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From the body

STEARDAN-stearoyl dopamine

An endogenous lipid, inactive on its own, which strengthens the effect of NADA and anandamide at the TRPV1 channel.

Endogenous
Level of detail

C₂₆H₄₅NO₃

CAS 105955-10-0

Family
Endocannabinoid or related mediatorEndocannabinoidome
Molar mass
419.60 g/mol

Updated on

In plain terms

N-stearoyl dopamine is a small fatty molecule the mammalian body makes itself, by joining a common fatty acid to dopamine. It does not come from hemp and is in no shop product. On its own it triggers nothing in the published assays: it merely strengthens the action of related molecules at a sensory sensor, and in humans data are lacking.

Receptors and activity

Target network

TRPV1Positive allosteric modulatorInactive on its own (no calcium influx in cells expressing the receptor, no effect on withdrawal latency in the rat; Chu 2003). Preincubated for five minutes at 0.1 to 10 µM, it lowers the EC50 of NADA from about 90 nM to about 30 nM, potentiates anandamide (50 nM) and acts synergistically with a pH of 6.0 to 6.7; in vivo, 5 µg co-injected with 0.5 µg of NADA shorten the heat withdrawal latency in the rat (De Petrocellis 2004)
  • Activates

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

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. TRPV1Positive allosteric modulatorno measured value cited

    Inactive on its own (no calcium influx in cells expressing the receptor, no effect on withdrawal latency in the rat; Chu 2003). Preincubated for five minutes at 0.1 to 10 µM, it lowers the EC50 of NADA from about 90 nM to about 30 nM, potentiates anandamide (50 nM) and acts synergistically with a pH of 6.0 to 6.7; in vivo, 5 µg co-injected with 0.5 µg of NADA shorten the heat withdrawal latency in the rat (De Petrocellis 2004)

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-stearoyl dopamine belongs to the N-acyl dopamines, the same family as NADA, but its saturated eighteen-carbon chain changes everything. On identifying it in bovine striatum in 2003, Chu and colleagues found that it does not activate the TRPV1 channel and causes no pain behaviour in the rat: the long unsaturated chain is missing, and with it the direct activity (Chu 2003). Its interest lies elsewhere. De Petrocellis and colleagues showed in 2004 that a five-minute pre-incubation, between 0.1 and 10 µM, lowers NADA's half-maximal effective concentration at human TRPV1 from about 90 nM to about 30 nM, amplifies the response to anandamide and acts in synergy with acidification of the medium. Co-injected with NADA into the rat hind paw, it accentuates thermal hyperalgesia, and it enhances carrageenan-induced nocifensive behaviour. This is the classic profile of an « entourage » compound: inactive by itself, it changes the target's sensitivity to active ligands. Beyond these two studies and one report on its sulfation, measured in rat liver only while its unsaturated congeners are also sulfated in nervous tissue (Akimov 2009), the literature is very thin: human data are lacking, no physiological role is established and no therapeutic indication can be invoked.

Key sources.

History

Source
An endogenous mammalian lipid, entirely absent from hemp. The molecule was demonstrated in bovine striatum (Chu 2003), and the N-acyl dopamines of this series have been reported in bovine and rat nervous tissues (De Petrocellis 2004). No reference tissue concentration has been published for N-stearoyl dopamine itself. In humans, it appears only as a target analyte of a serum assay method, with no published concentration value (Luque-Córdoba 2018).

Biosynthetic pathway

In vivo

The formation route is not established. By analogy with the other N-acyl dopamines, an enzymatic conjugation between dopamine and stearic acid is the working hypothesis; for NADA, the proposed routes run either through an N-acyl tyrosine processed by tyrosine hydroxylase and then by aromatic amino acid decarboxylase, or through direct conjugation of the fatty acid with dopamine, which requires tyrosine hydroxylase in the striatum (Grabiec & Dehghani 2017). No synthetic enzyme has been named for this molecule and its tissue levels have never been followed after pharmacological manipulation.

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: identification of STEARDA in the bovine striatum, inactivity at VR1 (new tab)PMID 12569099
  2. De Petrocellis et al. 2004, Br J Pharmacol: actions of two saturated N-acyl-dopamines on TRPV1 channels (« entourage » effect) (new tab)PMID 15289293
  3. Grabiec & Dehghani 2017, Cannabis Cannabinoid Res: NADA, endocannabinoid and endovanilloid (biosynthetic pathways of the family) (new tab)PMID 29082315
  4. Akimov et al. 2009, Biochemistry (Mosc): sulfation of N-acyl-dopamines in rat tissues (new tab)PMID 19645674
  5. Zajac et al. 2014, PLoS One: metabolism of N-acyl-dopamines, O-methylation by COMT (new tab)PMID 24465516
  6. Luque-Córdoba et al. 2018, Talanta: sample preparation for the serum determination of endocannabinoids and analogous compounds by LC-MS/MS (new tab)PMID 29759247
  7. PubChem CID 10025103, N-stearoyldopamine (new tab)

Identifiers

Names

Common name
N-stearoyl dopamine
IUPAC name
N-[2-(3,4-dihydroxyphenyl)ethyl]octadecanamide
Other names
N-stearoyldopamine · STEARDA · STERDA

Identifiers

Formula
C₂₆H₄₅NO₃
CAS
105955-10-0
PubChem CID
10025103(new tab)
InChIKey
KOCSVLPLQCBIGW-UHFFFAOYSA-N
SMILES
CCCCCCCCCCCCCCCCCC(=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.