22162-53-4

Basic information

• Product Name: 10,11-DIHYDRO-5H-BENZO[E]PYRROLO[1,2-A][1,4]DIAZEPINE
• Synonyms: 10,11-DIHYDRO-5H-BENZO[E]PYRROLO[1,2-A][1,4]DIAZEPINE;10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine;5H-Pyrrolo[2,1-c][1,4]benzodiazepine, 10,11-dihydro-;10,11-dihydro-5H-pyrrolo
• CAS NO: 22162-53-4
• Molecular Formula: C₁₂H₁₂N₂
• Molecular Weight: 184.2428
• Mol File: 22162-53-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 152-154 °C (decomp)
• Boiling Point: 381.7±31.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.72±0.20(Predicted)
• CAS DataBase Reference: 10,11-DIHYDRO-5H-BENZO[E]PYRROLO[1,2-A][1,4]DIAZEPINE(CAS DataBase Reference)
• NIST Chemistry Reference: 10,11-DIHYDRO-5H-BENZO[E]PYRROLO[1,2-A][1,4]DIAZEPINE(22162-53-4)
• EPA Substance Registry System: 10,11-DIHYDRO-5H-BENZO[E]PYRROLO[1,2-A][1,4]DIAZEPINE(22162-53-4)

Safety Data

• Hazardous Substances Data: 22162-53-4(Hazardous Substances Data)

Usage

General Description

10,11-Dihydro-5H-Benzo[E]pyrrolo[1,2-A][1,4]diazepine, also known as BZP, is a chemical compound that belongs to the class of piperazine derivatives. It is a psychoactive drug that acts as a stimulant and has been used as a recreational drug, often sold in the form of tablets or capsules. BZP is structurally similar to methamphetamine and has stimulant effects on the central nervous system, including increased alertness, euphoria, and improved mood. It is often used as a substitute for MDMA and has been linked to adverse effects such as increased heart rate, insomnia, and anxiety. BZP is classified as a controlled substance in some countries due to its potential for abuse and negative health effects.

Upstream product

• 22162-51-2 1-(2-Nitrobenzyl)-2-pyrrolecarboxaldehyde 
• 3958-60-9 2-nitrophenylmethyl bromide 
• 612-23-7 2-nitrobenzyl chloride 
• 64-17-5 ethanol 
• 1003-29-8 2-pyrrole aldehyde 

Downstream Products

• 473717-55-4 (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(3'-methyl-[1,1'-biphenyl]-4-yl)-methanone 
• 473717-60-1 (5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepin-10-yl)-(4'-methoxy-3-methyl-[1,1'-biphenyl]-4-yl)-methanone 
• 473717-56-5 (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(4'-methoxy-[1,1'-biphenyl]-4-yl)-methanone 
• 473264-08-3 10-(4-iodo-2-methoxybenzoyl)-10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepine 
• 473717-54-3 (2'-Methoxy-[1,1'-biphenyl]-4-yl)-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone 
• 473264-06-1 (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(2'-methoxy-2-methyl-[1,1'-biphenyl]-4-yl)-methanone 
• 473264-22-1 (10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepin-10-yl)-(2-methoxy-2'-trifluoromethyl-[1,1'-biphenyl]-4-yl)-methanone 
• 473260-72-9 10-{[6-Chloro-3-methoxy-2'-ethoxy-[1,1'-biphenyl]-4-yl]carbonyl}-10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepine 
• 473264-15-2 10-{[6-chloro-3-methoxy-2'-trifluoromethyl-[1,1'-biphenyl]-4-yl]carbonyl}-10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepine 
• 473476-78-7 10-{[2'-chloro-6-chloro-3-methoxy-[1,1'-biphenyl]-4-yl]carbonyl}-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine 
• 473264-19-6 10-{[6-chloro-3-methoxy-2'-fluoro-[1,1'-biphenyl]-4-yl]carbonyl}-10,11-dihydro-5H-pyrrolo [2,1-c][1,4]benzodiazepine 
• 473574-28-6 (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(2-methoxy-4-iodo-5-chlorophenyl)-methanone 
• 200879-07-8 [3-Methoxy-4-(5H,11H-pyrrolo[2,1-c][1,4]-benzodiazepine-10-carbonyl)-phenyl]-biphenyl-2-carboxylic acid-amide 
• 207670-48-2 [4-(5H,11H-Pyrrolo-[2,1-c][1,4]benzodiazepine-10-carbonyl)-3-chloro-phenyl]-2-phenyl-cyclopent-1-enecarboxylic acid amide 

Relevant articles and documents

Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold

Using a Tube-in-Tube device based on the amorphous Teflon AF-2400 fluoropolymer, a series of nitroarenes was hydrogenated to afford the corresponding aniline compounds. The system was then applied to the construction of a pyrrolobenzo[1,4]diazapene scaffold through a tandem hydrogenation-condensation-hydrogenation sequence.

An Improved, Scalable and Impurity-Free Process for Lixivaptan

An optimized synthetic method in high efficiency has been developed for the synthesis of lixivaptan from 2-nitrobenzyl bromide and pyrrole-2-carboxaldehyde. The byproducts among this procedure and an unknown impurity in crude product were investigated. The byproducts were speculated by 1H NMR or MS. The unknown impurity was characterized by 1H NMR, 13C NMR, and HRMS, confirming the structures as N-[3-chloro-4-(5H-pyrrolo[2,1-c][1,4]benzodiazepine-10(11H)-ylcarbonyl)phenyl]-N-(5-fluoro-2-methylbenzoyl)-5-fluoro-2-methylbenzamide. Afterwards, the impurity was synthesized to make comparisons. The target product lixivaptan was obtained with 47.6% overall yield and 99.93% purity. This cost-effective and environmentally friendly process is suitable for scale-up production.

DRUG DERIVATIVES

The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.