Why cyanide had no effect on Rasputin in the first murder attempt.
On the occasion of the 100th anniversary of the celebrated murder of the (in)famous Siberian peasant mystic Rasputin, Oxford Today has published several exciting articles lately. The pre-syllable “ras-“ in Russian, by the way, means “dis-“or “un-“ and the word “putnyj” (путный) “orderly”, or sensible. Rasputin thus means “the disordered” or “debauched one”. The murderer was the Oxford University College alumnus Felix Felixovich Yusupov, one of the many Oxford eccentrics through the ages, and his group of fellow conspirators. The story is very well told in Oxford Today and many times elsewhere.
A question that remains from the gloomy 30th December evening in 1916 is, why cyanide sprinkled over cakes and dissolved in Madeira wine had no effect on Rasputin in the first murder attempt, and Yusupov therefore had to resort to more violent means. Rasputin’s physical stamina has been suggested as a reason, but the chemistry of cyanide and carbohydrates may hold another clue.
The so-called Kiliani-Fischer synthesis (1885) is a well-known process in carbohydrate (sugar) chemistry. The process offers routes (highly innovative at the time) to synthesize carbohydrates which are difficult to obtain from natural sources. In this process cyanide, CN- binds to an available carbohydrate to form what is known as a cyanohydrin. This cyanohydrin molecule is brought to further reaction by heat and acid, leading to the desired new carbohydrates, and converting bound cyanide to harmless ammonia, NH3 as in the scheme
Potassium cyanide may not have reacted with the solid cake. Dissolved in the sweet Madeira, it is likely to have been converted from lethal cyanide form into harmless ammonia by the Kiliani-Fischer process before the Madeira was drunk, and left Rasputin unharmed. In other words, had Felix and his conspirators known their organic chemistry better and used instead dry wine and savory snacks, the job might have been much easier, and cleaner, and Rasputin would have passed away peacefully.
Jens Ulstrup is Professor of Inorganic Chemistry at the Technical University of Denmark. David Ackland Tanner is Professor of Organic Chemistry, also at the Technical University of Denmark