Indian snakeroot

But that was only one half of the logic behind the chemical-imbalance theory. The other half came from studies of reserpine, a drug that was extracted from Rauvolfia serpentina or the Indian snakeroot plant, which had historically been used to treat snakebite, hypertension, insomnia and insanity. In studies of animals, reserpine was reported to induce sedation and to decrease brain levels of norepinephrine, serotonin and dopamine. Clinical reports indicated that some people became severely depressed when taking reserpine.14 Putting these two findings together, it seemed likely that reserpine made people depressed because it decreased neurotransmitter levels. 

Reserpine Alkaloid Antihypertensive (reduces blood pressure) Rauvolfia serpentina (Indian snakeroot)... 

Rauwolfia serpentina Benth, which derives its name from Leonhart Rauwolf, a 16th century botanist, and its serpentine root (Figure 56.1), has long been used in India for a variety of ailments. The discovery of its tranquilizing action, particularly in lowering the blood pressure, led to its introduction into Western medicine. The Rauwolfia alkaloids are derived from a family of tropical and semitropical plants related to oleander and periwinkle. They vary from small shrubs to tall trees. The important species from which the alkaloids are derived include Rauwolfia serpentina (Ophioxylon serpentinum or Indian snakeroot), R. micrantha, R. vomitoria, and R. hirsuta (Canescens heterophylla). 

Reserpine, an alkaloid, and the active ingredient of Rauwolfia serpentina, the Indian snakeroot, was the basis of the first major tranquilizer. Reserpine was used in the treatment of snake bites, high blood pressure, and... 

INDIAN SNAKEROOT -- Rauwolfia serpentina. Family Aponcynaceae (Dogbane family). 

Catharanthus roseus (Madagascar periwinkle), Rauwolfia serpentina (Indian snakeroot), R. tetraphyllo (pinque-pinque, four-leaf devil pepper), R. vomitoria (African snakeroot), Vinca minor (periwinkle) (Apocynaceae)... 

Indian snakeroot was found to contain a reserpine -like constituent... 

Draw a stepwise mechanism for the following reactions, two steps in R. B. Woodward s classic synthesis of reserpine in 1958. Reserpine, which is isolated from the extracts of the Indian snakeroot Rauwolfia serpentina Benth, has been used to manage mild hypertension associated with anxiety. 

Among its first applications was the study of reserpine. Reserpine was isolated in 1952 from Rauwolfia serpentina (Indian snakeroot), which was used for centuries to treat insanity. Reserpine acts by blocking the reuptake NE back into presynaptic vesicles. The same year, Henri Laborit, a surgeon in Paris, administered reserpine to prepare his patients for surgery, because it maden them less anxious. Subsequently, it was widely used to treat patients with severe psychiatry diseases with impressive results. 

In 955yBernard Brodie and colleagues at the NIH discovered that the drug, reserpine, results in a decrease in serotonin in the brain. Reserpine was isolated in 1952 from the dried root of Rauwolfia Serpentina (Indian snakeroot), and introduced into clinical medicine inl954. Reserpine blocks the uptake and storage of NE and DA into synaptic vesicles by inhibiting the vesicular monoamine transporters. 

The goal of a retrosynthesis is to synthesize one and only one of those stereoisomers. This is not an easy task. If you wish to give it a try, please discuss your retrosynthesis with your instructor or it will be a very frustrating exercise. A total synthesis by R. B. Woodward (United States 1917-1979) can be found in the journal Tetrahedron. Reserpine is an indole alkaloid isolated from the roots of Rauwolfia serpentina (also known as Indian snakeroot). This plant has been used in India for the treatment of insanity as well as for the treatment of fevers or snakebite. In pure form, it has been used in the treatment of high blood pressure and it has antipsychotic properties. 

Reserpine is a natural product belonging to the family of alkaloids (see Special Topic F). Reserpine was isolated from the Indian snakeroot Rauwolfia serpentina. CUnical applications of reserpine include treatment of hypertension and nervous and mental disorders. The synthesis of reserpine, which contains six chirality centers, was a landmark accomplishment reported by R. B. Woodward in 1955. Incorporated in the synthesis are several reactions involving amines and related nitrogen-containing functional groups, as we shall see on the following page. 

Hindus have used the Indian snakeroot Rauwolfia serpentaria) for centuries as a febrifuge, an antidote to poisonous snakebites, and a treatment for dysentery and other intestinal afflictions. The plant is a perennial, evergreen shrub that grows in India, Pakistan, Sri Lanka, Burma and Thailand. Reserpine, the major indole alkaloid present in roots, stems and leaves of R. serpentina at levels of 1.7-3.0% (w/w), is an effective hypotensive. 

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