Linoleoyl Glycine

Linoleoyl Glycine

Cayman Chemical Item Number 9000326

N-Linoleoyl Glycine; LinGly; Glycine Linoleamide (CAS 2764-03-6)

Linoleoyl Glycine (CAS 2764-03-6)

Description

Arachidonyl glycine, the conjugate of arachidonic acid and glycine produced in mammalian brain, skin, and spinal cord, is a structural analog of anandamide (AEA) that is reported to have analgesic activities in whole animal experiments.^1,2,3 It has poor affinity for the central cannabinoid (CB₁) receptor, high-affinity for the G protein-coupled receptor GPR-18, and is metabolically regulated by fatty acid amide hydrolase (FAAH) activity.⁴ LinGly is an endogenous homolog of linoleoyl ethanolamide, an arachidonyl glycine. It inhibits the hydrolysis of AEA in FAAH-containing N18TG2 cell membranes with an IC₅₀ value of ~25 µM, which is less potent than that of arachidonyl glycine (IC₅₀ = 7 µM).³ The biological significance of LinGly has not yet been determined.

1 Burstein, S.H., Rossetti, R.G., Yagen, B., et al. Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat 61 29-41 (2000).

2 Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification and characterization of an endogenous anandamide-like compound: N-arachidonylglycine (NAGly). ICRS 2001 Symposium on the Cannabinoids 78 (2001).

3 Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. J Biol Chem 276(46) 42639-42644 (2001).

4 Rimmerman, N., Bradshaw, H.B., Hughes, H.V., et al. N-palmitoyl glycine, a novel endogenous lipid that acts as a modulator of calcium influx and nitric oxide production in sensory neurons. Mol Pharmacol 74(1) 213-224 (2008).

Synonyms

N-Linoleoyl Glycine
LinGly
Glycine Linoleamide

Formal Name

N-9Z,12Z-1-oxo-octadecadien-1-yl-glycine

CAS Number

2764-03-6

Molecular Formula

C₂₀H₃₅NO₃

Formula Weight

337.5

Formulation

A crystalline solid

Purity

≥98%

Stability

2 years

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

Copy SMILES to clipboard

CCCCC/C=C\C/C=C\CCCCCCCC(=O)NCC(=O)O

Background Reading

Burstein, S.H., Rossetti, R.G., Yagen, B., et al. Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat 61 29-41 (2000).

Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification and characterization of an endogenous anandamide-like compound: N-arachidonylglycine (NAGly). ICRS 2001 Symposium on the Cannabinoids 78 (2001).

Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. J Biol Chem 276(46) 42639-42644 (2001).

Rimmerman, N., Bradshaw, H.B., Hughes, H.V., et al. N-palmitoyl glycine, a novel endogenous lipid that acts as a modulator of calcium influx and nitric oxide production in sensory neurons. Mol Pharmacol 74(1) 213-224 (2008).

Show all 4 Hide all but first 3

Linoleoyl Glycine is available in the following screening library:

Fatty Acid Screening Library (96-Well)

Size

Global Purchasing

5 mg 
See a distributor in your region for pricing

10 mg 
See a distributor in your region for pricing

50 mg 
See a distributor in your region for pricing

100 mg 
See a distributor in your region for pricing