AM404

Names

[ Name ]:
AM404

[Synonym ]:
N-(4-Hydroxyphenyl)-arachidonylamide
5,8,11,14-Eicosatetraenamide, N-(4-hydroxyphenyl)-, (5Z,8Z,11Z,14Z)-
AM 404
(5Z,8Z,11Z,14Z)-N-(4-Hydroxyphenyl)icosa-5,8,11,14-tetraenamide
N-(4-Hydroxyphenyl)arachidonylamide
AM-404
AM404
(5Z,8Z,11Z,14Z)-N-(4-Hydroxyphenyl)-5,8,11,14-icosatetraenamide

Biological Activity

[Description]:

AM404, an inhibitor of endocannabinoid reuptake, blocks anandamide transport with IC50 values in the low micromolar range[1]. AM404 is able to relax rat isolated hepatic arteries contracted with Phenylephrine, with a pEC50 value of 7.4 (corresponding to an EC50 of 0.04 µM). Neuroprotective Effect[2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vitro]

AM404 reduces C6 glioma cell proliferation with IC50 values of 4.9 µM. AM404 non-specifically inhibit C6 glioma cell proliferation at concentrations used to block the cellular accumulation of the endocannabinoid anandamide[2]. Cell Viability Assay[2] Cell Line: Rat C6 glioma cells Concentration: 1, 3, 10 and 30 µM Incubation Time: 24, 48, 72 and 96 h Result: Produced a concentration-dependent reduction in cell proliferation that was seen with 24 h of exposure to 10 and 30 µM concentrations and after 48 h at 3 µM. The lowest concentration of AM404 tested, 1 µM, produced a significant, albeit small, reduction in cell proliferation at 72 h.

[In Vivo]

AM404 (1-5 mg/kg, i.p.) exerts dose-dependent anxiolytic-like effects in the three models: elevated plus maze, defensive withdrawal and separation-induced ultrasonic vocalizations. Animal Model: Adult male Sprague-Dawley rats (250-300 g)[2] Dosage: 2.5-10 mg/kg Administration: Intraperitoneal (i.p.) Result: Caused a dose-dependent increase in anandamide levels in prefrontal cortex, hippocampus and thalamus.

[References]

[1]. A Giuffrida, et al. Mechanisms of endocannabinoid inactivation: biochemistry and pharmacology. J Pharmacol Exp Ther. 2001 Jul;298(1):7-14.

[2]. Kent-Olov Jonsson, et al. AM404 and VDM 11 non-specifically inhibit C6 glioma cell proliferation at concentrations used to block the cellular accumulation of the endocannabinoid anandamide. Arch Toxicol. 2003 Apr;77(4):201-7.

[3]. Marco Bortolato, et al. Anxiolytic-like properties of the anandamide transport inhibitor AM404. Neuropsychopharmacology. 2006 Dec;31(12):2652-9.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
579.4±50.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₆H₃₇NO₂

[ Molecular Weight ]:
395.578

[ Flash Point ]:
304.2±30.1 °C

[ Exact Mass ]:
395.282440

[ PSA ]:
49.33000

[ LogP ]:
7.63

[ Vapour Pressure ]:
0.0±1.7 mmHg at 25°C

[ Index of Refraction ]:
1.555

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H319

[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
F: Flammable;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S7

[ RIDADR ]:
UN 1170 3/PG 2

Articles

Cannabidiol enhances anandamide signaling and alleviates psychotic symptoms of schizophrenia.

Transl. Psychiatry 2 , e94, (2012)

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 elevatio...

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

Br. J. Pharmacol. 165(8) , 2539-48, (2012)

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 (an...

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

Eur. J. Pharmacol. 408(2) , 161-8, (2000)

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 inhi...