N-Desalkylflurazepam

N-Desalkylflurazepam (also known as norflurazepam) is a benzodiazepine analog and an active metabolite of several other benzodiazepine drugs including flurazepam,^[2] flutoprazepam,^[3] fludiazepam,^[4] midazolam,^[5] flutazolam,^[6] quazepam,^[7] and ethyl loflazepate.^[8][9] It is long-acting, prone to accumulation, and binds unselectively to the various benzodiazepine receptor subtypes.^[7] It has been sold as a designer drug from 2016 onward.^[10]

N-Desalkylflurazepam

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-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one
CAS Number	2886-65-9
PubChem CID	4540
ChemSpider	4381
UNII	X9U41NXR6M
ChEMBL	ChEMBL974
CompTox Dashboard (EPA)	DTXSID30183057
ECHA InfoCard	100.018.863
Chemical and physical data
Formula	C15H10ClFN2O
Molar mass	288.71 g·mol−1
3D model (JSmol)	Interactive image
Melting point	205 to 206 °C (401 to 403 °F) [1]
SMILES Fc1ccccc1C2=NCC(=O)Nc3ccc(Cl)cc23

References

1. SciFinder record for CAS#2886-65-9
2. Riva R, de Anna M, Albani F, Baruzzi A (March 1981). "Rapid quantitation of flurazepam and its major metabolite, N-desalkylflurazepam, in human plasma by gas-liquid chromatography with electron-capture detection". Journal of Chromatography. 222 (3): 491–5. doi:10.1016/S0378-4347(00)84153-5. PMID 7228960.
3. Barzaghi N, Leone L, Monteleone M, Tomasini G, Perucca E (1989). "Pharmacokinetics of flutoprazepam, a novel benzodiazepine drug, in normal subjects". European Journal of Drug Metabolism and Pharmacokinetics. 14 (4): 293–8. doi:10.1007/bf03190114. PMID 2633923. S2CID 20710732.
4. Descotes J, ed. (December 1996). Human Toxicology (1st ed.). Elsevier Science. p. 43.
5. Vogt S, Kempf J, Buttler J, Auwärter V, Weinmann W (2013). "Desalkylflurazepam found in patients' samples after high-dose midazolam treatment". Drug Testing and Analysis. 5 (9–10): 745–7. doi:10.1002/dta.1484. PMID 23713025.
6. Miyaguchi H, Kuwayama K, Tsujikawa K, Kanamori T, Iwata YT, Inoue H, Kishi T (February 2006). "A method for screening for various sedative-hypnotics in serum by liquid chromatography/single quadrupole mass spectrometry". Forensic Science International. 157 (1): 57–70. doi:10.1016/j.forsciint.2005.03.011. PMID 15869852.
7. Nikaido AM, Ellinwood EH (1987). "Comparison of the effects of quazepam and triazolam on cognitive-neuromotor performance". Psychopharmacology. 92 (4): 459–64. doi:10.1007/bf00176478. PMID 2888152. S2CID 13162524.
8. Ba BB, Iliadis A, Cano JP (1989). "Pharmacokinetic modeling of ethyl loflazepate (Victan) and its main active metabolites". Annals of Biomedical Engineering. 17 (6): 633–46. doi:10.1007/bf02367467. PMID 2574017. S2CID 31310535.
9. Davi H, Guyonnet J, Necciari J, Cautreels W (July 1985). "Determination of circulating ethyl loflazepate metabolites in the baboon by radio-high-performance liquid chromatography with injection of crude plasma samples: comparison with solvent extraction and thin-layer chromatography". Journal of Chromatography. 342 (1): 159–65. doi:10.1016/S0378-4347(00)84498-9. PMID 2864352.
10. Manchester KR, Maskell PD, Waters L (March 2018). "a and plasma protein binding values for benzodiazepines appearing as new psychoactive substances" (PDF). Drug Testing and Analysis. 10 (8): 1258–1269. doi:10.1002/dta.2387. PMID 29582576.