Alstonine

Systematic (IUPAC) name
(19α,20α)-16-(Methoxycarbonyl)-19-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium
Identifiers
CAS Number	642-18-2
ATC code	none
PubChem	CID: 441979
ChemSpider	149308
Chemical data
Formula	C21H21N2O3
Molecular mass	349.402496 g/mol
SMILES O=C(OC)\C1=C\O[C@H]([C@H]5[C@@H]1Cc3[n+](ccc4c2ccccc2nc34)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 an indole alkaloid and putative antipsychotic constituent of various plant species including Alstonia boonei, Catharanthus roseus, Picralima nitida, Rauwolfia caffra and Rauwolfia vomitoria. In preclinical studies alstonine attenuates MK-801-induced hyperlocomotion, working memory deficit and social withdrawal. It also possesses anxiolytic-like effects in preclinical studies, attenuates amphetamine-induced lethality and stereotypy as well as apomorphine-induced stereotypy, and attenuates haloperidol-induced catalepsy. These effects appear to be mediated by stimulation of the 5-HT_2C receptor. In addition, alstonine, similarly to clozapine, indirectly inhibits the reuptake of glutamate in hippocampal slices. 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.