Ajmalicine

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
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • (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
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)
SMILES
  • O=C(OC)\C4=C\OC(C5CN3CCc1c([nH]c2ccccc12)C3CC45)C
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 Y
  • Key:GRTOGORTSDXSFK-XJTZBENFSA-N Y
 NY (what is this?)  (verify)

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. 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)


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