Rauwolscine hydrochloride
- CAS NO.:6211-32-1
- Empirical Formula: C21H27ClN2O3
- Molecular Weight: 390.9
- MDL number: MFCD00069342
- EINECS: 228-279-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 20:33:22
What is Rauwolscine hydrochloride?
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.
The Uses of Rauwolscine hydrochloride
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.
The Uses of Rauwolscine hydrochloride
Standard alpha-2 adrenergic antagonist
What are the applications of Application
Rauwolscine ? HCl is a standard α-2-adrenergic (AR) 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)
Properties of Rauwolscine hydrochloride
Melting point: | 270-280°C |
storage temp. | Store at RT |
solubility | H2O: soluble |
form | solid |
color | white |
Sensitive | Light Sensitive |
Safety information for Rauwolscine hydrochloride
Signal word | Warning |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
GHS Hazard Statements |
H300:Acute toxicity,oral H310:Acute toxicity,dermal H330:Acute toxicity,inhalation |
Precautionary Statement Codes |
P320:Specific treatment is urgent (see … on this label). P330:Rinse mouth. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P405:Store locked up. |
Computed Descriptors for Rauwolscine hydrochloride
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