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AM404 information


AM404
Identifiers
IUPAC name
  • (5Z,8Z,11Z,14Z)- N-(4-Hydroxyphenyl)icosa- 5,8,11,14-tetraenamide
CAS Number
  • 183718-77-6 ☒N 198022-70-7
PubChem CID
  • 6604822
ChemSpider
  • 5037081 checkY
UNII
  • XVJ94H0U21
ChEMBL
  • ChEMBL39878 checkY
CompTox Dashboard (EPA)
  • DTXSID60424985 Edit this at Wikidata
Chemical and physical data
FormulaC26H37NO2
Molar mass395.587 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- checkY
  • Key:IJBZOOZRAXHERC-DOFZRALJSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.

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AM404

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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...

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Cyclooxygenase

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to the COX-2 isozyme are called COX-2 inhibitors. The active metabolite (AM404) of paracetamol is a COX inhibitor, a fact to which some or all of its therapeutic...

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Paracetamol

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cyclooxygenase and actions of its metabolite N-arachidonoylphenolamine (AM404). Supporting the first mechanism, pharmacologically and in its side effects...

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Allodynia

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disinhibiting pain perception. However, this re-uptake can be blocked by AM404, elongating the duration of pain inhibition. Howard Hughes is thought to...

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Onion

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Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi) AM404 ASP-7663 Bradykinin Cannabichromene (cannabis) Cannabidiol (cannabis) Cannabigerol...

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Thyme

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Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi) AM404 ASP-7663 Bradykinin Cannabichromene (cannabis) Cannabidiol (cannabis) Cannabigerol...

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Anandamide

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Canada) is metabolically combined with arachidonic acid by FAAH to form AM404. This metabolite of paracetamol is a potent agonist at the TRPV1 vanilloid...

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Ruta graveolens

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Formaldehyde

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Cinnamon

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Black pepper

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Sichuan pepper

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Tobacco

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Ginger

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Horseradish

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Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi) AM404 ASP-7663 Bradykinin Cannabichromene (cannabis) Cannabidiol (cannabis) Cannabigerol...

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Mentha

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Camphor

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Wasabi

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Vanilla

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Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi) AM404 ASP-7663 Bradykinin Cannabichromene (cannabis) Cannabidiol (cannabis) Cannabigerol...

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Turmeric

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Cannabidiol

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Basil

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Analgesic

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Multiple; inhibits prostaglandin synthesis in the CNS, an active metabolite, AM404, is an anandamide reuptake inhibitor. PO, IV, IM, rectal. Protein binding...

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Nicotine

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Methyl salicylate

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Clove

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Cannabis

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TRPV1

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endocannabinoid anandamide has also been shown to act on TRPV1 receptors. AM404—an active metabolite of paracetamol (also known as acetaminophen)—that serves...

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Curcumin

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Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi) AM404 ASP-7663 Bradykinin Cannabichromene (cannabis) Cannabidiol (cannabis) Cannabigerol...

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