Rauwolscine HCl

Base Information

• Chemical Name: Rauwolscine HCl
• CAS No.: 6211-32-1
• Molecular Formula: C21H26N2O3^.HCl
• Molecular Weight: 390.90
• Hs Code.: 29339900
• European Community (EC) Number: 228-279-6
• Mol file: 6211-32-1.mol

Synonyms:6211-32-1;Rauwolscine HCl;Rauwolscine (hydrochloride);C21H26N2O3.ClH;Prestwick_660;20.alpha.-Yohimban-16.beta.-carboxylic acid, 17.alpha.-hydroxy-, methyl ester, monohydrochloride;Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, monohydrochloride, (16.beta.,17.alpha.,20.alpha.)-;MFCD00069342;AKOS032949623;C16096;-Yohimbine hydrochloride;Corynanthidine hydrochloride;Isoyohimbine hydrochloride

Chemical Property of Rauwolscine HCl

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 270-280 °C
• Boiling Point: 543 °C at 760 mmHg
• Flash Point: 282.2 °C
• PSA: 65.56000
• Density: 1.31 g/cm3
• LogP: 3.38700
• Storage Temp.: Store at RT
• Sensitive.: Light Sensitive
• Solubility.: H2O: soluble
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 390.1710204
• Heavy Atom Count: 27
• Complexity: 555

Purity/Quality:

99%, ^*data from raw suppliers

Rauwolscine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O.Cl
• Isomeric SMILES: COC(=O)C1[C@H](CC[C@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O.Cl
• 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. Standard alpha-2 adrenergic antagonist