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Rauwolscine hydrochloride

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Rauwolscine hydrochloride Basic information

Product Name:
Rauwolscine hydrochloride
Synonyms:
  • RAUWOLSCINE HYDROCHLORIDE (A-YOHIMBINE) A2 AD
  • α-Yohimbine hydrochloride, 17α-Hydroxy-20α-yohimban-16 β-carboxylic acid methyl ester hydrochloride
  • Corynanthidine hydrochloride
  • Isoyohimbine hydrochloride
  • Rauwolscine dot hydrochloride
  • ALPHA YOHIMBINE HCL 90% (Rauwolscine HCL 90%)
  • YohiMban-16-carboxylicacid, 17-hydroxy-, Methyl ester, hydrochloride (1:1), (16b,17a,20a)-
  • YOHIMBINE HCL, ALPHA-
CAS:
6211-32-1
MF:
C21H27ClN2O3
MW:
390.9
EINECS:
228-279-6
Product Categories:
  • Adrenoceptor
Mol File:
6211-32-1.mol
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Rauwolscine hydrochloride Chemical Properties

Melting point:
270-280°C
storage temp. 
Store at RT
solubility 
H2O: soluble
form 
solid
color 
white
Sensitive 
Light Sensitive
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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
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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]30D - 40° (EtOH). The alkaloid forms crystalline salts: the hydrochloride, m.p. 27S-2S00C (dec.); [α]30D + 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]23D + 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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