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. It is an active metabolite of phenazepam, as well as the active metabolite of the benzodiazepine prodrug cinazepam. 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. It has been sold online as a designer drug.

See also

• Lorazepam, licensed medication
• Nifoxipam
• Nitemazepam