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Synthetic

BAY 59-3074

A partial CB1/CB2 agonist designed by Bayer, studied in rodents only.

Unscheduled
Level of detail

Harm-reduction warning

No characterised human dose: animal / in vitro data only. Effect profile, safety margin and acute toxicity are not documented in human clinical practice. Extremely potent compound: severe effects, seizures and deaths reported in the literature.

C₁₈H₁₃F₆NO₄S

CAS 406205-74-1

Family
Synthetic CB receptor agonistResearch ligand or medicine
Molar mass
453.40 g/mol

Updated on

In plain terms

BAY 59-3074 is a laboratory molecule developed by the pharmaceutical group Bayer in the early 2000s. It does not exist in hemp: it was made to bind to the same receptors as THC, and it was studied in pain models in rats. No trial in humans was found and it is in no consumer product.

Receptors and activity

Target network

CB1Partial agonistEC50 = 46 nM · humancAMP inhibition, membranes of CHO cells overexpressing human CB1, efficacy 39 ± 11% of the maximal CP 55,940 signal (Amato et al. 2022); Ki of 48.3 nM (human CB1) and 55.4 nM (rat CB1) (De Vry et al. 2004)
  • Activates

The lower the cited value, the closer the target sits to BAY 59-3074: 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 BAY 59-3074.

Brain, side view
Body, front view
Blood

CB1CB1 found in 7 regions of the body

  1. Basal gangliadenseMost dense in basal ganglia outflow nuclei1
  2. CerebellumdenseVery dense in the cerebellum1
  3. HippocampusdenseVery high concentrations in the hippocampus2
  4. AmygdaladenseHigh concentrations in the amygdala2
  5. CortexpresentPresent throughout the neocortex2
  6. Adipose tissuepresentExpressed in adipose tissue3
  7. GutpresentColonic epithelium, smooth muscle and plexus4

Map sources

  1. Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
  2. Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
  3. Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
  4. Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)

Cited values

  1. CB1Partial agonistEC50 = 46 nM · human56 out of 100

    Amato et al., Molecules 2022 (table 1, compound 1) (new tab) · cAMP inhibition, membranes of CHO cells overexpressing human CB1, efficacy 39 ± 11% of the maximal CP 55,940 signal (Amato et al. 2022); Ki of 48.3 nM (human CB1) and 55.4 nM (rat CB1) (De Vry et al. 2004)

  2. CB2Partial agonistKi = 45.5 nM · human56 out of 100

    De Vry et al., J Pharmacol Exp Ther 2004 (new tab) · [3H]CP 55,940 displacement, human CB2; partial agonist properties in [35S]GTPγS

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

BAY 59-3074 is a partial agonist of the CB1 and CB2 cannabinoid receptors, of unusual structure: a diaryl ether carrying a sulfonic ester, unrelated to the dibenzopyran skeleton of THC or to the indoles and indazoles of synthetic cannabinoids on the illicit market. De Vry and colleagues reported in 2004 Ki values of 55.4 nM at rat CB1, 48.3 nM at human CB1 and 45.5 nM at human CB2, with a partial agonist profile in [35S]GTPγS; a more recent cAMP assay gives a maximal efficacy of 39% of that of CP 55,940 at human CB1 (Amato et al. 2022). In rats, at 0.3 to 3 mg/kg orally, the molecule produced antihyperalgesic and antiallodynic effects in several neuropathic and inflammatory pain models; cannabinoid-type side effects, including hypothermia, appeared above 1 mg/kg and tolerance developed within 5 days, with no sign of withdrawal after 14 days of daily administration of 1 to 10 mg/kg (De Vry et al. 2004). In drug discrimination in rats, its effects are reproduced by BAY 38-7271, CP 55,940, HU-210, WIN 55,212-2 and Δ9-THC, but not by morphine, gabapentin, carbamazepine, amitriptyline or baclofen, and are blocked by rimonabant: the action goes through CB1 (De Vry and Jentzsch 2004). No study in humans was found, nor any metabolism or chronic toxicology data.

Key sources.

History

Source
An entirely synthetic substance, absent from hemp and from any living organism, designed by Bayer as a ligand of cannabinoid receptors (De Vry et al. 2004). It is described only in the research literature.

Origin

Laboratory synthesis

No biosynthetic pathway: the molecule has no natural equivalent. It is a synthetic compound of the diaryl ether sulfonate ester class.

Classification

Family, origin and source verification

Family

Synthetic CB receptor agonist › Research ligand or medicine

Class

diaryl ether alkanesulfonate

Verification

Classification, sources and binding values checked on 20 October 2026; text read against its sources and Wikipedia.

Wikipedia (English)

BAY 59-3074 (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. De Vry J et al. 3-[2-Cyano-3-(trifluoromethyl)phenoxy]phenyl-4,4,4-trifluoro-1-butanesulfonate (BAY 59-3074): a novel cannabinoid CB1/CB2 receptor partial agonist with antihyperalgesic and antiallodynic effects. J Pharmacol Exp Ther, 2004 (new tab)PMID 15140913
  2. De Vry J, Jentzsch KR. Discriminative stimulus effects of the structurally novel cannabinoid CB1/CB2 receptor partial agonist BAY 59-3074 in the rat. Eur J Pharmacol, 2004 (new tab)PMID 15556145
  3. Amato G et al. Structure-activity relationship development efforts towards peripherally selective analogs of the cannabinoid receptor partial agonist BAY 59-3074. Molecules, 2022 (new tab)PMID 36080443
  4. Teng H, Thakur GA, Makriyannis A. Conformationally constrained analogs of BAY 59-3074 as novel cannabinoid receptor ligands. Bioorg Med Chem Lett, 2011 (new tab)PMID 21880487
  5. PubChem, BAY 59-3074, CID 10479060 (identifiers and properties) (new tab)

Identifiers

Names

IUPAC name
[3-[2-cyano-3-(trifluoromethyl)phenoxy]phenyl] 4,4,4-trifluorobutane-1-sulfonate
Other names
BAY-59-3074 · BAY59-3074

Identifiers

Formula
C₁₈H₁₃F₆NO₄S
CAS
406205-74-1
PubChem CID
10479060(new tab)
InChIKey
LWUSZIVDPJPVBW-UHFFFAOYSA-N
SMILES
C1=CC(=CC(=C1)OS(=O)(=O)CCCC(F)(F)F)OC2=CC=CC(=C2C#N)C(F)(F)F

Machine-readable entry (JSON)

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