Difludiazepam

Chemical compound
  • CA: Schedule IV
  • DE: NpSG (Industrial and scientific use only)
  • UK: Under Psychoactive Substances Act
Identifiers
  • 7-chloro-5-(2,6-difluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one
CAS Number
  • 39080-67-6 checkY
PubChem CID
  • 44366236
ChemSpider
  • 23222150
UNII
  • 7N3B9XEC7B
ChEMBL
  • ChEMBL346673
Chemical and physical dataFormulaC16H11ClF2N2OMolar mass320.72 g·mol−13D model (JSmol)
  • Interactive image
  • Fc3cccc(F)c3C2=NCC(=O)N(C)c1ccc(Cl)cc12
InChI
  • InChI=1S/C16H11ClF2N2O/c1-21-13-6-5-9(17)7-10(13)16(20-8-14(21)22)15-11(18)3-2-4-12(15)19/h2-7H,8H2,1H3
  • Key:DUNFPASORLTEGN-UHFFFAOYSA-N

Difludiazepam[1] (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.[2][3][4] Difludiazepam has subsequently been sold as a designer drug, and was first notified to the EMCDDA by Swedish authorities in 2017.[5][6]

See also

References

  1. ^ Maskell PD, Wilson NE. Designer Benzodiazepines: New Challenges and Treatment Options, in Corazza O, Roman-Urrestarazu. Handbook of Novel Psychoactive Substances: What Clinicians Should Know about NPS. Taylor & Francis, 2019. ISBN 978-1-138-06830-8
  2. ^ Winkler DA, Burden FR, Watkins AJ (January 1998). "Atomistic Topological Indices Applied to Benzodiazepines using Various Regression Methods". Quantitative Structure-Activity Relationships. 17 (1): 14–19. doi:10.1002/(SICI)1521-3838(199801)17:01<14::AID-QSAR14>3.0.CO;2-U.
  3. ^ So SS, Karplus M (December 1996). "Genetic neural networks for quantitative structure-activity relationships: improvements and application of benzodiazepine affinity for benzodiazepine/GABAA receptors". Journal of Medicinal Chemistry. 39 (26): 5246–5256. doi:10.1021/jm960536o. PMID 8978853.
  4. ^ Maddalena DJ, Johnston GA (February 1995). "Prediction of receptor properties and binding affinity of ligands to benzodiazepine/GABAA receptors using artificial neural networks". Journal of Medicinal Chemistry. 38 (4): 715–724. doi:10.1021/jm00004a017. PMID 7861419.
  5. ^ Europol 2017 Annual Report on the implementation of Council Decision 2005/387/JHA (PDF). Lisbon, Portugal: European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) and Europol. 2018. ISBN 978-92-9497-348-1.
  6. ^ 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.
  • v
  • t
  • e
1,4-Benzodiazepines
1,5-Benzodiazepines2,3-Benzodiazepines*TriazolobenzodiazepinesImidazobenzodiazepinesOxazolobenzodiazepinesThienodiazepinesThienotriazolodiazepinesThienobenzodiazepines*PyridodiazepinesPyridotriazolodiazepinesPyrazolodiazepinesPyrrolodiazepinesTetrahydroisoquinobenzodiazepinesPyrrolobenzodiazepines*Benzodiazepine prodrugs
* atypical activity profile (not GABAA receptor ligands)
  • v
  • t
  • e
GABAA receptor positive modulators
Alcohols
Barbiturates
Benzodiazepines
Carbamates
Flavonoids
Imidazoles
Kava constituents
  • 10-Methoxyyangonin
  • 11-Methoxyyangonin
  • 11-Hydroxyyangonin
  • Desmethoxyyangonin
  • 11-Methoxy-12-hydroxydehydrokavain
  • 7,8-Dihydroyangonin
  • Kavain
  • 5-Hydroxykavain
  • 5,6-Dihydroyangonin
  • 7,8-Dihydrokavain
  • 5,6,7,8-Tetrahydroyangonin
  • 5,6-Dehydromethysticin
  • Methysticin
  • 7,8-Dihydromethysticin
  • Yangonin
Monoureides
Neuroactive steroids
Nonbenzodiazepines
Phenols
Piperidinediones
Pyrazolopyridines
Quinazolinones
Volatiles/gases
Others/unsorted
  • Unsorted benzodiazepine site positive modulators: α-Pinene
  • MRK-409 (MK-0343)
  • TCS-1105
  • TCS-1205
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators