AM404

AM404
Identifiers
	IUPAC name (5Z,8Z,11Z,14Z)- N-(4-Hydroxyphenyl)icosa- 5,8,11,14-tetraenamide;
CAS Number	183718-77-6;
PubChem CID	6604822;
ChemSpider	5037081 ;
UNII	XVJ94H0U21;
ChEMBL	ChEMBL39878 ;
CompTox Dashboard (EPA)	DTXSID60424985 ;
Chemical and physical data
Formula	C26H37NO2
Molar mass	395.587 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(Nc1ccc(O)cc1)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC;
	InChI InChI=1S/C26H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26(29)27-24-20-22-25(28)23-21-24/h6-7,9-10,12-13,15-16,20-23,28H,2-5,8,11,14,17-19H2,1H3,(H,27,29)/b7-6-,10-9-,13-12-,16-15- ; Key:IJBZOOZRAXHERC-DOFZRALJSA-N ;
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AM404, also known as N-arachidonoylphenolamine,^[1]^[2] is an active metabolite of paracetamol (acetaminophen), responsible for all or part of its analgesic action^[3] and anticonvulsant effects.^[4] Chemically, it is the amide formed from 4-aminophenol and arachidonic acid. AM404 is one of the AM cannabinoids discovered by Alexandros Makriyannis and his team.

^ Nakamura S, Nonaka T, Komatsu S, Yamada T, Yamamoto T (February 2022). "Oral acetaminophen-induced spinal 5-hydroxytriyptamine release produces analgesic effects in the rat formalin test". Biomedicine & Pharmacotherapy. 146: 112578. doi:10.1016/j.biopha.2021.112578. PMID 34959121. S2CID 245483361.
^ Rogosch T, Sinning C, Podlewski A, Watzer B, Schlosburg J, Lichtman AH, et al. (January 2012). "Novel bioactive metabolites of dipyrone (metamizol)". Bioorganic & Medicinal Chemistry. 20 (1): 101–107. doi:10.1016/j.bmc.2011.11.028. PMC 3248997. PMID 22172309.
^ Ottani A, Leone S, Sandrini M, Ferrari A, Bertolini A (February 2006). "The analgesic activity of paracetamol is prevented by the blockade of cannabinoid CB1 receptors". European Journal of Pharmacology. 531 (1–3): 280–281. doi:10.1016/j.ejphar.2005.12.015. PMID 16438952.
^ Deshpande LS, DeLorenzo RJ (January 2011). "Acetaminophen inhibits status epilepticus in cultured hippocampal neurons". NeuroReport. 22 (1): 15–18. doi:10.1097/WNR.0b013e3283413231. PMC 3052417. PMID 21037491.