94421-68-8

Basic information

• Product Name: ANANDAMIDE
• Synonyms: Arachidonylethanolamide,AEA, Anandamide, Arachidonic acid N-(hydroxyethyl)amide;Anandamide (in Tocrisolve 100);Arachidonoyl Ethanolamide Lipid Maps MS Standard;(5Z,8Z,11Z,14Z)-N-(2-Hydroxyethyl)-5,8,11,14-eicosatetraenamide;ARACHIDONYLETHANOLAMIDE, >=97.0% (TL;11,14-eicosatetraenamide(all-z)-n-(2-hydroxyethyl)-8;14-eicosatetraenamide,n-(2-hydroxyethyl)-(all-z)-11;5,8,11,14-eicosatetraenoylethanolamide
• CAS NO: 94421-68-8
• Molecular Formula: C₂₂H₃₇NO₂
• Molecular Weight: 347.53
• EINECS: 200-578-6
• Product Categories: Cannabinoid receptor;Cannabinoid
• Mol File: 94421-68-8.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 522.3 ºCat 760 mmHg
• Flash Point: 14 °C
• Appearance: light yellow/oil
• Density: 0.92 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.33E-13mmHg at 25°C
• Refractive Index: 1.503
• Storage Temp.: −20°C
• Solubility: ethanol: soluble
• PKA: 14.48±0.10(Predicted)
• 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.
• CAS DataBase Reference: ANANDAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ANANDAMIDE(94421-68-8)
• EPA Substance Registry System: ANANDAMIDE(94421-68-8)

Safety Data

• Hazard Codes: F
• Statements: 11
• Safety Statements: 24/25-16-7
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 3
• RTECS: JX3842500
• Hazardous Substances Data: 94421-68-8(Hazardous Substances Data)

Usage

Description

Anandamide, also known as arachidonoylethanolamide, is an endogenous cannabinoid receptor agonist that naturally occurs in the body. It has a Ki value of 89 nM for CB1 receptors and 371 nM for CB2 receptors, indicating its high affinity for these receptors.

Uses

Used in Pharmaceutical Industry:
Anandamide is used as a therapeutic agent for various medical conditions due to its interaction with cannabinoid receptors. It has potential applications in the treatment of pain, inflammation, anxiety, and neurodegenerative disorders.
Used in Cosmetic Industry:
Anandamide is used as an active ingredient in cosmetic products for its potential anti-aging, moisturizing, and skin barrier repair properties. Its interaction with cannabinoid receptors in the skin may contribute to these benefits.
Used in Nutraceutical Industry:
Anandamide is used as a dietary supplement to support overall health and well-being. Its potential benefits include promoting relaxation, improving sleep quality, and modulating mood.
Used in Research:
Anandamide is used as a research tool to study the endocannabinoid system and its role in various physiological processes. It helps scientists understand the mechanisms of action and potential therapeutic applications of cannabinoids.

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.

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.

References

1) Devane?et al. (1992),?Isolation and structure of a brain constituent that binds to the cannabinoid receptor; Science,258?1946 2) Devane?et al. (1994),?New dawn of cannabinoid pharmacology; Trends Pharmacol.Sci.,?15?40 3) Hillard?et al. (1997),?Biochemistry and pharmacology of arachidonoylethanolamide, a putative endogenous cannabinoid; J. Lipid Res.,?38?2383

InChI:InChI=1/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,15-16,24H,2-5,8,11,14,17-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-,16-15-

Upstream product

• 141-43-5 ethanolamine 
• 57303-04-5 arachidonoyl chloride 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 2002-24-6 2-amino-ethanol hydrochloride 
• 543-27-1 isobutyl chloroformate 
• 2566-89-4 methyl arachidonate 
• 69205-93-2 arachidonic acid imidazolide 
• 95285-77-1 ethyl arachidonate 

Downstream Products

• 287937-12-6 virodhamine 
• 79551-85-2 19-Hydroxyarachidonic acid 
• 184488-43-5 4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienyl]oxiran-2-yl}butanoic acid 
• 184488-44-6 8,9-epoxyeicosa-5(Z),11(Z),14(Z)-trienoic acid 
• 197508-62-6 cis-14,15-epoxyeicosatrienoic acid 
• 200960-01-6 11,12-cis-epoxyeicosatrienoic acid 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 

Relevant articles and documents

Modification of the antitumor effect of doxorubicin by complexes of α-fetoprotein with amphiphilic compounds based on polyenoic fatty acids

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Methyl arachidonyl fluorophosphonate: A potent irreversible inhibitor of anandamide amidase

Anandamide amidase (EC 3.5.1.4) is responsible for the hydrolysis of arachidonoyl ethanolamide (anandamide). Relatively selective and potent enzyme reversible inhibitors effective in the low micromolar range, such as arachidonyl trifluoromethyl ketone (Arach-CF3), have been described (Koutek et al., J Biol Chem 269: 22937-22940, 1994). In the current study, methyl arachidonyl fluorophosphonate (MAFP), an arachidonyl binding site directed phosphonylation reagent, was tested as an inhibitor of anandamide amidase and as a ligand for the CB1 cannabinoid receptor. MAFP was 800 times more potent than Arach-CF3 and phenylmethylsulfonyl fluoride (PMSF) as an amidase inhibitor in rat brain homogenates. In intact neuroblastoma cells, MAFP was also approximately 1000-fold more potent than Arach-CF3. MAFP demonstrated selectivity towards anandamide amidase for which it was approximately 3000 and 30,000-fold more potent than it was towards chymotrypsin and trypsin, respectively. MAFP displaced [3H]CP-55940 binding to the CB1 cannabinoid receptor with an IC50 of 20 nM vs 40 nM for anandamide. It bound irreversibly and prevented subsequent binding of the cannabinoid radioligand [3H]CP-55940 at that locus. These studies suggest that MAFP is a potent and specific inhibitor of anandamide amidase and, in addition, can interact with the cannabinoid receptors at the cannabinoid binding site. This is the first report of a potent and relatively selective irreversible inhibitor of arachidonoyl ethanolamide amidase.

COMPOSITIONS HAVING AN AGENT AND AN ENHANCER THEREOF, METHODS OF USE, AND DELIVERY SYSTEMS

The present invention relates to compositions, and methods of use thereof, related to the endocannabinoid system and includes therapeutic compositions including an agent and an enhancer thereof, optionally, formulated for administration of the therapeutic compositions, preferably in a measured amount.

INHIBITORS OF N-ACYLPHOSPHATIDYLETHANOLAMINE PHOSPHOLIPASE D (NAPE-PLD)

The invention relates to a compound of the formula (I) as novel inhibitor of N-acylphosphatidylethanolamine phospholipase D (NAPE-PLD), and to use thereof for the prophylaxis or treatment of diseases associated with NAPE-PLD. wherein in a ring A, X1 is N, or CR4; X2 is N or CR5; X3 is N or CH; with the proviso that at least one of X1 and X3 is N.