Serinolamide A

Serinolamide A
Identifiers
  • (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−1
3D model (JSmol)
  • O=C(N(C)[C@H](CO)COC)CC/C=C/CCCCCCCCCCCCC
  • 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.[1]

  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.