PipISB

PipISB
Identifiers
	IUPAC name N-(4-fluorobenzyl)-4-(3-(piperidin-1-ylindole-1-sulfonyl)benzamide;
PubChem CID	58975213;
Chemical and physical data
Formula	C27H26FN3O3S
Molar mass	491.58 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(N1C2=CC=CC=C2C(N3CCCCC3)=C1)(C4=CC=C(C(NCC5=CC=C(F)C=C5)=O)C=C4)=O;

PipISB is a drug used in scientific research which acts as a potent and selective inverse agonist of the cannabinoid receptor CB₁. It is highly selective for the CB₁ receptor over CB₂, with a K_d at CB₁ of 1.5nM vs over 7000nM at CB₂, has good blood-brain barrier penetration, and can be conveniently radiolabelled with either ¹¹C or ¹⁸F, making it useful for mapping the distribution of CB₁ receptors in the brain.[1][2]

References

Donohue, Sean R.; Halldin, Christer; Schou, Magnus; Hong, Jinsoo; Phebus, Lee; Chernet, Eyassu; Hitchcock, Stephen A.; Gardinier, Kevin M.; Ruley, Kevin M.; Krushinski, Joseph H.; Schaus, John; Pike, Victor W. (2008). "Radiolabeling of a high potency cannabinoid subtype-1 receptor inverse agonist, N-(4-fluoro-benzyl)-4-(3-(piperidin-1-yl-indole-1-sulfonyl)benzamide (PipISB), with carbon-11 or fluorine-18". Journal of Labelled Compounds and Radiopharmaceuticals. 51 (3): 146. doi:10.1002/jlcr.1491.
Finnema, S. J.; Donohue, S. R.; Zoghbi, S. S.; Brown, A. K.; Gulyás, B. Z.; Innis, R. B.; Halldin, C.; Pike, V. W. (2009). "Evaluation of \11C]PipISB and \18F]PipISB in monkey as candidate radioligands for imaging brain cannabinoid type-1 receptors in vivo". Synapse. 63 (1): 22–30. doi:10.1002/syn.20578. PMC 2587077. PMID 18925657.

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[1] Donohue, Sean R.; Halldin, Christer; Schou, Magnus; Hong, Jinsoo; Phebus, Lee; Chernet, Eyassu; Hitchcock, Stephen A.; Gardinier, Kevin M.; Ruley, Kevin M.; Krushinski, Joseph H.; Schaus, John; Pike, Victor W. (2008). "Radiolabeling of a high potency cannabinoid subtype-1 receptor inverse agonist, N-(4-fluoro-benzyl)-4-(3-(piperidin-1-yl-indole-1-sulfonyl)benzamide (PipISB), with carbon-11 or fluorine-18". Journal of Labelled Compounds and Radiopharmaceuticals. 51 (3): 146. doi:10.1002/jlcr.1491.

[2] Finnema, S. J.; Donohue, S. R.; Zoghbi, S. S.; Brown, A. K.; Gulyás, B. Z.; Innis, R. B.; Halldin, C.; Pike, V. W. (2009). "Evaluation of \11C]PipISB and \18F]PipISB in monkey as candidate radioligands for imaging brain cannabinoid type-1 receptors in vivo". Synapse. 63 (1): 22–30. doi:10.1002/syn.20578. PMC 2587077. PMID 18925657.