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From the body

AEAAnandamide (N-arachidonoylethanolamine)

The first endocannabinoid identified (Devane et al., 1992): synthesised on demand, hydrolysed by FAAH.

Endogenous
Level of detail

C₂₂H₃₇NO₂

CAS 94421-68-8

Family
Endocannabinoid or related mediatorEstablished
Origin
Endogenous (established endocannabinoid)
First described
1992
Molar mass
347.53 g/mol

Updated on

In plain terms

Anandamide is a molecule the body makes itself, when it needs it, from the lipids of cell membranes. It activates the same CB1 receptors as the THC in cannabis. An enzyme, FAAH, then breaks it down.

Receptors and activity

Target network

CB1Partial agonistKi = 239 nM · humanmeta-analytic mean of 16 binding studies, human CB1
  • Activates

The lower the cited value, the closer the target sits to AEA: 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 AEA.

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. CB1Partial agonistKi = 239 nM · human44 out of 100

    McPartland, Glass & Pertwee 2007, Br J Pharmacol 152:583 (meta-analysis) (new tab) · meta-analytic mean of 16 binding studies, human CB1

  2. CB2Partial agonistKi = 440 nM · human39 out of 100

    McPartland, Glass & Pertwee 2007, Br J Pharmacol 152:583 (meta-analysis) (new tab) · meta-analytic mean of 22 binding studies, human CB2

  3. TRPV1AgonistEC50 = 1.2 µM · human32 out of 100

    Smart et al. 2000, Br J Pharmacol 129:227 (human TRPV1) (new tab) · calcium influx (FLIPR), HEK293-hTRPV1, pEC50 5.94

  4. PPARαAgonistno 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

The first endocannabinoid identified: arachidonylethanolamide was isolated from pig brain by Raphael Mechoulam's team (Devane, Hanuš et al., Science 1992, 258:1946); its structure was established by mass spectrometry and NMR and then confirmed by synthesis. Its name comes from the Sanskrit « ananda », bliss (Maccarrone et al. 2015). Like 2-AG, it is synthesised on demand, in response to a rise in intracellular calcium, rather than stored (Pertwee et al. 2010). Its precursor, an N-acyl-phosphatidylethanolamine, is cleaved mainly by a specific phospholipase D, NAPE-PLD (Okamoto et al. 2004), and FAAH hydrolyses it into arachidonic acid and ethanolamine (Cravatt et al. 1996). It is a partial agonist at CB1 and CB2, with lower intrinsic activity at CB2 (Pertwee et al. 2010). Published affinities depend on species and assay: the meta-analysis by McPartland et al. (2007) gives a mean Ki of 239.2 nM at human CB1, 87.7 nM at rat CB1 and 439.5 nM at human CB2. Anandamide also activates the TRPV1 channel (Zygmunt et al. 1999), where it is a full agonist at the human receptor (EC50 ≈ 1.15 µM; Smart et al. 2000), and binds the ligand-binding domain of PPAR-α (Sun et al. 2007). Its status as a GPR55 ligand is not established (Pertwee et al. 2010). In 2016, in Rennes, a phase 1 trial of the FAAH inhibitor BIA 10-2474 caused an acute neurological syndrome in healthy volunteers at 50 mg per day, including 1 death (Kerbrat et al. 2016); this compound inhibits several lipases that the selective inhibitor PF-04457845 does not touch (van Esbroeck et al. 2017).

Key sources.

Biosynthetic pathway

In vivo

Synthesised on demand (Pertwee et al. 2010) from a membrane N-acyl-phosphatidylethanolamine, mainly by NAPE-PLD (Okamoto et al. 2004); a two-step route (PLA2 then lysophospholipase D) has also been described. Hydrolysed mainly by FAAH into arachidonic acid and ethanolamine (Cravatt et al. 1996).

Classification

Family, origin and source verification

Family

Endocannabinoid or related mediator › Established

Chemistry

N-acylethanolamine (NAE 20:4)

Verification

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

Wikipedia (English)

Anandamide (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. Devane et al. 1992, Science 258:1946 (isolation and structure) (new tab)PMID 1470919
  2. McPartland, Glass & Pertwee 2007, Br J Pharmacol 152:583 (meta-analysis) (new tab)PMID 17641667
  3. Pertwee et al. 2010, Pharmacol Rev 62:588 (IUPHAR LXXIX) (new tab)PMID 21079038
  4. Smart et al. 2000, Br J Pharmacol 129:227 (human TRPV1) (new tab)PMID 10694225
  5. Okamoto et al. 2004, J Biol Chem 279:5298 (NAPE-PLD) (new tab)PMID 14634025
  6. Cravatt et al. 1996, Nature 384:83 (FAAH) (new tab)PMID 8900284
  7. Kerbrat et al. 2016, N Engl J Med 375:1717 (BIA 10-2474) (new tab)PMID 27806235
  8. Maccarrone et al. 2015, Trends Pharmacol Sci 36:277 (glossary: etymology) (new tab)PMID 25796370

Identifiers

Names

Common name
Anandamide (N-arachidonoylethanolamine)
IUPAC name
(5Z,8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-5,8,11,14-tetraenamide
Other names
Anandamide · AEA

Identifiers

Formula
C₂₂H₃₇NO₂
CAS
94421-68-8
PubChem CID
5281969(new tab)
ChEBI
CHEBI:2700(new tab)
InChIKey
LGEQQWMQCRIYKG-DOFZRALJSA-N
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO

Machine-readable entry (JSON)

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

Suggested products

Anandamide is endogenous, produced by your own body.

The phytocannabinoids we work with interact with the same system. See our CBD flowers.