A terpenoid indole alkaloid
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Ajmalicine

Item No. 31213

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(19α)-16,17-didehydro-19-methyl-oxayohimban-16-carboxylic acid, methyl ester
CAS Number
483-04-5
Synonyms
  • (–)-Ajmalicine
  • NSC 72133
  • NSC 95087
  • Raubasine
Molecular Formula
C21H24N2O3
Formula Weight
352.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
Methanol: soluble
λmax
227 nm
SMILES
O=C(OC)C1=CO[C@@H](C)[C@]2([H])[C@]1([H])C[C@]3([H])N(CCC4=C3NC5=CC=CC=C45)C2
InChi Code
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
InChi Key
GRTOGORTSDXSFK-XJTZBENFSA-N
Origin
Natural/Source unknown
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    25 mg

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    Product Description

    Ajmalicine is an terpenoid indole alkaloid that has been found in R. serpentina.1,2 It is an α1-adrenergic receptor antagonist, reducing the phenylephrine-induced pressor response in pithed rats when administered at doses ranging from 1 to 4 mg/kg.3 It also binds to α2A-, α2B-, α2C-, and α2D-adrenergic receptors (Kis = 8.2, 14.5, 5, and 289 nM, respectively).4 Ajmalicine, in combination with almitrine, improves hemodynamic and metabolic parameters following transient cerebral ischemia in dogs.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sharma, V., Chaudhary, S., Srivastava, S., et al. Characterization of variation and quantitative trait loci related to terpenoid indole alkaloid yield in a recombinant inbred line mapping population of Catharanthus roseus. J. Genet. 91(1), 49-69 (2012).

    2. Srivastava, A., Tripathi, A.K., Pandey, R., et al. Quantitative determination of reserpine, ajmaline, and ajmalicine in Rauvolfia serpentina by reversed-phase high-performance liquid chromatography. J. Chromatogr. Sci. 44(9), 557-560 (2006).

    3. Demichel, P., Gomond, P., and Roquebert, J. α-Adrenoceptor blocking properties of raubasine in pithed rats. Br. J. Pharmacol. 77(3), 449-454 (1982).

    4. Ruffolo, R.R., Jr., Bondinell, W., and Hieble, J.P. α- and β-adrenoceptors: From the gene to the clinic. 2. Structure-activity relationships and therapeutic applications. J. Med. Chem. 38(19), 3681-3716 (1995).

    5. Cahn, R., and Cahn, J. Curative effect of an almitrine-raubasine combination in the postischemic syndrome following transient cerebral ischemia in dogs. Pharmacology 36(3), 156-165 (1988).