Norketamine hydrochloride

CAS# 79499-59-5

Norketamine hydrochloride

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Chemical structure

Norketamine hydrochloride

3D structure

Chemical Properties of Norketamine hydrochloride

Cas No. 79499-59-5 SDF Download SDF
PubChem ID 25195026 Appearance Powder
Formula C12H15Cl2NO M.Wt 260.16
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in water
Chemical Name 2-amino-2-(2-chlorophenyl)cyclohexan-1-one;hydrochloride
SMILES C1CCC(C(=O)C1)(C2=CC=CC=C2Cl)N.Cl
Standard InChIKey CLPOJGPBUGCUKT-UHFFFAOYSA-N
Standard InChI InChI=1S/C12H14ClNO.ClH/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;1H
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Norketamine hydrochloride

DescriptionMajor metabolite of ketamine that is a potent non-competitive NMDA receptor antagonist (Ki = 3.6 μM for displacement of [3H]-MK 801 in rat brain). Antinociceptive and anesthetic in vivo.

Norketamine hydrochloride Dilution Calculator

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Norketamine hydrochloride Molarity Calculator

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Preparing Stock Solutions of Norketamine hydrochloride

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.8438 mL 19.2189 mL 38.4379 mL 76.8758 mL 96.0947 mL
5 mM 0.7688 mL 3.8438 mL 7.6876 mL 15.3752 mL 19.2189 mL
10 mM 0.3844 mL 1.9219 mL 3.8438 mL 7.6876 mL 9.6095 mL
50 mM 0.0769 mL 0.3844 mL 0.7688 mL 1.5375 mL 1.9219 mL
100 mM 0.0384 mL 0.1922 mL 0.3844 mL 0.7688 mL 0.9609 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Norketamine hydrochloride

Oral ketamine is antinociceptive in the rat formalin test: role of the metabolite, norketamine.[Pubmed:10353496]

Pain. 1999 May;81(1-2):85-93.

The present study was designed to evaluate the oral efficacy and bioavailability of ketamine. Antinociceptive efficacy was determined with the rat formalin test and oral bioavailability by the measurement of plasma and brain concentrations of ketamine and its major metabolite, norketamine. Oral ketamine in a dose range from 30 to 180 mg/kg or saline was given prior to intraplantar formalin and the flinching behavior was measured. Oral ketamine dose-dependently reduced the flinching during phase 2, while flinching during phase 1 was reduced only with the highest dose given. Following oral ketamine at 100 mg/kg, blood and brain samples were obtained and plasma and brain ketamine and norketamine levels were measured using high-performance liquid chromatography (HPLC). The average concentration ratio of norketamine/ketamine, as expressed by the area under the curve (AUC) value, was 6.4 for plasma and 2.9 for brain. These results demonstrate that a significant amount of norketamine is formed by first pass biotransformation of ketamine and is distributed to the brain. Competition binding assays for the [3H]MK-801-labeled non-competitive site of the N-methyl-D-aspartate receptor (NMDA) receptor revealed that both norketamine and ketamine displaced [3H]MK-801 at low micromolar concentrations with Ki values of 2.5 and 0.3 mM in the forebrain, and 4.2 and 1.0 mM in the spinal cord, respectively. Spinal norketamine was approximately equipotent to ketamine in producing antinociceptive effects during phase 2 of the formalin test. Thus, norketamine appears to contribute to the antinociceptive effects of oral ketamine through its NMDA receptor antagonist activity.

Norketamine, the main metabolite of ketamine, is a non-competitive NMDA receptor antagonist in the rat cortex and spinal cord.[Pubmed:9311667]

Eur J Pharmacol. 1997 Aug 20;333(1):99-104.

The enantiomers of the potent non-competitive NMDA receptor antagonist ketamine and its major metabolite, norketamine were evaluated as NMDA receptor antagonists using the rat cortical wedge preparation and the neonatal rat spinal cord preparation, respectively, for electrophysiological studies and [3H](RS)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-im ine ([3H]MK801) in homogenate binding experiments. In agreement with earlier studies (S)-ketamine (Ki 0.3 microM) was found to possess a 5 times higher affinity for the NMDA receptor complex than (R)-ketamine (Ki 1.4 microM). (S)-Norketamine (Ki 1.7 microM) had approximately an 8 times higher affinity than (R)-norketamine (Ki 13 microM) in the inhibition of [3H]MK-801 binding. All compounds inhibited responses to NMDA in the rat cortical wedge preparation and the hemisected neonatal rat spinal cord, being approximately four times more potent in the cortex than in the spinal cord except for (R)-norketamine being only twice as potent. In light of the clinically obtained concentrations of norketamine after oral administration of ketamine, these data strongly suggest that (S)-norketamine may contribute significantly to the clinical activity of (S)-ketamine, especially when given orally.

Comparative pharmacology in the rat of ketamine and its two principal metabolites, norketamine and (Z)-6-hydroxynorketamine.[Pubmed:3783598]

J Med Chem. 1986 Nov;29(11):2396-9.

(Z)-6-Hydroxynorketamine (3), a secondary metabolite of the dissociative anesthetic agent ketamine (1), was synthesized, and its central nervous system (CNS) properties were compared to those of the parent drug and the primary metabolite, norketamine (2). Administration of compounds 1 and 2 to rats (40 mg/kg iv) produced general anesthesia and also led to marked increases in spontaneous locomotor activity during the postanesthetic recovery phase. These effects were of significantly longer duration with 1 than with 2. In contrast, the same dose of 3 produced neither general anesthesia nor CNS excitation, despite the fact that 3 entered brain tissue readily from the systemic circulation. It is concluded that the CNS effects of 1 are attenuated by metabolism to 2 and are abolished by subsequent hydroxylation to produce 3. Moreover, the results suggest that the desirable anesthetic properties of 1 and related arylcyclohexylamines may be inseparable from their ability to produce adverse postanesthetic emergence reactions.

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