ANANDAMIDE Chemical Properties

Boiling point:

522.3±50.0 °C(Predicted)

Density 

0.92 g/mL at 25 °C (lit.)

Flash point:

14 °C

storage temp. 

-20°C

solubility 

ethanol: soluble

form 

oil

pka

14.48±0.10(Predicted)

color 

light yellow

Water Solubility 

413ug/L(25 ºC)

Stability:

Stable for 1 year from date of purchase as supplied. Subject to oxidation – protect from air. Solutions in degassed DMSO or ethanol may be stored under nitrogen or argon at -80°C for up to 1 month.

InChIKey

LGEQQWMQCRIYKG-DOFZRALJSA-N

SMILES

O=C(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)NCCO

Safety Information

Hazard Codes 

F

Risk Statements 

11

Safety Statements 

24/25-16-7

RIDADR 

UN 1170 3/PG 2

WGK Germany 

3

RTECS 

JX3842500

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

ANANDAMIDE Usage And Synthesis

Description

Anandamide (94421-68-8) is an endogenous cannabinoid receptor agonist.1-3?Ki=89 nM for CB1?and 371 nM for CB2?receptors.

Uses

Anandamide is an endogenous cannabinoid and TRPV1 receptor agonist. Findings suggest that endocannabinoids such as anandamide may help cause runner’s high, the feeling of euphoria, reduced anxiety and lessened ability to feel pain associated with exercise.

Definition

ChEBI: An N-(polyunsaturated fatty acyl)ethanolamine resulting from the formal condensation of carboxy group of arachidonic acid with amino group of ethanolamine.

Hazard

A reproductive hazard.

Biological Activity

Endogenous cannabinoid and vanilloid receptor agonist, in water-soluble emulsion (for details see TocrisolveTM 100). K i values are 89 and 371 nM for CB 1 and CB 2 receptors respectively; EC 50 values are 18, 31 and 27 nM at GPR55, CB 1 and CB 2 respectively; pK i = 5.68 for rVR1. Also blocks TNF- α -induced NF-kB activation via direct inhibition of IKK. Also available as the pure oil dissolved in ethanol (N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide ).

Biochem/physiol Actions

An arachidonic acid derivative that is an endogenous ligand for the CB cannabinoid receptor and for the VR1 vanilloid receptor. Inhibits calcium currents in neuroblastomas and neurons. Activates the MAP kinase signaling pathway. Inhibits proliferation and induces apoptosis of lymphocytes and human breast cancer cells.

Synthesis

Arachidonic acid-rich microbial algal oil (43.69% arachidonic acid, and other fatty acids such as 6.68% palmitic acid, 5.81% stearic acid, 5.95% oleic acid, 8.93% linoleic acid, 2.27% linolenic acid, 4.2% arachidonic acid, 3.2% behenic acid, and 10.62% lignocarboxylic acid, among others) was subjected to an amidation reaction with monoethanolamine. The molar ratio of microbial algal oil to monoethanolamine was 1:3, and the reaction medium (n-hexane:anhydrous ethanol = 1:1, v/v) was added according to the mass to volume ratio of 1:1, and a methanol solution of 0.3% sodium methanol was used as an alkaline catalyst, and the reaction was stirred for 2.5 h at 25 ??C to end the reaction. The fatty acid ethanolamide content was 62.5% by HPLC analysis. The reaction was heated and refluxed at 70 ?? according to urea: 95% ethanol = 1:2 (m/v), and after the urea was completely dissolved, the fatty acid monoethanolamide was added according to the mixed fatty acid monoethanolamide: urea = 1:2 (m/m), and refluxing was continued until the solution became clarified and transparent, and then the reaction was stopped and naturally cooled to room temperature. Then urea package at -40 ?? for 12h, remove and quickly filter separation, and wash the crystalline material with ethanol 2 to 3 times, combined filtrate, transferred to the partition funnel, then add anhydrous ether and hot water, gently shaking, fully extracted several times, and static layering. Get the aqueous phase is urea solution, after a low-temperature crystallization, filtrate concentration after the second crystallization can be obtained urea crystals recycling drying use. Combined with the organic phase, dried with anhydrous Na2SO4, spinning to remove the solvent, to obtain higher purity of arachidonic acid ethanolamine. The purity of the resulting arachidonic acid ethanolamine was increased from 42.17% to 63.18%.

Enzyme inhibitor

This lipid neurotransmitter and endocannabinoid receptor ligand (FW = 347.54 g/mol; CAS 94421-68-8), also known as arachidonylethanolamide, inhibits calcium ion currents and activates the MAP kinase signaling pathway. Anandamide is a naturally occurring effector of central and peripheral nervous systems, as mediated by CB1 and CB2 cannabinoid receptors, respectively. (These receptors were originally characterized as binding Δ9 -tetrahydrocannabinol, or THC, marijuana’s major psychoactive ingredient.) Anandamide, 2-arachidonoylglycerol, and congeners (N- oleoylethanolamide and N-palmitoylethanolamide) are lipophilic signalling molecules with multiple physiological roles in learning and memory, neuroinflammation, oxidative stress, neuroprotection and neurogenesis. Anandamide likewise plays a role in regulating uterine implantation of the early-stage embryo (blastocyst). Anandamide synthesis occurs from N- acetylphosphatidylethanolamine by multiple pathways that include phospholipase A2, phospholipase C, and NAPE-hydrolyzing phospholipase D (or NAPE-PLD). Target(s): adenylate cyclase; Na + channels; a7-nicotinic acetylcholine receptor; 5 HT3 receptors; Ca 2+ channels; K+ channels, voltage-gated; acylglycerol lipase, or monoacylglycerol lipase.

storage

Store at -20°C

References

[1] WILLIAM A. DEVANE. Isolation and Structure of a Brain Constituent That Binds to the Cannabinoid Receptor[J]. Science, 1992, 258 5090. DOI:10.1126/science.1470919
[2] DEVANE W A. New dawn of cannabinoid pharmacology.[J]. Trends in pharmacological sciences, 1994, 15 2: 40-41. DOI:10.1016/0165-6147(94)90106-6
[3] C J HILLARD  W B C. Biochemistry and pharmacology of arachidonylethanolamide, a putative endogenous cannabinoid.[J]. Journal of Lipid Research, 1997, 38 12: 2383-2398.

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