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| Routes of administration | Oral |
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| ECHA InfoCard | 100.006.900 |
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| Formula | C21H24N2O3 |
| Molar mass | 352.434 g·mol−1 |
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| Melting point | 262.5 to 263 °C (504.5 to 505.4 °F) |
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Ajmalicine, also known asδ-yohimbine orraubasine, is anantihypertensivedrug used in the treatment of highblood pressure.[1] It has been marketed under numerous brand names includingCard-Lamuran,Circolene,Cristanyl,Duxil,Duxor,Hydroxysarpon,Iskedyl,Isosarpan,Isquebral,Lamuran,Melanex,Raunatin,Saltucin Co,Salvalion, andSarpan.[1] It is analkaloid foundnaturally in various plants such asRauvolfia spp.,Catharanthus roseus, andMitragyna speciosa.[1][2][3]
Ajmalicine isstructurally related toyohimbine,rauwolscine, and otheryohimbanderivatives.[4] Likecorynanthine, it acts as aα1-adrenergic receptorantagonist with preferential actions overα2-adrenergic receptors, underlying its hypotensive rather than hypertensive effects.[1][5]
Additionally, it is a very strong inhibitor of theCYP2D6 liver enzyme, which is responsible for the breakdown of many drugs. Its binding affinity at this receptor is 3.30 nM.[6]
Two moieties are involved in the biosynthesis of ajmalicine, the terpenoid moiety and the indole moiety.[7] The terpenoid moiety is synthesized by the MEP pathway. The MEP pathway starts with pyruvate and D-glyceraldehyde-3-phosphate, followed by the involvement of DXS, DXR, MCT, MECS, HDS, and HDR genes. This results in isopentenyl diphosphate and dimethylallyl diphosphate which are then synthesized into secologanin. The indole moiety is brought about by the indole pathway, where tryptophan decarboxylase (TDC) catalyzes the formation of tryptamine from tryptophan. Strictosidine synthase (STR) then catalyzes the formation of strictosidine from the intermediates of the previous pathways. Strictosidine is the common precursor for all terpenoid indole alkaloids. Ajmalicine is finally synthesized under catalysis of strictosidine glucosidase (SGD).
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