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H1911

Sigma-Aldrich

N-(4-Hydroxyphenyl)-arachidonylamide

≥98%, ethanol solution

Synonym(s):

AM404

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About This Item

Empirical Formula (Hill Notation):
C26H37NO2
CAS Number:
183718-77-6
Molecular Weight:
395.58
MDL number:
MFCD03095721
UNSPSC Code:
12352200
PubChem Substance ID:
24895490
NACRES:
NA.32

Quality Level

200

Assay

≥98%

form

ethanol solution

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)Nc1ccc(O)cc1

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-

InChI key

IJBZOOZRAXHERC-DOFZRALJSA-N

Gene Information

human ... CNR1(1268) , CNR2(1269)
mouse ... Cnr2(12802)
rat ... Cnr1(25248) , Faah(29347) , Trpv1(83810)

Application

Potentiates the activity of endogenous anandamide by blocking its re-uptake into presynaptic membranes. AM404 selectively inhibits the carrier-mediated transport of anandamide without affecting anandamide hydrolysis.

Other Notes

To change the solvent, simply evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

55.4 °F

Flash Point(C)

13 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Maria Scherma et al.
British journal of pharmacology, 165(8), 2539-2548 (2011-05-12)
The fatty acid amide hydrolase inhibitor URB597 can reverse the abuse-related behavioural and neurochemical effects of nicotine in rats. Fatty acid amide hydrolase inhibitors block the degradation (and thereby magnify and prolong the actions) of the endocannabinoid anandamide (AEA), and
A Giuffrida et al.
European journal of pharmacology, 408(2), 161-168 (2000-11-18)
The biological actions of the endogenous cannabinoid anandamide are terminated by carrier-mediated transport into neurons and astrocytes, followed by enzymatic hydrolysis. Anandamide transport is inhibited by the compound N-(4-hydroxyphenyl)arachidonylamide (AM404). AM404 potentiates several responses elicited by administration of exogenous anandamide
M Beltramo et al.
Science (New York, N.Y.), 277(5329), 1094-1097 (1997-08-22)
Anandamide, an endogenous ligand for central cannabinoid receptors, is released from neurons on depolarization and rapidly inactivated. Anandamide inactivation is not completely understood, but it may occur by transport into cells or by enzymatic hydrolysis. The compound N-(4-hydroxyphenyl)arachidonylamide (AM404) was
F M Leweke et al.
Translational psychiatry, 2, e94-e94 (2012-07-27)
Cannabidiol is a component of marijuana that does not activate cannabinoid receptors, but moderately inhibits the degradation of the endocannabinoid anandamide. We previously reported that an elevation of anandamide levels in cerebrospinal fluid inversely correlated to psychotic symptoms. Furthermore, enhanced

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