBL | 1039 |
| dbo:fdaUniiCode | XQY6JVF94X |
| dbo:pubchem | 123767 |
| dbo:thumbnail | wiki-commons:Special:FilePath/Norketamine.svg?width=300 |
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| dbp:atcPrefix | None (en) |
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| dbp:casNumber | 35211 (xsd:integer) |
| dbp:casSupplemental | 79499 (xsd:integer) |
| dbp:chembl | 1039 (xsd:integer) |
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| dbp:legalCa | Schedule I (en) |
| dbp:legalUk | Class B (en) |
| dbp:n | 1 (xsd:integer) |
| dbp:o | 1 (xsd:integer) |
| dbp:pubchem | 123767 (xsd:integer) |
| dbp:smiles | C1CCCN (en) |
| dbp:stdinchi | 1 (xsd:integer) |
| dbp:stdinchikey | BEQZHFIKTBVCAU-UHFFFAOYSA-N (en) |
| dbp:title | dbr:Pharmacodynamics |
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| dbp:unii | XQY6JVF94X (en) |
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| dct:subject | dbc:Chloroarenes dbc:General_anesthetics dbc:Human_drug_metabolites dbc:Ketones dbc:Mu-opioid_receptor_agonists dbc:NMDA_receptor_antagonists dbc:Sedatives dbc:Kappa-opioid_receptor_agonists dbc:Nicotinic_antagonists dbc:Antidepressants dbc:Arylcyclohexylamines dbc:Dissociative_drugs |
| gold:hypernym | dbr:Metabolite |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 dbo:ChemicalCompound dbo:Drug |
| rdfs:comment | Norketamine, or N-desmethylketamine, is the major active metabolite of ketamine, which is formed mainly by CYP3A4. Similarly to ketamine, norketamine acts as a noncompetitive NMDA receptor antagonist (Ki = 1.7 μM and 13 μM for (S)-(+)-norketamine and (R)-(–)-norketamine, respectively), but is about 3–5 times less potent as an anesthetic in comparison. Also, similarly again to ketamine, norketamine binds to the μ- and κ-opioid receptors. Relative to ketamine, norketamine is much more potent as an antagonist of the α7-nicotinic acetylcholine receptor, and produces rapid antidepressant effects in animal models which have been reported to correlate with its activity at this receptor. However, norketamine is about 1/5 as potent as ketamine as an antidepressant in mice as per the forced swim tes (en) |
| rdfs:label | Norketamine (en) |
| owl:sameAs | freebase:Norketamine yago-res:Norketamine wikidata:Norketamine https://global.dbpedia.org/id/urND |
| prov:wasDerivedFrom | wikipedia-en:Norketamine?oldid=1100234138&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/Norketamine.svg |
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| is dbo:wikiPageRedirects of | dbr:C12H14ClNO dbr:N-Demethylketamine dbr:N-Desmethylketamine dbr:N-demethylketamine dbr:N-desmethylketamine |
| is dbo:wikiPageWikiLink of | dbr:Dehydronorketamine dbr:Hydroxynorketamine dbr:2-Bromodeschloroketamine dbr:C12H14ClNO dbr:Dwayne_Haskins dbr:Alpha-7_nicotinic_receptor dbr:Arketamine dbr:Ketamine dbr:N-Demethylketamine dbr:N-Desmethylketamine dbr:N-demethylketamine dbr:N-desmethylketamine |
| is foaf:primaryTopic of | wikipedia-en:Norketamine |
