Nifoxipam

Nifoxipam (3-hydroxydesmethylflunitrazepam, DP 370) is a benzodiazepine that is a minor metabolite of flunitrazepam and has been sold online as a designer drug.[1][2][3][4][5][6][7][8][9]

Nifoxipam

Legal status
Legal status	CA: Schedule IV DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 5-(2-fluorophenyl)-3-hydroxy-7-nitro-2,3-dihydro-1H-1,4-benzodiazepin-2-one
CAS Number	74723-10-7
PubChem CID	3058221
ChemSpider	2319383
UNII	9O6C9M3CH6
CompTox Dashboard (EPA)	DTXSID80996250
Chemical and physical data
Formula	C15H10FN3O4
Molar mass	315.260 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C1C(O)N=C(C2=CC=CC=C2F)C3=CC([N+]([O-])=O)=CC=C3N1
InChI InChI=1S/C15H10FN3O4/c16-11-4-2-1-3-9(11)13-10-7-8(19(22)23)5-6-12(10)17-14(20)15(21)18-13/h1-7,15,21H,(H,17,20) Key:UHFIFTRHLBAWGY-UHFFFAOYSA-N

Nifoxipam produces strong tranquillising and sleep-prolonging effects and has much lower toxicity compared to lormetazepam and flunitrazepam in mice.[1]

See also

• List of benzodiazepine designer drugs
• Nitrazolam
• Nitemazepam
• Phenazepam

References

1. EP 0158267, Posselt K, Wagener HH, Gruber K,, "Pharmaceutical composition containing 5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-7-nitro- or 5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-7-nitro-2H-1,4-benzodiazepin-2-one and process for their preparation", published 16 October 1985, assigned to Dolorgiet Beteiligungs-GmbH
2. "Nifoxipam". New Synthetic Drugs Database.
3. Kilicarslan T, Haining RL, Rettie AE, Busto U, Tyndale RF, Sellers EM (April 2001). "Flunitrazepam metabolism by cytochrome P450S 2C19 and 3A4". Drug Metabolism and Disposition. 29 (4 Pt 1): 460–5. PMID 11259331.
4. Moosmann B, King LA, Auwärter V (June 2015). "Designer benzodiazepines: A new challenge". World Psychiatry. 14 (2): 248. doi:10.1002/wps.20236. PMC 4471986. PMID 26043347.
5. Kevin Flemen (August 2015). "Drug Facts - Newer Unregulated Drugs" (PDF). KFx. Retrieved 15 August 2015.
6. "Nifoxipam". WEDINOS.
7. Meyer MR, Bergstrand MP, Helander A, Beck O (May 2016). "Identification of main human urinary metabolites of the designer nitrobenzodiazepines clonazolam, meclonazepam, and nifoxipam by nano-liquid chromatography-high-resolution mass spectrometry for drug testing purposes". Analytical and Bioanalytical Chemistry. 408 (13): 3571–91. doi:10.1007/s00216-016-9439-6. PMID 27071765. S2CID 25831532.
8. 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.
9. Katselou M, Papoutsis I, Nikolaou P, Spiliopoulou C, Athanaselis S (2016). "Metabolites replace the parent drug in the drug arena. The cases of fonazepam and nifoxipam". Forensic Toxicology. 35 (1): 1–10. doi:10.1007/s11419-016-0338-5. PMC 5214877. PMID 28127407.