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Research tools

WOBE437

Synthetic inhibitor of endocannabinoid reuptake, a research tool with no human data.

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.

C₂₂H₃₃NO₃

CID 137700154

Family
ECS pharmacological toolTransport inhibitor
Molar mass
359.50 g/mol

Updated on

In plain terms

WOBE437 is a laboratory molecule, developed by Swiss chemists from a substance found in echinacea. It does not come from hemp. Its role is to help researchers understand how cells recycle the cannabinoids the body makes itself; it has been tested only on cells and animals, and no study in humans was found.

Receptors and activity

Target network

CB1Binding (function not established)Ki = 17 µM · not specified in the text consultedradioligand binding; negligible binding (Ki of 17 µM)
  • Blocks or inhibits
  • Binds or modulates

The lower the cited value, the closer the target sits to WOBE437: 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 WOBE437.

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. Cellular reuptake of endocannabinoids (anandamide, 2-AG)InhibitorIC50 = 10 nM · human67 out of 100

    Chicca et al., PNAS 2017 (new tab) · anandamide reuptake, U937 cells; 55 nM in Neuro-2a cells (mouse), 137 nM in HMC-1 cells (human, FAAH-free); transport mechanism not identified

  2. CB1Binding (function not established)Ki = 17 µM · not specified in the text consulted13 out of 100

    Chicca et al., PNAS 2017 (new tab) · radioligand binding; negligible binding (Ki of 17 µM)

  3. CB2Binding (function not established)Ki = 48 µM · not specified in the text consulted5 out of 100

    Chicca et al., PNAS 2017 (new tab) · radioligand binding; negligible binding (Ki of 48 µM)

  4. SCCPDH, VAT1 and ferrochelatase (off-target proteins)Binding (function not established)no measured value cited

    Proteins bound by a photoactivatable probe derived from WOBE437 in Neuro-2a cells; no numerical value in the abstract (Gagestein et al. 2022)

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

WOBE437 is the lead compound of the selective endocannabinoid reuptake inhibitors. Instead of activating cannabinoid receptors, it would slow the entry of anandamide and 2-arachidonoylglycerol into cells, without inhibiting the FAAH and MAGL enzymes. The 2017 paper reports an IC50 of 10 nM on anandamide reuptake in U937 cells and negligible binding to CB1 and CB2 (Ki 17 and 48 µM). In mice, a dose of 10 mg/kg intraperitoneally produced a moderate cannabinoid tetrad, blocked by rimonabant (except hypolocomotion, partly), which makes it an indirect CB1 agonist (Chicca et al. 2017); orally (50 mg/kg), the molecule is bioavailable, with a plasma and brain peak within 20 minutes or less, brain clearance in about 180 minutes, a CB1-dependent antinociceptive effect and no catalepsy or effect on locomotion (Reynoso-Moreno et al. 2018). At 10 mg/kg per day for 20 days, it reduced clinical severity in a mouse model of experimental autoimmune encephalomyelitis, without desensitisation of the CB1 receptor (Reynoso-Moreno et al. 2021; the authors declare an interest in the company Synendos Therapeutics). This picture should be read with caution: in 2022, an independent team identified three off-target proteins and observed an increase, not a decrease, in anandamide reuptake in Neuro-2a cells (Gagestein et al.). The postulated transporter has not been isolated; no study in humans was found.

Key sources.

History

Source
A synthetic molecule from a medicinal chemistry programme starting from an N-alkylamide of dodeca-2,4-dienoic acid found in echinacea (Echinacea purpurea). It is not known in cannabis (Chicca et al. 2017).

Origin

Research tool

No known biological pathway: WOBE437 is a synthetic compound (an N-substituted dienamide), produced by no living organism. Only its N-alkylamide backbone is inspired by a natural product from echinacea.

Classification

Family, origin and source verification

Family

ECS pharmacological tool › Transport inhibitor

Verification

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

Wikipedia (English)

No dedicated article.

References

  1. Chicca A et al. Chemical probes to potently and selectively inhibit endocannabinoid cellular reuptake. PNAS, 2017 (new tab)PMID 28584105
  2. Reynoso-Moreno I et al. The endocannabinoid reuptake inhibitor WOBE437 is orally bioavailable and exerts indirect polypharmacological effects via different endocannabinoid receptors. Front Mol Neurosci, 2018 (new tab)PMID 29910713
  3. Mäder P et al. Synthesis and biological evaluation of endocannabinoid uptake inhibitors derived from WOBE437. ChemMedChem, 2021 (new tab)PMID 32369259
  4. Reynoso-Moreno I et al. Selective endocannabinoid reuptake inhibitor WOBE437 reduces disease progression in a mouse model of multiple sclerosis. ACS Pharmacol Transl Sci, 2021 (new tab)PMID 33860200
  5. Gagestein B et al. Chemical proteomics reveals off-targets of the anandamide reuptake inhibitor WOBE437. ACS Chem Biol, 2022 (new tab)PMID 35482948
  6. PubChem, WOBE437, CID 137700154 (identifiers and properties) (new tab)

Identifiers

Names

IUPAC name
(2E,4E)-N-[2-(3,4-dimethoxyphenyl)ethyl]dodeca-2,4-dienamide
Other names
WOBE-437

Identifiers

Formula
C₂₂H₃₃NO₃
PubChem CID
137700154(new tab)
InChIKey
LAHLFCSEHHJQRN-AQASXUMVSA-N
SMILES
CCCCCCC/C=C/C=C/C(=O)NCCC1=CC(=C(C=C1)OC)OC

Machine-readable entry (JSON)

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