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3-Hydroxyphenazepam

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3-Hydroxyphenazepam is a benzodiazepine with hypnotic, sedative, anxiolytic, and anticonvulsant properties.[1] It is an active metabolite of phenazepam,[1][2] as well as the active metabolite of the benzodiazepine prodrug cinazepam.[3] Relative to phenazepam, 3-hydroxyphenazepam has diminished myorelaxant properties, but is about equivalent in most other regards.[1] Like other benzodiazepines, 3-hydroxyphenazepam behaves as a positive allosteric modulator of the benzodiazepine site of the GABAA receptor with an EC50 value of 10.3 nM.[4][5][6] It has been sold as a designer drug.[7][8][9][10]

3-Hydroxyphenazepam
Clinical data
ATC code
  • None
Legal status
Legal status
Identifiers
  • 7-Bromo-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H10BrClN2O2
Molar mass365.61 g·mol−1
3D model (JSmol)
  • c1ccc(c(c1)C2=NC(C(=O)Nc3c2cc(cc3)Br)O)Cl
  • InChI=1S/C15H10BrClN2O2/c16-8-5-6-12-10(7-8)13(19-15(21)14(20)18-12)9-3-1-2-4-11(9)17/h1-7,15,21H,(H,18,20)
  • Key:KRJKJUWAZOWXNV-UHFFFAOYSA-N

See also

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References

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  1. ^ a b c Valdman AV, ed. (31 May 1986). Drug dependence and emotional behavior: neurophysiological and neurochemical approaches. Consultants Bureau. ISBN 978-0-306-10984-3.
  2. ^ Komsta L, Waksmundzka-Hajnos M, Sherma J, eds. (20 December 2013). Thin Layer Chromatography in Drug Analysis. CRC Press. pp. 299–. ISBN 978-1-4665-0715-9.
  3. ^ Schukin SI, Zinkovsky VG, Zhuk OV (2011). "Elimination kinetics of the novel prodrug cinazepam possessing psychotropic activity in mice". Pharmacological Reports. 63 (5): 1093–1100. doi:10.1016/s1734-1140(11)70628-4. PMID 22180351. S2CID 4744087.
  4. ^ "Phenazepam Pre-Review Report" (PDF). World Health Organization (WHO). November 2015.
  5. ^ Kopanitsa MV, Zbarska SM, Boychuk YA, Krishtal OA (2000). "Modulation of GABA-activated currents by phenazepam and its metabolites in isolated rat purkinje neurons". Neurophysiology. 32 (3): 192. doi:10.1007/BF02506568. ISSN 0090-2977. S2CID 32313668.
  6. ^ Golovenko NY, Larionov VB (2014). "Pharmacodynamical and Neuroreceptor Analysis of the Permeability of the Blood-Brain Barrier for Derivatives of 1,4-Benzodiazepine". Neurophysiology. 46 (3): 199–205. doi:10.1007/s11062-014-9429-2. ISSN 0090-2977. S2CID 33732669.
  7. ^ "3-hydroxyphenazepam". New Synthetic Drugs Database. Archived from the original on 2016-09-28. Retrieved 2016-05-30.
  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. ^ Moosmann B, Bisel P, Franz F, Huppertz LM, Auwärter V (November 2016). "Characterization and in vitro phase I microsomal metabolism of designer benzodiazepines - an update comprising adinazolam, cloniprazepam, fonazepam, 3-hydroxyphenazepam, metizolam and nitrazolam". Journal of Mass Spectrometry. 51 (11): 1080–1089. Bibcode:2016JMSp...51.1080M. doi:10.1002/jms.3840. PMID 27535017.
  10. ^ Manchester KR, Maskell PD, Waters L (March 2018). "Experimental versus theoretical log D7.4 , pKa and plasma protein binding values for benzodiazepines appearing as new psychoactive substances". Drug Testing and Analysis. 10 (8): 1258–1269. doi:10.1002/dta.2387. PMID 29582576. S2CID 31098917.
 

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