Raubasine

Raubasine Basic information
Product Name:Raubasine
Synonyms:RAUBASIN;RAUBASINE;YOHIMBINE, C-;, 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-;16,17-Didehydro-19alpha-methyloxayohimban-16-carboxylic acid methyl ester;16,17-Didehydro-19-methyloxayohimban-16-carboxylic acid methyl ester;16,17-didehydro-19-methyloxayohimban-16-carboxylicacidmethylester;19-Epiajmalicine
CAS:483-04-5
MF:C21H24N2O3
MW:352.43
EINECS:207-589-5
Product Categories:Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Alkaloids
Mol File:483-04-5.mol
Raubasine Structure
Raubasine Chemical Properties
Melting point 258°C (rough estimate)
Boiling point 486.04°C (rough estimate)
alpha D20 -60° (c = 0.5 in chloroform); D20 -45° (c = 0.5 in pyridine); D20 -39° (c = 0.25 in methanol)
density 1.1823 (rough estimate)
refractive index 1.6500 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly, Heated)
form Solid
pkapK1:10.55(+1) (25°C)
color Pale Yellow
optical activity[α]/D -65±3°, c = 1 in chloroform
Water Solubility insoluble in water
BRN 97268
LogP2.880 (est)
NIST Chemistry ReferenceAjmalicine(483-04-5)
Safety Information
Hazard Codes Xn
Risk Statements 25-22
Safety Statements 22-45
RIDADR 1544
WGK Germany 3
RTECS AX7875000
HazardClass 6.1(b)
PackingGroup III
MSDS Information
Raubasine Usage And Synthesis
DescriptionVinca rosea L. yields this alkaloid which crystallizes as colourless needles from MeOH. The base is laevorotatory having a specific rotation of [α]D_620 (MeOH) and forms a crystalline hydrochloride, m.p. 281-3°e. The structure given above has been elucidated from chemical and spectroscopic data.
UsesAntihypertensive, anti-ischemic.
UsesAntihypertensive, anti-ischemic (cerebral and peripheral)
DefinitionChEBI: Ajmalicine is a monoterpenoid indole alkaloid with formula C21H24N2O3, isolated from several Rauvolfia and Catharanthus species. It is a selective alpha1-adrenoceptor antagonist used for the treatment of high blood pressure. It has a role as an antihypertensive agent, an alpha-adrenergic antagonist and a vasodilator agent. It is a monoterpenoid indole alkaloid, a methyl ester and an organic heteropentacyclic compound. It is a conjugate base of an ajmalicine(1+).
targetP450 (e.g. CYP17)
Purification MethodsIt crystallises from MeOH, EtOH or EtOAc. [Beilstein 27 III/IV 7927.]
ReferencesJanot, Le Men, Cornpt. Rend., 243, 1786 (1956) Shamma, Moss, J. Arner. Chern. Soc., 83, 5038 (1961) Abdurakhsimova, Yuldashev, Yunusov, Khirn. Prir. Soedin., 1,224 (1965)
Raubasine Preparation Products And Raw materials
1,2,3,4,6,7,12,12b-octahydroindolo(2,3-a)quinolizine Methyl 2-[1-(Methylamino)ethyl]indole 1-Methyl-4-piperidineacetic acid CHEMBRDG-BB 4010855 TRANS-2,5-DIMETHYLPIPERIDINE BETA-ISOBUTOXYACROLEIN 5-AMINO CAPROIC ACID 1-METHYL-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE RAUBASINE HYDROCHLORIDE,δ-Yohimbine hydrochloride, Raubasine hydrochloride Vinyl isopropyl ether (1-Methyl-piperidin-4-yl)-acetaldehyde 3-Piperidinemethanol,1-methyl-,(3R)-(9CI) CARBOXYLIC ACID almitrine-raubasine defluina CHEMBRDG-BB 4010735 3-[2-(1-PIPERIDINYL)ETHYL]INDOLE

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