137596-53-3

Basic information

• Product Name: 3,7,8,10-Tetramethyl-4a-(3-oxo-3-phenyl-propyl)-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione
• Synonyms: 3,7,8,10-Tetramethyl-4a-(3-oxo-3-phenyl-propyl)-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione
• CAS NO: 137596-53-3
• Molecular Weight: 404.469
• Mol File: 137596-53-3.mol

Chemical Properties

• CAS DataBase Reference: 3,7,8,10-Tetramethyl-4a-(3-oxo-3-phenyl-propyl)-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7,8,10-Tetramethyl-4a-(3-oxo-3-phenyl-propyl)-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione(137596-53-3)
• EPA Substance Registry System: 3,7,8,10-Tetramethyl-4a-(3-oxo-3-phenyl-propyl)-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione(137596-53-3)

Safety Data

• Hazardous Substances Data: 137596-53-3(Hazardous Substances Data)

Upstream product

• 18636-32-3 3-methyllumiflavin 
• 210049-24-4 1-amino-2-phenylbut-3-en-2-ol 
• 41049-53-0 1-phenylcyclopropylamine 
• 67-56-1 methanol 

Relevant articles and documents

A new strategy for the design of monoamine oxidase inactivators. Exploratory studies with tertiary allylic and propargylic amino alcohols

A new strategy for the design of monoamine oxidase (MAO) inhibitors is proposed. The strategy is based on the premise that tertiary-amine containing MAO-inactivators which operate by alkylation of active site nucleophiles are activated in situ by single e

SET photochemistry of flavin-cyclopropylamine systems. Models for proposed monoamine oxidase inhibition mechanisms

Single electron transfer (SET) induced photochemical reactions of 3-methyllumiflavin (3-MLF) with the cyclopropylamines, trans-2-phenylcyclopropylamine (1) and 1-phenylcyclopropylamine (4), have been explored with the aim of defining the nature of and mechanisms for the reaction pathways followed. The excited-state SET processes probed in this investigation were designed to model those proposed previously for inactivation of the flavine-containing enzyme, monoamine oxidase, by these same cyclopropylamines. Irradiation of 3-MLF in an N2-purged solution containing cyclopropylamine 4 leads to generation of the C-4a,N-5-propanodihydrofiavin 14 as the major primary photoproduct. This substance, which is formed by an SET-promoted radical coupling mechanism, is transformed to the C-4a-(benzoylethyl)dihydroflavin 6 under hydrolytic conditions. Several other minor, cyclopropylamine-derived products are also generated in this reaction, again via radical pathways. In contrast, irradiation of an air-saturated solution of 3-MLF and 4 produces the epoxy ketone 8 efficiently. In this reaction, 3-MLF serves as an SET photosensitizer for the oxidative ring-opening reaction that converts 4 to 8. Finally, the C-4a,N-5-propanodihydroflavin adducts 17 and 18 are generated along with substances arising by secondary reaction of a primary product, cinnamaldehyde (20), when 3-MLF is irradiated in an N2-purged solution containing the cyclopropylamine 1. Mechanistic aspects of these bona fide SET flavin-cyclopropylamine reactions and their possible relationship to proposals made earlier about the nature of and mechanisms for monoamine oxidase inactivation by the same cyclopropylamines are discussed.