PipISB

PipISB
Identifiers
  • N-(4-fluorobenzyl)-4-(3-(piperidin-1-ylindole-1-sulfonyl)benzamide
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H26FN3O3S
Molar mass491.58 g·mol−1
3D model (JSmol)
  • O=S(N1C2=CC=CC=C2C(N3CCCCC3)=C1)(C4=CC=C(C(NCC5=CC=C(F)C=C5)=O)C=C4)=O
  • 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 Kd 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]

  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.