| Identification | Back Directory | [Name]
RAUWOLSCINE HYDROCHLORIDE | [CAS]
6211-32-1 | [Synonyms]
Nsc407307
RAUWOLSCINE
ISOYOHIMBINE
MESOYOHIMBINE
RAUWOLSCINE HCL
ALPHA-YOHIMBINE
ALPHA-YOHIMBINE HCL
YOHIMBINE HCL, ALPHA-
RAUWOLSCINE HYDROCHLORIDE
RAUWOLFSCINE HYDROCHLORIDE
Fauwolscine, hydrochloride
Isoyohimbine hydrochloride
alpha-yohimbinhydrochloride
Corynanthidine hydrochloride
Rauwolscine dot hydrochloride
ALPHA-YOHIMBINE HYDROCHLORIDE
Rauwolscine hydrochloride, 98%, from Yohimbe
ALPHA YOHIMBINE HCL 90% (Rauwolscine HCL 90%)
RAUWOLSCINE HYDROCHLORIDE (A-YOHIMBINE) A2 AD
17α-Hydroxy-20α-yohimban-16β-carboxylicacid,methylesterhydrochloride
17A-HYDROXY-20A-YOHIMBAN-16B-CARBOXYLIC ACID,METHYL ESTER HYDROCHLORIDE
20-alpha-yohimban-16-beta-carboxylicacid,17-alpha-hydroxy-,methylester,hyd
methyl (16beta,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylate hydrochloride
17ALPHA-HYDROXY-20ALPHA-YOHIMBAN-16 BETA-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE
YohiMban-16-carboxylicacid, 17-hydroxy-, Methyl ester, hydrochloride (1:1), (16b,17a,20a)-
20.alpha.-Yohimban-16.beta.-carboxylic acid, 17.alpha.-hydroxy-, methyl ester, monohydrochloride
α-Yohimbine hydrochloride, 17α-Hydroxy-20α-yohimban-16 β-carboxylic acid methyl ester hydrochloride
Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, monohydrochloride, (16.beta.,17.alpha.,20.alpha.)- | [EINECS(EC#)]
228-279-6 | [Molecular Formula]
C21H27ClN2O3 | [MDL Number]
MFCD00069342 | [MOL File]
6211-32-1.mol | [Molecular Weight]
390.9 |
| Chemical Properties | Back Directory | [Melting point ]
270-280°C | [storage temp. ]
Store at RT | [solubility ]
H2O: soluble
| [form ]
solid
| [color ]
white
| [Sensitive ]
Light Sensitive |
| Hazard Information | Back Directory | [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]
Standard α 2 -adrenergic antagonist (K i values are 3.5, 4.6 , and 0.6 nM at cloned human α 2A , α 2B , and α 2C -adrenoceptors respectively). Partial agonist at 5-HT 1A receptors. Also available as part of the α 2 -Adrenoceptor Tocriset™ . | [storage]
Store at RT | [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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