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Structure Database (LMSD)

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Common Name

Dihomo-gamma-linolenoyl-EA

Systematic Name

N-(8Z,11Z,14Z-eicosatrienoyl)-ethanolamine

Synonyms

dihomo-gamma-linolenoyl ethanolamide

LM ID

LMFA08040011

Formula

C₂₂H₃₉NO₂

Exact Mass

Calculate m/z

349.298079

Sum Composition

NAE 20:3

Status

Curated

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Classification

Biological Context

Dihomo-γ-linolenoyl ethanolamide is an endocannabinoid containing dihomo-γ-linoleate in place of the arachidonate moiety of AEA. Dihomo-γ-linolenoyl ethanolamide binds to recombinant human CB1 and CB2 receptors with Ki values of 857 and 598 nM, respectively.¹ Its specific role and relative importance as a cannabinergic neurotransmitter has not been elucidated.²

This information has been provided by Cayman Chemical

References

1. Hanus, L., Gopher, A., Almog, S., et al. Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor. J. Med. Chem. 36(20), 3032-3034 (1993).

2. Felder, C.C., Joyce, K.E., Briley, E.M., et al. Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol. Pharmacol. 48(3), 443-450 (1995).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Sus scrofa (#9823)

Mammalia (#40674)

Two new unsaturated fatty acid ethanolamides in brain that bind to the cannabinoid receptor.,
J Med Chem, 1993

Pubmed ID: 8411021

String Representations

InChiKey (Click to copy)

ULQWKETUACYZLI-QNEBEIHSSA-N

InChi (Click to copy)

InChI=1S/C22H39NO2/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/h6-7,9-10,12-13,24H,2-5,8,11,14-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-

SMILES (Click to copy)

C(/C/C=C\C/C=C\CCCCC)=C/CCCCCCC(=O)NCCO