Deserpidine Chemical Properties

Melting point:

228-232°; mp 230-232°; mp 138° and 226-232° with resolidification at 175°

alpha 

D20 -163° (c = 0.5 in pyridine)

Boiling point:

638.28°C (rough estimate)

Density 

1.2277 (rough estimate)

refractive index 

1.6260 (estimate)

storage temp. 

-20°C Freezer

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

6.68 in 40% methanol

form 

Solid

color 

White to Off-White

CAS DataBase Reference

131-01-1(CAS DataBase Reference)

NIST Chemistry Reference

Deserpidine(131-01-1)

Deserpidine Usage And Synthesis

Chemical Properties

Crystalline solid; exists in three crystallineforms; mp 228–232°C (442.4–449.6°F); soluble in chloroform and methanol, insolublein water; pK 6.68 in saturated solution of40% methanol in water.

Originator

Harmonyl,Abbott,US,1957

Uses

Deserpidine, is an antihypertensive drug related to Reserpine (R144600). It is naturally found in Rauvolfia spp.

Uses

Deserpidine is found and extracted fromthe roots of Rauwolfia canescens L., andApocyanaceae. Therapeutically, it is used asan antihypertensive agent.

Definition

ChEBI: Deserpidine is an alkaloid ester, a methyl ester, a benzoate ester, an organic heteropentacyclic compound and a yohimban alkaloid. It derives from a hydride of a yohimban.

Manufacturing Process

500 parts by weight of dried, finely ground roots of Rauwolfia canescens are extracted batchwise with methanol at its boiling point, using the following volumes and times, and filtering each extract while hot: 2,000 parts by volume, 1 hour; 1,000 parts by volume, 45 minutes; 1,000 parts by volume, 30 minutes; 1,000 parts by volume, 30 minutes. The extracts are combined and evaporated in vacuo to 75 parts by volume of a thick syrupy solution.
After the addition of 75 parts by volume of methanol and 150 parts by volume of acetic acid of 15% strength with adequate mixing, the solution is extracted with 2 portions each of 100 parts by volume of hexane. The combined hexane extracts are extracted with 15 parts by volume of acetic acid of 15% strength. The latter extract is added to the above acetic acid phase which is then extracted with 3 portions each of 75 parts by volume and 1 portion of 50 parts by volume of ethylene chloride.
The first three extracts are combined and washed with 60 parts by volume of 2 N sodium carbonate solution and then with 60 parts by volume of distilled water. These washing solutions are saved and used for the washing of the 4th and final ethylene chloride extract. The combined ethylene chloride extracts are dried over sodium sulfate, filtered and evaporated in vacuo to a constant weight of a tan, frothy solid. One part by weight of this residue is dissolved in 1.5 parts by volume of warm methanol and the solution cooled to 5°C for 18 hours, whereby crystallization of a mixture containing principally reserpine sets in. After filtering this mixture and washing it with cool methanol, the filtrate is freed of solvent in vacuo.
Two parts by weight of the resulting red-brown solid froth are triturated with 2 portions each of 25 parts by volume of benzene and filtered each time. The benzene insoluble material is saved for further treatment. The benzene soluble fraction is poured on to a column of 40 parts by weight of activated alumina (Woelm, Activity Grade I) which is then eluted first with 3 portions each of 50 parts by volume of benzene and then with 6 portions each of 50 parts by volume of benzene-acetone (9:1), the first of which benzene-acetone portions had been used for extraction of the abovementioned benzene insoluble material. The second of the 6 benzene-acetone elution fractions on removal of the solvents gives a light tan solid froth which on crystallization from methanol gives colorless prismatic needles of slightly impure deserpidine. Rechromatographing of 1 part by weight of this substance on 20 parts by weight of activated alumina (Woelm, Activity Grade I) using benzene and benzene containing 0.1% methanol as eluting agents followed by crystallization from methanol gives colorless prismatic needles of pure deserpidine, melting at 228-232°C. Deserpidine obtained according to this example can be made up into pharmaceutical preparations.

brand name

Harmonyl(Abbott).

Therapeutic Function

Antihypertensive

Health Hazard

The pharmacological properties of deserpi dine are similar to those of reserpine, causingsedation and tranquilization. Toxic effectsfrom high doses include drowsiness, depres sion, nausea, diarrhea, abdominal cramps,and hypotension. It is less toxic than reserpine. However, the poisoning effects may begreater than those of other Rauwolfia alka loids, such as rescinnamine. An oral LD50value in mice is 500 mg/kg.There is some evidence of its carcinogenic actions in animals and humans. Ratsgiven oral doses of 54 mg/kg over 77 weeksdeveloped blood tumor. In humans, it mayproduce tumors in skin and appendages.Cancer-causing properties of deserpidine,however, are not yet fully established.

Deserpidine(131-01-1)Related Product Information

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