Emopamil

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Emopamil
Names
IUPAC name
2-isopropyl-5-(methyl- (2-phenylethyl)amino)- 2-phenylpentanenitrile
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C23H30N2/c1-20(2)23(19-24,22-13-8-5-9-14-22)16-10-17-25(3)18-15-21-11-6-4-7-12-21/h4-9,11-14,20H,10,15-18H2,1-3H3 checkY
    Key: DWAWDSVKAUWFHC-UHFFFAOYSA-N checkY
  • InChI=1/C23H30N2/c1-20(2)23(19-24,22-13-8-5-9-14-22)16-10-17-25(3)18-15-21-11-6-4-7-12-21/h4-9,11-14,20H,10,15-18H2,1-3H3
    Key: DWAWDSVKAUWFHC-UHFFFAOYAK
  • N#CC(c1ccccc1)(C(C)C)CCCN(CCc2ccccc2)C
  • CC(C)C(CCCN(C)CCC1=CC=CC=C1)(C#N)C2=CC=CC=C2
Properties
C23H30N2
Molar mass 334.50 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Emopamil is a calcium channel blocker and a high-affinity ligand of human sterol isomerase.[1]

Structure

Emopamil's structure consists of an organic amino compound, nitrile compound and a member of two benzene rings.

Applications

Emopamil also known as EMP is a phenylalkylamine and inhibitor of 5-hydroxytryptamine 5-HT2 receptors.[2] EMP includes a chiral quaternary carbon center, and research has indicated that its optical isomers have different biological effects.[3] It interacts in an extracellular site of the nerve cell to inhibit calcium channel responses while other phenylalkylamines act at an intracellular site. The interaction site of emopamil suggests to its greater neuroprotective efficacy in research related to ischaemia.[4]

See also

References

  1. ^ Paul, Raymond; Silve, Sandra; De Nys, Nathalie; Dupuy, Pascal-Henry; Labit-Le Bouteiller, Christine; Rosenfeld, Jorge; Ferrara, Pascual; Le Fur, Gérard; Casellas, Pierre; Loison, Gérard (1998). "Both the Immunosuppressant SR31747 and the Antiestrogen Tamoxifen Bind to an Emopamil-Insensitive Site of Mammalian Δ8-Δ7 Sterol Isomerase". Journal of Pharmacology and Experimental Therapeutics. 285 (3): 1296–302. PMID 9618436.
  2. ^ "Emopamil - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2022-12-07.
  3. ^ Toyohara, J.; Okamoto, M.; Aramaki, H.; Zaitsu, Y.; Shimizu, I.; Ishiwata, K. (2016). "(R)-¹¹CEmopamil as a novel tracer for imaging enhanced P-glycoprotein function". Nuclear Medicine and Biology. 43 (1): 52–62. doi:10.1016/j.nucmedbio.2015.09.001. PMID 26429767.
  4. ^ Keith, R. A.; Mangano, T. J.; Defeo, P. A.; Ernst, G. E.; Warawa, E. J. (1994). "Differential inhibition of neuronal calcium entry and 3H-D-aspartate release by the quaternary derivatives of verapamil and emopamil". British Journal of Pharmacology. 113 (2): 379–384. doi:10.1111/j.1476-5381.1994.tb16999.x. PMC 1510140. PMID 7834187.
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