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Chemistry

Suxamethonium is an odorless, white crystalline substance. Aqueous solutions have a pH of about 4. The dihydrate melts at 160 °C, whereas the anhydrous melts at 190 °C. It is highly soluble in water (1 gram in about 1 mL), soluble in ethyl alcohol (1 gram in about 350 mL), slightly soluble in chloroform, and practically insoluble in ether. Suxamethonium is a hygroscopic compound. The compound consists of two acetylcholine molecules that are linked by their acetyl groups. It can also be viewed as a central moiety of succinic acid with two choline moieties, one on each end.

Synthesis

Nova Laboratories Synthesis Patent

Published in February of 2014, Neon Laboratories applied for a patent for a new method of synthesizing the succinylcholine chloride. In their method of synthesis they claim their method to be novel primarily because it avoids dealing with gaseous reactants or products both of which can be difficult to deal with in a large scale production setting. The new method involves the reaction of the molecule diakyl succinate with an excess of dimethlaminoethanol in the presence of an alkali metal. Several previous methods were discussed in the patent all of which had some downfalls that this new method remedies. The new method ideally takes between 1-3 hours for the full reaction to occur at a temperature of 70-80 degrees Celsius, with the purity of the compound reaching 99% after recrystallization.

Although the patent covers a variety of functional groups in order to protect their invention adequately, Neon Laboratories states that the preferred method of synthesis involves R₁ as an electron withdrawing group either N0₂ or CN, R₂ is hydrogen or electron withdrawing group selected from N0₂ or CN, while R₃ is a hydrogen. The patent listed five previous methods of synthesis which have been summarized below.

Synthesis of SUX Method I

Method I: Succinic acid reacts with dimethylaminoethanol and produces bis(2- dimethylaminoethyl)succinate. This product is then further reacted with methyl chloride to produce succinylcholine chloride. This synthesis is outlined in the pictures on the right.

Method II: bis(2-chloroethyl)succinate is reacted with dimethylamine to obtain bis(2-dimethylaminoethyl) succinate, which is then reacted with methyl chloride to give succinylcholine chloride.

Both Methods 1 & 2 requires methyl chloride which is difficult to handle.

Method III: Succinic acid is reacted with ethylene chlorohydrin to give bis(2-chloroethyl) succinate, followed by alkylation with trimethylamine to provide succinylcholine chloride.

The percent yield is relatively low in methods I through III.

Method IV: Succinyl dichloride is reacted with choline chloride.

This main disadvantage of method IV is that succinyl dichloride is hygroscopic and hence difficult to handle. Additionally Thionyl chloride, which is required for preparing succinyl dichloride, is a toxic reagent.

Method V: Succinic anhydride is reacted with choline chloride in presence of dry HC1 as a catalyst. The reaction occurs in benzene which is classified as human carcinogen.

History

Suxamethonium was first discovered in 1906 by Reid Hunt and René de M. Taveau. When studying the drug, animals were given curare and thus they missed the neuromuscular blocking properties of suxamethonium. Instead in 1949 an Italian group led by Daniel Bovet was first to describe succinylcholine induced paralysis. The clinical introduction of suxamethonium was described in 1951 by several groups. Papers published by Stephen Thesleff and Otto von Dardel in Sweden are important but also to be mentioned is work by Bruck, Mayrhofer and Hassfurther in Austria, Scurr and Bourne in UK, and Foldes in America.

Dr. Carl Coppolino

Coppolino was a poisoner who utilized succinyl choline in high doses to paralyze all muscles in the body, preventing victims from properly breathing leading to Asphyxia which was easily passed as a fatal heart attack. Since succinylcholine is broken down in the body to succinic acid and choline, both endogenously produced it was difficult to prove that there had been been foul play.

In his first trial he was accused of the murder of William Farber in the state of New Jersey, Army Col. William Farber husband of Marjorie Farber, a woman with whom he had a long-term affair with. However since the man had suffered from chronic coronary disease backed by several expert witnesses, the jury was not convinced of Coppolino’s guilt beyond a reasonable doubt, and he therefore walked free.

Yet he faced yet another trial for the murder of his wife in Florida, Dr. Carmela Musetto was found dead from a supposed heart attack at the young age of 30 years old. This time a toxicology expert was able to show definitively that the byproducts of succinyl choline, succinic acid and choline were found in abnormally high concentrations in the organs of the victim. This damning evidence led to a guilty verdict for Dr. Coppolino who was sentenced to life in prison, but was released 12.5 years later on parole.

Society and culture

Suxamethonium has been described as a "perfect poison" for murder, and has been used by criminals in murders. Suxamethonium chloride is the INN.

Other animals

It is sometimes used in combination with pain medications and sedatives for euthanasia and immobilization of horses.

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