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O2136

Sigma-Aldrich

Oleamide

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C18H35NO
Número de CAS:
301-02-0
Peso molecular:
281.48
EC Number:
206-103-9
MDL number:
MFCD00053638
UNSPSC Code:
12352200
PubChem Substance ID:
24897957
NACRES:
NA.77

product name

Oleamide, ≥99%

assay

≥99%

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage temp.

−20°C

SMILES string

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

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-

InChI key

FATBGEAMYMYZAF-KTKRTIGZSA-N

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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.

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.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk_germany

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Plastic additive 13 United States Pharmacopeia (USP) Reference Standard

USP

1545045

Plastic additive 13

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
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
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
Gayong Shim et al.
Journal of controlled release : official journal of the Controlled Release Society, 155(1), 60-66 (2010-10-26)
Oligolysine-based cationic lipid derivatives were synthesized for delivery of siRNA, and formulated into cationic liposomes. Among various oligolysine-based lipid derivatives differing in lysine residue number and lipid moiety, trilysinoyl oleylamide (TLO)-based liposomes (TLOL) showed the highest delivery efficiency combined with
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