Clozapine N-oxide

Clozapine N-oxide (CNO) is a synthetic drug used mainly in biomedical research as a ligand to activate DREADD receptors.[1] Although CNO was initially believed to be biologically inert, it has been shown to reverse metabolise into clozapine which has a series of effects on serotonin and dopamine receptors.[2]

Clozapine N-oxide

Names
IUPAC name 3-chloro-6-(4-methyl-4-oxidopiperazin-4-ium-1-yl)-11H-benzo[b][1,4]benzodiazepine
Identifiers
CAS Number	34233-69-7
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1688
ChemSpider	21169512
ECHA InfoCard	100.164.243
PubChem CID	135445691
UNII	MZA8BK588J
CompTox Dashboard (EPA)	DTXSID50955778
InChI 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 Key: OGUCZBIQSYYWEF-UHFFFAOYSA-N
SMILES C[N+]1(CCN(CC1)C2=NC3=C(C=CC(=C3)Cl)NC4=CC=CC=C42)[O-]
Properties
Chemical formula	C18H19ClN4O
Molar mass	342.83 g·mol^−1
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H315, H319, H335
GHS precautionary statements	P261, P264, P270, P271, P280, P301+310, P302+352, P304+340, P305+351+338, P312, P321, P330, P332+313, P337+313, P362, P403+233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References

1. Armbruster, B. N.; Li, X.; Pausch, M. H.; Herlitze, S.; Roth, B. L. (2007-03-02). "Evolving the lock to fit the key to create a family of G protein-coupled receptors potently activated by an inert ligand". Proceedings of the National Academy of Sciences. 104 (12): 5163–5168. doi:10.1073/pnas.0700293104. ISSN 0027-8424.
2. Manvich, Daniel F.; Webster, Kevin A.; Foster, Stephanie L.; Farrell, Martilias S.; Ritchie, James C.; Porter, Joseph H.; Weinshenker, David (2018-03-01). "The DREADD agonist clozapine N -oxide (CNO) is reverse-metabolized to clozapine and produces clozapine-like interoceptive stimulus effects in rats and mice". Scientific Reports. 8 (1): 1–10. doi:10.1038/s41598-018-22116-z. ISSN 2045-2322.