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O2136

Sigma-Aldrich

Oleamide

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

Synonym(s):

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

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100 MG
¥38,100
500 MG
¥61,000

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100 MG
¥38,100
500 MG
¥61,000

About This Item

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

¥38,100

Available to ship onMarch 31, 2025Details

Request a Bulk Order

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[1] or a brain fatty acid, that is found in the CSF (cerebrospinal fluid).[2] It is originally obtained from the cerebrospinal fluid of cats, that are sleep-deprived.[3]

Application

Oleamide has been used as a supplement in glucose and galactose media to prevent the rescue of galactose-induced Leigh syndrome (LS).[4]

Biochem/physiol Actions

Oleamide has the ability to stimulate sleep.[2] It possess several properties, like cannabinoid-like activity.[1] Oleamide can also disable the communication, facilitated by gap junction between rat glial cells.[3]
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.

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

404.6 °F - closed cup

Flash Point(C)

207 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

O2136-500MG:
O2136-100MG:
O2136-BULK:
O2136-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
0000428617
0000428616
0000428616
0000428617
0000405324

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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
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
Chemosensation in the Ventricles of the Central Nervous System
Chemosensory Transduction: The Detection of Odors, Tastes, and Other Chemostimuli, 339-357 (2016)
Oleamide and anandamide effects on food intake and sexual behavior of rats
Martinez-Gonzalez D, et al.
Neuroscience Letters, 364(1), 1-6 (2004)
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