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From the body

NATN-arachidonoyl taurine

An endogenous lipid regulated by FAAH, a micromolar agonist of TRPV1 and TRPV4, with no activity at CB1 or CB2.

Endogenous
Level of detail

C₂₂H₃₇NO₄S

CAS 119959-65-8

Family
Endocannabinoid or related mediatorEndocannabinoidome
Molar mass
411.60 g/mol

Updated on

In plain terms

N-arachidonoyl taurine is a small fatty molecule made by the body, formed by joining a fatty acid, arachidonic acid, to taurine. It does not exist in hemp and does not behave like CBD: it acts on heat and sensation sensors, the TRPV channels, not on cannabinoid receptors. Everything known comes from cell and animal experiments; human data are lacking.

Receptors and activity

Target network

TRPV1AgonistActivation reported among the TRP channels activated by N-acyl taurines (Saghatelian 2006). In mouse prefrontal cortex slices, 10 µM increased sEPSC frequency (about 130% at one minute, 150% at two minutes) and eEPSC amplitude, effects abolished by capsazepine (Zhang 2020)
  • Activates

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

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. TRPV1Agonistno measured value cited

    Activation reported among the TRP channels activated by N-acyl taurines (Saghatelian 2006). In mouse prefrontal cortex slices, 10 µM increased sEPSC frequency (about 130% at one minute, 150% at two minutes) and eEPSC amplitude, effects abolished by capsazepine (Zhang 2020)

  2. TRPV4Agonistno measured value cited

    Activation reported in the founding study, alongside TRPV1, both channels being expressed in the kidney where these lipids are abundant (Saghatelian 2006). Potency value not published in open access

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

This conjugate belongs to the N-acyl taurines, the second structural class of fatty acid amides controlled by FAAH, the enzyme that also degrades anandamide: tissues of FAAH-deficient mice accumulate them massively, and both liver and kidney contain the polyunsaturated forms, including this one (Saghatelian 2004; Saghatelian 2006). Its profile sets it apart from the endocannabinoids: these lipids activate several TRP channels, including TRPV1 and TRPV4, and N-arachidonoyl taurine does not activate cannabinoid receptors (Saghatelian 2006; Raboune 2014). The effects described appear at micromolar concentrations, well above tissue levels: in mouse prefrontal cortex slices, 10 µM raised the frequency of spontaneous excitatory currents by about 50 % at most, an effect abolished by capsazepine (Zhang 2020); in beta-cell lines, the molecule caused calcium oscillations and insulin secretion involving TRPV1 (Waluk 2013). Its hepatic synthesis was assigned in 2023 to BAAT, the peroxisomal bile acid-conjugating enzyme, whose knockout removes up to 90 % of N-acyl taurine synthase activity (Trammell 2023). The precise physiological function remains undetermined and human data are lacking; no therapeutic property is demonstrated.

Key sources.

History

Source
This compound is not present in hemp: it is an endogenous mammalian lipid, a conjugate of arachidonic acid and taurine. In the mouse, central nervous system N-acyl taurines are mostly long-chain saturated forms (≥ C20), whereas liver and kidney are enriched in polyunsaturated forms such as this one (C20:4, C22:6) (Saghatelian 2006). Human liver also synthesises N-acyl taurines, with an acyl-chain preference similar to that of mouse liver (Trammell 2023).

Biosynthetic pathway

In vivo

The molecule is formed by transfer of the arachidonoyl group from arachidonoyl-CoA onto taurine. In mouse liver this N-acyl taurine synthase activity is peroxisomal, depends on an active-site cysteine and has been assigned to bile acid-CoA:amino acid N-acyltransferase (BAAT): Baat knockout livers lose up to 90 % of the activity, and their polyunsaturated biliary N-acyl taurines are significantly reduced (Trammell 2023). Degradation is carried out by FAAH, releasing arachidonic acid and taurine (Saghatelian 2006).

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. Saghatelian et al. 2006, Biochemistry: a FAAH-regulated class of N-acyl taurines, activation of TRP channels (new tab)PMID 16866345
  2. Saghatelian et al. 2004, Biochemistry: assignment of endogenous FAAH substrates by metabolomic profiling (new tab)PMID 15533037
  3. Raboune et al. 2014, Front Cell Neurosci: endogenous N-acyl amides activating TRPV1-4; N-arachidonoyl taurine does not activate CB receptors (new tab)PMID 25136293
  4. Zhang et al. 2020, Front Neurosci: effects of N-arachidonoyl taurine on prefrontal cortex synaptic transmission, blockade by capsazepine (new tab)PMID 32116530
  5. Trammell et al. 2023, J Lipid Res: BAAT, the hepatic polyunsaturated fatty acid N-acyl taurine synthase (new tab)PMID 36958721
  6. Waluk et al. 2013, Biochem Biophys Res Commun: calcium oscillations and insulin secretion induced by N-acyl taurines in beta cell lines (new tab)PMID 23159632
  7. Grevengoed et al. 2019, PNAS: N-acyl taurines, endogenous lipid messengers (new tab)PMID 31740614
  8. Connor, Vaughan & Vandenberg 2010, Br J Pharmacol: N-acyl amino acids and neurotransmitter conjugates (review) (new tab)PMID 20649585
  9. PubChem CID 42607331, N-arachidonoyl taurine (new tab)

Identifiers

Names

Common name
N-arachidonoyl taurine
IUPAC name
2-[[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]amino]ethanesulfonic acid
Other names
NA-Tau · N-arachidonoyltaurine · NAT 20:4 · N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)taurine

Identifiers

Formula
C₂₂H₃₇NO₄S
CAS
119959-65-8
PubChem CID
42607331(new tab)
InChIKey
YUNYSWCRLRYOPO-DOFZRALJSA-N
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCS(=O)(=O)O

Machine-readable entry (JSON)

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