N -Arachidonoylphenolamine

Structural formula
General
Surname	N -Arachidonoylphenolamine
other names	(5 Z , 8 Z , 11 Z , 14 Z ) - N - (4-Hydroxyphenyl) icosa-5,8,11,14-tetraenamide; AM404;
Molecular formula	C 26 H 37 NO 2
External identifiers / databases
PubChem	6604822
Wikidata	Q4652517
Drug information
Drug class	Anxiolytic
properties
Molar mass	395.58 g · mol -1
safety instructions
H and P phrases	H: 225-319
	P: 210-280-305 + 351 + 338-337 + 313-403 + 235
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N -Arachidonoylphenolamine (also known as AM404 ) is a metabolic product that is formed in the brain and spinal cord after taking the drug paracetamol , with the participation of the enzyme fatty acid amide hydrolase , when paracetamol is conjugated with arachidonic acid after its deacetylation .

AM404 affects the intracellular transport of anandamide . The hypothesis that it also inhibits a putative transporter in the cell membrane for the reuptake of anandamide has been unproven for many years and - due to alternative concepts - is not necessary to explain the observations.

literature

National Research Council (US). Committee on Toxicology: Possible Long-term Health Effects of Short-term Exposure to Chemical Agents , National Academy Press , Washington 1984.

Individual evidence

↑ ^a ^b Data sheet N- (4-Hydroxyphenyl) -arachidonylamide from Sigma-Aldrich , accessed on February 26, 2016 ( PDF ).
^ A. Bertolini, A. Ferrari, A. Ottani, S. Guerzoni, R. Tacchi, S. Leone: Paracetamol: new vistas of an old drug. In: CNS Drug Rev 12, 2006, pp. 75-250, PMID 17227290 .
^ CJ Fowler: Transport of endocannabinoids across the plasma membrane and within the cell. In: The FEBS journal. Volume 280, number 9, May 2013, pp. 1895–1904, doi : 10.1111 / febs.12212 , PMID 23441874 (free full text) (review).
↑ CJ Fowler: Anandamide uptake explained? In: Trends in pharmacological sciences. Volume 33, Number 4, April 2012, pp. 181-185, doi : 10.1016 / j.tips.2012.01.001 , PMID 22297258 (review).

[SIGMA-1] Data sheet N- (4-Hydroxyphenyl) -arachidonylamide from Sigma-Aldrich , accessed on February 26, 2016 ( PDF ).

[PMID_17227290-2] A. Bertolini, A. Ferrari, A. Ottani, S. Guerzoni, R. Tacchi, S. Leone: Paracetamol: new vistas of an old drug. In: CNS Drug Rev 12, 2006, pp. 75-250, PMID 17227290 .

[PMID23441874-3] CJ Fowler: Transport of endocannabinoids across the plasma membrane and within the cell. In: The FEBS journal. Volume 280, number 9, May 2013, pp. 1895–1904, doi : 10.1111 / febs.12212 , PMID 23441874 (free full text) (review).

[PMID22297258-4] CJ Fowler: Anandamide uptake explained? In: Trends in pharmacological sciences. Volume 33, Number 4, April 2012, pp. 181-185, doi : 10.1016 / j.tips.2012.01.001 , PMID 22297258 (review).