ANANDAMIDE

Base Information

• Chemical Name: ANANDAMIDE
• CAS No.: 94421-68-8
• Molecular Formula: C22H37 N O2
• Molecular Weight: 347.541
• Hs Code.: 2924199090
• Mol file: 94421-68-8.mol

Synonyms:5,8,11,14-Eicosatetraenamide,N-(2-hydroxyethyl)-, (all-Z)-; Anandamide; Arachidonylethanolamide;N-(2-Hydroxyethyl)arachidonamide; N-(2-Hydroxyethyl)arachidonylamide;N-Arachidonoylethanolamide; N-Arachidonylethanolamide;N-Arachidonylethanolamine

Chemical Property of ANANDAMIDE

Chemical Property:

• Appearance/Colour: light yellow oil
• Vapor Pressure: 4.33E-13mmHg at 25°C
• Boiling Point: 522.3 ºCat 760 mmHg
• PKA: 14.48±0.10(Predicted)
• Flash Point: 269.7 ºC
• PSA: 49.33000
• Density: 0.92 g/mL at 25 °C(lit.)
• LogP: 5.63150
• Storage Temp.: −20°C
• Solubility.: ethanol: soluble
• Water Solubility.: 413ug/L(25 oC)

Purity/Quality:

98%,99%, ^*data from raw suppliers

Arachidonylethanolamide ≥97.0% (TLC), oil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 24/25-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: Anandamide, also known as arachidonylethanolamide or N-arachidonoylethanolamine, is an endogenous cannabinoid receptor ligand that exhibits structural and functional similarities to Δ9-tetrahydrocannabinol (THC). Research highlights its stereochemical selectivity for CB1 and CB2 receptors, with modifications such as methyl group substitutions enhancing receptor affinity, particularly for CB1, while offering limited improvements in metabolic stability. Hybrid analogs combining structural features of anandamide and THC demonstrate high binding affinity, suggesting shared pharmacophoric elements critical for cannabinoid receptor interaction. These findings underscore anandamide's role as a key endocannabinoid and its potential as a template for designing novel cannabinoid receptor modulators.

Technology Process of ANANDAMIDE

There total 11 articles about ANANDAMIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) + ethanolamine (141-43-5) → anandamide (94421-68-8)

Guidance literature:

all cis 5,8,11,14-eicosatetraenoic acid; With 1,1'-carbonyldiimidazole; In dichloromethane; at 20 ℃; for 0.5h;

ethanolamine; In dichloromethane; for 12h;

DOI:10.1055/s-0037-1611939

Reference yield: 94.0%

ethanolamine (141-43-5) + arachidonoyl chloride (57303-04-5) → anandamide (94421-68-8)

Guidance literature:

DOI:10.1016/0024-3205(95)00187-B

Reference yield: 81.0%

ethyl arachidonate (95285-77-1,1808-26-0) + ethanolamine (141-43-5) → anandamide (94421-68-8)

Guidance literature:

With Candida antarctica B lipase; Enzymatic reaction;

DOI:10.1002/ejoc.201501263

upstream raw materials:

ethanolamine

arachidonoyl chloride

all cis 5,8,11,14-eicosatetraenoic acid

2-amino-ethanol hydrochloride

Downstream raw materials:

virodhamine

all cis 5,8,11,14-eicosatetraenoic acid

19-Hydroxyarachidonic acid

4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trienyl]oxiran-2-yl}butanoic acid

Refernces

Stereochemical selectivity of methanandamides for the CB1 and CB2 cannabinoid receptors and their metabolic stability

10.1016/S0968-0896(01)00088-8

The research aimed to evaluate the stereoselectivity of chiral analogues of the endogenous cannabinoid receptor ligand, arachidonylethanolamide (anandamide), in binding to CB1 and CB2 cannabinoid receptors and their metabolic stability. The study synthesized several chiral anandamide analogues with methyl groups introduced at the 2,1 and 20 positions using asymmetric synthesis. The researchers found that the introduction of a single 2-methyl group increased affinity for CB1, but only modestly improved metabolic stability. However, the 2,1-dimethyl analogues exhibited high enantio- and diastereoselectivity, with (R)-N-(1-methyl-2-hydroxyethyl)-2-(R)-methyl-arachidonamide (4) showing the highest CB1 receptor affinity. The study concluded that a partial CB1 receptor site model could be proposed, featuring two hydrophobic pockets capable of accommodating 1- and 2-methyl groups. Key chemicals used in the process included arachidonic acid, various amino alcohols, and chiral auxiliaries like 4-benzyl-2-oxazolidinone, along with reagents such as oxalyl chloride, lithium hydroxide, and phenylmethanesulfonyl fluoride (PMSF) for enzyme inhibition during binding assays.

Novel, potent THC/anandamide (hybrid) analogs

10.1016/j.bmc.2007.08.039

The research focuses on the exploration of structural similarities between anandamide (AEA) and Δ9-tetrahydrocannabinol (Δ9-THC) by designing and synthesizing hybrid structures. The purpose of this study was to broaden the understanding of these structural similarities and to develop novel THC/AEA hybrid ligands with potential novel pharmacological properties. The researchers synthesized a series of hybrid compounds, among which Hybrid 1 (O-2220) demonstrated very high binding affinity to CB1 receptors. The study concluded that the high receptor affinity and pharmacological potency of O-2220 provide further insights into the structural requirements for biological activity shared by THC and AEA, and that the hybrids developed in this study show potential for developing new templates for cannabinoid receptor agonists and antagonists. The chemicals used in the process included various organic compounds such as anandamide, Δ9-THC, and their analogs, as well as reagents like ethanol, emulphor, and saline for drug preparation and administration. Additionally, a range of synthetic intermediates and final hybrid compounds were prepared using a variety of chemical reactions and techniques, as detailed in the chemistry section of the article.