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The biosynthesis of N-arachidonoyl dopamine (NADA), a putative endocannabinoid and endovanilloid, via conjugation of arachidonic acid with dopamine

Academic Article
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Overview

authors

  • Hu, S. S. J.
  • Bradshaw, H. B.
  • Benton, V. M.
  • Chen, J. S. C.
  • Huang, S. M.
  • Minassi, A.
  • Bisogno, T.
  • Masuda, K.
  • Tan, B.
  • Roskoski, R.
  • Cravatt, Benjamin
  • Di Marzo, V.
  • Walker, J. M.

publication date

  • October 2009

journal

  • Prostaglandins Leukotrienes and Essential Fatty Acids  Journal

abstract

  • N-arachidonoyl dopamine (NADA) is an endogenous ligand that activates the cannabinoid type 1 receptor and the transient receptor potential vanilloid type 1 channel. Two potential biosynthetic pathways for NADA have been proposed, though no conclusive evidence exists for either. The first is the direct conjugation of arachidonic acid with dopamine and the other is via metabolism of a putative N-arachidonoyl tyrosine (NA-tyrosine). In the present study we investigated these biosynthetic mechanisms and report that NADA synthesis requires TH in dopaminergic terminals; however, NA-tyrosine, which we identify here as an endogenous lipid, is not an intermediate. We show that NADA biosynthesis primarily occurs through an enzyme-mediated conjugation of arachidonic acid with dopamine. While this conjugation likely involves a complex of enzymes, our data suggest a direct involvement of fatty acid amide hydrolase in NADA biosynthesis either as a rate-limiting enzyme that liberates arachidonic acid from AEA, or as a conjugation enzyme, or both.

subject areas

  • Amidohydrolases
  • Animals
  • Arachidonic Acid
  • Arachidonic Acids
  • Brain
  • Cannabinoid Receptor Modulators
  • Dopamine
  • Endocannabinoids
  • Male
  • Rats
  • Rats, Sprague-Dawley
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Research

keywords

  • Biosynthesis
  • Dopamine
  • FAAH
  • NADA
  • TH
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Identity

PubMed Central ID

  • PMC2757501

International Standard Serial Number (ISSN)

  • 0952-3278

Digital Object Identifier (DOI)

  • 10.1016/j.plefa.2009.05.026

PubMed ID

  • 19570666
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Additional Document Info

start page

  • 291

end page

  • 301

volume

  • 81

issue

  • 4

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