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From the body

OLDAN-oleoyl dopamine

An endogenous amide of dopamine and oleic acid, a TRPV1 agonist at 36 nM, with no human data.

Endogenous
Level of detail

C₂₆H₄₃NO₃

CAS 105955-11-1

Family
Endocannabinoid or related mediatorEndocannabinoidome
Molar mass
417.60 g/mol

Updated on

In plain terms

OLDA is a molecule the body makes itself, by joining dopamine to a very common fatty acid, oleic acid, the one in olive oil. It was spotted in 2003 in mammalian brain. It does not come from hemp and is in no CBD product: it is a research substance, known mainly because it activates the burning-sensation sensor, the same one triggered by chilli.

Receptors and activity

Target network

TRPV1AgonistEC50 = 36 nM · humancalcium influx, HEK293 cells transfected with VR1 (TRPV1); blockade by iodo-resiniferatoxin 10 nM
  • Activates

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

Brain, side view
Body, front view
Blood

TRPV1TRPV1 found in 7 regions of the body

  1. Sensory gangliapresentExpressed in dorsal root ganglia1
  2. Spinal cordpresentNerve fibres in the spinal dorsal horn2
  3. CortexpresentParietal cortex neurons (layers 3 and 5)3
  4. SkinpresentWidely distributed in the skin4
  5. Blood vesselspresentPresent on dermal blood vessels4
  6. BonepresentPresent on osteoclasts5
  7. LiverpresentRNA enriched in the liver6

Map sources

  1. Cortright DN et al. The tissue distribution and functional characterization of human VR1. Biochem Biophys Res Commun, 2001 (new tab)
  2. Facer P et al. Differential expression of the capsaicin receptor TRPV1 and related novel receptors TRPV3, TRPV4 and TRPM8 in normal human tissues and changes in traumatic and diabetic neuropathy. BMC Neurol, 2007 (new tab)
  3. Mezey E et al. Distribution of mRNA for vanilloid receptor subtype 1 (VR1), and VR1-like immunoreactivity, in the central nervous system of the rat and human. Proc Natl Acad Sci U S A, 2000 (new tab)
  4. Ständer S et al. Expression of vanilloid receptor subtype 1 in cutaneous sensory nerve fibers, mast cells, and epithelial cells of appendage structures. Exp Dermatol, 2004 (new tab)
  5. Rossi F et al. The endovanilloid/endocannabinoid system in human osteoclasts: possible involvement in bone formation and resorption. Bone, 2009 (new tab)
  6. Human Protein Atlas. TRPV1 tissue expression (RNA consensus) (new tab)

Cited values

  1. TRPV1AgonistEC50 = 36 nM · human57 out of 100

    Chu et al. 2003, J Biol Chem (new tab) · calcium influx, HEK293 cells transfected with VR1 (TRPV1); blockade by iodo-resiniferatoxin 10 nM

  2. GPR119Agonistno measured value cited

    cAMP accumulation in cells transfected with GPR119, as effective as oleoylethanolamide and the agonist AR231453; cAMP and insulin release in HIT-T15; oral effect on glucose tolerance absent in the GPR119-deficient mouse. No EC50 published in the study (Chu 2010)

  3. CB1Agonistno measured value cited

    Binding only: the founding study describes it as « only a weak ligand for rat CB1 receptors », with no published value and no measurement of functional efficacy (Chu 2003)

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

OLDA belongs to the N-acyl dopamines, a family of endogenous lipids led by NADA. Its profile is primarily vanilloid: identified in 2003 in bovine striatal extracts, it activated the TRPV1 channel with an EC50 of 36 nM in transfected HEK293 cells and shortened paw withdrawal latency in the rat (EC50 0.72 µg), effects abolished by an antagonist of the receptor, while it was only a weak ligand of rat CB1 and a poor FAAH substrate (Chu 2003). A second target is well documented: OLDA activates the GPR119 receptor of pancreatic beta cells and intestinal L cells, and its oral administration improved glucose tolerance in wild-type but not GPR119-deficient mice (Chu 2010). The other reported effects — thermal hyperalgesia after spinal administration, sensitised by TNF-α (Spicarova 2010), cardiac recovery after ischaemia-reperfusion in isolated mouse hearts through CGRP and substance P release (Zhong & Wang 2008), interleukin-10 induction in an endotoxaemia model (Joffre 2022) — disappear in animals lacking TRPV1, which identifies that channel as the main relay. Its metabolism follows the dopamine routes: O-methylation by COMT, reversed by tolcapone (Zajac 2014), and sulfation, described as the most productive pathway for N-acyl dopamines in cytosolic fractions of rat liver and nervous tissue (Akimov 2009). All these data come from rodents or cell cultures: human data are lacking, no clinical trial has been conducted and no therapeutic benefit is established in humans.

Key sources.

History

Source
An endogenous mammalian substance, absent from cannabis. It was demonstrated in bovine striatum (Chu 2003) and N-acyl dopamines have been found in bovine and rat nervous tissues (De Petrocellis 2004). Research samples are synthetic and sold as laboratory reagents, never as ingredients of consumer products.

Biosynthetic pathway

In vivo

The molecule joins dopamine and oleic acid through an amide bond; no synthetic enzyme specific to OLDA has been characterised. For the family's lead compound NADA, two pathways are proposed: an N-acyl tyrosine processed by tyrosine hydroxylase and then by aromatic amino acid decarboxylase, or enzymatic conjugation of the fatty acid with dopamine, which requires tyrosine hydroxylase in the striatum; FAAH also appears rate-limiting for NADA biosynthesis (Grabiec & Dehghani 2017). OLDA's metabolism, for its part, follows the dopamine pathway (Zajac 2014).

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)

No dedicated article.

References

  1. Chu et al. 2003, J Biol Chem: N-oleoyl-dopamine, an endogenous capsaicin-like lipid that produces hyperalgesia (new tab)PMID 12569099
  2. Chu et al. 2010, Mol Endocrinol: OLDA improves glucose homeostasis through GPR119 activation (new tab)PMID 19901198
  3. De Petrocellis et al. 2004, Br J Pharmacol: actions of two saturated N-acyl-dopamines on TRPV1 (presence in bovine and rat nervous tissue) (new tab)PMID 15289293
  4. Zhong & Wang 2008, Am J Physiol Heart Circ Physiol: protection of the heart against ischaemia-reperfusion via TRPV1 (new tab)PMID 18567714
  5. Zajac et al. 2014, PLoS One: metabolism of N-acyl-dopamines, O-methylation by COMT (new tab)PMID 24465516
  6. Akimov et al. 2009, Biochemistry (Mosc): sulfation of N-acyl-dopamines in rat tissues (new tab)PMID 19645674
  7. Spicarova & Palecek 2010, J Neuroinflammation: TNF-α sensitises spinal TRPV1 to OLDA (new tab)PMID 20796308
  8. Joffre et al. 2022, J Neuroinflammation: IL-10 induction via central TRPV1 in endotoxaemia (new tab)PMID 35610647
  9. Grabiec & Dehghani 2017, Cannabis Cannabinoid Res: NADA, endocannabinoid and endovanilloid (biosynthetic pathways of the family) (new tab)PMID 29082315
  10. PubChem CID 5282106, N-oleoyldopamine (new tab)

Identifiers

Names

Common name
N-oleoyl dopamine
IUPAC name
(Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]octadec-9-enamide
Other names
N-oleoyldopamine · OLDA

Identifiers

Formula
C₂₆H₄₃NO₃
CAS
105955-11-1
PubChem CID
5282106(new tab)
InChIKey
QQBPLXNESPTPNU-KTKRTIGZSA-N
SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)NCCC1=CC(=C(C=C1)O)O

Machine-readable entry (JSON)

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