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Ajmalicine

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Ajmalicine
ajmalicine 2D skeletal
ajmalicine 3D BS
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • (19α)-16,17-didehydro- 19-methyloxayohimban- 16-carboxylic acid methyl ester
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.006.900
Chemical and physical data
Formula C21H24N2O3
Molar mass 352.434 g·mol−1
3D model (JSmol)
Melting point 262.5 to 263 °C (504.5 to 505.4 °F)
  • O=C(OC)\C4=C\OC(C5CN3CCc1c([nH]c2ccccc12)C3CC45)C
  • 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 checkY
  • Key:GRTOGORTSDXSFK-XJTZBENFSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ajmalicine, also known as δ-yohimbine or raubasine, is an antihypertensive drug used in the treatment of high blood pressure. It has been marketed under numerous brand names including Card-Lamuran, Circolene, Cristanyl, Duxil, Duxor, Hydroxysarpon, Iskedyl, Isosarpan, Isquebral, Lamuran, Melanex, Raunatin, Saltucin Co, Salvalion, and Sarpan. It is an alkaloid found naturally in various plants such as Rauvolfia spp., Catharanthus roseus, and Mitragyna speciosa.

Ajmalicine is structurally related to yohimbine, rauwolscine, and other yohimban derivatives. Like corynanthine, it acts as a α1-adrenergic receptor antagonist with preferential actions over α2-adrenergic receptors, underlying its hypotensive rather than hypertensive effects.

Additionally, it is a very strong inhibitor of the CYP2D6 liver enzyme, which is responsible for the breakdown of many drugs. Its binding affinity at this receptor is 3.30 nM.

See also



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