Serinolamide A

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 K_i of 1300 nM at CB₁ and five fold selectivity over the related CB₂ receptor.[1]

Serinolamide A

Identifiers
IUPAC name (R,E)-N-(1-Hydroxy-3-methoxypropan-2-yl)-N-methyloctadec-4-enamide
CAS Number	1342300-14-4^N
PubChem CID	56597771
ChemSpider	27025743
Chemical and physical data
Formula	C23H45NO3
Molar mass	383.617 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C(N(C)[C@H](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

See also

• Methanandamide
• O-1812
• Perrottetinene

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.