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Serinolamide A

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Chemical compound Pharmaceutical compound
Serinolamide A
Identifiers
IUPAC name
  • (R,E)-N-(1-Hydroxy-3-methoxypropan-2-yl)-N-methyloctadec-4-enamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H45NO3
Molar mass383.617 g·mol
3D model (JSmol)
SMILES
  • O=C(N(C)(CO)COC)CC/C=C/CCCCCCCCCCCCC
InChI
  • InChI=1S/C23H45NO3/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)24(2)22(20-25)21-27-3/h16-17,22,25H,4-15,18-21H2,1-3H3/b17-16+/t22-/m1/s1
  • Key:CJAVPRNATZCNLN-NBRGKURFSA-N

Serinolamide A is a naturally occurring eicosanoid derivative related to anandamide, which has been isolated from the marine cyanobacteria Lyngbya majuscula and related species in the Oscillatoria family.

Testing established that serinolamide A is an active cannabinoid agonist with moderate potency, having a Ki of 1300 nM at CB1 and five fold selectivity over the related CB2 receptor.

See also

References

  1. Gutiérrez M, Pereira AR, Debonsi HM, Ligresti A, Di Marzo V, Gerwick WH (October 2011). "Cannabinomimetic lipid from a marine cyanobacterium". Journal of Natural Products. 74 (10): 2313–7. doi:10.1021/np200610t. PMC 3325759. PMID 21999614.

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