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: | 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 |
| |
Please mouse over
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;
