Difludiazepam

Difludiazepam
Legal status
Legal status	CA: Schedule IV; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name 7-chloro-5-(2,6-difluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one;
CAS Number	39080-67-6 ;
PubChem CID	44366236;
ChemSpider	23222150;
UNII	7N3B9XEC7B;
ChEMBL	ChEMBL346673;
CompTox Dashboard (EPA)	DTXSID001135292 ;
Chemical and physical data
Formula	C16H11ClF2N2O
Molar mass	320.72 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 GABA_A 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]

References

^ 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
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[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.

[pmid36454409-6] 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.

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Legal status

Legal status	CA: Schedule IV DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 7-chloro-5-(2,6-difluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one
CAS Number	39080-67-6^Y
PubChem CID	44366236
ChemSpider	23222150
UNII	7N3B9XEC7B
ChEMBL	ChEMBL346673
CompTox Dashboard (EPA)	DTXSID001135292
Chemical and physical data
Formula	C₁₆H₁₁ClF₂N₂O
Molar mass	320.72 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES 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

See also

References