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Canna·wikiLY-2183240

ECS modulator (research)

Unscheduled

LY-2183240

N,N-diméthyl-5-[(4-phénylphényl)méthyl]tétrazole-1-carboxamide

Aliases.LY2183240 · LY 2183240

A covalent FAAH inhibitor long taken for a blocker of anandamide transport, and not very selective.

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
C₁₇H₁₇N₅O
Molar mass
307.35 g·mol⁻¹
CAS
874902-19-9
PubChem CID
11507802
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
GZNIYOXWFCDBBJ-UHFFFAOYSA-N

In plain terms

LY-2183240 was supposed to block the transport of anandamide into the cell. A study in 2006 showed that it does something quite different: it destroys the enzyme that degrades anandamide, and several other enzymes along the way. A classic case of a misunderstood tool.

Receptors and activity

  • FAAH
    Inhibition covalente par carbamylation de la sérine nucléophileAntagonist
  • Transporteur membranaire de l'anandamide
    Effet attribué à tort au transport ; expliqué par l'inhibition de la FAAHModulator
  • 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
    20
  • Clarity
    5
  • Sleep
    15
  • Appetite
    15
  • High
    10

Editorial estimate, not clinical.

Pharmacology

LY-2183240 illustrates the commonest risk of experimental pharmacology: that of drawing a conclusion about a mechanism from a tool whose target one believes one knows. The compound had been introduced as an inhibitor of the presumed anandamide transporter, and the fact that it reduced the cellular uptake of that endocannabinoid while producing analgesia was read as an argument in favour of the existence of such a transporter. Alexander and Cravatt showed in 2006 that it is in reality a potent covalent inhibitor of fatty acid amide hydrolase, the enzyme that hydrolyses anandamide, and that it inactivates it by carbamylation of the nucleophilic serine of its active site. The interpretive consequence is direct: the blockade of uptake observed with this compound is explained by inactivation of the enzyme, which on the contrary provides an argument in favour of the competing model, the one in which enzymatic hydrolysis constitutes the metabolic engine that sustains the diffusion of anandamide into the cell. The screening by activity-based proteomic probes carried out in the same study moreover revealed that the molecule inhibits several other serine hydrolases of the brain, which led the authors to warn against this heterocyclic urea chemotype, whose reactivity towards the proteome appears excessive for pharmaceutical development. The compound retains a historical value in the long-open debate on the existence of a membrane transporter for anandamide.

Key sources.

Origin (research tool)

An entirely chemical route, described here by class only. The molecule is a heterocyclic urea: a tetrazole core bears on one side a biphenylmethyl group and on the other a dimethylcarboxamide function. It is that tetrazole-carboxamide sequence which constitutes the reactive group, the tetrazole playing the role of leaving group in the reaction with the enzyme.

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.Alexander et Cravatt 2006 : le LY2183240, prétendu bloqueur du transport endocannabinoïde, est un inhibiteur de la FAAH et d'autres hydrolasesPMID 16866524

Structured data

InChIKey
GZNIYOXWFCDBBJ-UHFFFAOYSA-N
SMILES
CN(C)C(=O)N1C(=NN=N1)CC2=CC=C(C=C2)C3=CC=CC=C3
Formula
C17H17N5O
Molar mass
307.35 g·mol⁻¹
CAS
874902-19-9
PubChem CID
11507802
Machine-readable entry (JSON)

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