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AM 404

N-arachidonoylaminophenol

An Activator of TRPV1 Channels and a Ligand of CB1 Cannabinoid Receptors

Cat #: A-190
Alternative Name N-arachidonoylaminophenol
Lyophilized Powder yes
  • Bioassay Tested
    • Source Synthetic
    MW: 395.6
    Purity: >98% (HPLC)
    Form Lyophilized powder.
    Effective concentration 0.5 nM - 50 µM.
    Structure
    Chemical name N-(4-Hydroxyphenyl)-5Z,8Z,11Z,14Z-eicosatetraenamide.
    Molecular formula C26H37NO2.
    CAS No.: 198022-70-7
    Activity AM 404 activates TRPV1 channels with EC50 = 0.04 µM1, and serves as a ligand for CB1 cannabinoid receptors2.
    References-Activity
    1. Zygmunt, P.M. et al. (2000) Eur. J. Pharmacol. 396, 39.
    2. Fegley, D. et al. (2004) Proc. Natl. Acad. Sci. U.S.A. 101, 8756.
    Shipping and storage Shipped at room temperature. Product as supplied can be stored intact at room temperature for several weeks. For longer periods, it should be stored at -20°C.
    Solubility 100 mM in DMSO, 50 mM in ethanol (dissolves slowly). Centrifuge all product preparations before use (10000 x g 5 min).
    Storage of solutions Up to four weeks at 4°C or three months at -20°C.
    Our bioassay
    • Alomone Labs AM 404 activates TRPV1 channels heterologously expressed in C-6 cells.
      Alomone Labs AM 404 activates TRPV1 channels heterologously expressed in C-6 cells.
      Cells were loaded with Fluo-3AM and changes in intracellular Ca2+ were measured. Normalized fluorescence before (control, gray dotted line) and after application of 1 µM and 2 µM AM 404 (#A-190), (black lines, as indicated).
    References - Scientific background
    1. De Petrocellis, L. et al. (2000) FEBS Lett. 483, 52.
    2. Fegley, D. et al. (2004) Proc. Natl. Acad. Sci. U.S.A. 101, 8756.
    3. Glaser, S.T. et al. (2003) Proc. Natl. Acad. Sci. U.S.A. 100, 4269.
    4. Rogosch, T. et al. (2012) Bioorg. Med. Chem. 20, 101.
    5. Guhring, H. et al. (2002) Eur. J. Pharmacol. 454, 153.
    6. Beltramo, M. et al. (1997) Science 277, 1094.
    7. Rodella, L.F. et al. (2005) Eur. J. Pharmacol. 508, 139.
    Scientific background N-arachidonoylaminophenol (AM 404) belongs to a group of bioactive N-acylamines. It is a potent activator of TRPV1 (EC50 = 26 nM)1, and a CB1 cannabinoid receptor ligand2. Recent work on the mechanism of AM 404 has suggested that the inhibition of fatty acid amide hydrolase (FAAH) by AM 404 (IC50 = 6 μΜ) is likely responsible for all of its attributed "reuptake" properties, since intracellular FAAH hydrolysis of anandamide changes the intra/extracellular anandamide equilibrium3. AM 404 also inhibits cyclooxygenase COX-1 and COX-2, thus attenuating prostaglandin synthesis4. AM 404 produces analgesia in the mouse formalin and hot plate tests5 and potentiates the analgesic effect of anandamide in the mouse hot plate test6. Furthermore, AM 404 decreases the expression of c-fos in the spinal cord of neuropathic rats, an effect inhibited by both TRPV1 and cannabinoid receptor antagonists7.
    Target TRPV1, CB1 receptors
    Lyophilized Powder
    Last update: 02/01/2022

    AM 404 (#A-190) is a highly pure, synthetic, and biologically active compound.

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    For research purposes only, not for human use
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