Efficient N-Acyldopamine Synthesis

Chem Pharm Bull (Tokyo). 2016;64(7):935-40. doi: 10.1248/cpb.c16-00162.


N-Acyldopamines are endogenous analogs of capsaicin that exhibit cannabinoid-like activities and were identified from brain extracts. Among them, N-arachidonoyldopamine (AADA) and N-oleoyldopamine (ODA) were characterized as transient receptor potential vanilloid type V1 channel (TRPV1) ligands. Recently, it was shown that N-acyldopamines may possess diverse physiological roles in addition to their ligand activities. To study the multiple functions and action mechanisms of endogenous N-acyldopamines, a simple and efficient method of N-acyldopamine synthesis was investigated. The eighteen potentially endogenous N-acyldopamines and two deuterated ones, N-palmitoyl dopamine-d5 and N-stearoyl dopamine-d5, were efficiently synthesized without protective groups in CH2Cl2 under optimized conditions using propylphosphoric acid cyclic anhydride (PPACA) as a condensation agent.

MeSH terms

  • Dopamine / analogs & derivatives*
  • Dopamine / chemical synthesis*
  • Dopamine / chemistry
  • Molecular Structure
  • Phosphoric Acids / chemistry*


  • Phosphoric Acids
  • Dopamine