Metizolam

Last updated
Metizolam
Desmethyletizolam.svg
Clinical data
Dependence
liability 		Moderate
Routes of
administration 		Oral, sublingual, rectal
Legal status
Legal status
Identifiers
  • 4-(2-Chlorophenyl)-2-ethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C16H13ClN4S
Molar mass 328.82 g·mol−1
3D model (JSmol)
  • ClC1=C(C=CC=C1)C3=NCC2=NN=C[N]2C4=C3C=C(S4)CC
  • 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]

Contents

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

See also

Related Research Articles

<span class="mw-page-title-main">Adinazolam</span> Chemical compound

Adinazolam is a tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It possesses anxiolytic, anticonvulsant, sedative, and antidepressant properties. Adinazolam was developed by Jackson B. Hester, who was seeking to enhance the antidepressant properties of alprazolam, which he also developed. Adinazolam was never FDA approved and never made available to the public market; however, it has been sold as a designer drug.

<span class="mw-page-title-main">Etizolam</span> Chemical compound

Etizolam is a thienodiazepine derivative which is a benzodiazepine analog. The etizolam molecule differs from a benzodiazepine in that the benzene ring has been replaced by a thiophene ring and triazole ring has been fused, making the drug a thienotriazolodiazepine.

<span class="mw-page-title-main">Clotiazepam</span> Chemical compound

Clotiazepam is a thienodiazepine drug which is a benzodiazepine analog. The clotiazepam molecule differs from benzodiazepines in that the benzene ring has been replaced by a thiophene ring. It possesses anxiolytic, skeletal muscle relaxant, anticonvulsant, sedative properties. Stage 2 NREM sleep is significantly increased by clotiazepam.

<span class="mw-page-title-main">Brotizolam</span> Benzodiazepine

Brotizolam is a sedative-hypnotic thienotriazolodiazepine drug which is a benzodiazepine analog. It possesses anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties, and is considered to be similar in effect to other short-acting hypnotic benzodiazepines such as triazolam or midazolam. It is used in the short-term treatment of severe insomnia. Brotizolam is a highly potent and short-acting hypnotic, with a typical dose ranging from 0.125 to 0.25 milligrams, which is rapidly eliminated with an average half-life of 4.4 hours.

<span class="mw-page-title-main">Rilmazafone</span> Chemical compound

Rilmazafone is a water-soluble prodrug developed in Japan. Once metabolized, rilmazafone is converted into several benzodiazepine metabolites that have sedative and hypnotic effects. These metabolites induce impairment of motor function and have hypnotic properties.

<span class="mw-page-title-main">Ciclotizolam</span> Chemical compound

Ciclotizolam (WE-973) is a drug which is a thienotriazolodiazepine derivative. It is a partial agonist for the benzodiazepine site of the GABAA receptor, with similar binding affinity to related compounds like brotizolam, but a low efficacy.

<span class="mw-page-title-main">Pyrazolam</span> Benzodiazepine

Pyrazolam (SH-I-04) is a benzodiazepine derivative originally developed by a team led by Leo Sternbach at Hoffman-La Roche in the 1970s. It has since been "rediscovered" and sold as a designer drug since 2012.

<span class="mw-page-title-main">Clonazolam</span> Benzodiazepine derivative research chemical

Clonazolam is a drug of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. Little research has been done about its effects and metabolism, and is sold online as a designer drug.

<span class="mw-page-title-main">Flubromazolam</span> Triazolobenzodiazepine/Benzodiazepine derivative

Flubromazolam (JYI-73) is a triazolobenzodiazepine (TBZD), which are benzodiazepine (BZD) derivatives. Flubromazolam is reputed to be highly potent, and concerns have been raised that clonazolam and flubromazolam in particular may pose comparatively higher risks than other designer benzodiazepines, due to their ability to produce strong sedation and amnesia at oral doses of as little as 0.5 mg. Life-threatening adverse reactions have been observed at doses of only 3 mg of flubromazolam.

<span class="mw-page-title-main">Deschloroetizolam</span> Chemical compound

Deschloroetizolam is a thienotriazolodiazepine that is the dechlorinated analog of the closely related etizolam. The compound has been sold as a designer drug.

<span class="mw-page-title-main">Nifoxipam</span> Chemical compound

Nifoxipam is a benzodiazepine that is a minor metabolite of flunitrazepam and has been sold online as a designer drug.

<span class="mw-page-title-main">Desmethylflunitrazepam</span> Chemical compound

Desmethylflunitrazepam (also known as norflunitrazepam, Ro05-4435 and fonazepam) is a benzodiazepine that is a metabolite of flunitrazepam and has been sold online as a designer drug. It has an IC50 value of 1.499 nM for the GABAA receptor.

<span class="mw-page-title-main">Thienotriazolodiazepine</span> Chemical compound

A thienotriazolodiazepine is a heterocyclic compound containing a diazepine ring fused to thiophene and triazole rings. Thienotriazolodiazepine forms the central core of several pharmaceutical drugs including:

<span class="mw-page-title-main">Nitrazolam</span> Chemical compound

Nitrazolam is a triazolobenzodiazepine (TBZD) , which are benzodiazepine (BZD) derivatives, that has been sold online as a designer drug.

<span class="mw-page-title-main">Cloniprazepam</span> Chemical compound

Cloniprazepam is a benzodiazepine derivative and a prodrug of clonazepam, 7-aminoclonazepam, and other metabolites.

<span class="mw-page-title-main">Fluclotizolam</span> Chemical compound

Fluclotizolam is a thienotriazolodiazepine derivative which was first synthesised in 1979, but was never marketed. It has subsequently been sold as a designer drug, first being definitively identified in 2017.

<span class="mw-page-title-main">Flubrotizolam</span> Thienotriazolodiazepine

Flubrotizolam is a thienotriazolodiazepine derivative with potent sedative and anxiolytic effects, which has been sold as a designer drug.

<span class="mw-page-title-main">Fluetizolam</span> Chemical compound

Fluetizolam is a thienotriazolodiazepine derivative with potent sedative and anxiolytic effects, which has been sold as a designer drug.

<span class="mw-page-title-main">Clotizolam</span> Chemical compound

Clotizolam (Ro11-1465) is a thienotriazolodiazepine derivative first invented in the 1970s, which in more recent years has been sold as a designer drug. As with other related thienotriazolodiazepines, it produces sedative, anxiolytic, anticonvulsant and muscle relaxant effects, and also acts as an inhibitor of platelet-activating factor (PAF).

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.
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