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C0832

Sigma-Aldrich

Clozapine N-oxide

Synonym(s):

8-Chloro-11-(4-methyl-1-piperazinyl)-5H-dibenzo[b,e](1,4)diazepine N-oxide

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About This Item

Empirical Formula (Hill Notation):
C18H19ClN4O
CAS Number:
Molecular Weight:
342.82
MDL number:
UNSPSC Code:
12352119
PubChem Substance ID:
NACRES:
NA.77

form

solid

Quality Level

SMILES string

C[N+]1([O-])CCN(CC1)C2=Nc3cc(Cl)ccc3Nc4ccccc24

InChI

1S/C18H19ClN4O/c1-23(24)10-8-22(9-11-23)18-14-4-2-3-5-15(14)20-16-7-6-13(19)12-17(16)21-18/h2-7,12,20H,8-11H2,1H3

InChI key

OGUCZBIQSYYWEF-UHFFFAOYSA-N

General description

Clozapine N-oxide (CNO), inactive from of clozapine drug, activates G-protein-coupled receptors (GPCRs). CNO serves as a synthetic ligand for engineered human muscarinic receptor. It elicits clozapine-like effects upon metabolic conversion. Clozapine conversion to CNO favors its passage through blood-brain barrier.

Application

Clozapine N-oxide has been used:
  • for the activation of human M4 muscarinic (hM4Di) in primary motor cortex
  • for inducing in vivo chemogenetic manipulation and impairing locomotor activity in Th-cre transgenic mice
  • in behavioral testing in mice and for stimulating (HEK293) cells

Biochem/physiol Actions

5-HT2 serotonin receptor antagonist; major metabolite of clopazine that can be monitored by HPLC.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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Skull and crossbones

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Danger

Hazard Classifications

Acute Tox. 3 Oral - STOT SE 3

target_organs

Central nervous system

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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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Weizhe Hong et al.
Cell, 158(6), 1348-1361 (2014-09-13)
Animals display a range of innate social behaviors that play essential roles in survival and reproduction. While the medial amygdala (MeA) has been implicated in prototypic social behaviors such as aggression, the circuit-level mechanisms controlling such behaviors are not well
Branch-specific dendritic Ca2+ spikes cause persistent synaptic plasticity
Cichon J and Gan WB
Nature, 520(7546), 180-185 (2015)
Gram scale preparation of clozapine N-oxide (CNO), a synthetic small molecule actuator for muscarinic acetylcholine DREADDs
van der Peet PL, et al.
MethodsX, 5, 257-267 (2018)
Clozapine-n-oxide administration produces behavioral effects in Long-Evans rats-implications for designing DREADD experiments
MacLaren DAA, et al.
eNeuro, ENEURO-EN0219 (2016)
Mei-Hong Qiu et al.
Brain structure & function, 224(7), 2525-2535 (2019-07-22)
The midbrain dopamine system via the dorsal and ventral striatum regulates a wide range of behaviors. To dissect the role of dopaminergic projections to the dorsal striatum (nigrostriatal projection) and ventral striatum (mesolimbic projection) in sleep-wake behavior, we selectively chemogenetically

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