Cloniprazepam

Cloniprazepam
Clinical data
Other names	1-Cyclopropylmethylclonazepam, Kloniprazepam, 2-Chloro-7'-nitroprazepam
Drug class	Benzodiazepines
Legal status
Legal status	CA: Schedule IV; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name 5-(2-Chlorophenyl)-1-(cyclopropylmethyl)-7-nitro-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one;
CAS Number	1998158-84-1 ;
PubChem CID	137700140;
ChemSpider	68003855;
UNII	YSL4SM8QYP;
CompTox Dashboard (EPA)	DTXSID60893511 ;
Chemical and physical data
Formula	C19H16ClN3O3
Molar mass	369.81 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1N(CC2CC2)C3=CC=C([N+]([O-])=O)C=C3C(C4=CC=CC=C4Cl)=NC1;
	InChI InChI=1S/C19H16ClN3O3/c20-16-4-2-1-3-14(16)19-15-9-13(23(25)26)7-8-17(15)22(11-12-5-6-12)18(24)10-21-19/h1-4,7-9,12H,5-6,10-11H2; Key:CCSYKGYLSFXNTA-UHFFFAOYSA-N;

Cloniprazepam is a benzodiazepine derivative and a prodrug of clonazepam, 7-aminoclonazepam, and other metabolites.^[1]^[2]

Some of the minor metabolites include 3-hydroxyclonazepam and 6-hydroxyclonazepam, 3-hydroxycloniprazepam and ketocloniprazepam with ketone group formed where 3-hydroxy group was.^[1]

It is a designer drug and an NPS (short for "new psychoactive substance").^[1] At the end of 2017, cloniprazepam was an uncontrolled substance in most of the countries.

^ ^a ^b ^c Moosmann B, Bisel P, Franz F, Huppertz LM, Auwärter V (November 2016). "Characterization and in vitro phase I microsomal metabolism of designer benzodiazepines - an update comprising adinazolam, cloniprazepam, fonazepam, 3-hydroxyphenazepam, metizolam and nitrazolam". Journal of Mass Spectrometry. 51 (11): 1080–1089. Bibcode:2016JMSp...51.1080M. doi:10.1002/jms.3840. PMID 27535017.
^ Mortelé O, Vervliet P, Gys C, Degreef M, Cuykx M, Maudens K, et al. (May 2018). "In vitro Phase I and Phase II metabolism of the new designer benzodiazepine cloniprazepam using liquid chromatography coupled to quadrupole time-of-flight mass spectrometry". Journal of Pharmaceutical and Biomedical Analysis. 153: 158–167. doi:10.1016/j.jpba.2018.02.032. hdl:10067/1496330151162165141. PMID 29494888. S2CID 3946404.

[pmid27535017-1] Moosmann B, Bisel P, Franz F, Huppertz LM, Auwärter V (November 2016). "Characterization and in vitro phase I microsomal metabolism of designer benzodiazepines - an update comprising adinazolam, cloniprazepam, fonazepam, 3-hydroxyphenazepam, metizolam and nitrazolam". Journal of Mass Spectrometry. 51 (11): 1080–1089. Bibcode:2016JMSp...51.1080M. doi:10.1002/jms.3840. PMID 27535017.

[2] Mortelé O, Vervliet P, Gys C, Degreef M, Cuykx M, Maudens K, et al. (May 2018). "In vitro Phase I and Phase II metabolism of the new designer benzodiazepine cloniprazepam using liquid chromatography coupled to quadrupole time-of-flight mass spectrometry". Journal of Pharmaceutical and Biomedical Analysis. 153: 158–167. doi:10.1016/j.jpba.2018.02.032. hdl:10067/1496330151162165141. PMID 29494888. S2CID 3946404.

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