Archive for November 9th, 2019

The Structure of Tetrodotoxin as a free base.

Saturday, November 9th, 2019

The notorious neurotoxin Tetrodotoxin is often chemically represented as a zwitterion, shown below as 1. This idea seems to originate from a famous article written in 1964 by the legendary organic chemist, Robert Burns Woodward.[1] This structure has propagated on to Wikipedia and is found in many other sources.
With the elegance and the unique style that is typical Woodward, his article is a tour de force because of the way in which he deploys a large armoury of spectroscopic (X-ray crystal, NMR, IR) as well as physicochemical (pKa) tools to infer this structure; an approach that has been subsequently widely emulated. The article a well worth a read for the elegant logic that slowly builds to a climax on page 73 (sic!) of the article, when he unveils his final structure (XXXVIII, or 38). The lecture(s) from which the article is apparently derived must have been one hell of an occasion.



  1. R.B. Woodward, "The structure of tetrodotoxin", Pure and Applied Chemistry, vol. 9, pp. 49-74, 1964.