Deschloroetizolam

Last updated

Deschloroetizolam
Deschloroetizolam.svg
Deschloroetizolam.png
Clinical data
Dependence
liability
Moderate
Routes of
administration
Oral, sublingual, rectal
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class C
  • Illegal in Sweden
Identifiers
  • 4-phenyl-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H16N4S
Molar mass 308.40 g·mol−1
3D model (JSmol)
  • CCC1=CC2=C(S1)N3C(=NN=C3CN=C2C4=CC=CC=C4)C
  • InChI=1S/C17H16N4S/c1-3-13-9-14-16(12-7-5-4-6-8-12)18-10-15-20-19-11(2)21(15)17(14)22-13/h4-9H,3,10H2,1-2H3
  • Key:JIOBORXCOGMHSV-UHFFFAOYSA-N

Deschloroetizolam (also known as Etizolam-2) is a thienotriazolodiazepine that is the dechlorinated analog of the closely related etizolam. [1] [2] [3] The compound has been sold as a designer drug. [4] [5] [6] [7]

Contents

Deschloroetizolam is classified and controlled as a hazardous substance in Sweden as of on October 15, 2015. [8]

Deschloroetizolam was made schedule I at the state level in Alabama on July 15th, 2024. [9]

See also

Related Research Articles

<span class="mw-page-title-main">Etizolam</span> Benzodiazepine analog drug

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 The etizolam molecule differs from a benzodiazepine in that the benzene ring has been replaced by a thiophene ring and triazole ring has been fused, making the drug a thienotriazolodiazepine.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">Phenazepam</span> Benzodiazepine drug

Phenazepam is a benzodiazepine drug, first developed in the Soviet Union in 1975, and now produced in Russia and several other countries.

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

Meclonazepam ((S)-3-methylclonazepam) was discovered by a team at Hoffmann-La Roche in the 1970s and is a drug which is a benzodiazepine derivative similar in structure to clonazepam. It has sedative and anxiolytic actions like those of other benzodiazepines, and also has anti-parasitic effects against the parasitic worm Schistosoma mansoni.

<span class="mw-page-title-main">Ro5-4864</span> Chemical compound

Ro5-4864 (4'-chlorodiazepam) is a drug which is a benzodiazepine derivative of diazepam. However unlike most benzodiazepine derivatives, Ro5-4864 lacks affinity for GABAA receptors and lacks typical benzodiazepine effects, instead being sedative yet also convulsant and anxiogenic in effects. Ro5-4864 was found to be a potent ligand for the "peripheral benzodiazepine receptor", later renamed to mitochondrial translocator protein 18kDa (TSPO). Despite its convulsant effects, at lower doses Ro5-4864 has proved to be neuroprotective and has become widely used for research into the role of the TSPO protein in neurotoxicity. In vitro studies and rodent models also suggest the possibility of analgesic, antidepressant, cardioprotective, and anti-cancer effects.

<i>N</i>-Desalkylflurazepam Benzodiazepine analog

N-Desalkylflurazepam is a benzodiazepine analog and an active metabolite of several other benzodiazepine drugs including flurazepam, flutoprazepam, fludiazepam, midazolam, flutazolam, quazepam, and ethyl loflazepate. It is long-acting, prone to accumulation, and binds unselectively to the various benzodiazepine receptor subtypes. It has been sold as a designer drug from 2016 onward.

<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">Diclazepam</span> Benzodiazepine medication

Diclazepam (Ro5-3448), also known as chlorodiazepam and 2'-chloro-diazepam, is a benzodiazepine and functional analog of diazepam. It was first synthesized by Leo Sternbach and his team at Hoffman-La Roche in 1960. It is not currently approved for use as a medication, but rather sold as an unscheduled substance. Efficacy and safety have not been tested in humans.

<span class="mw-page-title-main">Flubromazepam</span> Benzodiazepine designer drug

Flubromazepam is a benzodiazepine derivative which was first synthesized in 1960, but was never marketed and did not receive any further attention or study until late 2012 when it appeared on the grey market as a novel designer drug.

<span class="mw-page-title-main">3-Hydroxyphenazepam</span> Benzodiazepine medication

3-Hydroxyphenazepam is a benzodiazepine with hypnotic, sedative, anxiolytic, and anticonvulsant properties. It is an active metabolite of phenazepam, as well as the active metabolite of the benzodiazepine prodrug cinazepam. Relative to phenazepam, 3-hydroxyphenazepam has diminished myorelaxant properties, but is about equivalent in most other regards. Like other benzodiazepines, 3-hydroxyphenazepam behaves as a positive allosteric modulator of the benzodiazepine site of the GABAA receptor with an EC50 value of 10.3 nM. It has been sold online as a designer drug.

<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. Although little research has been done about its effects and metabolism, it is sold online as a designer drug.

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

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">Metizolam</span> Chemical compound

Metizolam is a thienotriazolodiazepine that is the demethylated analogue of the closely related etizolam.

<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">Bromazolam</span> Triazolobenzodiazepine

Bromazolam (XLI-268) is a triazolobenzodiazepine (TBZD) which was first synthesised in 1976, but was never marketed. It has subsequently been sold as a designer drug, first being definitively identified by the EMCDDA in Sweden in 2016. It is the bromo instead of chloro analogue of alprazolam and has similar sedative and anxiolytic effects to it and other benzodiazepines. Bromazolam is a non subtype selective agonist at the benzodiazepine site of GABAA receptors, with a binding affinity of 2.81 nM at the α1 subtype, 0.69 nM at α2 and 0.62 nM at α5. The "common" dosage range for users of bromazolam was reported to be 1–2 mg, suggesting its potency is similar to alprazolam.

<span class="mw-page-title-main">Flualprazolam</span> Triazolobenzodiazepine drug

Flualprazolam is a tranquilizer of the triazolobenzodiazepine (TBZD) class, which are benzodiazepines (BZDs) fused with a triazole ring. It was first synthesised in 1976, but was never marketed. It can be seen as the triazolo version of fludiazepam. It has subsequently been sold as a designer drug, first being definitively identified as such in Sweden in 2018. It can be described as the 2'-fluoro derivative of alprazolam or the fluoro instead of chloro analogue of triazolam, and has similar sedative and anxiolytic effects.

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

Difludiazepam (Ro07-4065) is a benzodiazepine derivative which is the 2',6'-difluoro derivative of fludiazepam. It was invented in the 1970s but was never marketed, and has been used as a research tool to help determine the shape and function of the GABAA receptors, at which it has an IC50 of 4.1nM. Difludiazepam has subsequently been sold as a designer drug, and was first notified to the EMCDDA by Swedish authorities in 2017.

<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.

References

  1. Weber KH, Bauer A, Langbein A, Daniel H (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.
  2. US 3904641,Nakanishi M, Tahara T, Araki K, Shiroki M,"Triazolothienodiazepine compounds",published 1975-09-09, assigned to Yoshitomi Pharmaceutical Industries, Ltd.
  3. EP 0776892,Hiroshi K, Syuji E, Hideaki S, Minoru M, Kenichi O,"Thienylazole compound and thienotriazolodiazepine compound",published 4 June 1997, assigned to Yoshitomi Pharmaceutical Industries, Ltd.
  4. "Deschloroetizolam". New Synthetic Drugs Database. 9 November 2023.
  5. Pettersson Bergstrand M, Helander A, Hansson T, Beck O (April 2017). "Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays". Drug Testing and Analysis. 9 (4): 640–645. doi:10.1002/dta.2003. PMID   27366870.
  6. Manchester KR, Maskell PD, Waters L (March 2018). "Experimental versus theoretical log D7.4 , pKa and plasma protein binding values for benzodiazepines appearing as new psychoactive substances". Drug Testing and Analysis. 10 (8): 1258–1269. doi:10.1002/dta.2387. PMID   29582576. S2CID   31098917.
  7. Manchester KR, Waters L, Haider S, Maskell PD (July 2022). "The blood-to-plasma ratio and predicted GABAA-binding affinity of designer benzodiazepines". Forensic Toxicology. 40 (2): 349–356. doi:10.1007/s11419-022-00616-y. PMC   9715504 . PMID   36454409. S2CID   247455284.
  8. "Nya substanser klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. 18 August 2015.
  9. https://www.alabamapublichealth.gov/blog/assets/controlledsubstanceslist.pdf [ bare URL PDF ]