TETRANDRINI DIMETHIODIDUM Property

alpha 

D22 +148 to +158° (c = 0.25)

Safety

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

Hazard and Precautionary Statements (GHS)

TETRANDRINI DIMETHIODIDUM Chemical Properties,Usage,Production

Originator

Metubine Iodide,Lilly,US,1949

Uses

Metocurine Iodide is used as Zika virus protease inhibitor.

Uses

Neuromuscular blocking agent.

Definition

ChEBI: Metocurine iodide is an aromatic ether.

Manufacturing Process

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.

brand name

Metubine Iodide (Lilly).

Therapeutic Function

Muscle relaxant

General Description

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.