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Canna·wikiLY-320135

ECS modulator (research)

Unscheduled

LY-320135

4-[[6-méthoxy-2-(4-méthoxyphényl)-1-benzofuran-3-yl]carbonyl]benzonitrile

Aliases.LY320135 · LY 320135

A benzofuran-skeleton CB1 antagonist, Ki of 224 nM and selectivity greater than 70 times over CB2.

Updated on

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.

Identifiers

Formula
C₂₄H₁₇NO₄
Molar mass
383.40 g·mol⁻¹
CAS
176977-56-3
PubChem CID
5311257
Origin
A wholly synthetic compound with no natural occurrence. It is produced as a pharmacological research reagent and has never been the subject of clinical development.
InChIKey
RYNSGDFWBJWWSZ-UHFFFAOYSA-N

In plain terms

LY-320135 blocks the CB1 receptor without chemically resembling it. It served to reveal an unexpected behaviour of that receptor, able to stimulate an enzyme it normally inhibits. It is a laboratory tool, never a medicine.

Receptors and activity

  • CB1
    Ki = 224 nM (lignée stable) ; 203 nM sur membranes de cerveletAntagonist
  • CB2
    Ki supérieur à 10 µM ; sélectivité CB1 supérieure à 70 foisModulator
  • Agonist
  • Partial agonist
  • Antagonist
  • Modulator
  • Inverse agonist

Hover over a row for the precise value (Ki, EC50…)

Subjective signature

Hover over an axis to read its definition.

  • Calm
    5
  • Clarity
    30
  • Sleep
    5
  • Appetite
    3
  • High
    5

Editorial estimate, not clinical.

Pharmacology

LY-320135 is a CB1 receptor antagonist described in 1998 by Felder and colleagues, remarkable for its benzofuran skeleton, unrelated to the pyrazoles of the rimonabant lineage or to the classical cannabinoids. Its selectivity is clear: the inhibition constant stands at 224 nanomolar at the CB1 receptor expressed in a stable line, against more than 10 micromolar at CB2, a factor greater than seventy, and neighbouring values are found on cerebellum and spleen membranes. Its main interest is, however, methodological. By treating CB1-expressing cells with pertussis toxin, the authors neutralised the Gi and Go proteins that carry the inhibition of adenylyl cyclase by anandamide, and then saw a stimulatory effect of that same anandamide on the enzyme appear. The compound blocked that stimulatory component, which made it possible to attribute it unambiguously to the CB1 receptor rather than to a parallel target. That result helped establish that CB1 is not coupled to a single signalling pathway and that it can recruit Gs proteins depending on cellular context, a notion that today structures the reading of biased cannabinoid signalling. The compound moreover blocks the inhibition of N-type calcium channels and the activation of inwardly rectifying potassium channels produced by WIN 55212-2. It remained a pharmacological tool and was not developed further.

Key sources.

Origin (research tool)

An entirely chemical route, described here by class only. The molecule is built on a benzofuran core bearing an aromatic ketone function and a nitrile, a structure unrelated to the pyrazoles of the rimonabant lineage or to the classical cannabinoids. It is that originality of skeleton that the authors emphasised.

Structural classification

Class
ECS modulator (research)
Origin
A wholly synthetic compound with no natural occurrence. It is produced as a pharmacological research reagent and has never been the subject of clinical development.
Status
Unscheduled

References

  1. 1.Felder et coll. 1998 : le LY320135, antagoniste CB1 révélant le couplage du récepteur à la stimulation de l'AMP cycliquePMID 9435190

Structured data

InChIKey
RYNSGDFWBJWWSZ-UHFFFAOYSA-N
SMILES
COC1=CC=C(C=C1)C2=C(C3=C(O2)C=C(C=C3)OC)C(=O)C4=CC=C(C=C4)C#N
Formula
C24H17NO4
Molar mass
383.40 g·mol⁻¹
CAS
176977-56-3
PubChem CID
5311257
Machine-readable entry (JSON)

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

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