In the realm of pharmaceutical research and development, understanding the precise chemical mechanisms of action for drug components is fundamental. N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-2-propenamide, identified by its CAS number 130929-57-6, is a prime example of a molecule whose chemical structure dictates its vital role as a catechol-O-methyltransferase (COMT) inhibitor.

The Role of COMT in Neurotransmission

Catechol-O-methyltransferase (COMT) is an enzyme found in various tissues, including the brain and peripheral organs. It plays a significant role in the metabolism of catecholamines, such as dopamine, norepinephrine, and epinephrine, by methylating their hydroxyl groups. In the context of Parkinson's disease treatment, COMT is particularly important because it metabolizes levodopa (L-DOPA), the precursor to dopamine. By breaking down levodopa in the periphery, COMT reduces the amount of levodopa that can cross the blood-brain barrier and exert its therapeutic effects.

CAS 130929-57-6: A Targeted Chemical Intervention

N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-2-propenamide is designed to selectively inhibit COMT. Its chemical structure, particularly the presence of the nitrocatechol moiety, allows it to bind to the active site of the COMT enzyme. This binding effectively blocks the enzyme's catalytic activity, preventing it from methylating levodopa. The chemical design ensures that the inhibition is primarily peripheral, minimizing central nervous system side effects while maximizing levodopa's availability in the brain.

Drug Design Implications

The efficacy of N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-2-propenamide as a COMT inhibitor stems from its:

  • High Affinity for COMT: Its molecular structure is optimized to bind strongly to the enzyme.
  • Peripheral Action: Limited ability to cross the blood-brain barrier ensures targeted peripheral inhibition.
  • Reversible Inhibition: Typically, COMT inhibitors like this act reversibly, allowing for predictable pharmacokinetics.
  • Synergy with Levodopa: By extending levodopa's half-life, it significantly improves motor control in Parkinson's patients, reducing 'off' times.

For researchers and formulators, procuring this intermediate from a reliable manufacturer is crucial to ensure the chemical integrity and effectiveness of the final drug product. Understanding the chemistry allows for better formulation strategies and therapeutic outcomes.

Conclusion

The chemical ingenuity behind N,N-diethyl-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-2-propenamide (CAS 130929-57-6) has made it a cornerstone in managing Parkinson's disease. Its targeted COMT inhibition exemplifies how precise chemical design can lead to significant therapeutic advancements. We offer this high-quality intermediate to support your drug design and development efforts.