Ascaridole

Ascaridole is a natural organic compound classified as a bicyclic monoterpenoid that has an unusual bridging peroxide functional group.

Ascaridole determines the specific flavor of the Chilean tree boldo and is a major constituent of the oil of Mexican tea (wormseed).

As part of the oil, ascaridole is used as an anthelmintic drug that expels parasitic worms from plants, domestic animals, and the human body.

He found that when heated to between 130° and 150 °C "there occurs, with sudden boiling in which the temperature momentarily rises to about 250°, a decomposition of an explosive character, occasionally accompanied by ignition.

Nelson also predicted the chemical structure of ascaridole which was almost correct, but had the peroxide bridge not along the molecular axis, but between the other, off-axis carbon atoms.

[1][6][12] Ascaridole (organic peroxide) is forbidden to be shipped as listed in the US Department of Transportation Hazardous Materials Table 49 CFR 172.101.

In the early 1900s, it was a major remedy against intestinal parasites in humans, cats, dogs, goats, sheep, chickens, horses, and pigs, and it is still used in livestock, particularly in the Central American countries.

[17] It is also part of tonic drinks and infusions to expel intestinal parasites and treat asthma, arthritis, dysentery, stomach ache, malaria, and nervous diseases in folk medicine practiced in North and South America, China, and Turkey.

In high doses, wormseed oil causes irritation of skin and mucous membranes, nausea, vomiting, constipation, headache, vertigo, tinnitus, temporary deafness and blindness.

Long-term effects include pulmonary edema (fluid accumulation in the lungs), hematuria, and albuminuria (presence of red blood cells and proteins in the urine, respectively) and jaundice (yellowish pigmentation of the skin).

Skeletal formula
Ball-and-stick model
Mexican Tea plant