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Merck

O2136

Oleamide

≥99% (TLC), powder, sleep-inducing brain lipid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C18H35NO
CAS Number:
301-02-0
Molecular Weight:
281.48
NACRES:
NA.77
PubChem Substance ID:
24897957
UNSPSC Code:
12352200
EC Number:
206-103-9
MDL number:
MFCD00053638

Product Name

Oleamide, ≥99%

Quality Level

200

InChI key

FATBGEAMYMYZAF-KTKRTIGZSA-N

InChI

1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-

SMILES string

CCCCCCCC\C=C/CCCCCCCC(N)=O

assay

≥99%

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage temp.

−20°C

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Application

Oleamide has been used as a supplement in glucose and galactose media to prevent the rescue of galactose-induced Leigh syndrome (LS).

Biochem/physiol Actions

Oleamide has the ability to stimulate sleep. It possess several properties, like cannabinoid-like activity. Oleamide can also disable the communication, facilitated by gap junction between rat glial cells.
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.

General description

Oleamide is a lipid or a brain fatty acid, that is found in the CSF (cerebrospinal fluid). It is originally obtained from the cerebrospinal fluid of cats, that are sleep-deprived.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

404.6 °F - closed cup

flash_point_c

207 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000492762
0000492761
0000492761
0000492762
0000467370

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Varadarajan Sudhahar et al.
European journal of pharmacology, 607(1-3), 143-150 (2009-03-28)
Fatty acid amides are a new class of signaling lipids that have been implicated in diverse physiological and pathological conditions. Oleamide is a fatty acid amide that induces vasorelaxation. Here, we investigated the mechanisms behind the vasorelaxation effect of oleamide
Edgar Soria-Gómez et al.
The international journal of neuropsychopharmacology, 13(9), 1247-1254 (2010-07-29)
The central nervous system control of food intake has been extensively studied, hence, several neurotransmitter systems regulating this function are now clearly identified, for example, the endocannabinoid and serotoninergic systems. The former stimulates feeding while the latter inhibits it. Oleamide
Andrea Herrera-Solís et al.
Pharmacology, biochemistry, and behavior, 95(1), 106-112 (2010-01-09)
Anandamide and oleamide, induce sleep when administered acutely, via the CB1 receptor. Their subchronic administration must be tested to demonstrate the absence of tolerance to this effect, and that the sudden withdrawal of these endocannabinoids (eCBs) does not affect sleep
Mónica Méndez-Díaz et al.
Addiction biology, 17(4), 725-735 (2010-12-25)
Endocannabinoids (eCBs) are mediators of the homeostatic and hedonic systems that modulate food ingestion. Hence, eCBs, by regulating the hedonic system, may be modulating the valence of the emotion associated to food ingestion (positive: pleasant or negative: unpleasant). Our first
Lidong Zhang et al.
Langmuir : the ACS journal of surfaces and colloids, 29(1), 65-74 (2012-12-12)
A series of oleamide derivatives, (C(18)H(34)NO)(2)(CH(2))(n) [n = 2 (1a), 3 (1b), 4 (1c), or 6 (1d); C(18)H(34)NO = oleic amide fragment] and (C(18)H(34)NO)(CH(2))(6)NH(2) (2), have been synthesized and their self-assembly is investigated in ethanol/water media. Self-assembly of 1a and
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