Mepindolol

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

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

Synthesis

Halogenation of 4-Benzyloxyindole-2-carboxylic acid [39731-09-4] (1) with thionyl chloride gave PC54108402 (2). Addition of dimethylamine gave the amide, PC134990474 (3). Reduction of the amide with lithium aluminium hydride led to PC134990355 (4). Addition of iodomethane gave the quaternary cation, PC134990594 (5). Displacement of trimethylamine leaving group by cyanide anion led to PC134990354 (6). Hydrolysis of the nitrile to the carboxylic acid in alkali led to PC134990475 (7). Splitting off carbon dioxide occurred on heating to give 2-methyl-4-[(phenylmethyl)oxy]-1H-indole [35308-72-6] (8). Removal of the benzyl protecting group occurred upon catalytic hydrogenation giving 4-Hydroxy-2-methylindole [35320-67-3] (9). Treatment with epichlorohydrin led to 2-methyl-4-(oxiran-2-ylmethoxy)-1H-indole [62119-47-5] (10). Further reaction with isopropylamine completed the synthesis of mepindolol (11).

See also

References
  1. Schmid MG, Gecse O, Szabo Z, Kilár F, Gübitz G, Ali I, Aboul-Enein HY (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. Weetman, D.F.; Castaer, J.; Mepindolol. Drugs Fut 1978, 3, 5, 381.
  3. Seemann, F.; Wiskott, E.; Niklaus, P.; Troxler, F. (1971). "Beiträge zur Chemie der 4-Hydroxyindol-Verbindungen 10. Mitteilung über synthetische indolverbindungen [1]". Helvetica Chimica Acta. 54 (8): 2411–2419. doi:10.1002/hlca.19710540805.
  4. Franz Dr Troxler & Albert Dr Hofmann, CH502337 (1971 to Sandoz AG).
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