62932-96-1

Basic information

• Product Name: 1-(3,4-DIBENZYLOXYPHENYL)-2-NITROPROPENE
• Synonyms: 4-(2-Nitro-1-propen-1-yl)-1,2-bis(phenylMethoxy)benzene;4-(2-Nitro-1-propenyl)-1,2-bis(phenylMethoxy)benzene;1-(3,4-DIBENZYLOXYPHENYL)-2-NITROPROPENE;1,2-Bis(benzyloxy)-4-(2-nitropropenyl)benzene
• CAS NO: 62932-96-1
• Molecular Formula: C₂₃H₂₁NO₄
• Molecular Weight: 375.42
• Product Categories: Propanes/propenes;Aromatics;Intermediates;Miscellaneous Reagents
• Mol File: 62932-96-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: 1-(3,4-DIBENZYLOXYPHENYL)-2-NITROPROPENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-DIBENZYLOXYPHENYL)-2-NITROPROPENE(62932-96-1)
• EPA Substance Registry System: 1-(3,4-DIBENZYLOXYPHENYL)-2-NITROPROPENE(62932-96-1)

Safety Data

• Hazardous Substances Data: 62932-96-1(Hazardous Substances Data)

Usage

Chemical Properties

Orange Solid

Uses

Different sources of media describe the Uses of 62932-96-1 differently. You can refer to the following data:
1. Intermediate in the preparation of 3,4-Methylenedioxymethamphetamine and its metabolites.
2. Intermediate in the preparation of 3,4-Methylenedioxymethamphetamine

Upstream product

• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 79-24-3 Nitroethane 
• 412278-47-8 1,2-bis-benzyloxy-4-(2-nitro-1-nitroso-propyl)-benzene 
• 408337-91-7 1-acetoxy-1-(3,4-bis-benzyloxy-phenyl)-2-nitro-propane 

Downstream Products

• 1616297-01-8 (R)-ethyl [1-(3,4-dibenzyloxyphenyl)propan-2-yl]carbamate 
• 440366-97-2 (S)-1-(3,4-bis(benzyloxy)phenyl)propan-2-amine 
• 1616296-99-1 (R,R_S)-N-[1-(3,4-dibenzyloxyphenyl)propan-2-yl]-N-methyltert-butylsulfinamide 
• 1616297-04-1 (S,S_S)-N-[1-(3,4-dibenzyloxyphenyl)propan-2-yl]tertbutylsulfinamide 
• 1616296-98-0 (R,R_S)-N-[1-(3,4-dibenzyloxyphenyl)propan-2-yl]tertbutylsulfinamide 
• 1616297-05-2 (S,R_S)-N-[1-(3,4-dibenzyloxyphenyl)propan-2-yl]tertbutylsulfinamide 
• 62932-76-7 1-(3,4-bis(benzyloxy)phenyl)propan-2-one 
• 66142-89-0 (S)-3,4-methylenedioxymethamphetamine 
• 42542-10-9 (-)-3,4-Methylenedioxymethamphetamine 
• 440366-99-4 (S)-N-ethoxycarbonyl-1-(3,4-dihydroxyphenyl)-2-aminopropane 
• 1616297-02-9 (R)-ethyl [1-(3,4-dihydroxyphenyl)propan-2-yl]carbamate 
• 440366-92-7 (S)-N-ethoxycarbonyl-1-(3,4-dibenzyloxyphenyl)-2-aminopropane 
• 14513-20-3 (-)-alpha-Methyldopamine 
• 14513-20-3 (+)-alpha-Methyldopamine 

Relevant articles and documents

Molecular basis of the selective binding of MDMA enantiomers to the alpha4beta2 nicotinic receptor subtype: Synthesis, pharmacological evaluation and mechanistic studies

The α4β2 nicotinic acetylcholine receptor (nAChR) is a molecular target of 3,4-methylenedioxymethamphetamine (MDMA), a synthetic drug also known as ecstasy, and it modulates the MDMA-mediated reinforcing properties. However, the enantioselective preference of the α4β2 nAChR subtype still remains unknown. Since the two enantiomers exhibit different pharmacological profiles and stereoselective metabolism, the aim of this study is to assess a possible difference in the interaction of the MDMA enantiomers with this nAChR subtype. To this end, we report a novel simple, yet highly efficient enantioselective synthesis of the MDMA enantiomers, in which the key step is the diastereoselective reduction of imides derived from optically pure tert-butylsulfinamide. The enantioselective binding to the receptor is examined using [3H]epibatidine in a radioligand assay. Even though the two enantiomers induced a concentration-dependent binding displacement, (S)-MDMA has an inhibition constant 13-fold higher than (R)-MDMA, which shows a Hill's coefficient not significantly different from unity, implying a competitive interaction. Furthermore, when NGF-differentiated PC12 cells were pretreated with the compounds, a significant increase in binding of [3H] epibatidine was found for (R)-MDMA, indicating up-regulation of heteromeric nAChR in the cell surface. Finally, docking and molecular dynamics studies have been used to identify the binding mode of the two enantiomers, which provides a structural basis to justify the differences in affinity from the differential interactions played by the substituents at the stereogenic centre of MDMA. The results provide a basis to explore the distinct psychostimulant profiles of the MDMA enantiomers mediated by the α4β2 nAChR subtype.

Synthesis and capillary electrophoretic analysis of enantiomerically enriched reference standards of MDMA and its main metabolites

Enantiomerically-enriched (S)-3,4-methylenedioxymethamphetamine (MDMA) and its main metabolites (S)-4-hydroxy-3-methoxymethamphetamine (HMMA) and (S)-3,4-dihydroxymethamphetamine (HHMA) were prepared or unequivocal identification of the differential enantioselective metabolism of these compounds as well as for its application in the analysis of biological samples. Capillary electrophoresis with cyclodextrin derivatives and a chemical correlation of (S)-MDMA, (S)-HMMA and (S)-HHMA has been performed to assign the absolute stereochemistry of major isomers in analytical standards enriched with such enantiomers. Copyright