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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Atypical Antipsychotics-Advances in Research and Application (2012)
Frontiers in Clinical Drug Research- Central Nervous System, 19-19 (2013)
Plasma clozapine levels and clinical response in treatment-refractory Chinese schizophrenic patients
Wong JO, et al.
Progress in Neuro-Psychopharmacology & Biological Psychiatry, 30(2), 251-264 (2006)
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
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
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