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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
Structure of NORKETAMINE

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

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 ( + / - )

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.

Originator

Curator's Comment: European Journal of Pharmacology Volume 49, Issue 1, 1 May 1978, Pages 15-23

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.7 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Norketamine, the main metabolite of ketamine, is a non-competitive NMDA receptor antagonist in the rat cortex and spinal cord.
1997 Aug 20
Interaction between morphine and norketamine enantiomers in rodent models of nociception.
2008 Oct
Podocyte glutamatergic signaling contributes to the function of the glomerular filtration barrier.
2009 Sep
(R,S)-Ketamine metabolites (R,S)-norketamine and (2S,6S)-hydroxynorketamine increase the mammalian target of rapamycin function.
2014 Jul
Patents

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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:20:16 GMT 2023
Edited
by admin
on Sat Dec 16 11:20:16 GMT 2023
Record UNII
XQY6JVF94X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORKETAMINE
Common Name English
J397.916D
Code English
(±)-NORKETAMINE
Common Name English
2-AMINO-2-(O-CHLOROPHENYL)CYCLOHEXANONE
Common Name English
N-DEMETHYLKETAMINE
Common Name English
CYCLOHEXANONE, 2-AMINO-2-(2-CHLOROPHENYL)-
Systematic Name English
N-DESMETHYLKETAMINE
Common Name English
Code System Code Type Description
CAS
65329-10-4
Created by admin on Sat Dec 16 11:20:16 GMT 2023 , Edited by admin on Sat Dec 16 11:20:16 GMT 2023
SUPERSEDED
CAS
35211-10-0
Created by admin on Sat Dec 16 11:20:16 GMT 2023 , Edited by admin on Sat Dec 16 11:20:16 GMT 2023
PRIMARY
EPA CompTox
DTXSID40891434
Created by admin on Sat Dec 16 11:20:16 GMT 2023 , Edited by admin on Sat Dec 16 11:20:16 GMT 2023
PRIMARY
PUBCHEM
123767
Created by admin on Sat Dec 16 11:20:16 GMT 2023 , Edited by admin on Sat Dec 16 11:20:16 GMT 2023
PRIMARY
WIKIPEDIA
NORKETAMINE
Created by admin on Sat Dec 16 11:20:16 GMT 2023 , Edited by admin on Sat Dec 16 11:20:16 GMT 2023
PRIMARY
SMS_ID
100000176238
Created by admin on Sat Dec 16 11:20:16 GMT 2023 , Edited by admin on Sat Dec 16 11:20:16 GMT 2023
PRIMARY
FDA UNII
XQY6JVF94X
Created by admin on Sat Dec 16 11:20:16 GMT 2023 , Edited by admin on Sat Dec 16 11:20:16 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
BINDER->LIGAND
ENANTIOMER -> RACEMATE
Related Record Type Details
PARENT -> METABOLITE ACTIVE