57435-86-6

Basic information

• Product Name: Premazepam
• Synonyms: Premazepam;3,7-Dihydro-6,7-dimethyl-5-phenylpyrrolo[3,4-e]-1,4-diazepin-2(1H)-one;MDL-181;Pyrrolo[3,4-e]-1,4-diazepin-2(1H)-one,3,7-dihydro-6,7-diMethyl-5-phenyl-;(Z)-6,7-dimethyl-5-phenylpyrrolo[3,4-e][1,4]diazepin-2(1H,3H,7H)-one;6,7-dimethyl-5-phenyl-1,3-dihydropyrrolo[3,4-e][1,4]diazepin-2-one
• CAS NO: 57435-86-6
• Molecular Formula: C15H15 N3 O
• Molecular Weight: 253.3
• Mol File: 57435-86-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 451.9°C at 760 mmHg
• Flash Point: 227.1°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 2.34E-08mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: Premazepam(CAS DataBase Reference)
• NIST Chemistry Reference: Premazepam(57435-86-6)
• EPA Substance Registry System: Premazepam(57435-86-6)

Safety Data

• Hazardous Substances Data: 57435-86-6(Hazardous Substances Data)

Usage

General Description

Premazepam is a benzodiazepine derivative medication that is primarily used for its anxiolytic, sedative, and hypnotic properties. It is a prodrug for the active metabolite desmethyldiazepam, which acts on the central nervous system to increase the inhibitory effects of the neurotransmitter gamma-aminobutyric acid (GABA). This leads to a reduction in symptoms of anxiety and promotes a state of relaxation and drowsiness. Premazepam is commonly prescribed for the short-term treatment of anxiety disorders and insomnia, but it is also used off-label for other conditions such as alcohol withdrawal and muscle spasms. It is typically administered in oral form, and its effects can last for several hours. However, prolonged use of premazepam can lead to tolerance, dependence, and withdrawal symptoms, and it carries a risk of abuse and addiction. Therefore, it is important to use this medication only as directed by a healthcare professional and to be aware of its potential for misuse.

InChI:InChI=1/C15H15N3O/c1-10-14-12(9-18(10)2)17-13(19)8-16-15(14)11-6-4-3-5-7-11/h3-7,9H,8H2,1-2H3,(H,17,19)

Synthetic route

Premazepam (57435-86-6) → 8-bromo-3,7-dihydro-6,7-dimethyl-5-phenylpyrrolo[3,4-e][1,4]diazepin-2(1H)-one

Conditions	Yield
With bromine; sodium hydrogencarbonate In methanol

Premazepam (57435-86-6) → 8-chloro-3,7-dihydro-6,7-dimethyl-5-phenylpyrrolo[3,4-e][1,4]diazepin-2(1H)-one

Conditions	Yield
With sulfuryl dichloride; sodium hydrogencarbonate In dichloromethane

Premazepam (57435-86-6) → 3,7-dihydro-6,7-dimethyl-8-nitro-5-phenylpyrrolo[3,4-e][1,4]diazepin-2(1H)-one

Conditions	Yield
With trifluorormethanesulfonic acid; nitric acid In dichloromethane

Downstream Products

• 84829-75-4 3,7-dihydro-6,7-dimethyl-8-nitro-5-phenylpyrrolo[3,4-e][1,4]diazepin-2(1H)-one 
• 84829-74-3 8-chloro-3,7-dihydro-6,7-dimethyl-5-phenylpyrrolo[3,4-e][1,4]diazepin-2(1H)-one 
• 84829-73-2 8-bromo-3,7-dihydro-6,7-dimethyl-5-phenylpyrrolo[3,4-e][1,4]diazepin-2(1H)-one 

Relevant articles and documents

Pharmacologically active pyrrolodiazepines

Compounds of the following formula STR1 wherein R is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl or tert.-butyl; R1 is hydrogen, methyl, ethyl or phenyl; R2 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec.-butyl or tert.-butyl; R3 is hydrogen, methoxy, trifluoromethyl, chloro, bromo or fluoro; and R4 is methyl. The new compounds are useful as CNS depressants, anticonvulsants, anti-inflammatories and inhibitors of the enzymes which promote the synthesis of prostaglandins.