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Systematic (IUPAC) name
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Formula C26H37NO2 
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Metabolite of OTC drug

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AM404 also known as N-arachidonoylphenolamine is an active metabolite of paracetamol (acetaminophen) responsible for all or part of its analgesic action.[1]


AM404 has been noted as an endogenous cannabinoid reuptake inhibitor, preventing the transport of anandamide and other related compounds back from the synaptic cleft, much in the same way that common SSRI antidepressants prevent the reuptake of serotonin. AM404 is also TRPV1 agonist, and also prevents cyclooxygenase COX-1 and COX-2 and prostaglandin synthesis. AM404 is thought to induce its analgesic action through its activity on the cannabinoid, COX and TRPV systems, all of which are present in pain and thermoregulatory pathways.[2]


  1. ^ Ottani A, Leone S, Sandrini M, Ferrari A, Bertolini A (2006). "The analgesic activity of paracetamol is prevented by the blockade of cannabinoid CB1 receptors". Eur. J. Pharmacol. 531 (1-3): 280–1. doi:10.1016/j.ejphar.2005.12.015. PMID 16438952.
  2. ^ Högestätt, E. D., B. A. G. Jönsson, A. Ermund, D. A. Andersson, H. Björk, J. P. Alexander, B. F. Cravatt, A. I. Basbaum, P. M. Zygmunt (September 9, 2005). "Conversion of Acetaminophen to the Bioactive N-Acylphenolamine AM404 via Fatty Acid Amide Hydrolase-dependent Arachidonic Acid Conjugation in the Nervous System". Journal of Biological Chemistry 280 (36): 31405–31412. doi:10.1074/jbc.M501489200. Retrieved on 2006-04-25.
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "AM404". A list of authors is available in Wikipedia.
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