Structure Database (LMSD)

Common Name
Arachidonoyl-EA(d8)
Systematic Name
N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine(d8)
Synonyms
  • Arachidonoyl-ethanolamine(d8)
LM ID
LMFA08040044
Formula
Exact Mass
Calculate m/z
355.332645
Status
Curated

Classification

Biological Context

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 Ki value of 52 nM, compared to 46 nM for Δ9-THC.1

This information has been provided by Cayman Chemical

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).

References

Comments
Synthetic deuterated standard

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Synthetic deuterated standard

String Representations

InChiKey (Click to copy)
LGEQQWMQCRIYKG-FBFLGLDDSA-N
InChi (Click to copy)
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-/i6D,7D,9D,10D,12D,13D,15D,16D
SMILES (Click to copy)
C(NCCO)(=O)CCC/C(/[2H])=C(/[2H])\C/C(/[2H])=C(/[2H])\C/C(/[2H])=C(/[2H])\C/C(/[2H])=C(/[2H])\CCCCC

Other Databases

CHEBI ID
PubChem CID
Cayman ID

Admin

Created at
-
Updated at
29th Jan 2021