7-Aminoflunitrazepam

7-Aminoflunitrazepam
Names
IUPAC name
7-Amino-5-(2-fluorophenyl)-1-methyl-3H-1,4-benzodiazepin-2-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.218.190
EC Number
  • 690-803-8
UNII
  • InChI=1S/C16H14FN3O/c1-20-14-7-6-10(18)8-12(14)16(19-9-15(20)21)11-4-2-3-5-13(11)17/h2-8H,9,18H2,1H3
    Key: LTCDLGUFORGHGY-UHFFFAOYSA-N
  • CN1C(=O)CN=C(C2=C1C=CC(=C2)N)C3=CC=CC=C3F
Properties
C16H14FN3O
Molar mass 283.306 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

7-Aminoflunitrazepam is a benzodiazepine and a major metabolite of the drug flunitrazepam.[1]

Pharmacology

While it possesses the core benzodiazepine structure like its parent drug flunitrazepam, it is generally regarded as being inactive,[2] with an assay determining it to have an IC50 value of 15381.5 μM at GABAA receptors.[3] As a reference, the more potent parent drug flunitrazepam displaces diazepam binding with an IC50 quantified as 0.001700 μM.[4]

Pharmacokinetics

The presence of 7-aminoflunitrazepam can be detected for up to 4 weeks in urine.[5] Detection in oral fluid is also possible, but for considerably less time than in urine.[6]

Use

Due to being relatively inactive and a metabolite of flunitrazepam, it is usually instead used as a biomarker to confirm flunitrazepam poisoning/intoxication.[7] Due to benzodiazepines, notably flunitrazepam, being frequently used as drugs to facilitate sexual assault, testing for the presence of flunitrazepam metabolites can be important steps in sexual assault investigations, where it is suspected that a drug has been used to facilitate the crime.[8][9][10]

References

  1. ^ Feely, J.; Kavanagh, P. V.; McNamara, S. M. (1999). "The detection and quantitation of 7-aminoflunitrazepam, the major urinary metabolite of flunitrazepam, by gas chromatography/mass spectrometry". Irish Journal of Medical Science. 168 (3): 189–192. doi:10.1007/BF02945851. PMID 10540786.
  2. ^ Bylund, David B. (2017). "Flunitrazepam". Reference Module in Biomedical Sciences. doi:10.1016/B978-0-12-801238-3.98271-0. ISBN 978-0-12-801238-3.
  3. ^ "AID 40995 - Binding affinity towards benzodiazepine/GABA A receptor. - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-02.
  4. ^ "AID 40826 - Inhibition of [3H]diazepam binding to GABA-A benzodiazepine receptor of rat brain - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-02.
  5. ^ Verstraete, Alain G. (April 2004). "Detection times of drugs of abuse in blood, urine, and oral fluid". Therapeutic Drug Monitoring. 26 (2): 200–205. doi:10.1097/00007691-200404000-00020. PMID 15228165.
  6. ^ Samyn, Nele; De Boeck, Gert; Cirimele, Vincent; Verstraete, Alain; Kintz, Pascal (2002). "Detection of flunitrazepam and 7-aminoflunitrazepam in oral fluid after controlled administration of rohypnol". Journal of Analytical Toxicology. 26 (4): 211–215. doi:10.1093/jat/26.4.211. PMID 12054361.
  7. ^ "LOINC 105950-0 7-Aminoflunitrazepam [Presence] in Urine by Confirmatory method". LOINC. Retrieved 2026-01-02.
  8. ^ Negrusz, A.; Moore, C. M.; Hinkel, K. B.; Stockham, T. L.; Verma, M.; Strong, M. J.; Janicak, P. G. (September 2001). "Deposition of 7-aminoflunitrazepam and flunitrazepam in hair after a single dose of Rohypnol". Journal of Forensic Sciences. 46 (5): 1143–1151. doi:10.1520/JFS15113J. PMID 11569557.
  9. ^ Ohshima, T. (2006). "A case of drug-facilitated sexual assault by the use of flunitrazepam". Journal of Clinical Forensic Medicine. 13 (1): 44–45. doi:10.1016/j.jcfm.2005.05.006. PMID 16087387.
  10. ^ "Detection of "Date-Rape" Drugs in Hair and Urine, Final Report | National Institute of Justice". nij.ojp.gov. Retrieved 2026-01-02.
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