Rauwolscine hydrochloride Chemical Properties

Melting point:

270-280°C

storage temp. 

Store at RT

solubility 

H₂O: soluble

form 

solid

color 

white

Sensitive 

Light Sensitive

Safety Information

Hazard Codes 

T

Risk Statements 

23/24/25

Safety Statements 

22-36/37/39-45

RIDADR 

UN 1544 6.1/PG 2

WGK Germany 

3

RTECS 

ZG1035000

HazardClass 

6.1

HS Code 

29339900

Rauwolscine hydrochloride Usage And Synthesis

Description

This alkaloid is isolated as the oxalate from the leaf extract of Rauwolfia canescens L. from which the free base may be obtained as colourless needles which are laevorotatory with [α]³⁰_D - 40° (EtOH). The alkaloid forms crystalline salts: the hydrochloride, m.p. 27S-2S00C (dec.); [α]³⁰_D + 74° (H20); nitrate, m.p. 257-SoC (dec.); oxalate, m.p. 245-6°C and the picrate, m.p. 20SoC. Two active hydrogens are present and the alkaloid furnishes a monoacetyl derivative, m.p. 2l6-SoC (dec.). Treatment with concentrated ammonia solution at room temperature converts the base into rauwolscinic acid, C2oH2403N2.H20, m.p. 262-4°C (dec.); [α]²³_D + l36.So (H20) which yields a crystalline hydrochloride, m.p. 255.5-257.5°C (dec.) and on esterification with MeOH reverts to the original alkaloid. On distillation with Zn dust, rauwolscine yields harman, 2-methylindole (skatole) and isoquinoline.
Chakravarti has shown that the alkaloid is a cardiovascular depressant, shows hypotensive activity and is relatively highly toxic.

Uses

Rauwolscine is a natural alkaloid that acts as a selective and reversible α2-adrenergic receptor antagonist (Ki = 12 nM). It is a stereoisomer of yohimbine, which potently antagonizes both α1- and α2-adrenergic receptors. Rauwolscine also acts as a receptor antagonist at the serotonin 5-HT2B receptor (Ki = 14.3 nM) and as a weak partial agonist at 5-HT1A (IC50 = 1.3 μM).The α2-adrenergic receptor has diverse physiological functions and antagonists like rauwolscine have numerous applications, including the modulation of mood and behavior.

Uses

Standard alpha-2 adrenergic antagonist

Biological Activity

Rauwolscine hydrochloride is a standard α2-adrenergic antagonist (Ki values are 3.5, 4.6, and 0.6 nM at cloned human α2A, α2B, and α2C-adrenoceptors respectively). Partial agonist at 5-HT1A receptors. Also available as part of the α2-Adrenoceptor Tocriset? .

References

Mukherjee., J. Ind. Chern. Soc., 18, 33, 485 (1941)
Mukherjee., ibid, 20, 11 (1943)
Mukherjee., ibid, 23, 6 (1946)
Pharmacology:
Chakravarti., Sci. Cult., (Calcutta), 7, 45S (1942)

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