3-Hydroxyphenazepam Explained

3-Hydroxyphenazepam is a benzodiazepine with hypnotic, sedative, anxiolytic, and anticonvulsant properties.^[1] It is an active metabolite of phenazepam,^[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. Like other benzodiazepines, 3-hydroxyphenazepam behaves as a positive allosteric modulator of the benzodiazepine site of the GABA_A receptor with an EC₅₀ value of 10.3 nM.^{[4] [5] [6]} It has been sold online as a designer drug.^{[7] [8] [9] [10]}

See also

• Lorazepam, licensed medication
• Nifoxipam
• Nitemazepam

Notes and References

1. Book: Valdman AV . Drug dependence and emotional behavior: neurophysiological and neurochemical approaches. 31 May 1986. Consultants Bureau. 978-0-306-10984-3.
2. Book: Komsta L, Waksmundzka-Hajnos M, Sherma J . Thin Layer Chromatography in Drug Analysis. 20 December 2013. CRC Press. 978-1-4665-0715-9. 299–.
3. Schukin SI, Zinkovsky VG, Zhuk OV . Elimination kinetics of the novel prodrug cinazepam possessing psychotropic activity in mice . Pharmacological Reports . 63 . 5 . 1093–1100 . 2011 . 22180351 . 10.1016/s1734-1140(11)70628-4 . 4744087 .
4. Web site: Phenazepam Pre-Review Report . World Health Organization (WHO) . November 2015.
5. Kopanitsa MV, Zbarska SM, Boychuk YA, Krishtal OA . Modulation of GABA-activated currents by phenazepam and its metabolites in isolated rat purkinje neurons. Neurophysiology. 32. 3. 2000. 192. 0090-2977. 10.1007/BF02506568. 32313668.
6. Golovenko NY, Larionov VB . Pharmacodynamical and Neuroreceptor Analysis of the Permeability of the Blood-Brain Barrier for Derivatives of 1,4-Benzodiazepine. Neurophysiology. 46. 3. 2014. 199–205. 0090-2977. 10.1007/s11062-014-9429-2. 33732669.
7. Web site: 3-hydroxyphenazepam . New Synthetic Drugs Database . 2016-05-30 . https://web.archive.org/web/20160928192828/http://nsddb.eu/substance/589/ . 2016-09-28 . dead .
8. Pettersson Bergstrand M, Helander A, Hansson T, Beck O . Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays . Drug Testing and Analysis . 9 . 4 . 640–645 . April 2017 . 27366870 . 10.1002/dta.2003 .
9. Moosmann B, Bisel P, Franz F, Huppertz LM, Auwärter V . 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 . November 2016 . 27535017 . 10.1002/jms.3840 . 2016JMSp...51.1080M .
10. Manchester KR, Maskell PD, Waters L . Experimental versus theoretical log D_7.4, pK_a and plasma protein binding values for benzodiazepines appearing as new psychoactive substances . Drug Testing and Analysis . 10 . 8 . 1258–1269 . March 2018 . 29582576 . 10.1002/dta.2387 . 31098917 .