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ALX-340-029 [ALEXIS] Revised 08-Jul-08
Anandamide SYNONYMS    AEA N-Arachidonoylethanolamine (all-Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide PRODUCT LINE    Neurobiology PRODUCT FAMILIES    Anandamide & Anandamide Analogs Ordering Information  Product Numbers Format Size Unit Price Quantity  ALX-340-029-M005 5 mg     Product Specification FORMULA:    C22H37NO2   MW:    347.5   CAS NUMBER:    94421-68-8   MERCK INDEX:    14: 624   RTECS:    JX3842500   CONCENTRATION:    50mg/ml    PURITY:    ≥98%   FORMULATION:    Liquid. Solution in ethanol.   SOLUBILITY:    10mg/ml soluble in DMSO or dimethyl formamide.   SHIPPING:    SHIPPED ON BLUE ICE   LONG TERM STORAGE:    -20°C   USE/STABILITY:    Stable for at least 1 year after receipt when stored at -20°C. Stable for at least 6 months in other organic solvents when stored at -20°C.   HANDLING:    Protect from light and oxygen. Product Description 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]. Product Specific Literature References [1] Isolation and structure of a brain constituent that binds to the cannabinoid receptor: W.A. Devane, et al.; Science 258, 1946 (1992) Abstract [2] 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 [3] Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide: P.M. Zygmunt, et al.; Nature 400, 452 (1999) Abstract [4] 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 [5] Anandamide inhibits nuclear factor-kappaB activation through a cannabinoid receptor-independent pathway: R. Sancho, et al.; Mol. Pharmacol. 63, 429 (2003) Abstract [6] 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 [7] The MAP kinase signal transduction pathway is activated by the endogenous cannabinoid anandamide: M. Wartmann, et al.; FEBS Lett. 359, 133 (1995) 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 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 Endocannabinoids: a new class of vasoactive substances: M.D. Randall & D.A. Kendall; TIPS 19, 55 (1998), (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 Anandamide: a candidate neurotransmitter heads for the big leagues: D.W. Self; Nat. Neurosci. 2, 303 (1999), (Review) Abstract New perspectives on enigmatic vanilloid receptors: A. Szallasi & V. Di Marzo; TINS 23, 491 (2000), (Review) Abstract Anandamide: some like it hot: V. Di Marzo, et al.; TIPS 22, 346 (2001), (Review) 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-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 Arachidonylethanolamide induces apoptosis of human glioma cells through vanilloid receptor-1: E. Contassot, et al.; J. Neuropathol. Exp. Neurol. 63, 956 (2004) Abstract Preferred conformations of endogenous cannabinoid ligand anandamide: J.Z. Chen, et al.; Life Sci. 76, 2053 (2005) Abstract The cardiovascular actions of anandamide: more targets?: M.D. Randall; Br. J. Pharmacol. 145, 565 (2005) Full Text; http://www.nature.com/bjp/journal/v145/n5/pdf/0706234a.pdf Accumulation of anandamide: Evidence for cellular diversity: C.J. Hillard and A. Jarrahian; Neuropharmacology 48, 1072 (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 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 inhibits adhesion and migration of breast cancer cells: C. Grimaldi, et al.; Exp. Cell Res. 312, 363 (2006) Abstract General Information Background/Technical Information    To change the solvent, evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice. RELATED PRODUCT GROUPS    Neurobiology > TRPVs [Vanilloid Receptors] / Related Products > Endovanilloids / Signal Transduction > NF-kB Pathway > NF-kB Pathway Inhibitors / Neurobiology > Cannabinoid Receptors / Related Products > Endocannabinoids / Cell Death / Apoptosis / Autophagy > Apoptosis Inducers & Inhibitors > Apoptosis Inducers & Inhibitors Other Products / Signal Transduction > MAP Kinase Pathways > MAPK Pathway Activators