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Endogenous CB1 receptor ligand
Endogenous [1] ligand for the CB1 receptor (CB1: Ki=52nm; CB2: Ki=1930nm [2]) and TRPV1 (Ki=5.78µM [3,4]). Inhibits NF-κB activation through direct binding to IKKβ [5] and induces apoptosis independently of cannabinoid or vanilloid receptors [6]. Activates the MAP kinase (MAPK/ERK) signalling pathway [7].
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Product Details
| Alternative Name |
AEA, N-Arachidonoylethanolamine, (all-Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide |
|---|---|
| Appearance |
Colorless oil. |
| CAS |
94421-68-8 |
| Couple Target |
Cannabinoid receptor, IKK, MAPK, TRP channel |
| Couple Type |
Activator, Inhibitor, Ligand |
| Formula |
C22H37NO2 |
| MI |
14: 624 |
| MW |
347.54 |
| Purity |
≥98% (TLC) |
| Solubility |
Soluble in ethanol (e.g. at a concentration of 50 mg/ml). It is also soluble in DMSO and dimethyl formamide. |
Handling & Storage
| Use/Stability |
As indicated on product label or CoA when stored as recommended. Stable for at least 1 year after receipt when stored, as supplied, under an inert atmosphere at -80°C. |
|---|---|
| Handling |
Protect from light and oxygen. Keep under inert gas. |
| Long Term Storage |
-80°C |
| Shipping |
Dry Ice |
| Regulatory Status |
RUO – Research Use Only |
|---|
- Direct interrogation of context-dependent GPCR activity with a universal biosensor platform: R. Janicot, et al.; Cell 187, 1527 (2024), Abstract
- Anandamide inhibits adhesion and migration of breast cancer cells: C. Grimaldi, et al.; Exp. Cell Res. 312, 363 (2006), Abstract
- Anandamide reduces infarct size in rat isolated hearts subjected to ischaemia-reperfusion by a novel cannabinoid mechanism: N.J. Underdown, et al.; Br. J. Pharmacol. 146, 809 (2005), Abstract
- Anandamide as an intracellular messenger regulating ion channel activity: M. van der Stelt and V. Di Marzo; Prostaglandins Other Lipid Mediat. 77, 111 (2005), Abstract
- Accumulation of anandamide: Evidence for cellular diversity: C.J. Hillard and A. Jarrahian; Neuropharmacology 48, 1072 (2005), Abstract
- The cardiovascular actions of anandamide: more targets?: M.D. Randall; Br. J. Pharmacol. 145, 565 (2005), Abstract — Full Text
- Preferred conformations of endogenous cannabinoid ligand anandamide: J.Z. Chen, et al.; Life Sci. 76, 2053 (2005), Abstract
- Arachidonylethanolamide induces apoptosis of human glioma cells through vanilloid receptor-1: E. Contassot, et al.; J. Neuropathol. Exp. Neurol. 63, 956 (2004), Abstract
- Anandamide-induced cell death in primary neuronal cultures: role of calpain and caspase pathways: V.A. Movsesyan, et al.; Cell Death Differ. 11, 1121 (2004), Abstract
- Anandamide is an endogenous inhibitor for the migration of tumor cells and T lymphocytes: J. Joseph, et al.; Cancer Immunol. Immunother. 53, 723 (2004), Abstract
- Anandamide induces cell death independently of cannabinoid receptors or vanilloid receptor 1: possible involvement of lipid rafts: K.P. Sarker, et al.; Cell Mol. Life Sci. 60, 1200 (2003), Abstract
- Anandamide inhibits nuclear factor-kappaB activation through a cannabinoid receptor-independent pathway: R. Sancho, et al.; Mol. Pharmacol. 63, 429 (2003), Abstract
- Anandamide: some like it hot: V. Di Marzo, et al.; TIPS 22, 346 (2001), (Review), Abstract
- Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens: R.A. Ross, et al.; Br. J. Pharmacol. 132, 631 (2001), Abstract
- New perspectives on enigmatic vanilloid receptors: A. Szallasi & V. Di Marzo; TINS 23, 491 (2000), (Review), Abstract
- Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide: P.M. Zygmunt, et al.; Nature 400, 452 (1999), Abstract
- Anandamide: a candidate neurotransmitter heads for the big leagues: D.W. Self; Nat. Neurosci. 2, 303 (1999), (Review), Abstract
- Metabolism of anandamide and 2-arachidonoylglycerol: an historical overview and some recent developments: V. Di Marzo, et al.; Lipids 34, S319 (1999), (Review), Abstract
- Endocannabinoids: a new class of vasoactive substances: M.D. Randall & D.A. Kendall; TIPS 19, 55 (1998), (Review), Abstract
- Novel analogues of arachidonylethanolamide (anandamide): affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability: S. Lin, et al.; J. Med. Chem. 41, 5353 (1998), Abstract
- The endogenous cannabinoid anandamide inhibits human breast cancer cell proliferation: L. De Petrocellis, et al.; PNAS 95, 8375 (1998), Abstract
- Cannabinoid receptors and their endogenous agonist, anandamide: J. Axelrod & C.C. Felder; Neurochem. Res. 23, 575 (1998), (Review), Abstract
- Endocannabinoids: endogenous cannabinoid receptor ligands with neuromodulatory action: V. Di Marzo, et al.; TINS 21, 521 (1998), (Review), Abstract
- Biochemistry and pharmacology of arachidonylethanolamide, a putative endogenous cannabinoid: C.J. Hillard & W.B. Campbell; J. Lipid Res. 38, 2383 (1997), (Review), Abstract
- The MAP kinase signal transduction pathway is activated by the endogenous cannabinoid anandamide: M. Wartmann, et al.; FEBS Lett. 359, 133 (1995), Abstract
- New dawn of cannabinoid pharmacology: W.A. Devane; Trends Pharmacol. Sci. 15, 40 (1994), Abstract
- Anandamide, an endogenous ligand of the cannabinoid receptor, induces hypomotility and hypothermia in vivo in rodents: J.N. Crawley, et al.; Pharmacol. Biochem. Behav. 46, 967 (1993), Abstract
- Pharmacological activity of the cannabinoid receptor agonist, anandamide, a brain constituent: E. Fride & R. Mechoulam; Eur. J. Pharmacol. 231, 313 (1993), Abstract
- Molecular characterization of a peripheral receptor for cannabinoids: S. Munro, et al.; Nature 365, 61 (1993), Abstract
- Isolation and structure of a brain constituent that binds to the cannabinoid receptor: W.A. Devane, et al.; Science 258, 1946 (1992), Abstract
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