Metizolam

Metizolam

Clinical data
Dependence liability	Moderate
Routes of administration	Oral, sublingual, rectal
Legal status
Legal status	CA: Unscheduled DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act Illegal in Sweden
Identifiers
IUPAC name 4-(2-Chlorophenyl)-2-ethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine
CAS Number	40054-68-0^Y
PubChem CID	12434325
ChemSpider	59207712
UNII	K1C6XI9LLX
ChEMBL	ChEMBL4782672
CompTox Dashboard (EPA)	DTXSID101032847
Chemical and physical data
Formula	C16H13ClN4S
Molar mass	328.82 g·mol^−1
3D model (JSmol)	Interactive image
SMILES ClC1=C(C=CC=C1)C3=NCC2=NN=C[N]2C4=C3C=C(S4)CC
InChI InChI=1S/C16H13ClN4S/c1-2-10-7-12-15(11-5-3-4-6-13(11)17)18-8-14-20-19-9-21(14)16(12)22-10/h3-7,9H,2,8H2,1H3 Key:NQSSWDKQLVBUQN-UHFFFAOYSA-N

Metizolam (also known as desmethyletizolam) is a thienotriazolodiazepine that is the demethylated analogue of the closely related etizolam.^{[1][2][3][4][5][6]}

Legal status

Following its sale as a designer drug,^[7] metizolam was classified as controlled substance in Sweden on 26. January 2016.^[8]

See also

• List of benzodiazepine designer drugs

References

1. Weber K, Bauer A, Langbein A, Daniel H (20 September 1978). "Heteroaromaten mit anellierten Siebenringen, III. Umwandlung von Thienotriazolooxazepinen in Diazepine". Justus Liebigs Annalen der Chemie (in German). 1978 (8): 1257–1265. doi:10.1002/jlac.197819780806. ISSN 1099-0690.
2. US 3904641, Nakanishi M, Tahara T, Araki K, Shiroki M, "Triazolothienodiazepine compounds", issued 9 September 1975, assigned to Welfide Corp 
3. EP 0776892, Hiroshi K, Ehara Syuji E, Hideaki S, Moriwaki Minoru M, Kenichi O, "Thienylazole compound and thienotriazolodiazepine compound", published 1997-06-04, assigned to Yoshitomi Pharmaceutical Industries, Ltd. 
4. EP 0315698, Moriwaki M, Abe M, Mikashima H, Tahara T, "Thieno(triazolo)diazepine compounds and medicinal application of the same", published 1993-03-03, assigned to Yoshitomi Pharmaceutical Industries, Ltd. 
5. 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.
6. Kintz P, Richeval C, Jamey C, Ameline A, Allorge D, Gaulier JM, Raul JS (July 2017). "Detection of the designer benzodiazepine metizolam in urine and preliminary data on its metabolism". Drug Testing and Analysis. 9 (7): 1026–1033. doi:10.1002/dta.2099. PMID 27671107.
7. "Desmethyletizolam". New Synthetic Drugs Database. Archived from the original on 2016-06-25. Retrieved 2016-01-16.
8. "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.