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Emopamil

From Wikipedia, the free encyclopedia
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 mass334.50 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Emopamil is acalcium channel blocker and a high-affinityligand of humansterolisomerase.[1]

Structure

[edit]

Emopamil's structure consists of an organicamino compound,nitrile compound and a member of twobenzene rings.

Applications

[edit]

Emopamil also known as EMP is aphenylalkylamine and inhibitor of5-hydroxytryptamine 5-HT2 receptors.[2] EMP includes a chiral quaternary carbon center, and research has indicated that itsoptical isomers have different biological effects.[3] It interacts in an extracellular site of thenerve 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 toischaemia.[4]

See also

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References

[edit]
  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. Retrieved2022-12-07.
  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.
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
KCaTooltip Calcium-activated potassium channel
Blockers
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
Activators
CFTRTooltip Cystic fibrosis transmembrane conductance regulator
Blockers
Activators
Unsorted
Blockers
Others
TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels
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