Nifoxipam

Nifoxipam
Legal status
Legal status	AU: Unscheduled; BR: Class B1 (Psychoactive drugs); CA: Schedule IV; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act; US: Unscheduled; UN: Unscheduled; In general legal for medical and research uses.;
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 (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 produces strong tranquillising and sleep-prolonging effects and has much lower toxicity compared to lormetazepam and flunitrazepam in mice.^[1]

References

^ ^a ^b 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
^ "Nifoxipam". New Synthetic Drugs Database. Archived from the original on 2016-11-01. Retrieved 2016-07-08.
^ 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.
^ 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.
^ Kevin Flemen (August 2015). "Drug Facts - Newer Unregulated Drugs" (PDF). KFx. Retrieved 15 August 2015.
^ "Nifoxipam". WEDINOS.
^ 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.
^ 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.
^ 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.

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[Kosselt_1985-1] 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. Archived from the original on 2016-11-01. Retrieved 2016-07-08.

[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.

[MoosmannKing2015-4] 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.

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Legal status


Legal status	AU: Unscheduled BR: Class B1 (Psychoactive drugs) CA: Schedule IV DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act US: Unscheduled UN: Unscheduled In general legal for medical and research uses.
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

See also

References