3-Hydroxyphenazepam

3-Hydroxyphenazepam
Clinical data
ATC code	None;
Legal status
Legal status	CA: Schedule IV; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name 7-Bromo-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-2H-1,4-benzodiazepin-2-one;
CAS Number	70030-11-4;
PubChem CID	125820;
ChemSpider	111897;
UNII	1KJ8MP77JK;
CompTox Dashboard (EPA)	DTXSID10990281 ;
Chemical and physical data
Formula	C15H10BrClN2O2
Molar mass	365.61 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1ccc(c(c1)C2=NC(C(=O)Nc3c2cc(cc3)Br)O)Cl;
	InChI 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-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 GABA_A receptor with an EC₅₀ value of 10.3 nM.^[4]^[5]^[6] It has been sold as a designer drug.^[7]^[8]^[9]^[10]