SKF-64139

Chemical compound From Wikipedia, the free encyclopedia

SKF-64139 is a synthetic tetrahydroisoquinoline (THIQ) derivative that functions as a potent and selective inhibitor of phenylethanolamine N-methyltransferase (PNMT), the enzyme that catalyzes the conversion of norepinephrine to epinephrine in both the adrenal medulla and the central nervous system. By lowering epinephrine levels through PNMT inhibition, SKF-64139 has been widely used as a research tool to study the physiological functions of epinephrine, particularly its roles in cardiovascular regulation and metabolic processes.[1]

Other namesSK&F 64139, DCTQ.
CAS Number
Quick facts Clinical data, Other names ...
SKF-64139
Clinical data
Other namesSK&F 64139, DCTQ.
Identifiers
  • 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC9H9Cl2N
Molar mass202.08 g·mol−1
3D model (JSmol)
  • C1CNCC2=C1C=CC(=C2Cl)Cl
  • InChI=1S/C9H9Cl2N/c10-8-2-1-6-3-4-12-5-7(6)9(8)11/h1-2,12H,3-5H2
  • Key:WFPUBEDBBOGGIQ-UHFFFAOYSA-N
Close

This compound also exhibits additional actions, such as weak monoamine oxidase (MAO) inhibition at higher doses, which may contribute to broader neurochemical and hemodynamic effects.[2] Additionally, SKF-64139 is an alpha-2 blocker[3] that lowers the blood pressure in hypertensive rats.[4]

Synthesis

The isoquinoline core of SKF-64139 is prepared by a stepwise Pomeranz–Fritsch reaction, in which the benzaldehyde (1) and 2,2-dimethoxyethylamine (2) undergo condensation followed by cyclization:[5]

See also

References

Related Articles

Wikiwand AI