A0580

Arachidonylethanolamide

≥97.0% (TLC), oil

• Synonym(s): Anandamide (20:4, n-6), AEA, Anandamide, Arachidonic acid N-(hydroxyethyl)amide
• Empirical Formula (Hill Notation): C₂₂H₃₇NO₂
• CAS Number: 94421-68-8
• Molecular Weight: 347.53
• MDL number: MFCD00153766
• UNSPSC Code: 12352211
• PubChem Substance ID: 24890438
• NACRES: NA.25

Properties

• Quality Level: 200
• Assay: ≥97.0% (TLC)
• form: oil
• drug control: regulated under CDSA - not available from Sigma-Aldrich Canada
• color: colorless to light yellow
• solubility: ethanol: soluble
• density: 0.92 g/mL at 25 °C (lit.)
• lipid type: omega FAs
• shipped in: dry ice
• storage temp.: −20°C
• SMILES string: O=C(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)NCCO
• InChI: 1S/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-
• InChI key: LGEQQWMQCRIYKG-DOFZRALJSA-N
• Gene Information: rat ... Cnr1(25248)

Description

Application

• Interactions Between Endocannabinoid and Endogenous Opioid Systems Prospectively Influence Postoperative Opioid Use in Pregnant Patients Undergoing Cesarean Delivery: Investigates Arachidonylethanolamide′s interactions with opioid systems, providing insights that could lead to better management of postoperative pain and opioid use (Stone et al., 2024).

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.

Caution

Protect from light and moisture.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves