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PipISB

Identifiers
IUPAC name N-(4-fluorobenzyl)-4-(3-(piperidin-1-ylindole-1-sulfonyl)benzamide
CAS Number	859165-19-8
PubChem CID	58975213
ChemSpider	65322455
CompTox Dashboard (EPA)	DTXSID101045311
Chemical and physical data
Formula	C27H26FN3O3S
Molar mass	491.58 g·mol
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
InChI InChI=1S/C27H26FN3O3S/c28-22-12-8-20(9-13-22)18-29-27(32)21-10-14-23(15-11-21)35(33,34)31-19-26(30-16-4-1-5-17-30)24-6-2-3-7-25(24)31/h2-3,6-15,19H,1,4-5,16-18H2,(H,29,32) Key:RXTQWWFLLRSBCM-UHFFFAOYSA-N

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 C or F, making it useful for mapping the distribution of CB₁ receptors in the brain.

References

1. Donohue SR, Halldin C, Schou M, Hong J, Phebus L, Chernet E, et al. (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 SJ, Donohue SR, Zoghbi SS, Brown AK, Gulyás B, Innis RB, et al. (January 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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