Catalog Number: 1116
Chemical Name: N-(4-Hydroxyphenyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Biological Activity
Competitive and selective inhibitor of carrier-mediated anandamide transport (IC50 = 1 μM). Does not activate CB1 receptors or inhibit anandamide hydrolysis but has been shown to activate native and cloned vanilloid receptors (pEC50 = 7.4). Active in vivo. Also available in water soluble emulsion (Cat. No. 1685).
Technical Data
  • M.Wt:
    395.58
  • Formula:
    C26H37NO2
  • Solubility:
    Soluble to 50 mM in ethanol and to 50 mM in DMSO
  • Purity:
    >98%
  • Storage:
    Store at -20°C
  • CAS No:
    198022-70-7
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis. All Tocris products are intended for laboratory research use only.
Background References
  1. Functional role of high-affinity anandamide transport, as revealed by selective inhibition.
    Beltramo et al.
    Science, 1997;277:1094
  2. Potentiation of anandamide hypotension by the transport inhibitor, AM 404.
    Calignano et al.
    Eur.J.Pharmacol., 1997;337:R1
  3. The anandamide transport inhibitor AM404 activates vanilloid receptors.
    Zygmunt et al.
    Eur.J.Pharmacol., 2000;396:39
  4. Structural determinants for recognition and translocation by the anandamide transporter.
    Piomelli et al.
    Proc.Natl.Acad.Sci.U.S.A., 1999;96:5802
Citations:

The citations listed below are publications that use Tocris products. Selected citations for AM 404 include:

11 Citations: Showing 1 - 10
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  1. Molecular components and functions of the endocannabinoid system in mouse prefrontal cortex.
    Authors: Lafourcade Et al.
    PLoS One ;2:e709
  2. Sex Differences in Molecular Signaling at Inhibitory Synapses in the Hippocampus.
    Authors: Tabatadze Et al.
    J Neurosci 2015;35:11252
  3. Effects of cannabinoid drugs on the deficit of prepulse inhibition of startle in an animal model of schizophrenia: the SHR strain.
    Authors: Levin Et al.
    Circulation 2014;5:10
  4. Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses.
    Authors: Caiati Et al.
    Sci Rep 2012;2:285
  5. A putative 'pre-nervous' endocannabinoid system in early echinoderm development.
    Authors: Buznikov Et al.
    Dev Neurosci 2010;32:1
  6. Differential endocannabinoid regulation of baroreflex-evoked sympathoinhibition in normotensive versus hypertensive rats.
    Authors: Brozoski Et al.
    Auton Neurosci 2009;150:82
  7. Blockade of THC-seeking behavior and relapse in monkeys by the cannabinoid CB(1)-receptor antagonist rimonabant.
    Authors: Justinova Et al.
    Neuropsychopharmacology 2008;33:2870
  8. Differential effect of cannabinoid agonists and endocannabinoids on histamine release from distinct regions of the rat brain.
    Authors: Cenni Et al.
    Eur J Neurosci 2006;24:1633
  9. Is there a temperature-dependent uptake of anandamide into cells?
    Authors: Thors and Fowler
    Br J Pharmacol 2006;149:73
  10. Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension.
    Authors: Bátkai Et al.
    Br J Pharmacol 2004;110:1996
  11. A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus.
    Authors: Craib Et al.
    Br J Pharmacol 2001;134:42581
Expand to show all 11 Citations

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