Clozapine N-oxide

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

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]

Alternatives to CNO with more inert character and faster kinetics include Compound 21 (C21)[3] and deschloroclozapine (DCZ).[4]

References

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.
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.
Bonaventura, Jordi; Eldridge, Mark A. G.; Hu, Feng; Gomez, Juan L.; Sanchez-Soto, Marta; Abramyan, Ara M.; Lam, Sherry; Boehm, Matthew A.; Ruiz, Christina; Farrell, Mitchell R.; Moreno, Andrea (2019-10-11). "High-potency ligands for DREADD imaging and activation in rodents and monkeys". Nature Communications. 10 (1): 4627. doi:10.1038/s41467-019-12236-z. ISSN 2041-1723.
Nagai, Yuji; Miyakawa, Naohisa; Takuwa, Hiroyuki; Hori, Yukiko; Oyama, Kei; Ji, Bin; Takahashi, Manami; Huang, Xi-Ping; Slocum, Samuel T.; DiBerto, Jeffrey F.; Xiong, Yan (September 2020). "Deschloroclozapine, a potent and selective chemogenetic actuator enables rapid neuronal and behavioral modulations in mice and monkeys". Nature Neuroscience. 23 (9): 1157–1167. doi:10.1038/s41593-020-0661-3. ISSN 1546-1726.

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[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.

[3] Bonaventura, Jordi; Eldridge, Mark A. G.; Hu, Feng; Gomez, Juan L.; Sanchez-Soto, Marta; Abramyan, Ara M.; Lam, Sherry; Boehm, Matthew A.; Ruiz, Christina; Farrell, Mitchell R.; Moreno, Andrea (2019-10-11). "High-potency ligands for DREADD imaging and activation in rodents and monkeys". Nature Communications. 10 (1): 4627. doi:10.1038/s41467-019-12236-z. ISSN 2041-1723.

[4] Nagai, Yuji; Miyakawa, Naohisa; Takuwa, Hiroyuki; Hori, Yukiko; Oyama, Kei; Ji, Bin; Takahashi, Manami; Huang, Xi-Ping; Slocum, Samuel T.; DiBerto, Jeffrey F.; Xiong, Yan (September 2020). "Deschloroclozapine, a potent and selective chemogenetic actuator enables rapid neuronal and behavioral modulations in mice and monkeys". Nature Neuroscience. 23 (9): 1157–1167. doi:10.1038/s41593-020-0661-3. ISSN 1546-1726.