Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C12H14ClNO |
| Molecular Weight | 223.699 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1(CCCCC1=O)C2=C(Cl)C=CC=C2
InChI
InChIKey=BEQZHFIKTBVCAU-UHFFFAOYSA-N
InChI=1S/C12H14ClNO/c13-10-6-2-1-5-9(10)12(14)8-4-3-7-11(12)15/h1-2,5-6H,3-4,7-8,14H2
Norketamine is one of the major metabolites of Ketamine, which is routinely used as an anesthetic. Norketamine is a potent antagonist of the N-methyl-D-aspartate receptor and is believed to contribute to the analgesic effects of ketamine. In animal models, norketamine has been noted to increase the glomerular filtration rate by remodeling the cellular cytoskeleton, and it has been identified as having possible antidepressant effects.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacokinetics and analgesic effects of i.m. and oral ketamine. | 1981 Aug |
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| Family history of cancer and mortality among patients gastrectomized because of benign gastric diseases. | 1990 Jul |
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| (R,S)-Ketamine metabolites (R,S)-norketamine and (2S,6S)-hydroxynorketamine increase the mammalian target of rapamycin function. | 2014 Jul |
|
| Antidepressant-like effects of ketamine, norketamine and dehydronorketamine in forced swim test: Role of activity at NMDA receptor. | 2015 Dec |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: It should be noted that this dosage is approximately 20 times less than the metabolic dose when ketamine is administered as an anesthetic. https://www.ncbi.nlm.nih.gov/pubmed/17439422
Balb/c mice were treated with norketamine for 3 days at a dose of 0.3 mg/100g delivered by intraperitoneal injection. Urinary excretion of albumin and creatine were both increased over the next 24 hours.
Route of Administration:
Intraperitoneal
Podocyte cells were cultured and extracted from rat Kidneys. Cells were cultured for 1 week with collagen type IV at 37°C in 5% CO2 atmosphere. An NMDA receptor blockade was established by adding 50 microM of Norketamine Hydrochloride to the cell media. After 30 minutes a profound remodeling of podocyte cytoskeleton was observed, highlighted by the disappearance of actin stress fibers and redistribution of myosin-IIA. When the same concentration of norketamine was added to isolated rat glomeruli there was a significant increase in glomerular albumin permeability.
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65329-10-4
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35211-10-0
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DTXSID40891434
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123767
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NORKETAMINE
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100000176238
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XQY6JVF94X
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PARENT (METABOLITE ACTIVE)
SUBSTANCE RECORD
