Cat. No. 1339

Anandamide C22H37NO2 [94421-68-8]

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Alternative Names: Arachidonylethanolamide, AEA

Chemical Name: N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide

Biological Activity

Endogenous cannabinoid and TRPV1 receptor agonist (Ki values are 89 and 371 nM at CB1 and CB2 receptors respectively; EC50 values are 18, 31 and 27 nM at GPR55, CB1 and CB2 respectively; pKi = 5.68 for rTRPV1). Also blocks TNF-α-induced NF-κB activation via direct inhibition of IKK. Also available in water soluble emulsion (Cat. No. 1017).

Technical Data

Soluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 5mg/ml)
Store at -20°C

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
All Tocris products are intended for laboratory research use only.

Certificate of Analysis / Safety Data Sheet

Certificate of Analysis: View current batch
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Safety Data Sheet: View Safety Data Sheet

Ryberg et al (2007) The orphan receptor GPR55 is a novel cannabinoid receptor. Br.J.Pharmacol. 152 1092. PMID: 17876302.

Sancho et al (2003) Anandamide inhibits nuclear factor-κB activation through a cannabinoid receptor-independent pathway. Mol.Pharmacol. 63 429. PMID: 12527815.

Ross et al (2001) Structure-activity relationship for the endogenous cannabinoid, anandamide, and certain of its analogues at vanilloid receptors in transfected cells and vas deferens. Br.J.Pharmacol. 132 631. PMID: 11159715.

Pertwee (1999) Pharmacology of cannabinoid receptor ligands. Curr.Med.Chem. 6 635. PMID: 10469884.

Devane et al (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258 1946. PMID: 1470919.

If you know of a relevant reference for this product please let us know.

Citations are publications that use Tocris products. Selected citations for Anandamide include:

Malek et al (2015) Anandamide, Acting via CB2 Receptors, Alleviates LPS-Induced Neuroinflammation in Rat Primary Microglial Cultures. Neural Plast 2015 130639. PMID: 26090232.

Smith et al (2015) The Effects of the Endocannabinoids Anandamide and 2-Arachidonoylglycerol on Human Osteoblast Proliferation and Differentiation. PLoS One 10 e0136546. PMID: 26414859.

Baranowska-Kuczko et al (2014) Mechanisms of endothelium-dependent relaxation evoked by anandamide in isolated human pulmonary arteries. J Biomed Sci 387 477. PMID: 24682422.

Malenczyk et al (2013) CB1 cannabinoid receptors couple to focal adhesion kinase to control insulin release. J Biol Chem 288 32685. PMID: 24089517.

Valdeolivas et al (2013) The inhibition of 2-arachidonoyl-glycerol (2-AG) biosynthesis, rather than enhancing striatal damage, protects striatal neurons from malonate-induced death: a potential role of cyclooxygenase-2-dependent metabolism of 2-AG. Cell Death Dis 4 e862. PMID: 24136226.

Caiati et al (2012) Developmental regulation of CB1-mediated spike-time dependent depression at immature mossy fiber-CA3 synapses. Sci Rep 2 285. PMID: 22368777.

Okine et al (2012) Lack of effect of chronic pre-treatment with the FAAH inhibitor URB597 on inflammatory pain behaviour: evidence for plastic changes in the endocannabinoid system. Am J Physiol Heart Circ Physiol 167 627. PMID: 22595021.

Morera-Herreras et al (2011) Nigrostriatal denervation changes the effect of cannabinoids on subthalamic neuronal activity in rats. Psychopharmacology (Berl) 214 379. PMID: 20959968.

Zschenderlein et al (2011) Capsaicin-induced changes in LTP in the lateral amygdala are mediated by TRPV1. PLoS One 6 e16116. PMID: 21249195.

Bhaskaran and Smith (2010) Effects of TRPV1 activation on synaptic excitation in the dentate gyrus of a mouse model of temporal lobe epilepsy. Cell Death Differ 223 529. PMID: 20144892.

Rajesh et al (2010) Cannabinoid-1 receptor activation induces reactive oxygen species-dependent and -independent mitogen-activated protein kinase activation and cell death in human coronary artery endothelial cells. Br J Pharmacol 160 688. PMID: 20590572.

Brozoski et al (2009) Differential endocannabinoid regulation of baroreflex-evoked sympathoinhibition in normotensive versus hypertensive rats. Auton Neurosci 150 82. PMID: 19464961.

Mendiguren and Pineda (2009) Effect of the CB(1) receptor antagonists rimonabant and AM251 on the firing rate of dorsal raphe nucleus neurons in rat brain slices. Br J Pharmacol 158 1579. PMID: 19845674.

Wang et al (2009) Pretreatment with electroacupuncture induces rapid tolerance to focal cerebral ischemia through regulation of endocannabinoid system. Stroke 40 2157. PMID: 19372445.

Zhang et al (2009) Developmental expression of a functional TASK-1 2P domain K+ channel in embryonic chick heart. Br J Pharmacol 16 104. PMID: 19930646.

Justinova et al (2008) Blockade of THC-seeking behavior and relapse in monkeys by the cannabinoid CB(1)-receptor antagonist rimonabant. Neuropsychopharmacology 33 2870. PMID: 18305459.

Meuth et al (2008) TWIK-related acid-sensitive K+ channel 1 (TASK1) and TASK3 critically influence T lymphocyte effector functions. J Biol Chem 283 14559. PMID: 18375952.

Bátkai et al (2007) Decreased age-related cardiac dysfunction, myocardial nitrative stress, inflammatory gene expression, and apoptosis in mice lacking fatty acid amide hydrolase. Am J Physiol Heart Circ Physiol 293 H909. PMID: 17434980.

Cuypers et al (2007) TRPV1 as a key determinant in ciguatera and neurotoxic shellfish poisoning. Exp Neurol 361 214. PMID: 17659256.

Hillard et al (2007) Inhibition of 2-arachidonoylglycerol catabolism modulates vasoconstriction of rat middle cerebral artery by the thromboxane mimetic, U-46619. Br J Pharmacol 152 691. PMID: 17891162.

Ho and Randall (2007) Endothelium-dependent metabolism by endocannabinoid hydrolases and cyclooxygenases limits vasorelaxation to anandamide and 2-arachidonoylglycerol. Naunyn Schmiedebergs Arch Pharmacol 150 641. PMID: 17245358.

Saitoh et al (2007) The differential contractile responses to capsaicin and anandamide in muscle strips isolated from the rat urinary bladder. Br J Pharmacol 570 182. PMID: 17586490.

Bender et al (2006) Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex. J Neurosci 26 4166. PMID: 16624937.

Raduner et al (2006) Alkylamides from Echinacea are a new class of cannabinomimetics. Cannabinoid type 2 receptor-dependent and -independent immunomodulatory effects. J Biol Chem 281 14192. PMID: 16547349.

Kwolek et al (2005) Central and peripheral components of the pressor effect of anandamide in urethane-anaesthetized rats. Br J Pharmacol 145 567. PMID: 15834445.

Pacher et al (2005) Hemodynamic profile, responsiveness to anandamide, and baroreflex sensitivity of mice lacking fatty acid amide hydrolase. Br J Pharmacol 289 H533. PMID: 15821037.

Bátkai et al (2004) Endocannabinoids acting at cannabinoid-1 receptors regulate cardiovascular function in hypertension. Eur J Pharmacol 110 1996. PMID: 15451779.

Movsesyan et al (2004) Anandamide-induced cell death in primary neuronal cultures: role of calpain and caspase pathways. Br J Pharmacol 11 1121. PMID: 15375383.

Price et al (2004) Cannabinoid receptor-independent actions of the aminoalkylindole WIN 55,212-2 on trigeminal sensory neurons. Br J Pharmacol 142 257. PMID: 15155534.

Smart et al (2002) 'Entourage' effects of N-acyl ethanolamines at human vanilloid receptors. Comparison of effects upon anandamide-induced vanilloid receptor activation and upon anandamide metabolism. J Biomol Screen 136 452. PMID: 12023948.

Jamshidi and Taylor (2001) Anandamide administration into the ventromedial hypothalamus stimulates appetite in rats. Br J Pharmacol 134 1151. PMID: 11704633.

Fowler et al (2000) Differences in the pharmacological properties of rat and chicken brain fatty acid amidohydrolase. Circulation 131 498. PMID: 11015300.

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Keywords: Anandamide, supplier, Endogenous, CB, receptor, agonists, vanilloids, cannabinoids, Non-Selective, Receptors, VR1, TRPV, Channels, Transient, Receptor, Potential, cb2r, cb1r, endocannabinoids, AEA, Tocris Bioscience, Non-selective Cannabinoid Agonist products

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