ChemicalBook--->CAS DataBase List--->483-04-5

483-04-5

483-04-5 Structure

483-04-5 Structure
IdentificationBack Directory
[Name]

Raubasine
[CAS]

483-04-5
[Synonyms]

Sarpan
Tensyl
Lamuran
Ranitol
Vincain
Vincein
Vinceine
Vincaine
Rauvasan
Raubasil
RAUBASIN
RAUBASINE
Ajmalicin
alkaloidc
alkaloidf
Circolene
Raumalina
Raubaserp
NSC 72133
NSC 95087
Vinceinen
AJMALICINE
Isoarteril
alkaloidii
Alkaloid C
Alkaloid F
Alkaloid II
Hydrosarpan
substanceii
D-YOHIMBINE
Substance II
YOHIMBINE, C-
ALPHA-YOHIMBIN
delta-Yohimbine
gamma-Yohimbine
19-Epiajmalicine
AJMALICINE HCl(RG)
Tetrahydroserpentine
AJMALICINE(-YOHIMBINE)
Py-tetrahydroserpentine
Ajmalicine (base and/or unspecified salts)
, 7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]-
Methyl 19-methyl-16,17-didehydrooxayohimban-16-carboxylate
16,17-didehydro-19-methyloxayohimban-16-carboxylicacidmethylester
16,17-Didehydro-19-methyloxayohimban-16-carboxylic acid methyl ester
oxayohimban-16-carboxylicacid,16,17-didehydro-19-methyl-,methylester,(19
16,17-Didehydro-19alpha-methyloxayohimban-16-carboxylic acid methyl ester
(19α)-16,17-Didehydro-19-Methyl-oxayohiMban-16-carboxylic Acid Methyl Ester
(19alpha)-16,17-Didehydro-19-methyloxayohimban-16-carboxylic acid methyl ester
4H-Indolo[2,3-a]pyrano[3,4-g]quinolizine, oxayohimban-16-carboxylic acid deriv.
Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19alpha)-
[EINECS(EC#)]

207-589-5
[Molecular Formula]

C21H24N2O3
[MDL Number]

MFCD00042748
[MOL File]

483-04-5.mol
[Molecular Weight]

352.43
Chemical PropertiesBack Directory
[Melting point ]

258°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)
[Boiling point ]

486.04°C (rough estimate)
[density ]

1.1823 (rough estimate)
[refractive index ]

1.6500 (estimate)
[storage temp. ]

2-8°C
[solubility ]

Chloroform (Slightly), Methanol (Slightly, Heated)
[form ]

Solid
[pka]

pK1:10.55(+1) (25°C)
[color ]

Pale Yellow
[Optical Rotation]

[α]/D -65±3°, c = 1 in chloroform
[Water Solubility ]

insoluble in water
[BRN ]

97268
[LogP]

2.880 (est)
[NIST Chemistry Reference]

Ajmalicine(483-04-5)
Hazard InformationBack Directory
[Uses]

Antihypertensive, anti-ischemic (cerebral and peripheral)
[Description]

Vinca 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.
[Definition]

ChEBI: 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+).
[target]

P450 (e.g. CYP17)
[Purification Methods]

It crystallises from MeOH, EtOH or EtOAc. [Beilstein 27 III/IV 7927.]
[References]

Janot, 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)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

25-22
[Safety Statements ]

22-45
[RIDADR ]

1544
[WGK Germany ]

3
[RTECS ]

AX7875000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
Spectrum DetailBack Directory
[Spectrum Detail]

Raubasine(483-04-5)MS
Raubasine(483-04-5)1HNMR
Raubasine(483-04-5)13CNMR
Raubasine(483-04-5)IR1
Raubasine(483-04-5)IR2
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