AEA-D8

Product NameAEA-D8
CAS924894-98-4
MFC22H37NO2
MW355.58
EINECS
MOL FileMol File

Chemical Properties

Boiling point	522.258±50.00 °C(Press: 760.00 Torr)(predicted)
Density	0.940±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
solubility	1 mg/ml EtOH:PBS pH 7.2: can dilute 1:1.6 (>380 μg/ml); 10 mg/ml EtOH:PBS pH 7.2: can dilute 1:1 (>5 mg/ml) (fro; 100 g/ml EtOH:PBS pH 7.2: can dilute 1:1.6 (>38 μg/ml) (; DMF: >10 mg/ml (from AEA); DMSO: >30 mg/ml (from AEA); Ethanol: >100 mg/ml (from AEA); PBS pH 7.2: <100 μg/ml (from AEA)
pka	14.483±0.10(predicted)
form	Liquid
color	Colorless to light yellow

Usage And Synthesis

Description

Arachidonoyl ethanolamide-d₈ (AEA-8) contains eight deuterium atoms at the 5, 6, 8, 9, 11, 12, 14, and 15 positions. It is intended for use as an internal standard for the quantification of AEA by GC- or LC-mass spectrometry. AEA is the ethanolamine amide of arachidonic acid, first isolated from porcine brain.¹ It is an endogenous cannabinoid neurotransmitter that binds to both CB₁ and CB₂ receptors.² AEA inhibits the specific binding of [³H]-HU-243 to synaptosomal membranes with a K_i value of 52 nM, compared to 46 nM for Δ⁹-THC.¹

Uses

Anandamide-d8 is a deuterated labeled Anandamide[1]. Anandamide is an endocannabinoid. Anandamide modulates both neuronal and immune functions through two protein-coupled cannabinoid receptors (CB1 and CB2). Anandamide can activate numerous other receptors like PPARS, TRPV1, and GPR18/GPR55. Anandamide also has potential anti-fungal and anti-inflammatory activities. Anandamide can be used for the research of Alzheimer’s disease (AD) and ulcerative colitis[2][3][4][5][6].

Definition

ChEBI: Anandamide is an N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine. It has a role as a neurotransmitter, a vasodilator agent and a human blood serum metabolite. It is an endocannabinoid and a N-acylethanolamine 20:4. It is functionally related to an arachidonic acid.

in vivo

Anandamide (10 mg/kg, IP, once) considerably lowers the increase of glycemia in response to glucose ingestion compared with control, and this is associated with an improvement of glucose tolerance^[3].
Anandamide (100 ng, ICV bilateral injection, single) partially prevents streptozotocin (STZ)-induced cognitive impairments, changes in synaptic markers and ventricle enlargement^[4].
Anandamide exerts anti-inflammatory activities, attenuating the development of inflammation in a mouse model of ulcerative colitis^[5].
Anandamide alleviates lipopolysaccharide (LPS)-induced neuroinflammation in rat primary microglial cultures^[2].

References

1. Devane, W.A., Hanus, L., Breuer, A., et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor Science 258(5090),1946-1949(1992).
2. Felder, C.C., Briley, E.M., Axelrod, J., et al. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction Proc. Natl. Acad. Sci. USA 90(16),7656-7660(1993).

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