Structure via PubChem · Public domain (PubChem)
AM-404
Sign in to saveAlso known as N-arachidonoylphenolamine, AM404
AM404, also known as '''N-arachidonoylphenolamine''', is an active metabolite of paracetamol (acetaminophen), responsible for all or part of its analgesic action and anticonvulsant effects. 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.
Chemical data
- Formula
- C26H37NO2
- Molecular weight
- 395.6 g/mol
- IUPAC name
- (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide
- SMILES
- CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC1=CC=C(C=C1)O
- InChIKey
- IJBZOOZRAXHERC-DOFZRALJSA-N
- XLogP
- 7.2
- Polar surface area
- 49.3 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 395.282
Show 3 more facts
- chemical formula
- C₂₆H₃₇NO₂
- canonical SMILES
- CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC1=CC=C(C=C1)O
- isomeric SMILES
- CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NC1=CC=C(C=C1)O
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
8 sectionsContents
- Pharmacokinetics
- Pharmacodynamics
- CB<sub>1</sub> and CB<sub>2</sub>
- Endocannabinoid concentration
- TRPV1
- Sodium channels
- See also
- References
AM404, also known as '''N-arachidonoylphenolamine', is an active metabolite of paracetamol (acetaminophen), responsible for all or part of its analgesic action and anticonvulsant effects. 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.
== Pharmacokinetics == AM404 is found in the brains of animals and cerebrospinal fluid of humans taking paracetamol. It is produced from 4-aminophenol by the action of FAAH.
Excerpted from Wikipedia’s “AM-404” article, available under the CC BY-SA 4.0 licence.