Mepindolol

Last updated

Mepindolol
Mepindolol.svg
Clinical data
ATC code
Identifiers
  • (RS)-1-[(2-Methyl-1H-indol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.041.650 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H22N2O2
Molar mass 262.353 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)C)O
  • InChI=1S/C15H22N2O2/c1-10(2)16-8-12(18)9-19-15-6-4-5-14-13(15)7-11(3)17-14/h4-7,10,12,16-18H,8-9H2,1-3H3
  • Key:NXWGWUVGUSFQJC-UHFFFAOYSA-N

Mepindolol (Betagon) is a non-selective beta blocker. It is used to treat glaucoma. [1]

Contents

Synthesis

Mepindolol synthesis.svg

The first reported synthesis of mepindolol in 1971 used 4-hydroxy-2-methylindole {9) with epichlorohydrin and then isopropylamine to add the sidechain which was known to produce beta blockers, by analogy with drugs discovered by Imperial Chemical Industries, such as propanolol. [2] The requisite intermediate was synthesized in a multi-step procedure from 4-benzyloxyindole-2-carboxylic acid (1) which was converted into (9) by conventional chemistry. [3] [4]

See also

References

  1. ↑ Schmid MG, Gecse O, Szabo Z, Kilár F, Gübitz G, Ali I, et al. (September 2001). "Comparative study of the chiral resolution of β-blockers on cellulose tris (3,5-dimethyl-phenylcarbamate) phases in normal and reversed phase modes". Journal of Liquid Chromatography & Related Technologies. 24 (16): 2493–2504. doi:10.1081/JLC-100105955.
  2. ↑ Lednicer D (1998). Strategies for Organic Drug Synthesis and Design. Canada: John Wiley & Sons. pp. 37–41. ISBN   0-471-19657-6.
  3. ↑ Seemann F, Wiskott E, Niklaus P, Troxler F (1971). "Beiträge zur Chemie der 4-Hydroxyindol-Verbindungen 10. Mitteilung über synthetische indolverbindungen" [Contributions to the chemistry of 4-hydroxyindole compounds 10. Report on synthetic indole compounds]. Helvetica Chimica Acta (in German). 54 (8): 2411–2419. doi:10.1002/hlca.19710540805.
  4. ↑ "Mepindolol". Pharmaceutical Substances. Georg Thieme Verlag KG. Retrieved 2024-06-30.
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