AM 404

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Cat.No. 1116 - AM 404 | C26H37NO2 | CAS No. 198022-70-7
Description: Anandamide transport inhibitor
Chemical Name: N-(4-Hydroxyphenyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Purity: ≥98% (HPLC)
Datasheet
Citations (11)
Literature

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
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 198022-70-7
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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 19.78 50
ethanol 19.78 50

Preparing Stock Solutions

The following data is based on the product molecular weight 395.58. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.53 mL 12.64 mL 25.28 mL
5 mM 0.51 mL 2.53 mL 5.06 mL
10 mM 0.25 mL 1.26 mL 2.53 mL
50 mM 0.05 mL 0.25 mL 0.51 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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


If you know of a relevant reference for AM 404, please let us know.

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Keywords: Vanilloid receptors agonists anandamide transport inhibitors inhibits VR1 TRPV TRP Channels Transient Receptor Potential AMT Transporters Cannabinoids Monoamine Neurotransmitter AM404 Cannabinoid Transporters

11 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

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

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

Brozoski et al (2009) Differential endocannabinoid regulation of baroreflex-evoked sympathoinhibition in normotensive versus hypertensive rats. Auton Neurosci 150 82 PMID: 19464961

Justinova et al (2008) Blockade of THC-seeking behavior and relapse in monkeys by the cannabinoid CB(1)-receptor antagonist rimonabant. Neuropsychopharmacology 33 2870 PMID: 18305459

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

Bátkai et al (2004) Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension. Br J Pharmacol 110 1996 PMID: 15451779

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


Do you know of a great paper that uses AM 404 from Tocris? If so please let us know.

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