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O2136 Sigma

Oleamide

≥99%

Synonym: cis-9,10-Octadecenoamide, cis-9-Octadecenamide, Oleic acid amide

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Description

Biochem/physiol Actions

Sleep-inducing brain lipid, which allosterically modulates GABAA receptors and potentiates 5-HT7 serotonin receptor responses. Selective endogenous agonist of rat and human CB1 cannabinoid receptor.

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36-37
WGK Germany 
1

Protocols & Articles

Peer-Reviewed Papers

References

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Trilysinoyl oleylamide-based cationic liposomes for systemic co-delivery of siRNA and an anticancer drug. Shim G, Han SE, Yu YH, et al. J. Control. Release 155(1), 60-6, (2011)

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The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications. Didier M Lambert et al J. Med. Chem. 48, 5059-87, (2005)

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The role of gap junctions in megakaryocyte-mediated osteoblast proliferation and differentiation. Wendy A. Ciovacco et al Bone 44, 80-6, (2009)

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The hypnotic actions of the fatty acid amide, oleamide. Mendelson WB and Basile AS Biol. Psychiatry 25(5 Suppl), S36-9, (2001)

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The palmitoylethanolamide and oleamide enigmas : are these two fatty acid amides cannabimimetic? Lambert DM and Di Marzo V Curr. Med. Chem. 6(8), 757-73, (1999)

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Oleamide: a fatty acid amide signaling molecule in the cardiovascular system? Hiley CR and Hoi PM Cardiovasc. Drug Rev. 25(1), 46-60, (2007)

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Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation. Sumner Burstein et al Bioorg. Med. Chem. 16, 9644-51, (2008)

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Insights into the mechanism and inhibition of fatty acid amide hydrolase from quantum mechanics/molecular mechanics (QM/MM) modelling. Lodola A, Mor M, Sirirak J, et al. Biochem. Soc. Trans. 37(Pt 2), 363-7, (2009)

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Modulation of GABAA receptors and inhibitory synaptic currents by the endogenous CNS sleep regulator cis-9,10-octadecenoamide (cOA). Lees, et al. Br. J. Pharmacol. 124, 873-882, (1998)

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Oleamide potentiates benzodiazepine-sensitive gamma-aminobutyric acid receptor activity but does not alter minimum alveolar anesthetic concentration. Yost, C.S., et al. Anesth. Analg. 86, 1294-1300, (1998)

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Berberine potentizes apoptosis induced by X-rays irradiation probably through modulation of gap junctions. Liu B, Wang Q, Yuan DD, et al. Chin. Med. J. 124(8), 1221-8, (2011)

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The endocannabinoid system modulates the valence of the emotion associated to food ingestion. Méndez-Díaz M, Rueda-Orozco PE, Ruiz-Contreras AE, et al. Addict. Biol. 17(4), 725-35, (2012)

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Acute and subchronic administration of anandamide or oleamide increases REM sleep in rats. Herrera-Solís A, Vásquez KG, and Prospéro-García O Pharmacol. Biochem. Behav. 95(1), 106-12, (2010)

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Oleamide derivatives are prototypical anti-metastasis drugs that act by inhibiting Connexin 26. Nojima H, Ohba Y, and Kita Y Curr. Drug Saf. 2(3), 204-11, (2007)

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Oleamide is a selective endogenous agonist of rat and human CB1 cannabinoid receptors. Leggett, J.D., et al. Br. J. Pharmacol. 141, 253-262, (2004)

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Oleamide: a member of the endocannabinoid family? Fowler CJ Br. J. Pharmacol. 141(2), 195-6, (2004)

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Fatty acid amide hydrolase: biochemistry, pharmacology, and therapeutic possibilities for an enzyme hydrolyzing anandamide, 2-arachidonoylglycerol, palmitoylethanolamide, and oleamide. Fowler CJ, Jonsson KO, and Tiger G Biochem. Pharmacol. 62(5), 517-26, (2001)

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Stereoselective modulatory actions of oleamide on GABA(A) receptors and voltage-gated Na(+) channels in vitro: a putative endogenous ligand for depressant drug sites in CNS. Verdon, B., et al. Br. J. Pharmacol. 129, 283, (2000)

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The endogenous lipid oleamide activates serotonin 5-HT7 neurons in mouse thalamus and hypothalamus. Thomas, E.A., et al. J. Neurochem. 72, 2370-2378, (1999)

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Oleamide: an endogenous sleep-inducing lipid and prototypical member of a new class of biological signaling molecules. Boger, et al. Curr. Pharm. Des. 4, 303, (1998)

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Discovery and development of fatty acid amide hydrolase (FAAH) inhibitors. Mark Seierstad et al J. Med. Chem. 51, 7327-43, (2008)

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Fabrication of microspheres via solvent volatization induced aggregation of self-assembled nanomicellar structures and their use as a pH-dependent drug release system. Zhang L, Jeong YI, Zheng S, et al. Langmuir 29(1), 65-74, (2013)

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Primary fatty acid amide metabolism: conversion of fatty acids and an ethanolamine in N18TG2 and SCP cells. Farrell EK, Chen Y, Barazanji M, et al. J. Lipid Res. 53(2), 247-56, (2012)

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Oleamide administered into the nucleus accumbens shell regulates feeding behaviour via CB1 and 5-HT2C receptors. Soria-Gómez E, Márquez-Diosdado MI, Montes-Rodríguez CJ, et al. Int. J. Neuropsychopharmacol. 13(9), 1247-54, (2010)

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One-step formation of straight nanostripes from a mammal lipid-oleamide directly on highly oriented pyrolytic graphite. Zhang R, Möhwald H, and Kurth DG Langmuir 25(4), 2290-3, (2009)

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The endogenous cannabinoid anandamide shares discriminative stimulus effects with ∆(9)-tetrahydrocannabinol in fatty acid amide hydrolase knockout mice. Walentiny DM, Gamage TF, Warner JA, et al. Eur. J. Pharmacol. 656(1-3), 63-7, (2011)

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Oleamide activates peroxisome proliferator-activated receptor gamma (PPARγ) in vitro. Dionisi M, Alexander SP, and Bennett AJ Lipids Health Dis. 11, 51, (2012)

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Enhanced vasorelaxant effects of the endocannabinoid-like mediator, oleamide, in hypertension. Hopps JJ, Dunn WR, and Randall MD Eur. J. Pharmacol. 684(1-3), 102-7, (2012)

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Mechanisms involved in oleamide-induced vasorelaxation in rat mesenteric resistance arteries. Sudhahar V, Shaw S, and Imig JD Eur. J. Pharmacol. 607(1-3), 143-50, (2009)

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The structure of oleamide films at the aluminum/oil interface and aluminum/air interface studied by Sum Frequency Generation (SFG) vibrational spectroscopy and Reflection Absorption Infrared Spectroscopy (RAIRS). Casford MT and Davies PB ACS Appl. Mater. Interfaces 1(8), 1672-81, (2009)

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Gap junctions favor normal rat kidney epithelial cell adaptation to chronic hypertonicity. Desforges B, Savarin P, Bounedjah O, et al. Am. J. Physiol. Cell Physiol. 301(3), C705-16, (2011)

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Chemical synthesis of 9(Z)-octadecenamide and its hypolipidemic effect: a bioactive agent found in the essential oil of mountain celery seeds. Cheng MC, Ker YB, Yu TH, et al. J. Agric. Food Chem. 58(3), 1502-8, (2010)

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Oleamide restores sleep in adult rats that were subjected to maternal separation. Reyes Prieto NM, Romano López A, Pérez Morales M, et al. Pharmacol. Biochem. Behav. 103(2), 308-12, (2012)

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Oleamide suppresses lipopolysaccharide-induced expression of iNOS and COX-2 through inhibition of NF-kappaB activation in BV2 murine microglial cells. Oh YT, Lee JY, Lee J, et al. Neurosci. Lett. 474(3), 148-53, (2010)

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Biosynthesis of oleamide. Mueller GP and Driscoll WJ Vitam. Horm. 81, 55-78, (2009)

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A novel hypothesis about mechanisms affecting conduction velocity of central myelinated fibers. Adriano E, Perasso L, Panfoli I, et al. Neurochem. Res. 36(10), 1732-9, (2011)

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Therapeutic effects of connexin inhibitors on detrusor overactivity induced by bladder outlet obstruction in rats. Kim SJ, Park EY, Hwang TK, et al. Urology 78(2), 475.e1-7, (2011)

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Low concentrations of alendronate increase the local invasive potential of osteoblastic sarcoma cell lines via connexin 43 activation. Yoshitani K, Kido A, Honoki K, et al. Pathol. Res. Pract. 207(7), 417-22, (2011)

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Connexin 32 and its derived homotypic gap junctional intercellular communication inhibit the migration and invasion of transfected HeLa cells via enhancement of intercellular adhesion. Yang J, Liu B, Wang Q, et al. Mol. Med. Report. 4(5), 971-9, (2011)

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Effect of oleamide on pentylenetetrazole-induced seizures in rats. Solomonia R, Nozadze M, Mikautadze E, et al. Bull. Exp. Biol. Med. 145(2), 225-7, (2008)

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Lipopolysaccharide effects on the proliferation of NRK52E cells via alternations in gap-junction function. Hei Z, Zhang A, Wei J, et al. J. Trauma Acute Care Surg. 73(1), 67-72, (2012)

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