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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;YohiMban-16-carboxylicacid, 17-hydroxy-, Methyl ester, hydrochloride (1:1), (16b,17a,20a)-;YOHIMBINE HCL, ALPHA-;20-alpha-yohimban-16-beta-carboxylicacid,17-alpha-hydroxy-,methylester,hyd;alpha-yohimbinhydrochloride;RAUWOLFSCINE HYDROCHLORIDE;RAUWOLSCINE HYDROCHLORIDE | | CAS: | 6211-32-1 | | MF: | C21H27ClN2O3 | | MW: | 390.9 | | EINECS: | 228-279-6 | | Product Categories: | Adrenoceptor | | Mol File: | 6211-32-1.mol |  |
| | Rauwolscine hydrochloride Chemical Properties |
| Melting point | 270-280°C | | storage temp. | Store at RT | | solubility | H2O: soluble | | form | solid | | color | white | | Sensitive | Light Sensitive |
| 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]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 | Standard alpha-2 adrenergic antagonist | | 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. | | 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) |
| | Rauwolscine hydrochloride Preparation Products And Raw materials |
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