Chemical Properties
White Solid
Originator
Sanorex ,Sandoz ,US ,1973
Uses
Clinical trials as appetite depressant. Anorexic; CNS stimulant.
Controlled substance (stimulant).
Definition
ChEBI: Mazindol is an organic molecular entity.
Manufacturing Process
Step 1: 1-(p-Chlorophenyl)-3-Ethoxy-11H-Isoindole - Crystalline triethyloxonium borontetrafluoride (21 g) (prepared from 23 g of borontrifluoride etherate and 11 g of epichlorohydrin) is dissolved in 100 ml of
absolute methylenechloride. 3-(p-Chlorophenyl) phthalimidine (21 g) is added
and the reaction mixture is stirred overnight at room temperature. The
resulting solution is poured onto 50 ml of saturated sodium carbonate,
extracted with 500 ml of ether and dried. Upon evaporation of the solvent
there is obtained crude material which is recrystallized from methylene
chloride/hexane (1:1) to yield 1-(p-chlorophenyl)-3-ethoxy-1H-isoindole; MP
102° to 103°C.
Step 2: 5-(p-Chlorophenyl)-5-Hydroxy-2,3-Dihydro-5H-Imidazo[2,1-
a]Isoindole - 1-(p-Chlorophenyl)-3-ethoxy-1H-isoindole (1 g), 2 g of
ethyleneimine hydrotetrafluoroborate moistened with methylene chloride
(containing approximately 0.66 g of dry salt) is refluxed in 25 ml of absolute
toluene for 2 hours in an atmosphere of nitrogen. The resulting mixture is
poured into 2 N sodium carbonate solution (25 ml) and extracted with ether.
The ether solution is contacted with air for 6 days at room temperature to
give the desired product. The crude material is recrystallized from
acetone/hexane (1:1) to give 5-(p-chlorophenyl)-5-hydroxy-2,3-dihydro-5Himidazo[2,1-a]isoindole; MP 198° to 199°C.
brand name
Mazanor (Wyeth); Sanorex (Novartis);Dasten;Degonon;Fagolipo;Lipese;Magrilan;Mazanor tablets;Mazeldene;Mazinil;Maznor;Tenorac.
Therapeutic Function
Antiobesity
World Health Organization (WHO)
Mazindol, an anorectic agent, was introduced into medicine in
1970 as an aid to weight reduction. It is controlled under Schedule IV of the 1971
Convention on Psychotropic Substances. It remains available in many countries
with highly evolved drug regulatory authorities.
(Reference: (UNCPS4) United Nations Convention on Psychotropic Substances (IV),
, , 1971)
