Pseudotropine

Pseudotropine

Pseudotropine is an alkaloid that is a structural isomer of tropine. It is a secondary metabolite found in a variety of plants, including those in the Solanaceae family. Pseudotropine is also known as isotropine and has been used in the synthesis of various pharmaceuticals.

Chemistry

Pseudotropine is a tropane alkaloid, a class of alkaloids that also includes atropine and cocaine. It is a bicyclic compound, consisting of a six-membered piperidine ring fused to a five-membered pyrrolidine ring. The compound is chiral, with the natural form being the (R)-enantiomer.

Biosynthesis

The biosynthesis of pseudotropine begins with the amino acids ornithine and arginine, which are converted into putrescine by the enzyme ornithine decarboxylase. Putrescine is then converted into N-methylputrescine by the enzyme putrescine N-methyltransferase. N-methylputrescine is then oxidized to form N-methyl-Δ1-pyrroline, which is then reduced to form tropinone. Tropinone is then rearranged to form pseudotropine by the enzyme tropinone reductase.

Pharmacology

Pseudotropine has been used as a starting material in the synthesis of various pharmaceuticals, including atropine, scopolamine, and hyoscyamine. These drugs are used to treat a variety of conditions, including gastrointestinal disorders, motion sickness, and certain eye diseases.

Toxicology

Like other tropane alkaloids, pseudotropine can be toxic if ingested in large amounts. Symptoms of overdose can include dry mouth, blurred vision, tachycardia, and hallucinations. In severe cases, overdose can lead to coma or death.

See also

• Tropane
• Tropine
• Atropine
• Scopolamine
• Hyoscyamine