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Canna·wikiPipISB

ECS modulator (research)

Unscheduled

PipISB

N-[(4-fluorophenyl)methyl]-4-(3-piperidin-1-ylindol-1-yl)sulfonylbenzamide

Aliases.[11C]PipISB · [18F]PipISB

A radiotracer of the CB1 receptor for positron emission tomography, evaluated in primates.

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
C₂₇H₂₆FN₃O₃S
Molar mass
491.17 g·mol⁻¹
CAS
-
PubChem CID
58975213
Origin
A wholly synthetic compound with no natural occurrence. It is produced as a radiotracer for positron emission tomography and has no therapeutic use.
InChIKey
RXTQWWFLLRSBCM-UHFFFAOYSA-N

In plain terms

PipISB is not a medicine but a tracer: made radioactive, it makes it possible to photograph CB1 receptors in the living brain. It serves to count those receptors in animals and to understand how their number varies.

Receptors and activity

  • CB1
    Agoniste inverse sélectif de haute affinité ; employé comme radioligand (Finnema et coll. 2009)Inverse agonist
  • CB2
    Sélectivité CB1 ; valeur non détaillée dans les sources retenuesModulator
  • 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
    10
  • Sleep
    5
  • Appetite
    5
  • High
    5

Editorial estimate, not clinical.

Pharmacology

PipISB belongs to a category of molecules whose purpose is not to heal but to measure. Counting CB1 receptors in a living brain requires a compound that satisfies several hard-to-reconcile constraints at once: high and selective affinity for the target, rapid brain penetration, elimination swift enough for the specific signal to stand out from background, and a chemical position in which to lodge a positron-emitting isotope without altering molecular recognition. That last constraint explains why the field has produced few usable tracers despite an obvious clinical interest, the CB1 receptor being implicated in dependence, obesity, schizophrenia and several neurodegenerative conditions. PipISB, a CB1 inverse agonist built on a sulfonylated indole, was prepared in two radiolabelled forms, one with carbon 11 whose very short half-life requires production at the very site of the examination, the other with fluorine 18 whose longer half-life permits transport. Finnema and colleagues evaluated both in the macaque in 2009, comparing brain uptake at baseline and after saturation of the receptors by a blocking dose, the reference method for establishing the specific fraction of the signal. The compound has remained a research tracer, without moving into routine clinical use.

Key sources.

Origin (research tool)

An entirely chemical route, described here by class only. The molecule is a sulfonylated indole: an indole core bearing a piperidine at position 3 is linked through a sulfonyl function to a benzamide whose nitrogen carries a fluorobenzyl group. It is the two labellable positions, the carbonyl of the amide and the fluorine of the benzyl, that determine the two radioactive variants used in imaging.

Structural classification

Class
ECS modulator (research)
Origin
A wholly synthetic compound with no natural occurrence. It is produced as a radiotracer for positron emission tomography and has no therapeutic use.
Status
Unscheduled

References

  1. 1.Finnema et coll. 2009 : évaluation du [11C]PipISB et du [18F]PipISB chez le singe comme radioligands candidats pour l'imagerie des récepteurs CB1 cérébraux in vivoPMID 18925657

Structured data

InChIKey
RXTQWWFLLRSBCM-UHFFFAOYSA-N
SMILES
C1CCN(CC1)C2=CN(C3=CC=CC=C32)S(=O)(=O)C4=CC=C(C=C4)C(=O)NCC5=CC=C(C=C5)F
Formula
C27H26FN3O3S
Molar mass
491.17 g·mol⁻¹
PubChem CID
58975213
Machine-readable entry (JSON)

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

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