NORKETAMINE HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H14ClNO.ClH
Molecular Weight	260.16
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.NC1(CCCCC1=O)C2=CC=CC=C2Cl

InChI

InChIKey=CLPOJGPBUGCUKT-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C12H14ClNO
Molecular Weight	223.699
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9311667 | https://www.ncbi.nlm.nih.gov/pubmed/24936922 | http://adisinsight.springer.com/drugs/800021669 | https://www.ncbi.nlm.nih.gov/pubmed/19578006 | https://www.ncbi.nlm.nih.gov/pubmed/26240948 | https://www.ncbi.nlm.nih.gov/pubmed/2269237

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate NMDA receptor 47 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9311667	Antagonist 2849		1.7 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Persistent pain 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18586315	Primary	Preclinical	Unknown Approved Use Unknown
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27028535	Primary	Preclinical	Unknown Approved Use Unknown
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26240948	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antidepressant-like effects of ketamine, norketamine and dehydronorketamine in forced swim test: Role of activity at NMDA receptor.	2015-12	26240948
(R,S)-Ketamine metabolites (R,S)-norketamine and (2S,6S)-hydroxynorketamine increase the mammalian target of rapamycin function.	2014-07	24936922
Podocyte glutamatergic signaling contributes to the function of the glomerular filtration barrier.	2009-09	19578006
Interaction between morphine and norketamine enantiomers in rodent models of nociception.	2008-10	18582492
Norketamine, the main metabolite of ketamine, is a non-competitive NMDA receptor antagonist in the rat cortex and spinal cord.	1997-08-20	9311667
Family history of cancer and mortality among patients gastrectomized because of benign gastric diseases.	1990-07	2269237
Pharmacokinetics and analgesic effects of i.m. and oral ketamine.	1981-08	7272143

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:06:54 GMT 2025` Edited by `admin` on `Mon Mar 31 23:06:54 GMT 2025`
Record UNII	QA4F2IDL56
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NORKETAMINE HYDROCHLORIDE

Common Name

English

(±)-NORKETAMINE HYDROCHLORIDE

Preferred Name

English

CYCLOHEXANONE, 2-AMINO-2-(2-CHLOROPHENYL)-, HYDROCHLORIDE

Systematic Name

English

CYCLOHEXANONE, 2-AMINO-2-(2-CHLOROPHENYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

Code System Code Type Description

CAS

79499-59-5