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From the body

Oleamide

Endogenous fatty amide isolated from sleep-deprived cats, a micromolar and selective CB1 agonist.

Endogenous
Level of detail

C₁₈H₃₅NO

CAS 301-02-0

Family
Endocannabinoid or related mediatorPutative
Molar mass
281.50 g/mol

Updated on

In plain terms

Oleamide is a small fatty molecule the body makes itself. It was discovered in the fluid around the brain of sleep-deprived cats, and its synthetic version induced sleep in rats. It does not come from hemp; industry also produces it as a slip additive for plastics.

Receptors and activity

Target network

CB1AgonistKi = 8.1 µM · human[3H]CP55,940, hCB1 membranes (1140 nM on rat brain; GTPγS EC50 1640 nM)
  • Activates
  • Blocks or inhibits
  • Binds or modulates

The lower the cited value, the closer the target sits to Oleamide: one ring per factor of 100. A target with no measured value stays on the edge.

Where these targets live

Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of Oleamide.

Brain, side view
Body, front view
Blood

CB1CB1 found in 7 regions of the body

  1. Basal gangliadenseMost dense in basal ganglia outflow nuclei1
  2. CerebellumdenseVery dense in the cerebellum1
  3. HippocampusdenseVery high concentrations in the hippocampus2
  4. AmygdaladenseHigh concentrations in the amygdala2
  5. CortexpresentPresent throughout the neocortex2
  6. Adipose tissuepresentExpressed in adipose tissue3
  7. GutpresentColonic epithelium, smooth muscle and plexus4

Map sources

  1. Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
  2. Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
  3. Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
  4. Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)

Cited values

  1. CB1AgonistKi = 8.1 µM · human18 out of 100

    Leggett J.D. et al., Br J Pharmacol 2004 (new tab) · [3H]CP55,940, hCB1 membranes (1140 nM on rat brain; GTPγS EC50 1640 nM)

  2. GABA-APositive allosteric modulatorno measured value cited
  3. Glycine receptorPositive allosteric modulatorno measured value cited
  4. 5-HT2Modulatorno measured value cited
  5. 5-HT7Modulatorno measured value cited
  6. Voltage-gated sodium channelsModulatorno measured value cited
  7. FAAHInhibitorno measured value cited
Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

Pharmacology

Oleamide (cis-9,10-octadecenamide) is an endogenous fatty acid primary amide, isolated in 1995 from the cerebrospinal fluid of sleep-deprived cats. At the CB1 receptor, Leggett et al. (2004) measured micromolar affinity (Ki 1.14 µM on rat brain, 8.13 µM at human CB1) and full agonist activity abolished by SR141716A, with no notable CB2 binding. IUPHAR (Pertwee 2010) lists it among molecules that may also serve as endocannabinoids: its status remains putative. Its other described targets are GABA-A and glycine receptors, 5-HT2 and 5-HT7 receptors and sodium channels; as an FAAH substrate, it might also act indirectly by slowing anandamide hydrolysis. In rats, synthetic oleamide induced physiological sleep (Cravatt 1995); human data are lacking. It is also a common industrial additive in plastics.

Key sources.

History

Source
An endogenous mammalian lipid, not reported in cannabis. Cravatt et al. (1995) isolated it from the cerebrospinal fluid of sleep-deprived cats and identified fatty acid primary amides in the cerebrospinal fluid of cat, rat and human. Produced industrially, oleamide is used as a slip agent in plastics; it leaches from disposable laboratory plasticware (McDonald 2008) and has been detected as a non-cannabinoid adulterant in herbal mixtures containing synthetic cannabinoids (Alves 2021).

Biosynthetic pathway

In vivo

The best-studied route starts from oleic acid: formation of N-oleoylglycine, then conversion to oleamide by peptidylglycine α-amidating monooxygenase (PAM), a route the review by Hiley and Hoi (2007) calls probable. Degradation is carried out by FAAH, the enzyme that also hydrolyses anandamide.

Classification

Family, origin and source verification

Family

Endocannabinoid or related mediator › Putative

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

Oleamide (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

References

  1. Cravatt B.F. et al., Chemical characterization of a family of brain lipids that induce sleep, Science 1995 (new tab)PMID 7770779
  2. Leggett J.D. et al., Oleamide is a selective endogenous agonist of rat and human CB1 cannabinoid receptors, Br J Pharmacol 2004 (new tab)PMID 14707029
  3. Hiley C.R., Hoi P.M., Oleamide: a fatty acid amide signaling molecule in the cardiovascular system?, Cardiovasc Drug Rev 2007 (new tab)PMID 17445087
  4. Coyne L. et al., The sleep hormone oleamide modulates inhibitory ionotropic receptors in mammalian CNS in vitro, Br J Pharmacol 2002 (new tab)PMID 11959801
  5. Cheer J.F. et al., Modification of 5-HT2 receptor mediated behaviour in the rat by oleamide and the role of cannabinoid receptors, Neuropharmacology 1999 (new tab)PMID 10221757
  6. McDonald G.R. et al., Bioactive contaminants leach from disposable laboratory plasticware, Science 2008 (new tab)PMID 18988846
  7. Alves V.L. et al., Highly sensitive screening and analytical characterization of synthetic cannabinoids in nine different herbal mixtures, Anal Bioanal Chem 2021 (new tab)PMID 33575815
  8. Pertwee R.G. et al., International Union of Basic and Clinical Pharmacology. LXXIX. Cannabinoid receptors and their ligands: beyond CB1 and CB2, Pharmacological Reviews, 2010 (new tab)PMID 21079038
  9. PubChem CID 5283387: Oleamide (identity, formula, InChIKey) (new tab)
  10. EUR-Lex: consolidated Regulation (EU) No 10/2011 on plastic materials and articles in contact with food (new tab)

Identifiers

Names

IUPAC name
(Z)-octadec-9-enamide
Other names
ODA · 9-Octadecenamide

Identifiers

Formula
C₁₈H₃₅NO
CAS
301-02-0
PubChem CID
5283387(new tab)
ChEBI
CHEBI:116314(new tab)
InChIKey
FATBGEAMYMYZAF-KTKRTIGZSA-N
SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)N

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.