Mepindolol

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

Mepindolol

Clinical data
ATC code	C07AA14 (WHO)
Identifiers
IUPAC name (RS)-1-[(2-Methyl-1H-indol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol
CAS Number	23694-81-7
PubChem CID	71698
ChemSpider	64750
UNII	00Q31ER368
KEGG	D07181
CompTox Dashboard (EPA)	DTXSID40865110
ECHA InfoCard	100.041.650
Chemical and physical data
Formula	C15H22N2O2
Molar mass	262.353 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES CC1=CC2=C(N1)C=CC=C2OCC(CNC(C)C)O
InChI 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

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

• Pindolol
• Bopindolol