| Identification | Back 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 Properties | Back 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 activity]
[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 Information | Back 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) |
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