| 词条 | 3-Hydroxyphenazepam |
| 释义 |
| IUPAC_name = 7-Bromo-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one | image = 3-Hydroxyphenazepam.svg | width = 222 | image2 = 3-Hydroxyphenazepam ball-and-stick model.png | CAS_number = 70030-11-4 | ATC_prefix = None | ATC_suffix = | PubChem = 125820 | DrugBank = | ChemSpiderID = 111897 | C=15 | H=10 | Br=1 | Cl=1 | N=2 | O=2 | molecular_weight = 365.609 g/mol | smiles = c1ccc(c(c1)C2=NC(C(=O)Nc3c2cc(cc3)Br)O)Cl | StdInChI = 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) | StdInChIKey = KRJKJUWAZOWXNV-UHFFFAOYSA-N | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = Schedule IV | legal_UK = | legal_US = | legal_status = | routes_of_administration = }}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 online as a designer drug.[7][8][9][10] See also
References1. ^1 2 {{cite book|author=Artur Viktorovich Valʹdman|title=Drug dependence and emotional behavior: neurophysiological and neurochemical approaches|url=https://books.google.com/books?id=GiNtAAAAMAAJ|date=31 May 1986|publisher=Consultants Bureau|isbn=978-0-306-10984-3}} {{Benzodiazepines}}{{GABAAR PAMs}}{{DEFAULTSORT:Hydroxyphenazepam, 3-}}{{sedative-stub}}2. ^{{cite book|author1=Lukasz Komsta|author2=Monika Waksmundzka-Hajnos|author3=Joseph Sherma|title=Thin Layer Chromatography in Drug Analysis|url=https://books.google.com/books?id=LSEtAgAAQBAJ&pg=PA299|date=20 December 2013|publisher=CRC Press|isbn=978-1-4665-0715-9|pages=299–}} 3. ^{{cite journal |vauthors=Schukin SI, Zinkovsky VG, Zhuk OV | title = Elimination kinetics of the novel prodrug cinazepam possessing psychotropic activity in mice | journal = Pharmacol Rep | volume = 63 | issue = 5 | pages = 1093–100 | year = 2011 | pmid = 22180351 | doi = 10.1016/s1734-1140(11)70628-4| url = http://www.if-pan.krakow.pl/pjp/pdf/2011/5_1093.pdf}} 4. ^{{cite web | url=http://www.who.int/medicines/access/controlled-substances/5.8_Phenazepam_PreRev.pdf | title=Phenazepam Pre-Review Report | publisher=World Health Organisation (WHO) | date=November 2015}} 5. ^{{cite journal|last1=Kopanitsa|first1=M. V.|last2=Zbarska|first2=S. M.|last3=Boychuk|first3=Ya. A.|last4=Krishtal|first4=O. A.|title=Modulation of GABA-activated currents by phenazepam and its metabolites in isolated rat purkinje neurons|journal=Neurophysiology|volume=32|issue=3|year=2000|pages=192|issn=0090-2977|doi=10.1007/BF02506568}} 6. ^{{cite journal|last1=Golovenko|first1=N. Ya|last2=Larionov|first2=V. B.|title=Pharmacodynamical and Neuroreceptor Analysis of the Permeability of the Blood-Brain Barrier for Derivatives of 1,4-Benzodiazepine|journal=Neurophysiology|volume=46|issue=3|year=2014|pages=199–205|issn=0090-2977|doi=10.1007/s11062-014-9429-2}} 7. ^{{cite web | url=http://nsddb.eu/substance/589/ | title=3-hydroxyphenazepam | publisher=New Synthetic Drugs Database}} 8. ^{{cite journal | title=Detectability of designer benzodiazepines in CEDIA, EMIT II Plus, HEIA, and KIMS II immunochemical screening assays | author=Madeleine Pettersson Bergstrand |author2=Anders Helander |author3=Therese Hansson |author4=Olof Beck | journal=Drug Testing and Analysis |volume = 9| issue=4 | pages=640–645 | date=2016 | doi=10.1002/dta.2003 | pmid=27366870}} 9. ^{{cite journal|first1=Bjoern|last1=Moosmann|first2=Philippe|last2=Bisel|first3=Florian|last3=Franz|first4=Laura M.|last4=Huppertz|title=Characterization and in vitro phase I microsomal metabolism of designer benzodiazepines – an update comprising adinazolam, cloniprazepam, fonazepam, 3-hydroxyphenazepam, metizolam, and nitrazolam|journal=Journal of Mass Spectrometry|date=2016|issn=1096-9888|volume=51|issue=11|pages=1080–1089|doi=10.1002/jms.3840|pmid=27535017|first5=Volker|last5=Auwärter}} 10. ^{{cite journal|first1=Kieran R.|last1=Manchester|first2=Peter D.|last2=Maskell|first3=Laura|last3=Waters|title=Experimental versus theoretical log D7.4, pKa and plasma protein binding values for benzodiazepines appearing as new psychoactive substances|journal=Drug Testing and Analysis|volume=10|issue=8|pages=1258–1269|issn=1942-7611|doi=10.1002/dta.2387|pmid=29582576|date=2018}} 10 : Hypnotics|Anticonvulsants|Sedatives|Anxiolytics|Benzodiazepines|GABAA receptor positive allosteric modulators|Chloroarenes|Bromoarenes|Human drug metabolites|Designer drugs |
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