Article · Wikipedia archive · Last revised Aug 7, 2026

Mepindolol

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

Last revised
Aug 7, 2026
Read time
≈ 1 min
Length
224 w
Citations
4
Source
Wikipedia ↗
Mepindolol
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 InfoCard100.041.650
Chemical and physical data
FormulaC15H22N2O2
Molar mass262.353 g·mol−1
3D model (JSmol)
ChiralityRacemic 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

Synthesis

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.34

See also

See also

References

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.