Diclazepam

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.[3] It is not currently approved for use as a medication, but rather sold as an unscheduled substance.[4][5][6][7] Efficacy and safety have not been tested in humans.

Diclazepam
Clinical data
Routes of
administration		Oral, sublingual
Legal status
Legal status
  • CA: Schedule IV
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class C
  • US: The DEA has announced intent to place Diclazepam under control in Schedule I. [1]
Pharmacokinetic data
Bioavailability?
MetabolismHepatic
Elimination half-life~42 hours[2]
ExcretionRenal
Identifiers
  • 7-Chloro-5-(2-chlorophenyl)-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H12Cl2N2O
Molar mass319.19 g·mol−1
3D model (JSmol)
  • CN1C2=C(C=C(C=C2)Cl)C(C3=C(Cl)C=CC=C3)=NCC1=O
  • InChI=1S/C16H12Cl2N2O/c1-20-14-7-6-10(17)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)18/h2-8H,9H2,1H3
  • Key:VPAYQWRBBOGGPY-UHFFFAOYSA-N
 NY (what is this?)  (verify)

In animal models, its effects are similar to diazepam, possessing long-acting anxiolytic, anticonvulsant, hypnotic, sedative, skeletal muscle relaxant, and amnestic properties.

Metabolism

Metabolism of this compound has been assessed,[2] revealing diclazepam has an approximate elimination half-life of 42 hours and undergoes N-demethylation to delorazepam, which can be detected in urine for 6 days following administration of the parent compound.[8] Other metabolites detected were lorazepam and lormetazepam which were detectable in urine for 19 and 11 days, respectively, indicating hydroxylation by cytochrome P450 enzymes occurring concurrently with N-demethylation.

United Kingdom

In the UK, diclazepam has been classified as a Class C drug by the May 2017 amendment to The Misuse of Drugs Act 1971 along with several other benzodiazepine drugs.[9]

United States

On the 23rd of December 2022, the Drug Enforcement Administration announced its intent to place Diclazepam into Schedule I.

See also

References
  1. "(Proposed Rule) Schedules of Controlled Substances: Temporary Placement of Etizolam, Flualprazolam, Clonazolam, Flubromazolam, and Diclazepam in Schedule I". Drug Enforcement Administration. December 23, 2022.
  2. Moosmann B, Bisel P, Auwärter V (July–August 2014). "Characterization of the designer benzodiazepine diclazepam and preliminary data on its metabolism and pharmacokinetics". Drug Testing and Analysis. 6 (7–8): 757–63. doi:10.1002/dta.1628. PMID 24604775.
  3. US 3136815, "Amino substituted benzophenone oximes and derivatives thereof"
  4. Madeleine Pettersson Bergstrand; Anders Helander; Therese Hansson; Olof Beck (2016). "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.
  5. Høiseth, Gudrun; Tuv, Silja Skogstad; Karinen, Ritva (2016). "Blood concentrations of new designer benzodiazepines in forensic cases". Forensic Science International. 268: 35–38. doi:10.1016/j.forsciint.2016.09.006. PMID 27685473.
  6. Manchester, Kieran R.; Maskell, Peter D.; Waters, Laura (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. ISSN 1942-7611. PMID 29582576.
  7. Manchester, Kieran R.; Waters, Laura; Haider, Shozeb; Maskell, Peter D. (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. ISSN 1860-8973. S2CID 247455284.
  8. Bareggi SR, Truci G, Leva S, Zecca L, Pirola R, Smirne S (1988). "Pharmacokinetics and bioavailability of intravenous and oral chlordesmethyldiazepam in humans". European Journal of Clinical Pharmacology. 34 (1): 109–112. doi:10.1007/bf01061430. PMID 2896126. S2CID 1574555.
  9. "The Misuse of Drugs Act 1971 (Amendment) Order 2017".
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