Metubine Iodide,Lilly,US,1949
Metocurine Iodide is used as Zika virus protease inhibitor.
Neuromuscular blocking agent.
ChEBI: Metocurine iodide is an aromatic ether.
50 grams of crude, tarry curare as received in commerce and containing
about 20% of d-tubocurarine are suspended in 400 cc of 0.5 N methanolic
potassium hydroxide, and the mixture is boiled for ten minutes. The dark
own insoluble material is filtered off and the filtrate is treated with 50 cc of
methyl iodide and refluxed gently for about 8 hours. An additional amount of
25 cc of methyl iodide is added to the reaction mixture and the refluxing is
continued for 8 hours.
The reaction mixture is evaporated to a small volume, whereupon the dtubocurarine dimethyl ether iodide precipitates. The precipitate is filtered off
and dissolved in boiling water. The hot solution is treated with a small amount
of decolorizing carbon, the carbon filtered off and the filtrate cooled to about
0°C. The dimethyl ether of d-tubocurarine iodide crystallizes in white crystals
which melt at about 267°-270°C with decomposition.
Metocurine iodide, ( )-O,O -dimethylchondrocurarine diiodide (Metubine iodide),is prepared from natural crude curare by extracting the curarewith methanolic potassium hydroxide. When theextract is treated with an excess of methyl iodide, the ( )-tubocurarine is converted to the diquaternary dimethylether and crystallizes out as the iodide (see “TubocurarineChloride”). Other ethers besides the dimethyl ether havebeen made and tested. For example, the dibenzyl ether wasone third as active as tubocurarine chloride, and the diisopropylcompound had only one half the activity. For comparison,the dimethyl ether has approximately 4 times theactivity of tubocurarine chloride.
The pharmacological action of this compound is the sameas that of tubocurarine chloride, namely, a nondepolarizingcompetitive blocking effect on the motor end plate of skeletalmuscles. It is considerably more potent than d-tubocurarine,however, and has the added advantage of exerting much lesseffect on respiration. The effect on respiration is not a significantfactor in therapeutic doses. Accidental overdosage iscounteracted best by forced respiration.
