An endocannabinoid analog that does not bind to CB1, CB2, or TRPV1; at 5 mg/kg antagonizes the hypotensive effects of a 10 mg/kg IV bolus of abnormal cannabidiol (Abn-CBD) in an anesthetized rat blood pressure model; relaxes isolated rat mesenteric arteries and abdominal aorta, and increases the…

DGLA is a metabolite produced by chain elongation of the essential fatty acid γ-linolenic acid. Ethyl DGLA is an esterified version of the free acid which is less water soluble, but more ammenable for the formulation of DGLA-containing diets and dietary supplements. DGLA has been advanced as…

A homolog of DHEA, characterized by the addition of an (R)-β-methyl group at the terminal ethanolamine carbon.

A substrate for cPLA₂.

A minor alkaloid produced in plants of the Solanaceae family, including tobacco; detection in urine is used as an indicator of tobacco use; diminishes Aβ production, reduces the transcription and protein levels of β-secretase, and dose dependently inhibits NF-κB activation.

A homolog of EPEA, characterized by the addition of an (R)-β-methyl group at the terminal ethanolamine carbon.

An elongation product of γ-linolenic acid (18:3), rapidly metabolized by fatty acid desaturases to produce arachidonic acid (20:4); metabolized through the cyclooxygenase pathway to produce 1-series prostaglandins; can reduce atopic dermatitis and atherosclerosis when added to the diet of mice.

Oleyloxyethyl phosphorylcholine is an inhibitor of PLA2 with an IC₅₀ value of 6.2 µM for porcine pancreatic PLA2.

A selective calcium ionophore that mobilizes intracellular calcium stores. It is used as a research tool to raise the intracellular level of calcium, to study calcium transport across biological membranes, and to stimulate the intracellular production of cytokines.

A lipid peroxidation product derived from oxidized ω-6 PUFAs such as linoleic acid and arachidonic acid which is widely used as a marker of lipid peroxidation.

An isomer of Vitamin E that has less potent antioxidant properties than α-tocotrienol.

An EPA-containing MAG amide analog that inhibits the growth of human lung carcinoma A549 cells, producing 98.4% growth inhibition when applied at 3 µM; an analog of EPEA, a natural N-acylethanolamide that impacts aging and inflammation.

A natural isothiocyanate which induces the expression of phase II detoxification enzymes and activates Nrf2, promoting the expression of antioxidant and phase II genes; acts as a quorum sensing inhibitor, blocking acyl-homoserine lactone signaling in P. aeruginosa without affecting growth…

A naturally occurring phospholipid produced by cells upon inflammatory stimulation; less potent than PAF C-16 and PAF C-18 in the induction of neutrophil chemotaxis, but is equipotent to PAF C-16 and PAF C-18 in promoting eosinophil migration.

Ameliorates depression, reduces dopamine-induced neurotoxicity, and attenuates damage in a model of stroke; blocks autophagy, reduces inflammation, and inhibits apoptosis in isolated neurons and in brains; induces apoptosis in colon cancer cells.

A natural sesquiterpene that inhibits the proliferation of a wide range of tumors and enhances the effects of various chemotherapies; 10-40 µg/ml dose-dependently induces apoptosis and cell cycle arrest in the G2/M phase in HepG2 cells, upregulating Fas/FasL expression.

A water soluble prodrug analog of AEA with similar activity to that of AEA in the growth inhibition of C6 glioma cells; also a structural variant of LPA, however, its effects on the various LPA receptors have not been tested.

An alkaloid metabolite of nicotine as well as a major product of its pyrolysis; binds comparably to CYP2A6 and CYP2A13 (Kis = 7.5 and 5.6 µM, respectively), but appears to more effectively inactivate CYP2A6.

An inhibitor of Ras-mediated signaling that inhibits the growth of PANC-1 and U87 tumor cells with IC₅₀ values of 20 and 10 µM, respectively.

Unnatural C-15 epimer of Travoprost.

NAM is a potent, irreversible inhibitor of MAGL or MAGL-like activity in rat cerebellar membranes, exhibiting an IC50 value of 140 nM. Inhibition of MAGL by the sulfhydryl-reactive maleimide group of NAM suggests a critical cysteine residue is present in the substrate-binding site of the enzyme.

A homolog of DHEA, characterized by the addition of an (S)-β-methyl group at the terminal ethanolamine carbon.

A potent, stable, and selective agonist analog of AEA with a Ki value of 2.2 nM at the isolated rat CB1 receptor; 325 times more potent at the CB1 receptor compared with the CB2 receptor; induces hypothermia in mice with the same efficacy as AEA, in spite of its much higher affinity for the CB1…

A natural monoacylglycerol that is metabolized by monoacylglycerol lipase; an agonist of GPR119 (EC₅₀ = 2.5 µM), stimulating the release of glucagon-like peptide-1 from intestinal L-cells.

3-HPA is an analog of AM404, which is a selective inhibitor of carrier-mediated transport of AEA. 3-HPA is metabolized by both COX-1 and COX-2 and also selectively and irreversibly inhibits COX-2 with an IC50 value of 2 µM.

An ester of the free acid that is less water soluble, but more amenable for the formulation of stearidonate-containing diets and dietary supplements.

A more lipid-soluble form of DPA amenable to analysis using gas chromatography; may serve as a prodrug, since it should facilitate uptake of DPA and then be hydrolyzed by esterases to generate the free acid after uptake into cells.

A hybrid molecule patterned after N-arachidonoyl serotonin; inhibits capsaicin-induced TRPV1 channel activation (IC₅₀ = 2.57 μM) without blocking FAAH-mediated hydrolysis of arachidonoyl ethanolamine (IC₅₀ > 50 μM).

Cloprostenol is a synthetic PGF2α analog and a potent FP receptor agonist. (+)-15-epi Cloprostenol is the 15(S), or 15β-hydroxy enantiomer of (+)-cloprostenol. This epimer is less active by several orders of magnitude as an FP receptor ligand when compared to 15(R)-cloprostenol. However,…

Travoprost is the Alcon trade name for fluprostenol isopropyl ester, an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug. Fluprostenol isopropyl ester is a prodrug which is converted by esterase enzymatic activity in the cornea to yield the corresponding…

(+)-15(R)-Fluprostenol isopropyl ester is a prodrug (Travoprost) which is converted by esterase enzymatic activity in the cornea to yield the corresponding free acid. The free acid, (+)-15(R)-fluprostenol, is a potent FP receptor agonist. The 15(R)-epimers of most PGs are about 100 times less…

A potent anti-mitotic drug that is 100-fold more active than resveratrol at inhibiting the growth of human colon cancer Caco-2 cells; inhibits tubulin polymerization in a dose-dependent manner (IC₅₀ = 4 μM) and enzymes involved in the synthesis of the polyamines, putrescine, and spermidine.