EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes

(Z)-octadec-9-enoic acid amide

Supplier Sponsors

CAS Number: 301-02-0Picture of molecule3D/inchi
Other(deleted CASRN):181057-55-6
ECHA EINECS - REACH Pre-Reg:206-103-9
Nikkaji Web:J36.613G
XlogP3-AA:6.60 (est)
Molecular Weight:281.48315000
Formula:C18 H35 N O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:opacifying agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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DG SANTE Food Contact Materials:oleamide
FDA Mainterm (IAUFC):301-02-0 ; OLEAMIDE
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 433.34 °C. @ 760.00 mm Hg (est)
Flash Point: 421.00 °F. TCC ( 215.90 °C. ) (est)
logP (o/w): 6.882 (est)
Soluble in:
 water, 0.04591 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: opacifying agents
viscosity controlling agents
American International Chemical, LLC.
Oleamide Finawax-O Beads
BOC Sciences
For experimental / research use only.
Oleicamide 97%
Odor: characteristic
Use: A brain lipid that induces physiological sleep at nanomolar quantities when injected into rats. This lipid may repr
Kao Corporation
Odor: characteristic
Use: Lubricant use, anti-blocking agent and slipping agent.
Sigma-Aldrich: Sigma
For experimental / research use only.
Oleamide ≥99%
Safety Information:
Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
opacifying agents
Recommendation for oleamide usage levels up to:
 not for fragrance use.
Recommendation for oleamide flavor usage levels up to:
 not for flavor use.
Safety References:
European Food Safety Authority (EFSA) reference(s):

Safety assessment of the mixture of methyl-branched and linear C14C18 alkanamides, derived from fatty acids, for use in food contact materials
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):301-02-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5283387
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:301-02-0
Pubchem (cid):5283387
Pubchem (sid):134975607
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Indirect Additives used in Food Contact Substances:View
KEGG (GenomeNet):C19670
HMDB (The Human Metabolome Database):HMDB02117
Potential Blenders and core components note
None Found
Potential Uses:
 opacifying agents
 viscosity controlling agents
Occurrence (nature, food, other):note
 not found in nature
 adogen 73
 armoslip CP
 crodamide O
 crodamide OR
 fatty amide O-N
(Z)-octadec-9-enoic acid amide
9-octadecenamide, (9Z)-
9-octadecenamide, (Z)-
 oleamide finawax-O beads


PubMed:Preventive Effects of a Fermented Dairy Product against Alzheimer's Disease and Identification of a Novel Oleamide with Enhanced Microglial Phagocytosis and Anti-Inflammatory Activity.
PubMed:Characterisation of the metabolites of an antibacterial endophyte Botryodiplodia theobromae Pat. of Dracaena draco L. by LC-MS/MS.
PubMed:Antidepressant-like effects of the cannabinoid receptor ligands in the forced swimming test in mice: Mechanism of action and possible interactions with cholinergic system.
PubMed:Irsogladine Maleate Regulates Gap Junctional Intercellular Communication-Dependent Epithelial Barrier in Human Nasal Epithelial Cells.
PubMed:Endocannabinoids modulate human blood-brain barrier permeability in vitro.
PubMed:Differential proteomic analysis of the anti-depressive effects of oleamide in a rat chronic mild stress model of depression.
PubMed:Downregulation of Connexin 32 Attenuates Hypoxia/Reoxygenation Injury in Liver Cells.
PubMed:Metabolomics reveals that aldose reductase activity due to AKR1B10 is upregulated in hepatitis C virus infection.
PubMed:Prymnesium parvum revisited: relationship between allelopathy, ichthyotoxicity, and chemical profiles in 5 strains.
PubMed:2-Arachidonoylglycerol into the lateral hypothalamus improves reduced sleep in adult rats subjected to maternal separation.
PubMed:Role of gap junction intercellular communication in testicular leydig cell apoptosis induced by oxaliplatin via the mitochondrial pathway.
PubMed:Adhesion force interactions between cyclopentane hydrate and physically and chemically modified surfaces.
PubMed:Evidence for Transfer of Membranes from Mesenchymal Stem Cells to HL-1 Cardiac Cells.
PubMed:Synthesis and biological evaluation of a new series of N-acyldiamines as potential antibacterial and antifungal agents.
PubMed:Carriage of the V279F homozygous genotype, a rare allele, within the gene encoding Lp-PLA2 leads to changes in circulating intermediate metabolites in individuals without metabolic syndrome.
PubMed:Metabolomic study of lipids in serum for biomarker discovery in Alzheimer's disease using direct infusion mass spectrometry.
PubMed:Connexin-dependent gap junction enhancement is involved in the synergistic effect of sorafenib and all-trans retinoic acid on HCC growth inhibition.
PubMed:Stimulation of nitrogen removal in the rhizosphere of aquatic duckweed by root exudate components.
PubMed:A Metabolomic Approach to the Pathogenesis of Ventilator-induced Lung Injury.
PubMed:Propofol inhibits gap junctions by attenuating sevoflurane-induced cytotoxicity against rat liver cells in vitro.
PubMed:Contact allergy from metalworking fluid traced to tall oil fatty acids monoethanolamide.
PubMed:Macamides and their synthetic analogs: evaluation of in vitro FAAH inhibition.
PubMed:Human liver tissue metabolic profiling research on hepatitis B virus-related hepatocellular carcinoma.
PubMed:Role of heteromeric gap junctions in the cytotoxicity of cisplatin.
PubMed:Regulation of gap junctions in melanoma and their impact on Melan-A/MART-1-specific CD8⁺ T lymphocyte emergence.
PubMed:Nonempirical energetic analysis of reactivity and covalent inhibition of fatty acid amide hydrolase.
PubMed:Quantum mechanics/molecular mechanics modeling of fatty acid amide hydrolase reactivation distinguishes substrate from irreversible covalent inhibitors.
PubMed:Lipid profiling for early diagnosis and progression of colorectal cancer using direct-infusion electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry.
PubMed:Fabrication of microspheres via solvent volatization induced aggregation of self-assembled nanomicellar structures and their use as a pH-dependent drug release system.
PubMed:[Expression of connexin 43 and functional modulation of gap junction in neonatal rat astrocytes in vitro].
PubMed:Beta-D-glucoside protects against advanced glycation end products (AGEs)-mediated diabetic responses by suppressing ERK and inducing PPAR gamma DNA binding.
PubMed:Oleamide restores sleep in adult rats that were subjected to maternal separation.
PubMed:Probing gender-specific lipid metabolites and diagnostic biomarkers for lung cancer using Fourier transform ion cyclotron resonance mass spectrometry.
PubMed:Rat and human fatty acid amide hydrolases: overt similarities and hidden differences.
PubMed:Lipopolysaccharide effects on the proliferation of NRK52E cells via alternations in gap-junction function.
PubMed:Oleamide activates peroxisome proliferator-activated receptor gamma (PPARγ) in vitro.
PubMed:Metabolic disorders of fatty acids and fatty acid amides associated with human gastric cancer morbidity.
PubMed:Enhanced vasorelaxant effects of the endocannabinoid-like mediator, oleamide, in hypertension.
PubMed:[Influence of Cx26/Cx32 gap junction channel on antineoplastic effect of etoposide in Hela cells].
PubMed:In situ imaging of the autonomous intracellular Ca(2+) oscillations of osteoblasts and osteocytes in bone.
PubMed:Antimalarial natural products drug discovery in Panama.
PubMed:Primary fatty acid amide metabolism: conversion of fatty acids and an ethanolamine in N18TG2 and SCP cells.
PubMed:Ascaridole, a sensitizing component of tea tree oil, patch tested at 1% and 5% in two series of patients.
PubMed:Anandamide modulates carotid sinus nerve afferent activity via TRPV1 receptors increasing responses to heat.
PubMed:Therapeutic effects of connexin inhibitors on detrusor overactivity induced by bladder outlet obstruction in rats.
PubMed:A serum metabonomic study on the difference between alcohol- and HBV-induced liver cirrhosis by ultraperformance liquid chromatography coupled to mass spectrometry plus quadrupole time-of-flight mass spectrometry.
PubMed:Connexin 32 and its derived homotypic gap junctional intercellular communication inhibit the migration and invasion of transfected HeLa cells via enhancement of intercellular adhesion.
PubMed:Low concentrations of alendronate increase the local invasive potential of osteoblastic sarcoma cell lines via connexin 43 activation.
PubMed:Identification of oleamide in Guatteria recurvisepala by LC/MS-based Plasmodium falciparum thioredoxin reductase ligand binding method.
PubMed:Berberine potentizes apoptosis induced by X-rays irradiation probably through modulation of gap junctions.
PubMed:Discovery and molecular basis of potent noncovalent inhibitors of fatty acid amide hydrolase (FAAH).
PubMed:Application of a SCC-DFTB QM/MM approach to the investigation of the catalytic mechanism of fatty acid amide hydrolase.
PubMed:The endogenous cannabinoid anandamide shares discriminative stimulus effects with ∆(9)-tetrahydrocannabinol in fatty acid amide hydrolase knockout mice.
PubMed:The endocannabinoid system modulates the valence of the emotion associated to food ingestion.
PubMed:Oleamide administered into the nucleus accumbens shell regulates feeding behaviour via CB1 and 5-HT2C receptors.
PubMed:Major involvement of connexin 43 in seminiferous epithelial junction dynamics and male fertility.
PubMed:Fractionation and identification of organic nitrogen species from bio-oil produced by fast pyrolysis of sewage sludge.
PubMed: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).
PubMed:Oleamide suppresses lipopolysaccharide-induced expression of iNOS and COX-2 through inhibition of NF-kappaB activation in BV2 murine microglial cells.
PubMed:Chemical analysis of synthetic cannabinoids as designer drugs in herbal products.
PubMed:Chemical synthesis of 9(Z)-octadecenamide and its hypolipidemic effect: a bioactive agent found in the essential oil of mountain celery seeds.
PubMed:Acute and subchronic administration of anandamide or oleamide increases REM sleep in rats.
PubMed:Extracellular ATP and P2Y2 receptors mediate intercellular Ca(2+) waves induced by mechanical stimulation in submandibular gland cells: Role of mitochondrial regulation of store operated Ca(2+) entry.
PubMed:Method for determination of fatty acid amides in polyethylene packaging materials--gas chromatography/mass spectrometry.
PubMed:Serum metabolite profiling of human colorectal cancer using GC-TOFMS and UPLC-QTOFMS.
PubMed:Biosynthesis of oleamide.
PubMed:Gap junctions at the dendritic cell-T cell interface are key elements for antigen-dependent T cell activation.
PubMed:Mechanisms involved in oleamide-induced vasorelaxation in rat mesenteric resistance arteries.
PubMed:Insights into the mechanism and inhibition of fatty acid amide hydrolase from quantum mechanics/molecular mechanics (QM/MM) modelling.
PubMed:Properties of gap junction blockers and their behavioural, cognitive and electrophysiological effects: animal and human studies.
PubMed:One-step formation of straight nanostripes from a mammal lipid-oleamide directly on highly oriented pyrolytic graphite.
PubMed:Effect of oleamide on pentylenetetrazole-induced seizures in rats.
PubMed:Bioactive contaminants leach from disposable laboratory plasticware.
PubMed:The role of gap junctions in megakaryocyte-mediated osteoblast proliferation and differentiation.
PubMed:Oleamide derivatives are prototypical anti-metastasis drugs that act by inhibiting Connexin 26.
PubMed:Skin permeation enhancement of diclofenac by fatty acids.
PubMed:Functional role of gap junctions in cytokine-induced leukocyte adhesion to endothelium in vivo.
PubMed:Biosynthesis, degradation and pharmacological importance of the fatty acid amides.
PubMed:The role of the CB1 receptor in the regulation of sleep.
PubMed:On the lipid composition of human meibum and tears: comparative analysis of nonpolar lipids.
PubMed:Overview of the chemical families of fatty acid amide hydrolase and monoacylglycerol lipase inhibitors.
PubMed:Ca2+ signaling in injured in situ endothelium of rat aorta.
PubMed:Fatty acid amide hydrolase: from characterization to therapeutics.
PubMed:Evaluation of fatty acid amides in the carrageenan-induced paw edema model.
PubMed:Lipids of human meibum: mass-spectrometric analysis and structural elucidation.
PubMed:Engineering of Pseudomonas aeruginosa lipase by directed evolution for enhanced amidase activity: mechanistic implication for amide hydrolysis by serine hydrolases.
PubMed:Neuropharmacological effects of oleamide in male and female mice.
PubMed:Does rat granulation tissue maturation involve gap junction communications?
PubMed:Interferon-gamma inhibits intestinal restitution by preventing gap junction communication between enterocytes.
PubMed:The functional interrelationship between gap junctions and fenestrae in endothelial cells of the liver organoid.
PubMed:In vitro synthesis of oleoylglycine by cytochrome c points to a novel pathway for the production of lipid signaling molecules.
PubMed:Anxiolytic-like effects of oleamide in group-housed and socially isolated mice.
PubMed:Camellia oil and its distillate fractions effectively inhibit the spontaneous metastasis of mouse melanoma BL6 cells.
PubMed:Oleamide synthesizing activity from rat kidney: identification as cytochrome c.
PubMed:Oleamide: a fatty acid amide signaling molecule in the cardiovascular system?
PubMed:Oleamide derivatives suppress the spontaneous metastasis by inhibiting connexin 26.
PubMed:Potent and selective alpha-ketoheterocycle-based inhibitors of the anandamide and oleamide catabolizing enzyme, fatty acid amide hydrolase.
PubMed:Identification of fatty acids and fatty acid amides in human meibomian gland secretions.
PubMed:Elucidation of hydrolysis mechanisms for fatty acid amide hydrolase and its Lys142Ala variant via QM/MM simulations.
PubMed:Synthesis of colloidal uranium-dioxide nanocrystals.
PubMed:Comparison of three gas chromatography methods for the determination of slip agents in polyethylene films.
PubMed:Fatty acids and sleep in depressed inpatients.
PubMed:Injector-internal thermal desorption from edible oils performed by programmed temperature vaporizing (PTV) injection.
PubMed:Cardiac mitochondrial connexin 43 regulates apoptosis.
PubMed:Secretory proteins as potential semiochemical carriers in the horse.
PubMed:In vivo evidence that N-oleoylglycine acts independently of its conversion to oleamide.
PubMed:Chemical characteristics and origins of nitrogen-containing organic compounds in PM2.5 aerosols in the Lower Fraser Valley.
PubMed:[The role of gap junction communication in metastatic B16 melanoma in C57BL mice].
PubMed:A second fatty acid amide hydrolase with variable distribution among placental mammals.
PubMed:Connexin 26 expression prevents down-regulation of barrier and fence functions of tight junctions by Na+/K+-ATPase inhibitor ouabain in human airway epithelial cell line Calu-3.
PubMed:Solution structure of a chemosensory protein from the desert locust Schistocerca gregaria.
PubMed:A potential novel mechanism involving connexin 43 gap junction for control of sertoli cell proliferation by thyroid hormones.
PubMed:High-throughput screening for the discovery of inhibitors of fatty acid amide hydrolase using a microsome-based fluorescent assay.
PubMed:Subcellular localization and tissue specific expression of amidase 1 from Arabidopsis thaliana.
PubMed:Determination of oleamide and erucamide in polyethylene films by pressurised fluid extraction and gas chromatography.
PubMed:Signaling mechanisms of down-regulation of voltage-activated Ca2+ channels by transient receptor potential vanilloid type 1 stimulation with olvanil in primary sensory neurons.
PubMed:Enhanced radiosensitization of p53 mutant cells by oleamide.
PubMed:Possible involvement of gap junctions in the barrier function of tight junctions of brain and lung endothelial cells.
PubMed:Gap junction communications influence upon fibroblast synthesis of Type I collagen and fibronectin.
PubMed:Vasorelaxant effects of oleamide in rat small mesenteric artery indicate action at a novel cannabinoid receptor.
PubMed:Fatty acid amide hydrolase (-/-) mice exhibit an increased sensitivity to the disruptive effects of anandamide or oleamide in a working memory water maze task.
PubMed:Elucidation of fatty acid amide hydrolase inhibition by potent alpha-ketoheterocycle derivatives from Monte Carlo simulations.
PubMed:Sample preparation and gas chromatography of primary fatty acid amides.
PubMed:Fatty acid amide hydrolase controls mouse intestinal motility in vivo.
PubMed:QM/MM modelling of oleamide hydrolysis in fatty acid amide hydrolase (FAAH) reveals a new mechanism of nucleophile activation.
PubMed:Focus on the three key enzymes hydrolysing endocannabinoids as new drug targets.
PubMed:Targeted lipidomics: fatty acid amides and pain modulation.
PubMed:Structure and function of fatty acid amide hydrolase.
PubMed:Pharmacological enhancement of cannabinoid CB1 receptor activity elicits an antidepressant-like response in the rat forced swim test.
PubMed:A spectrophotometric assay for fatty acid amide hydrolase suitable for high-throughput screening.
PubMed:Discovery of a potent, selective, and efficacious class of reversible alpha-ketoheterocycle inhibitors of fatty acid amide hydrolase effective as analgesics.
PubMed:Allergic contact dermatitis from cocamidopropyl betaine, cocamidoamine, 3-(dimethylamino)propylamine, and oleamidopropyl dimethylamine: co-reactions or cross-reactions?
PubMed:Heterocyclic sulfoxide and sulfone inhibitors of fatty acid amide hydrolase.
PubMed:Fatty acid amide hydrolase in brain ventricular epithelium: mutually exclusive patterns of expression in mouse and rat.
PubMed:Characterization of the sleep-wake patterns in mice lacking fatty acid amide hydrolase.
PubMed:Oleic acid derived metabolites in mouse neuroblastoma N18TG2 cells.
PubMed:Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: evidence for an unprecedented combination of potency and selectivity.
PubMed:Mast cells promote fibroblast populated collagen lattice contraction through gap junction intercellular communication.
PubMed:A derivative of oleamide potently inhibits the spontaneous metastasis of mouse melanoma BL6 cells.
PubMed:Oleamide and anandamide effects on food intake and sexual behavior of rats.
PubMed:Functional characterization of Cx43 based gap junctions during spermatogenesis.
PubMed:The sleep lipid oleamide may represent an endogenous anticonvulsant: an in vitro comparative study in the 4-aminopyridine rat brain-slice model.
PubMed:Differential effects of the sleep-inducing lipid oleamide and cannabinoids on the induction of long-term potentiation in the CA1 neurons of the rat hippocampus in vitro.
PubMed:Oleamide is a selective endogenous agonist of rat and human CB1 cannabinoid receptors.
PubMed:Oleamide: a member of the endocannabinoid family?
PubMed:The sleep inducing brain lipid cis-oleamide (cOA) does not modulate serotonergic transmission in the CA1 pyramidal neurons of the hippocampus in vitro.
PubMed:The serotonergic system may be involved in the sleep-inducing action of oleamide in rats.
PubMed:Inhibition of fatty acid amidohydrolase, the enzyme responsible for the metabolism of the endocannabinoid anandamide, by analogues of arachidonoyl-serotonin.
PubMed:Selective effect of oleamide, an endogenous sleep-inducing lipid amide, on pentylenetetrazole-induced seizures in mice.
PubMed:Effects of oleamide on choline acetyltransferase and cognitive activities.
PubMed:A high-throughput-compatible assay for determining the activity of fatty acid amide hydrolase.
PubMed:Evidence for distinct roles in catalysis for residues of the serine-serine-lysine catalytic triad of fatty acid amide hydrolase.
PubMed:Biochemical regulation of non-rapid-eye-movement sleep.
PubMed:Expression of connexin 43 mRNA in microisolated murine osteoclasts and regulation of bone resorption in vitro by gap junction inhibitors.
PubMed:Economically pertinent continuous amide formation by direct lipase-catalyzed amidation with ammonia.
PubMed:Erucamide as a modulator of water balance: new function of a fatty acid amide.
PubMed:NTP Toxicology and Carcinogenesis Studies of Oleic Acid Diethanolamine Condensate (CAS No. 93-83-4) in F344/N Rats and B6C3F1 Mice (Dermal Studies).
PubMed:No hypothermic response to serotonin in 5-HT7 receptor knockout mice.
PubMed:Endocannabinoids and related fatty acid derivatives in pain modulation.
PubMed:The enzymatic inactivation of the fatty acid amide class of signaling lipids.
PubMed:Block of erg current by linoleoylamide, a sleep-inducing agent, in pituitary GH3 cells.
PubMed:Membrane protein crystallization in meso: lipid type-tailoring of the cubic phase.
PubMed:Induction of Oct-3/4 expression in somatic cells by gap junction-mediated cAMP signaling from blastomeres.
PubMed:Endocannabinoid hydrolases.
PubMed:Patterns of dye coupling in lumbar motor nuclei of the rat.
PubMed:Conjugated linoleic acid (CLA) inhibits growth of Caco-2 colon cancer cells: possible mediation by oleamide.
PubMed:Oleamide attenuates apoptotic death in cultured rat cerebellar granule neurons.
PubMed:Functional role for cannabinoids in respiratory stability during sleep.
PubMed:Pharmacological activity of fatty acid amides is regulated, but not mediated, by fatty acid amide hydrolase in vivo.
PubMed:Gap junction intercellular communication propagates cell death in cancerous cells.
PubMed:The sleep hormone oleamide modulates inhibitory ionotropic receptors in mammalian CNS in vitro.
PubMed:Fatty acid amide hydrolase, an enzyme with many bioactive substrates. Possible therapeutic implications.
PubMed:Selective inhibitors of fatty acid amide hydrolase relative to neuropathy target esterase and acetylcholinesterase: toxicological implications.
PubMed:The biohydrogenation of linoleamide in vitro and its effects on linoleic acid concentration in duodenal contents of sheep.
PubMed:Deletion of the GABA(A) receptor beta 3 subunit eliminates the hypnotic actions of oleamide in mice.
PubMed:Effect of oleamide on Ca(2+) signaling in human bladder cancer cells.
PubMed:Characterization of the 5'-sequence of the mouse fatty acid amide hydrolase.
PubMed:Oleamide modulates memory in rats.
PubMed:The hypnotic actions of the fatty acid amide, oleamide.
PubMed:Effect of oleamide on sleep and its relationship to blood pressure, body temperature, and locomotor activity in rats.
PubMed:A catalytic antibody produces fluorescent tracers of gap junction communication in living cells.
PubMed:Fatty acid amide hydrolase: biochemistry, pharmacology, and therapeutic possibilities for an enzyme hydrolyzing anandamide, 2-arachidonoylglycerol, palmitoylethanolamide, and oleamide.
PubMed:Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems.
PubMed:Gap junctions modulate survival-promoting effects of fibroblast growth factor-2 on cultured midbrain dopaminergic neurons.
PubMed:alpha-Keto heterocycle inhibitors of fatty acid amide hydrolase: carbonyl group modification and alpha-substitution.
PubMed:Direct methylation procedure for converting fatty amides to fatty acid methyl esters in feed and digesta samples.
PubMed:Characterization and manipulation of the acyl chain selectivity of fatty acid amide hydrolase.
PubMed:Fatty acid amide hydrolase inhibition by neurotoxic organophosphorus pesticides.
PubMed:Proteins regulating the biosynthesis and inactivation of neuromodulatory fatty acid amides.
PubMed:Gap-junctional communication is required for the maturation process of osteoblastic cells in culture.
PubMed:Inhibition of gap-junctional communication induces the trans-differentiation of osteoblasts to an adipocytic phenotype in vitro.
PubMed:Anesthetic-like interaction of the sleep-inducing lipid oleamide with voltage-gated sodium channels in mammalian brain.
PubMed:Fatty acid amide hydrolase substrate specificity.
PubMed:Endocannabinoids and fatty acid amides in cancer, inflammation and related disorders.
PubMed:The fatty acid amide hydrolase (FAAH).
PubMed:Site of administration and duration of feeding oleamide to cattle on feed intake and ruminal fatty acid concentrations.
PubMed:Connexin mimetic peptides reversibly inhibit Ca(2+) signaling through gap junctions in airway cells.
PubMed:Early migratory rat neural crest cells express functional gap junctions: evidence that neural crest cell survival requires gap junction function.
PubMed:pH Sensitivity of non-synaptic field bursts in the dentate gyrus.
PubMed:Exceptionally potent inhibitors of fatty acid amide hydrolase: the enzyme responsible for degradation of endogenous oleamide and anandamide.
PubMed:Anandamide amidohydrolase (fatty acid amide hydrolase).
PubMed:Clarifying the catalytic roles of conserved residues in the amidase signature family.
PubMed:Feeding oleamide to lactating Jersey cows. 2. Effects on nutrient digestibility, plasma fatty acids, and hormones.
PubMed:Feeding oleamide to lactating Jersey cows 1. Effects on lactation performance and milk fatty acid composition.
PubMed:Fatty acid amide hydrolase expression in rat choroid plexus: possible role in regulation of the sleep-inducing action of oleamide.
PubMed:Physiological role of gap-junctional hemichannels. Extracellular calcium-dependent isosmotic volume regulation.
PubMed: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.
PubMed:Induction of peptidylglycine alpha-amidating monooxygenase in N(18)TG(2) cells: a model for studying oleamide biosynthesis.
PubMed:Oleamide-mediated sleep induction does not depend on perturbation of membrane homeoviscosity.
PubMed:The hypnotic actions of oleamide are blocked by a cannabinoid receptor antagonist.
PubMed:Allosteric regulation by oleamide of the binding properties of 5-hydroxytryptamine7 receptors.
PubMed:Identification of two serine residues involved in catalysis by fatty acid amide hydrolase.
PubMed:Anandamide amidohydrolase of porcine brain: cDNA cloning, functional expression and site-directed mutagenesis(1).
PubMed:Studies on the sedative and hypnotic effects of oleamide in mice.
PubMed:The palmitoylethanolamide and oleamide enigmas : are these two fatty acid amides cannabimimetic?
PubMed:Chemical and mutagenic investigations of fatty acid amide hydrolase: evidence for a family of serine hydrolases with distinct catalytic properties.
PubMed:Lactation performance and fatty acid composition of milk from Holstein cows fed 0 to 5% oleamide.
PubMed:The endogenous lipid oleamide activates serotonin 5-HT7 neurons in mouse thalamus and hypothalamus.
PubMed:A gas chromatographic-mass spectral assay for the quantitative determination of oleamide in biological fluids.
PubMed:Characterization of the hypnotic properties of oleamide.
PubMed:Modification of 5-HT2 receptor mediated behaviour in the rat by oleamide and the role of cannabinoid receptors.
PubMed:Electron cryo-crystallography of a recombinant cardiac gap junction channel.
PubMed:Oleamide: an endogenous sleep-inducing lipid and prototypical member of a new class of biological signaling molecules.
PubMed:Trifluoromethyl ketone inhibitors of fatty acid amide hydrolase: a probe of structural and conformational features contributing to inhibition.
PubMed:Oleamide-induced modulation of 5-hydroxytryptamine receptor-mediated signaling.
PubMed:Anandamide transport inhibition by the vanilloid agonist olvanil.
PubMed:Conserved chromosomal location and genomic structure of human and mouse fatty-acid amide hydrolase genes and evaluation of clasper as a candidate neurological mutation.
PubMed:Gap junction-mediated cell-cell communication modulates mouse neural crest migration.
PubMed:Comparative characterization of a wild type and transmembrane domain-deleted fatty acid amide hydrolase: identification of the transmembrane domain as a site for oligomerization.
PubMed:Arachidonoylserotonin and other novel inhibitors of fatty acid amide hydrolase.
PubMed:Biosynthesis and degradation of bioactive fatty acid amides in human breast cancer and rat pheochromocytoma cells--implications for cell proliferation and differentiation.
PubMed:Oleamide potentiates benzodiazepine-sensitive gamma-aminobutyric acid receptor activity but does not alter minimum alveolar anesthetic concentration.
PubMed:Chemical requirements for inhibition of gap junction communication by the biologically active lipid oleamide.
PubMed:Structural requirements for 5-HT2A and 5-HT1A serotonin receptor potentiation by the biologically active lipid oleamide.
PubMed:Fatty acid composition of milk from Holstein cows fed oleamide or canola oil.
PubMed:Bioactive amides of fatty acids.
PubMed:Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand.
PubMed:Unique allosteric regulation of 5-hydroxytryptamine receptor-mediated signal transduction by oleamide.
PubMed:The sleep-inducing lipid oleamide deconvolutes gap junction communication and calcium wave transmission in glial cells.
PubMed:Fatty acid amide hydrolase, the degradative enzyme for anandamide and oleamide, has selective distribution in neurons within the rat central nervous system.
PubMed:The sleep inducing factor oleamide is produced by mouse neuroblastoma cells.
PubMed:Reversible hydrolysis and synthesis of anandamide demonstrated by recombinant rat fatty-acid amide hydrolase.
PubMed:Molecular characterization of human and mouse fatty acid amide hydrolases.
PubMed:Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides.
PubMed:Enzymatic synthesis of oleamide (cis-9, 10-octadecenoamide), an endogenous sleep-inducing lipid, by rat brain microsomes.
PubMed:Hydrolysis studies on oleamide in simulated gastrointestinal fluids.
PubMed:Contact allergy to oleamidopropyl dimethylamine and related substances.
PubMed:The patch test dilution of oleamidopropyl dimethylamine.
PubMed:[Allosterism of acidic alcohol dehydrogenase (class III ADH) of mouse liver and its role in alcohol metabolism].
PubMed:Application of liquid chromatography with on-line radiochemical detection to metabolism studies on a novel class of analgesics.
PubMed:Oleamidopropyl dimethylamine.
PubMed:Determination of quaternary ammonium surfactants in pharmaceutical formulations by the hypochromic effect.
PubMed:Cross-reaction pattern of the cationic emulsifier oleamidopropyl dimethylamine.
PubMed:NE-19550: a novel, orally active anti-inflammatory analgesic.
PubMed:Contact allergy to oleamidopropyl dimethylamine.
PubMed:Inhibition of chymase activity by long chain fatty acids.
plastic additive; can cause contact urticaria; a sleep inducing factor. Release agent migrating from food packaging Oleamide is an amide of the fatty acid oleic acid. It is an endogenous substance: it occurs naturally in the body of animals. It accumulates in the cerebrospinal fluid during sleep deprivation and induces sleep in animals. It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression.; The mechanism of action of oleamide's sleep inducing effects is an area of current research. It is likely that oleamide interacts with multiple neurotransmitter systems. Oleamide is structurally related to the endogenous cannabinoid anandamide, and has the ability to bind to the CB1 receptor as a full agonist.
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