Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

SKF-64139

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
SKF-64139
Clinical data
Other namesSK&F 64139, DCTQ.
Identifiers
  • 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline
CAS Number
PubChemCID
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

SKF-64139 is a synthetictetrahydroisoquinoline (THIQ) derivative that functions as a potent and selective inhibitor ofphenylethanolamine N-methyltransferase (PNMT), the enzyme that catalyzes the conversion ofnorepinephrine toepinephrine in both theadrenal medulla and thecentral 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]

This compound also exhibits additional actions, such as weakmonoamine oxidase (MAO) inhibition at higher doses, which may contribute to broaderneurochemical andhemodynamic effects.[2] Additionally, SKF-64139 is analpha-2 blocker[3] that lowers the blood pressure in hypertensive rats.[4]

Synthesis

[edit]

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

See also

[edit]

References

[edit]
  1. ^Park DH, Ruggiero DA, Anwar M, Joh TH (January 1988). "Possible mechanism of action of SKF 64139 in vivo on rat adrenal and brain phenylethanolamine N-methyltransferase activity".Biochemical Pharmacology.37 (2):313–318.doi:10.1016/0006-2952(88)90734-4.PMID 3342087.
  2. ^Mefford IN, Roth KA, Gilberg M, Barchas JD (March 1981). "In vivo intraneuronal MAO inhibition in rat brain SKF 64139, comparison to other potent PNMT inhibitors".European Journal of Pharmacology.70 (3):345–353.doi:10.1016/0014-2999(81)90168-0.PMID 7227455.
  3. ^Drew GM (March 1981). "α2-adrenoceptor-blocking action of the phenylethanolamine-N-methyltransferase inhibitor SKF 64139".The Journal of Pharmacy and Pharmacology.33 (3):187–188.doi:10.1111/j.2042-7158.1981.tb13750.x.PMID 6116766.
  4. ^Goldstein M, Kinguasa K, Hieble JP, Pendleton RG (June 1982). "Lowering of blood pressure in hypertensive rats by SKF 64139 and SKF 72223".Life Sciences.30 (23):1951–1957.doi:10.1016/0024-3205(82)90433-7.PMID 6125862.
  5. ^Bondinell WE, Chapin FW, Girard GR, Kaiser C, Krog AJ, Pavloff AM, et al. (May 1980). "Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-substituted 1,2,3,4-tetrahydroisoquinolines".Journal of Medicinal Chemistry.23 (5):506–511.doi:10.1021/jm00179a007.PMID 7381849.Compound #13 Method A
Retrieved from "https://en.wikipedia.org/w/index.php?title=SKF-64139&oldid=1329465936"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2026 Movatter.jp