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From the body

NAGlyN-arachidonoyl glycine

Endogenous lipoamino acid, a T-type calcium channel inhibitor with no affinity for CB1 or CB2.

Endogenous
Level of detail

C₂₂H₃₅NO₃

CAS 179113-91-8

Family
Endocannabinoid or related mediatorEndocannabinoidome
Molar mass
361.50 g/mol

Updated on

In plain terms

N-arachidonoyl glycine is a small fatty molecule the body makes by joining a fatty acid to an amino acid, glycine. It does not come from hemp and does not bind cannabis receptors. Animal studies link it to pain regulation, but human data are lacking.

Receptors and activity

Target network

GPR55Agonistno measured value
  • Activates
  • Blocks or inhibits

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

Brain, side view
Body, front view
Blood

GPR55GPR55 found in 4 regions of the body

  1. Basal gangliapresentmRNA found in the caudate nucleus and putamen1
  2. BonepresentOsteoclasts and osteoblasts2
  3. Adipose tissuepresentExpressed in visceral adipose tissue3
  4. LiverpresentExpressed in the liver3

Map sources

  1. Sawzdargo M et al. Identification and cloning of three novel human G protein-coupled receptor genes GPR52, PsiGPR53 and GPR55: GPR55 is extensively expressed in human brain. Brain Res Mol Brain Res, 1999 (new tab)
  2. Whyte LS et al. The putative cannabinoid receptor GPR55 affects osteoclast function in vitro and bone mass in vivo. Proc Natl Acad Sci U S A, 2009 (new tab)
  3. Moreno-Navarrete JM et al. The L-α-lysophosphatidylinositol/GPR55 system and its potential role in human obesity. Diabetes, 2012 (new tab)

Cited values

  1. Cav3.2 (canal calcique de type T)Antagonistno measured value cited
  2. GLYT2 (transporteur de la glycine)Inhibitorno measured value cited
  3. GPR18Agonistno measured value cited
  4. GPR55Agonistno measured value cited
  5. FAAH (fatty acid amide hydrolase)Inhibitorno 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

N-arachidonoyl glycine is a lipoamino acid, an amide formed between a fatty acid and an amino acid. It is the carboxylic analogue of anandamide: the alcohol of the ethanolamide is oxidised to an acid. According to Burstein's review (2018), N-acyl amino acids do not bind CB1 and CB2 receptors, which places the molecule in the endocannabinoidome rather than among the endocannabinoids. Its described targets lie elsewhere: in mice, the thermal analgesia it produced disappeared in animals lacking the Cav3.2 channel, which points to inhibition of T-type calcium channels (Barbara 2009); it also inhibits the glycine transporter GLYT2 (Edington 2009). The receptor side remains uncertain: GPR18 agonism, proposed in 2006, was not reproduced by other teams (Lu 2013), and an action at GPR55 was described in 2017. None of this has been tested in humans: there is no clinical trial and no tolerability data.

Key sources.

History

Source
An endogenous mammalian lipid, not reported in cannabis. Huang et al. (2001) detected it in bovine and rat brain and in other tissues; McHugh et al. (2010) describe it as an abundant endogenous lipid.

Biosynthetic pathway

In vivo

Two routes are proposed: direct conjugation of arachidonic acid with glycine, and oxidation of anandamide, whose terminal alcohol becomes a carboxylic acid (review by Burstein 2018). The secreted enzyme PM20D1 catalyses in vitro the condensation of fatty acids and amino acids into N-acyl amino acids, as well as the reverse reaction (Long 2016). Biosynthesis of N-arachidonoyl glycine and its degradation by FAAH were observed in rat brain tissue (Huang 2001).

Classification

Family, origin and source verification

Family

Endocannabinoid or related mediator › Endocannabinoidome

Verification

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

Wikipedia (English)

N-Arachidonylglycine (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. Huang S.M. et al., Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain, J Biol Chem 2001 (new tab)PMID 11518719
  2. Kohno M. et al., Identification of N-arachidonylglycine as the endogenous ligand for orphan G-protein-coupled receptor GPR18, Biochem Biophys Res Commun 2006 (new tab)PMID 16844083
  3. Burstein S.H., N-Acyl Amino Acids (Elmiric Acids): Endogenous Signaling Molecules with Therapeutic Potential, Mol Pharmacol 2018 (new tab)PMID 29138268
  4. Lu V.B., Puhl H.L., Ikeda S.R., N-Arachidonyl glycine does not activate G protein-coupled receptor 18 signaling via canonical pathways, Mol Pharmacol 2013 (new tab)PMID 23104136
  5. Barbara G. et al., T-type calcium channel inhibition underlies the analgesic effects of the endogenous lipoamino acids, J Neurosci 2009 (new tab)PMID 19846698
  6. Console-Bram L. et al., N-arachidonoyl glycine, another endogenous agonist of GPR55, Biochem Biophys Res Commun 2017 (new tab)PMID 28698140
  7. Long J.Z. et al., The Secreted Enzyme PM20D1 Regulates Lipidated Amino Acid Uncouplers of Mitochondria, Cell 2016 (new tab)PMID 27374330
  8. Edington A.R. et al., Extracellular loops 2 and 4 of GLYT2 are required for N-arachidonylglycine inhibition of glycine transport, J Biol Chem 2009 (new tab)PMID 19875446
  9. McHugh D. et al., N-arachidonoyl glycine, an abundant endogenous lipid, potently drives directed cellular migration through GPR18, BMC Neurosci 2010 (new tab)PMID 20346144
  10. PubChem CID 5283389, N-Arachidonoyl glycine (new tab)

Identifiers

Names

Common name
N-arachidonoyl glycine
IUPAC name
2-[[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]amino]acetic acid
Other names
NAGly · N-arachidonylglycine

Identifiers

Formula
C₂₂H₃₅NO₃
CAS
179113-91-8
PubChem CID
5283389(new tab)
ChEBI
CHEBI:58961(new tab)
InChIKey
YLEARPUNMCCKMP-DOFZRALJSA-N
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC(=O)O

Machine-readable entry (JSON)

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