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3-Hydroxyphenazepam

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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
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC15H10BrClN2O2
Molar mass365.61g·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

3-Hydroxyphenazepamis abenzodiazepinewithhypnotic,sedative,anxiolytic,andanticonvulsantproperties.[1]It is anactive metaboliteofphenazepam,[1][2]as well as the active metabolite of the benzodiazepineprodrugcinazepam.[3]Relative to phenazepam, 3-hydroxyphenazepam has diminishedmyorelaxantproperties, but is about equivalent in most other regards.[1]Like other benzodiazepines, 3-hydroxyphenazepam behaves as apositive allosteric modulatorof thebenzodiazepine siteof theGABAAreceptorwith an EC50value of 10.3 nM.[4][5][6]It has been sold online as adesigner drug.[7][8][9][10]

See also[edit]

References[edit]

  1. ^abcValdman AV, ed. (31 May 1986).Drug dependence and emotional behavior: neurophysiological and neurochemical approaches.Consultants Bureau.ISBN978-0-306-10984-3.
  2. ^Komsta L, Waksmundzka-Hajnos M, Sherma J, eds. (20 December 2013).Thin Layer Chromatography in Drug Analysis.CRC Press. pp. 299–.ISBN978-1-4665-0715-9.
  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.PMID22180351.S2CID4744087.
  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.ISSN0090-2977.S2CID32313668.
  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.ISSN0090-2977.S2CID33732669.
  7. ^"3-hydroxyphenazepam".New Synthetic Drugs Database. Archived fromthe originalon 2016-09-28.Retrieved2016-05-30.
  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.PMID27366870.
  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.PMID27535017.
  10. ^Manchester KR, Maskell PD, Waters L (March 2018)."Experimental versus theoretical log D7.4,pKaand plasma protein binding values for benzodiazepines appearing as new psychoactive substances ".Drug Testing and Analysis.10(8): 1258–1269.doi:10.1002/dta.2387.PMID29582576.S2CID31098917.
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