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What is an Alkyne

An alkyne is an unsaturated hydrocarbon, that contains at least one triple bond between carbon atoms.

They are commonly referred to as acetylenes.

Cicutoxin

C17H22O2

Many of the alkynes that are found in nature are helpful. We have figured out how to use several in the medical field presently.

Another of the killer alkynes that are found in nature is cicutoxin. This chemical is especially dangerous to humans and grazing animals. Cicuta, also known as water hemlock, is in the apiaceae family of plants. This plant grows in the northern hemisphere, typically found in North America and Europe. The plant grows in moist habitats, such as in ditches or near swamps or marshes. Water hemlock has small white or green flowers, a compound leaf structure, and large hollow roots. The plant can grow to 2.5m in height. Water hemlock is considered the most poisonous plant in North America.

Chemical Formula for

an Alkyne

CnH2n-2

Capillin

Here are some examples

Parsalmide is used as a pain reliever

Pargyline is used as an antihypertensive

17-ethynylestradiol is used as an oral contraceptive

C12H8O

The toxin is most concentrated in the roots, and a section as small as two square centimeters can kill an adult. Children just using the roots as a whistle have died as a result. The toxin effects the central nervous system, causing convulsions and seizures followed by death.

Treatment if ingested involves the use of activated charcoal, barbiturates, tranquilizers, and respiration support.

Livestock, and grazing animals are at the highest risk for contact with cicutoxin. They can pull up a root ball and die within fifteen minutes.

There are very few reports of human contact with the toxin these days. However the plant can be confused with wild carrots, pignut, sweet flag, watercress, wild parsnips, wild celery, wild ginseng, and kvane.

The water hemlock plant does have some positive aspects as well. Today the plant is used in the medical field to help treat migraines, painful menstruation, and intestinal worms.

Unfortunately not all of the alkynes that are found in nature are helpful or even benign. Many of the alkynes are just the opposite, harmful and in some cases deadly. Plants produce these alkynes as a defense mechanism against predators. Because of this some of the compounds effect plants and animals in different ways.

The natives and tribes people use the chemical just as anyone would expect, to catch fish. Some tribes use the extract by coating their arrow heads and darts with it, then hunting the fish with these deadly weapons. Others use it in baits made with locusts or manioc flour that are thrown into the water for the fish to ingest. Either way it is used, the fish die almost immediately from the toxin, while the people who eat the fish suffer no consequences. When tested on dogs the effects were typically convulsive.

The oriental wormwood plant produces the alkyne capillin. It is thought to inhibit the growth of certain fungi. In the future it may be useful for fighting fungus infections in humans. Right now the the oriental wormwood plant is already being used in holistic and Chinese medicines to treat liver and gallbladder imbalances.

Icthyothereol

Falcarinol

C17H24O

Icthyothereol is one of the killer alkynes found in nature. It is produced from the leaves of the Icthyothere, a flowering plant found in Central and South America. The name icthyothere literally translates to fish poison. Natives of Brazil and Guyana who often use the alkyne, commonly refer to the plant as "cunabi, cunami, or cunambi."

Falcarinol is another of the killer alkynes found in nature, and it is structurally related to cicutoxin. Falcarinol can be found in Ivy, red ginseng, and carrots. It has been found to have antibacterial, analgesic and sedative effects, as well as an anti-tumor effect being researched for cancer treatment.

Chemical Formula

C14H14O2

The anti-tumor possibilities were being studied using lab rats. Three groups of rats were given either an extract of falcarinol found in carrots, raw carrots, or their regular diet. The rats that were given the falcarinol as well as the rats that were given raw carrots both showed a 1/3 less chance for developing large lesions in the colon.

Bibliography

  • Ichthyothereol and Its Acetate, the Active Polyacetylene Constituents of Ichthyothere terminalis (Spreng.) Malme, a Fish Poison from the Lower Amazon1,2. Journal of the American Chemical Society.
  • United States Department of Agriculture, Agricultural Research Servic. Water Hemlock
  • General organic and biochemistry, Dennison 8th edition

Killer Alkynes in Nature

by Benjamin Jones

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