Rauwolfia root

Alseroxylon (Rauwiloid), an alkaloidal fraction from Rauwolfia root, is a reddish-brown amorphous powder with a characteristic odor. 

Deserpidine (Harmonyl) is an alkaloid from Rauwolfia root. 

Rescinnamine (Moderil) is an alkaloid of the alseroxylon fraction of Rauwolfia root. Syrosingopine (Singoserp) is a preparation made from reserpine by hydrolysis and... 

For laboratory purposes, methanol is the usual solvent, and procedures based on its use have been described in detail (21, 39, 81). Of great practical usefulness for the separation of the weakly basic fraction is the solubility of certain alkaloidal acetates in chloroform, e.g., reserpine, ajmalicine, and aricine, whereas other acetates are insoluble in this solvent, e.g., ajmaline, yohimbine, and a-yohimbine. Since the anhyd-ronium alkaloids are extremely strong bases, they can only be extracted into an organic solvent in their tertiary base form at pH 11. For industrial purposes, the best process extracts water-moistened Rauwolfia root with hydrocarbons such as benzene, toluene, or xylene. In this procedure, only the weak bases are extracted. No complicated separation processes are involved, and reserpine is obtained in high yields (122). 

Yohimbine (yocon), a competitive a2 antagonist, is an indolealkylamine alkaloid found in the bark of the tree Pausinystalia yohimbe and in Rauwolfia root structurally, yohimbine resembles reserpine. 

Yohimbine, an indole alkaloid isolated from PausinystUa yohimbe bark and Rauwolfia roots is an a2-antagonist with greater selectivity for q2- than for... 

Many alkaloids have pronounced biological properties, and a substantial number of the pharmaceutical agents used today are derived from naturally occurring amines. As a few examples, morphine, an analgesic agent, is obtained from the opium poppy Papaver somnifemm. Cocaine, both an anesthetic and a central nervous system stimulant, is obtained front the coca bush Erythroxylon coca, endemic to upland rain forest areas of Colombia, Ecuador, Peru, Bolivia, and western Brazil. Reserpine, a tranquilizer and antihypertensive, comes from powdered roots of the semitropical plant Rauwolfia serpentina. Ephedrine, a bronchodilator and decongestant, is obtained front the Chinese plant Ephedra sinica. 

By extraction from the pulverized roots of Rauwolfia serpentina (L.) Beuth. 

Other plants known to contain psychoactive compounds include hellebore, which was used for centuries in Europe to treat mania, violent temper, mental retardation and epilepsy. However, a drug of major importance in modern psychopharmacology arose from the discovery by medicinal chemists of the alkaloids of Rauwolfia serpentina, a root which had been used in the Indian subcontinent for centuries, not only for the treatment of snake bite but also for alleviating "insanity". Understandably, the mechanism of action of reserpine, the alkaloid purified from Rauwolfia serpentina, helped to lay the basis to psychopharmacology by demonstrating how the depletion of central and peripheral stores of biogenic amines was correlated with a reduction in blood pressure and tranquillization. 

Following the passage of the FD C Act, FDA was authorized to permit NDAs for new drugs, but the agency could not approve them affirmatively (see Section 505 of the FD C Act). One such NDA was for the botanical rauwolfia Rauwolfia serpentina), first marketed in the United States in 1953. Used in India for centuries, root of rauwolfia was sold in the United States as a treatment for hypertension. More than a dozen NDAs were subsequently recorded for the drug, all of which were discontinued by 1982, as better antihypertensives came to market (Table 1). 

Reserpine, an alkaloid extracted from the roots of an Indian plant, Rauwolfia serpentina, was one of the first effective drugs used on a large scale in the treatment of hypertension. At present, it is rarely used owing to its adverse effects. 

Reserpine is a raulwolfia alkaloid isolated from the roots of the plant Rauwolfia Serpentina. It is used for the treatment of mild essential hypertension or psychosis. 

Rauwolfia is the dried rhizome and roots of Rauwolfia (sometimes Rauvolfia) serpentina (Apocynaceae) or snakeroot, a small shrub from India, Pakistan, Burma, and Thailand. Other species used in commerce include R. vomitoria from tropical Africa, a small tree whose leaves after ingestion cause violent vomiting, and R. canescens = R. tetraphylla) from India and the... 

Ajmalicine (see rauwolfia, page 353) is present in the roots of Catharanthus roseus at a level of about 0.4%, and this plant is used as a commercial source in addition to Rauwolfia serpentina. 

Rauwolfia (Raudixin, Rauserpa, etc.), the powdered whole root of the Rauwolfia plant, is a tan, bitter, fine amorphous powder with a slight odor, sparingly soluble in alcohol and only very slightly soluble in water. 

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). 

FIGURE 56.1 A flowering Rauwolfia serpentina plant. Note the serpentine root from which the plant obtains... 

The known alkaloid heptaphylline has been isolated from the roots of Clausena harmandiana Pierre (Rutaceae) along with two new carbazole alkaloids identified as 2-hydroxy-3-formyl-7-methoxycarbazole (58) and 7-methoxyheptaphylline (59). The H- and l3C-NMR spectra have been analyzed and used to position the various functional groups (54,55). Other carbazole alkaloids isolated from the roots of Murraya siamensis Craib are identified as murrayanine, girinimbine, and mukonal, which occur together with heptaphylline and compounds 58 and 59 (56-55). Three new alkaloids have also been isolated from M. siamensis and named 3-formyl-2,7-dimethoxycarbazole (60), 3-formyl-2-methoxylcarbazole (O-methylmukonal) (61), and 7-methoxymurrayacine (62) (59). From the roots of Rauwolfia serpentina, the new alkaloid indobine (63) (60), the benzyl ester, and indobinine (64) (61), the cyclohexyl ester of indolepropionic acid, have been isolated and identified. 

From the roots of Rauwolfia cambodiana, the alkaloids pelirine and ajmaline have been isolated (73). The alkaloids akuammicine, akuammi-cine Nb-oxide, akuammicine Nb-methiodide, pseudoakuammigine, and tubotaiwine have been newly recorded from the root bark of Alstonia scholaris R.Br. (Apocynaceae) echitamine is isolated as the major alkaloid, along with Nb-demethylechitamine, as well as three unidentified echitamidine isomers, and other known alkaloids. The stems of the same plant yielded echitamine, Nb-demethylechitamine, tubotaiwine, pricri-nine, and other unidentified echitamidine isomers (81,82). Apart from the alkaloids in the heteroyohimbine group from roots of Rauwolfia serpentina, a new base, named ajmalimine (73) (53), and ajmalinimine (74)... 

---