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From the body

NADAN-arachidonoyl-dopamine

Endogenous brain lipid, a moderate CB1 agonist and a potent agonist of the TRPV1 channel.

Endogenous
Level of detail

C₂₈H₄₁NO₃

CAS 199875-69-9

Family
Endocannabinoid or related mediatorPutative
Molar mass
439.60 g/mol

Updated on

In plain terms

NADA is a small fatty molecule made by joining a fatty acid to dopamine. It has been found in rat brain, not in hemp, and its presence in humans has not been shown. In the laboratory, it acts on the CB1 receptor and above all on TRPV1, the sensor for heat and chilli.

Receptors and activity

Target network

TRPV1AgonistEC50 = 40 nM · humanCa2+, HEK293 cells expressing TRPV1 (48 nM at rat TRPV1)
  • Activates
  • Blocks or inhibits

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

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 = 40 nM · human57 out of 100

    Huang S.M. et al., PNAS 2002 (new tab) · Ca2+, HEK293 cells expressing TRPV1 (48 nM at rat TRPV1)

  2. CB1AgonistKi = 250 nM · rat43 out of 100

    Bisogno T. et al., Biochem J 2000 (new tab) · [3H]SR141716A, brain membranes

  3. TRPM8Antagonistno measured value cited
  4. PPARγAgonistno measured value cited
  5. 12-lipoxygenaseInhibitorIC50 = 150 nM47 out of 100

    Grabiec U., Dehghani F., Cannabis Cannabinoid Res 2017 (new tab) · enzymatic activity (review table)

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

NADA belongs to the N-acyl-dopamines, lipids at the border between the endocannabinoid and vanilloid systems. Bisogno et al. described it in 2000 within a series of synthetic N-acyl-dopamines: a Ki of 250 nM at the rat brain CB1 receptor, about 40-fold selectivity over CB2 and, in mice (1 to 10 mg/kg), hypothermia, reduced locomotion, catalepsy and analgesia, the tetrad of CB1 agonists. In 2002, Huang et al. detected it in rat nervous tissue and measured TRPV1 activation with an EC50 close to 50 nM, comparable to capsaicin, which makes it the main endovanilloid candidate. IUPHAR (Pertwee 2010) lists it among molecules that may also serve as endocannabinoids: its status remains putative. In vitro, cell death appears at micromolar concentrations (EC50 of about 30 µM on blood mononuclear cells). Human data are lacking: NADA was not found in human plasma or post-mortem human brain, and there is no therapeutic indication.

Key sources.

History

Source
An endogenous mammalian lipid, not reported in cannabis. Huang et al. (2002) detected it in rat nervous tissue, with the highest concentrations in the striatum, hippocampus and cerebellum and the lowest in the dorsal root ganglion; about 2 pmol per gram of wet tissue was measured in the rat substantia nigra pars compacta. According to the review by Grabiec and Dehghani (2017), chromatographic analyses of human plasma and post-mortem human brain found no NADA: its presence in humans is not established.

Biosynthetic pathway

In vivo

The route of formation is still debated. Two routes have been proposed (review by Grabiec and Dehghani 2017): an enzymatic conjugation of arachidonic acid with dopamine, dependent on tyrosine hydroxylase in the striatum, and a route through N-arachidonoyl-tyrosine, converted to N-arachidonoyl-DOPA by tyrosine hydroxylase and then to NADA by aromatic L-amino acid decarboxylase. In 2024, Yang et al. reported that the enzyme PM20D1 catalyses the conversion of dopamine to NADA.

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)

N-Arachidonoyl dopamine (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. Bisogno T. et al., N-acyl-dopamines: novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo, Biochemical Journal, 2000 (new tab)PMID 11042139
  2. Huang S.M. et al., An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors, Proceedings of the National Academy of Sciences, 2002 (new tab)PMID 12060783
  3. Grabiec U., Dehghani F., N-Arachidonoyl Dopamine: A Novel Endocannabinoid and Endovanilloid with Widespread Physiological and Pharmacological Activities, Cannabis and Cannabinoid Research, 2017 (new tab)PMID 29082315
  4. Yang Y. et al., The PM20D1-NADA pathway protects against Parkinson's disease, Cell Death and Differentiation, 2024 (new tab)PMID 39174646
  5. 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
  6. PubChem CID 5282105, N-Arachidonoyldopamine, National Library of Medicine (new tab)

Identifiers

Names

Common name
N-arachidonoyl-dopamine
IUPAC name
(5Z,8Z,11Z,14Z)-N-[2-(3,4-dihydroxyphenyl)ethyl]icosa-5,8,11,14-tetraenamide
Other names
N-arachidonoyl dopamine · NADA · N-arachidonoyldopamine · AA-DA

Identifiers

Formula
C₂₈H₄₁NO₃
CAS
199875-69-9
PubChem CID
5282105(new tab)
ChEBI
CHEBI:31231(new tab)
InChIKey
MVVPIAAVGAWJNQ-DOFZRALJSA-N
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=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.