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Structure Database (LMSD)

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Common Name

N-methyl arachidonoyl amine

Systematic Name

N-methyl-5Z,8Z,11Z,14Z-eicosatetraenoyl amine

Synonyms

N-methyl arachidonoylamide

LM ID

LMFA08020007

Formula

C₂₁H₃₅NO

Exact Mass

Calculate m/z

317.271864

Sum Composition

NA 21:4

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

Anandamide (AEA) is an endogenous cannabinoid that binds to both central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors. The biological actions of AEA are terminated by cellular uptake and hydrolysis of the amide bond by the enzyme fatty acid amide hydrolase. Arachidonoyl-N-methyl amide is an analog of anandamide that binds to the human central cannabinoid (CB1) receptor with a Ki of 60 nM.¹ It inhibits rat glial gap junction cell-cell communication 100% at a concentration of 50 µM.²

This information has been provided by Cayman Chemical

References

1. Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J. Med. Chem. 40(5), 659-667 (1997).

2. Boger, D.L., Sato, H., Lerner, A.E., et al. Arachidonic acid amide inhibitors of gap junction cell-cell communication. Bioorg. Med. Chem. Lett. 9(8), 1151-1154 (1999).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor.,
J Med Chem, 1997

Pubmed ID: 9057852

String Representations

InChiKey (Click to copy)

HTAWYBRCXMQDBL-ZKWNWVNESA-N

InChi (Click to copy)

InChI=1S/C21H35NO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(23)22-2/h7-8,10-11,13-14,16-17H,3-6,9,12,15,18-20H2,1-2H3,(H,22,23)/b8-7-,11-10-,14-13-,17-16-

SMILES (Click to copy)

C(/C/C=C\C/C=C\CCCCC)=C/C/C=C\CCCC(=O)NC