Ajmalicine

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	483-04-5 ;
PubChem CID	251561;
ChemSpider	390541 ;
ChEBI	CHEBI:2524;
ChEMBL	ChEMBL123325 ;
CompTox Dashboard (EPA)	DTXSID60904151 ;
ECHA InfoCard	100.006.900
Chemical and physical data
Formula	C21H24N2O3
Molar mass	352.434 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	262.5 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 ; Key:GRTOGORTSDXSFK-XJTZBENFSA-N ;
	(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]

References

^ ^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.
^ 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.
^ 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. PMID 19731590.
^ 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.

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[isbn0-306-45465-3-1] Wink, Michael; Roberts, M. W. (1998). Alkaloids: biochemistry, ecology, and medicinal applications. New York: Plenum Press. ISBN 0-306-45465-3.

[pmid17401876-2] 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.

[pmid19731590-3] 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. PMID 19731590.

[pmid6099269-4] 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.

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[2]

[3]

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See also

References