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Submit ReviewAM 404
Description: Anandamide transport inhibitor
Chemical Name: N-(4-Hydroxyphenyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Purity: ≥98% (HPLC)
Biological Activity for AM 404
AM 404 is a 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). Also FABP inhibitor. Active in vivo.
Technical Data for AM 404
| M. Wt | 395.58 |
| Formula | C26H37NO2 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 183718-77-6 |
| PubChem ID | 6604822 |
| InChI Key | IJBZOOZRAXHERC-DOFZRALJSA-N |
| Smiles | CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC1=CC=C(O)C=C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for AM 404
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| ethanol | 19.78 | 50 | |
| DMSO | 19.78 | 50 |
Preparing Stock Solutions for AM 404
The following data is based on the product molecular weight 395.58. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.5 mM | 5.06 mL | 25.28 mL | 50.56 mL |
| 2.5 mM | 1.01 mL | 5.06 mL | 10.11 mL |
| 5 mM | 0.51 mL | 2.53 mL | 5.06 mL |
| 25 mM | 0.1 mL | 0.51 mL | 1.01 mL |
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Product Datasheets for AM 404
References for AM 404
References are publications that support the biological activity of the product.
Beltramo et al (1997) Functional role of high-affinity anandamide transport, as revealed by selective inhibition. Science 277 1094 PMID: 9262477
Calignano et al (1997) Potentiation of anandamide hypotension by the transport inhibitor, AM 404. Eur.J.Pharmacol. 337 R1 PMID: 9389389
Piomelli et al (1999) Structural determinants for recognition and translocation by the anandamide transporter. Proc.Natl.Acad.Sci.U.S.A. 96 5802 PMID: 10318965
Zygmunt et al (2000) The anandamide transport inhibitor AM404 activates vanilloid receptors. Eur.J.Pharmacol. 396 39 PMID: 10822052
Deutsch (2017) A personal retrospective: Elevating Anandamide (AEA) by targeting fatty acid amide hydrolase (FAAH) and the fatty acid binding proteins (FABPs). Front.Pharmacol. 7 370 PMID: 27790143
If you know of a relevant reference for AM 404, please let us know.
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Keywords: AM 404, AM 404 supplier, Vanilloid, receptors, agonists, anandamide, transport, inhibitors, inhibits, VR1, TRPV, TRP, Channels, Transient, Receptor, Potential, AMT, Transporters, Cannabinoids, Monoamine, Neurotransmitter, AM404, 198022-70-7, FABPs, FABP, fatty, acid, binding, proteins, Cannabinoid, Fatty, Acid, Binding, Proteins, 1116, Tocris Bioscience
14 Citations for AM 404
Citations are publications that use Tocris products. Selected citations for AM 404 include:
Tabatadze et al (2015) Sex Differences in Molecular Signaling at Inhibitory Synapses in the Hippocampus. J Neurosci 35 11252 PMID: 26269634
Saliba (2017) AM404, paracetamol metabolite, prevents prostaglandin synthesis in activated microglia by inhibiting COX activity. J Neuroinflammation 14 246 PMID: 29237478
Levin et al (2014) Effects of cannabinoid drugs on the deficit of prepulse inhibition of startle in an animal model of schizophrenia: the SHR strain. Circulation 5 10 PMID: 24567721
Brozoski et al (2009) Differential endocannabinoid regulation of baroreflex-evoked sympathoinhibition in normotensive versus hypertensive rats. Auton Neurosci 150 82 PMID: 19464961
Caiati et al (2012) Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses. Sci Rep 2 285 PMID: 22368777
Buznikov et al (2010) A putative 'pre-nervous' endocannabinoid system in early echinoderm development. Dev Neurosci 32 1 PMID: 19907129
Cenni et al (2006) Differential effect of cannabinoid agonists and endocannabinoids on histamine release from distinct regions of the rat brain. Eur J Neurosci 24 1633 PMID: 17004927
Thors and Fowler (2006) Is there a temperature-dependent uptake of anandamide into cells? Br J Pharmacol 149 73 PMID: 16865094
Herradón et al (2007) Characterization of the vasorelaxant mechanisms of the endocannabinoid anandamide in rat aorta. Br J Pharmacol 152 699 PMID: 17704831
Justinova et al (2008) Blockade of THC-seeking behavior and relapse in monkeys by the cannabinoid CB(1)-receptor antagonist rimon. Neuropsychopharmacology 33 2870 PMID: 18305459
Craib et al (2001) A possible role of lipoxygenase in the activation of vanilloid receptors by anandamide in the guinea-pig bronchus. Br J Pharmacol 134 42581 PMID: 11522594
Lafourcade et al Molecular components and functions of the endocannabinoid system in mouse prefrontal cortex. PLoS One 2 e709 PMID: 17684555
Ronesi et al (2004) Disruption of endocannabinoid release and striatal long-term depression by postsynaptic blockade of endocannabinoid membrane transport. J Neurosci 24 1673 PMID: 14973237
Bátkai et al (2004) Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension. Br J Pharmacol 110 1996 PMID: 15451779
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