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H1911

N-(4-Hydroxyphenyl)-arachidonylamide

Name: N-(4-Hydroxyphenyl)-arachidonylamide
Brand: SIGMA

≥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

NACRES:

NA.32

PubChem Substance ID:

24895490

UNSPSC Code:

12352200

MDL number:

MFCD03095721

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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)

Related Categories

Bioactive Small Molecule Inhibitors

Application

Blocks anandamide re-uptake.

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.

Disclaimer

Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.

pictograms

GHS02,GHS07

signalword

Danger

hcodes

H225,H319

pcodes

P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

55.4 °F

flash_point_c

13 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品

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The anandamide transport inhibitor AM404 reduces the rewarding effects of nicotine and nicotine-induced dopamine elevations in the nucleus accumbens shell in rats.

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

Functional role of high-affinity anandamide transport, as revealed by selective inhibition.

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

Elevated circulating levels of anandamide after administration of the transport inhibitor, AM404.

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

Cannabidiol enhances anandamide signaling and alleviates psychotic symptoms of schizophrenia.

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

Global Trade Item Number

SKU	GTIN
H1911-10MG	04061838064677

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