AM-404

BML-CR106

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Anandamide transport inhibitor

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).

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Product Details

Alternative Name	N-(4-Hydroxyphenyl)-5Z,8Z,11Z,14Z-eicosatetraenamide, N-(4-Hydroxyphenyl)arachidonoylamide
Appearance	Waxy solid.
CAS	183718-77-6
Couple Target	Anandamide transporter, TRP channel
Couple Type	Activator, Inhibitor
Formula	C₂₆H₃₇NO₂
MW	395.6
Purity	≥98% (HPLC)
Solubility	Soluble in DMSO (>25mg/ml) or 100% ethanol (>25mg/ml).

Handling & Storage

Use/Stability	As indicated on product label or CoA when stored as recommended. 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.
Long Term Storage	-20°C
Shipping	Blue Ice

Regulatory Status	RUO – Research Use Only

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

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AM-404

BML-CR106

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