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 InfoCard100.006.900 Edit this at Wikidata
Chemical and physical data
FormulaC21H24N2O3
Molar mass352.434 g·mol−1
3D model (JSmol)
Melting point262.5 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.[1] 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.[1] It is an alkaloid found naturally in various plants such as Rauvolfia spp., Catharanthus roseus, and Mitragyna speciosa.[1][2][3]

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.[1][4]

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.[5]

See also

References

  1. ^ a b c d Wink, Michael; Roberts, M. W. (1998). Alkaloids: biochemistry, ecology, and medicinal applications. New York: Plenum Press. ISBN 0-306-45465-3.
  2. ^ Kurz WG, Chatson KB, Constabel F, et al. (May 1981). "Alkaloid Production in Catharanthus roseus Cell Cultures VIII1". Planta Medica. 42 (5): 22–31. doi:10.1055/s-2007-971541. PMID 17401876.
  3. ^ León F, Habib E, Adkins JE, Furr EB, McCurdy CR, Cutler SJ (July 2009). "Phytochemical characterization of the leaves of Mitragyna speciosa grown in U.S.A". Natural Product Communications. 4 (7): 907–10. doi:10.1177/1934578X0900400705. PMID 19731590. S2CID 37709142.
  4. ^ Roquebert J, Demichel P (October 1984). "Inhibition of the alpha 1 and alpha 2-adrenoceptor-mediated pressor response in pithed rats by raubasine, tetrahydroalstonine and akuammigine". European Journal of Pharmacology. 106 (1): 203–5. doi:10.1016/0014-2999(84)90698-8. PMID 6099269.
  5. ^ Strobl GR, von Kruedener S, Stöckigt J, Guengerich FP, Wolff T (1993). "Development of a pharmacophore for inhibition of human liver cytochrome P-450 2D6: molecular modeling and inhibition studies". J Med Chem. 36 (9): 1136–45. doi:10.1021/jm00061a004. PMID 8487254.((cite journal)): CS1 maint: multiple names: authors list (link)