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AM-404

Anandamide transport inhibitor



BML-CR106-0010	10 mg	80.00 USD

BML-CR106-0050	50 mg	327.00 USD
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Replaces Prod. #: ALX-340-032

Analog of anandamide (Prod. No. BML-FA017). Potentiates the activity of endogenous anandamide by blocking its re-uptake into presynaptic membranes. Activates TRPV1 (EC₅₀=0.04µM) at concentrations lower than those required to inhibit anandamide transport into the cell (neuronal (C6 glioma cells): IC₅₀=10µM; non-neuronal (rat RBL-2H3 cells): IC₅₀=11µM). Low affinity to FAAH (IC₅₀=5.9µM), to CB₁ receptor (IC₅₀=1.76µM) and to CB₂ receptor (IC₅₀>1µM).

Product Details

Alternative Name:	N-(4-Hydroxyphenyl)-5Z,8Z,11Z,14Z-eicosatetraenamide, N-(4-Hydroxyphenyl)arachidonoylamide

Formula:	C₂₆H₃₇NO₂

MW:	395.6

CAS:	183718-77-6

Purity:	≥98% (HPLC)

Appearance:	Waxy solid.

Solubility:	Soluble in DMSO (>25mg/ml) or 100% ethanol (>25mg/ml).

Shipping:	Shipped on Blue Ice

Long Term Storage:	-20°C

Use/Stability:	Stable for up to one year after receipt when stored at -20°C. Solutions are stable for up to 3 months when stored at -20°C under an inert atmosphere of nitrogen or argon.

Handling:	Protect from air. Keep under inert gas.

Regulatory Status:	RUO - Research Use Only

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Product Literature References

AM404, an inhibitor of anandamide uptake, prevents pain behaviour and modulates cytokine and apoptotic pathways in a rat model of neuropathic pain: B. Costa, et al.; Br. J. Pharmacol. 148, 1022 (2006), Abstract;

Modulation of neuropathic and inflammatory pain by the endocannabinoid transport inhibitor AM404 [N-(4-hydroxyphenyl)-eicosa-5,8,11,14-tetraenamide]: G. La Rana, et al.; J. Pharmacol. Exp. Ther. 317, 1365 (2006), Abstract;

Paracetamol: new vistas of an old drug: A. Bertolini, et al.; CNS Drug Rev. 12, 250 (2006), Abstract;

The analgesic activity of paracetamol is prevented by the blockade of cannabinoid CB1 receptors: A. Ottani, et al.; Eur. J. Pharmacol. 531, 280 (2006), Abstract;

Conversion of acetaminophen to the bioactive N-acylphenolamine AM404 via fatty acid amide hydrolase-dependent arachidonic acid conjugation in the nervous system: E.D. Hogestatt, et al.; J. Biol. Chem. 280, 31405 (2005), Abstract;

Anandamide transport inhibitor AM404 and structurally related compounds inhibit synaptic transmission between rat hippocampal neurons in culture independent of cannabinoid CB1 receptors: B.G. Kelley and S.A. Thayer; Eur. J. Pharmacol. 496, 33 (2004), Abstract;

Experimental parkinsonism alters anandamide precursor synthesis, and functional deficits are improved by AM404: a modulator of endocannabinoid function: E. Fernandez-Espejo, et al.; Neuropsychopharmacology 29, 1134 (2004), Abstract;

Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity: L. De Petrocellis, et al.; FEBS Lett. 483, 52 (2000), Abstract;

The anandamide transport inhibitor AM404 activates vanilloid receptors: P.M. Zygmunt, et al.; Eur. J. Pharmacol. 396, 39 (2000), Abstract;

Structural determinants for recognition and translocation by the anandamide transporter: D. Piomelli, et al.; PNAS 96, 5802 (1999), Abstract;

Functional role of high-affinity anandamide transport, as revealed by selective inhibition: M. Beltramo, et al.; Science 277, 1094 (1997), Abstract;

Potentiation of anandamide hypotension by the transport inhibitor, AM404: A. Calignano, et al.; Eur. J. Pharmacol. 337, R1 (1997), Abstract;