Anandamide

Pricing Availability Delivery Time Qty
Cat.No. 1339 - Anandamide | C22H37NO2 | CAS No. 94421-68-8
Description: Endogenous CB receptor agonist
Alternative Names: Arachidonylethanolamide, AEA
Chemical Name: N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide
Datasheet
Citations (34)

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

M. Wt 347.54
Formula C22H37NO2
Storage Store at -20°C
CAS Number 94421-68-8
PubChem ID 5281969
InChI Key LGEQQWMQCRIYKG-DOFZRALJSA-N
Smiles O=C(NCCO)CCC\C=C/C\C=C/C/C=C\C/C=C\CCCCC

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.

Solubility Data

SolubilitySoluble in ethanol (supplied pre-dissolved in anhydrous ethanol, 5mg/ml)

Preparing Stock Solutions

The following data is based on the product molecular weight 347.54. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.88 mL 14.39 mL 28.77 mL
5 mM 0.58 mL 2.88 mL 5.75 mL
10 mM 0.29 mL 1.44 mL 2.88 mL
50 mM 0.06 mL 0.29 mL 0.58 mL

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

Product Datasheets

Certificate of Analysis / Product Datasheet
Select another batch:
Safety Datasheet

References

References are publications that support the products' biological activity.

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

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

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

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


If you know of a relevant reference for Anandamide, please let us know.

View Related Products by Target

View Related Products by Product Action

View all Non-selective Cannabinoid Agonists

Keywords: Endogenous CB receptor agonists vanilloids cannabinoids Non-Selective Receptors VR1 TRPV Channels Transient Receptor Potential cb2r cb1r endocannabinoids AEA Arachidonylethanolamide AEA Non-selective Cannabinoids

34 Citations for Anandamide

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Almada (2017) The synthetic cannabinoid WIN-55,212-55,212 induced-apoptosis in cytotrophoblasts cells by a mechanism dependent on CB1 receptor. Toxicology 385 67 PMID: 28495606

King-Himmelreich (2017) AMPK contributes to aerobic exercise-induced antinociception downstream of endocannabinoids. Neuropharmacology 124 134 PMID: 28479394

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

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

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

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

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

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


Do you know of a great paper that uses Anandamide from Tocris? If so please let us know.

Commented out for usability testing

Reviews

TODO: Add Reviews

Literature in this Area

Pathways for Anandamide

Protocols

TODO: Add Protocols