Alstonine

Alstonine
Clinical data
ATC code	none;
Identifiers
	IUPAC name (19α,20α)-16-(Methoxycarbonyl)-19-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium;
CAS Number	642-18-2;
PubChem CID	441979;
ChemSpider	149308;
UNII	SB0M27Q90X;
ChEBI	CHEBI:2612;
CompTox Dashboard (EPA)	DTXSID201115727 ;
Chemical and physical data
Formula	C21H21N2O3
Molar mass	349.410 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OC)\C1=C\O[C@H]([C@H]5[C@@H]1Cc3[n+](ccc4c2ccccc2[nH]c34)C5)C;
	InChI InChI=InChI=1S/C21H20N2O3/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/h3-8,11-12,15-16H,9-10H2,1-2H3/p+1/t12-,15-,16-/m0/s1; Key:WYTGDNHDOZPMIW-RCBQFDQVSA-O;

Alstonine is a pentacyclic alkaloid and putative antipsychotic constituent of various plant species including Alstonia boonei, Catharanthus roseus, Picralima nitida, Rauvolfia afra and Rauvolfia vomitoria.^[1] In preclinical studies alstonine attenuates MK-801-induced hyperlocomotion, working memory deficit and social withdrawal.^[2] It also possesses anxiolytic-like effects in preclinical studies,^[1] attenuates amphetamine-induced lethality and stereotypy as well as apomorphine-induced stereotypy,^[1] and attenuates haloperidol-induced catalepsy.^[3] These effects appear to be mediated by stimulation of the 5-HT_2C receptor.^[4] In addition, alstonine, similarly to clozapine, indirectly inhibits the reuptake of glutamate in hippocampal slices.^[5] Unlike clozapine however, the effect of which is abolished by the D₂ receptor agonist apomorphine, alstonine requires 5-HT_2A and 5-HT_2C receptors to produce this effect, as it is abolished by antagonists of these receptors. Also unlike clozapine, alstonine lacks pro-convulsant activity in mice.^[6]

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