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 ;
UNII	4QJL8OX71Z;
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 ;
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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.

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