Emopamil

Emopamil
Names
	IUPAC name 2-isopropyl-5-(methyl- (2-phenylethyl)amino)- 2-phenylpentanenitrile
Identifiers
CAS Number	78370-13-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEMBL	ChEMBL173809 ;
ChemSpider	64360 ;
KEGG	C13766 ;
PubChem CID	71225;
UNII	M514041RF7 ;
CompTox Dashboard (EPA)	DTXSID90868474 ;
	InChI 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 Key: DWAWDSVKAUWFHC-UHFFFAOYSA-N ; 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;
	SMILES 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
Chemical formula	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). verify (what is ?) Infobox references

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]

References

^ 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.
^ "Emopamil - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2022-12-07.
^ 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.
^ 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.

[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.

[1]

[2]

[3]

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Structure

Applications

See also

References