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Ajmalicine (Standard)

CAT: 0804-HY-N1919RSize: 1 EachDry Ice: NoHazardous: No
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Description
Ajmalicine (Standard) is the analytical standard of Ajmalicine. This product is intended for research and analytical applications. Ajmalicine (Raubasine) is a potent adrenolytic agent which preferentially blocks α1-adrenoceptor. Ajmalicine is an reversible but non-competitive nicotine receptor full inhibitor, with an IC50 of 72.3 μM. Ajmalicine also can be used as anti-hypertensive, and serpentine, with sedative activity[1][2].
CAS Number
483-04-5
Product Name Alternative
Raubasine (Standard)
UNSPSC
12352005
Target
Adrenergic Receptor; Cholinesterase (ChE) ; Reference Standards
Type
Reference Standards
Related Pathways
GPCR/G Protein; Neuronal Signaling; Others
Field of Research
Endocrinology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/ajmalicine-standard.html
Smiles
O=C(C1=CO[C@@H](C)[C@](CN2CC3)([H])[C@]1([H])C[C@@]2([H])C4=C3C5=CC=CC=C5N4)OC
Molecular Formula
C21H24N2O3
Molecular Weight
352.43
References & Citations
[1]Roquebert J, et al. Inhibition of the alpha 1 and alpha 2-adrenoceptor-mediated pressor response in pithed rats by raubasine, tetrahydroalstonine and akuammigine. Eur J Pharmacol. 1984 Oct 30;106 (1) :203-5.|[2]Pereira DM, et al. Pharmacological effects of Catharanthus roseus root alkaloids in acetylcholinesterase inhibition and cholinergic neurotransmission. Phytomedicine. 2010 Jul;17 (8-9) :646-52.|[3]Demichel P, et al. Effects of raubasine stereoisomers on pre- and postsynaptic alpha-adrenoceptors in the rat vas deferens. Br J Pharmacol. 1984 Oct;83 (2) :505-10
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Ajmalicine

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 a vasodilator agent, an antihypertensive agent and an alpha-adrenergic antagonist. It is a methyl ester, an organic heteropentacyclic compound and a monoterpenoid indole alkaloid. It is a conjugate base of an ajmalicine(1+).

CAS Number483-04-5
PubChem CID441975
IUPAC Namemethyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate
Molecular FormulaC21H24N2O3
Molecular Weight352.4
XLogP2.7
Topological Polar Surface Area54.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Heavy Atom Count26
Formal Charge0
Complexity606
SMILES
C[C@H]1[C@H]2CN3CCC4=C([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC=CC=C45
InChI
InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1
InChIKey
GRTOGORTSDXSFK-XJTZBENFSA-N
Chemical Structure
2D Structure
2D structure of Ajmalicine
CAS: 483-04-5
CID: 441975
Formula: C21H24N2O3
MW: 352.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight352.4
XLogP32.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass352.17869263
Monoisotopic Mass352.17869263
Topological Polar Surface Area54.6 Ų
Heavy Atom Count26
Formal Charge0
Complexity606
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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GP5210-250mgAjmalicine
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