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AM 404 (Synonyms: 4HPA, N(4hydroxyphenyl)Arachidonoyl Amide)

Catalog No.GC12071

Anandamide transport inhibitor

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AM 404 Chemical Structure

Cas No.: 198022-70-7

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5mg
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10mg
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50mg
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100mg
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Sample solution is provided at 25 µL, 10mM.

Description of AM 404

AM 404 is a selective inhibitor of anandamide transport [1]. Also, it is an agonist of CB1 cannabinoid receptor and potential vanilloid type 1 (TRPV1).

The endocannabinoid transporter (eCBT) is a transporter for the endocannabinoid. The blockade of anandamide transport has anti-nociceptive effects.

AM 404 is a selective anandamide transport inhibitor. AM404 inhibited anandamide transport with IC50 values of 1 and 5 μM in neurons and astrocytes, respectively. However, AM404 had no effect on FAAH activity or on uptake of arachidonate or ethanolamine. Also, AM404 exhibited affinity for CB1 receptors with Ki value of 1.8 μM [1]. In rat hepatic artery contracted with phenylephrine, AM404 evoked relaxations in a concentration-dependent way, which was inhibited by capsazepine, a vanilloid receptor antagonist. These results suggested that AM404 activated vanilloid receptors [2]. In SK-N-SH neuroblastoma cells, AM404 inhibited NFAT and NF-κB signaling pathways [3].

In mice, AM404 (10 mg/kg) significantly prolonged and enhanced anandamide-induced analgesia [1]. In rats, AM404 inhibited motor behaviors induced by quinpirole, a D2 family receptor agonist. In juvenile spontaneously hypertensive rats, AM404 inhibited hyperactivity [4].

References:
[1].  Beltramo M, Stella N, Calignano A, et al. Functional role of high-affinity anandamide transport, as revealed by selective inhibition. Science, 1997, 277(5329): 1094-1097.
[2].  Zygmunt PM, Chuang H, Movahed P, et al. The anandamide transport inhibitor AM404 activates vanilloid receptors. Eur J Pharmacol, 2000, 396(1): 39-42.
[3].  Caballero FJ, Soler-Torronteras R, Lara-Chica M, et al. AM404 inhibits NFAT and NF-κB signaling pathways and impairs migration and invasiveness of neuroblastoma cells. Eur J Pharmacol, 2015, 746: 221-232.
[4].  Beltramo M, de Fonseca FR, Navarro M, et al. Reversal of dopamine D(2) receptor responses by an anandamide transport inhibitor. J Neurosci, 2000, 20(9): 3401-3407.

Chemical Properties of AM 404

Cas No. 198022-70-7 SDF
Synonyms 4HPA, N(4hydroxyphenyl)Arachidonoyl Amide
Chemical Name (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide
Canonical SMILES O=C(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)NC(C=C1)=CC=C1O
Formula C26H37NO2 M.Wt 395.58
Solubility <19.78mg/ml in ethanol; <19.78mg/ml in DMSO Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of AM 404

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1 mg 5 mg 10 mg
1 mM 2.5279 mL 12.6397 mL 25.2793 mL
5 mM 0.5056 mL 2.5279 mL 5.0559 mL
10 mM 0.2528 mL 1.264 mL 2.5279 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 38 reference(s) in Google Scholar.)

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