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]
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| Other names | SK&F 64139, DCTQ. |
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| Formula | C9H9Cl2N |
| Molar mass | 202.08 g·mol−1 |
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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]
