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D5676

Sigma-Aldrich

N-Desmethylclozapine

Synonym(s):

8-Chloro-11-piperazinyl-5H-dibenzo[b,e][1,4]diazepine, Norclozapine, Normethylclozapine

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About This Item

Empirical Formula (Hill Notation):
C17H17ClN4
CAS Number:
6104-71-8
Molecular Weight:
312.80
MDL number:
MFCD00210189
UNSPSC Code:
12352200
PubChem Substance ID:
24893957
NACRES:
NA.77

form

powder

Quality Level

200

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

SMILES string

Clc1ccc2Nc3ccccc3C(=Nc2c1)N4CCNCC4

InChI

1S/C17H17ClN4/c18-12-5-6-15-16(11-12)21-17(22-9-7-19-8-10-22)13-3-1-2-4-14(13)20-15/h1-6,11,19-20H,7-10H2

InChI key

JNNOSTQEZICQQP-UHFFFAOYSA-N

Gene Information

human ... KCNH1(3756)

Application

N-Desmethylclozapine has been used as standard to quantify the clozapine plasma levels in treatment-refractory Chinese schizophrenic patients.

Biochem/physiol Actions

N-Desmethylclozapine serves as an agonist to muscarinic acetylcholine receptors, and is known to exert its antipsychotic action. It blocks synaptic transmission by antagonizing synaptic GABA (γ-aminobutyric acid) receptors.
Major metabolite of clozapine; potent 5-HT2 serotonin receptor antagonist and a ligand for the cloned 5-HT6 and 5-HT7 serotonin receptors. Also an allosteric potentiator of M1 muscarinic receptors.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Robert L Smith et al.
CNS drugs, 31(11), 991-997 (2017-09-28)
Clozapine is restricted to use in patients with treatment-refractory schizophrenia due to the risk of a serious drop in absolute neutrophil granulocyte count (ANC). The formation of reactive, unstable metabolites (adducts) has been suggested as a mechanism of clozapine-induced granulocyte
Atypical Antipsychotics-Advances in Research and Application (2012)
Luiz G M Beloti et al.
Molecules (Basel, Switzerland), 24(2) (2019-01-19)
This manuscript describes a sensitive, selective, and online in-tube solid-phase microextraction coupled with an ultrahigh performance liquid chromatography-tandem mass spectrometry (in-tube SPME-UHPLC-MS/MS) method to determine chlopromazine, clozapine, quetiapine, olanzapine, and their metabolites in plasma samples from schizophrenic patients. Organic poly(butyl
K Koda et al.
British journal of pharmacology, 162(3), 763-772 (2010-10-21)
We have previously reported that galantamine, a weak acetylcholinesterase inhibitor, improves prepulse inhibition (PPI) deficits in mice reared in social isolation. ACh receptors are involved in the underlying mechanism of PPI, but whether rearing in social isolation causes dysfunction of
Cyrille Sur et al.
Proceedings of the National Academy of Sciences of the United States of America, 100(23), 13674-13679 (2003-11-05)
The molecular and neuronal substrates conferring on clozapine its unique and superior efficacy in the treatment of schizophrenia remain elusive. The interaction of clozapine with many G protein-coupled receptors is well documented but less is known about its biologically active
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