Alstonine

Title: Alstonine
CAS Registry Number: 642-18-2
CAS Name: 3,4,5,6,16,17-Hexadehydro-16-(methoxycarbonyl)-19a-methyl-20a-oxayohimbanium
Molecular Formula: C21H20N2O3
Molecular Weight: 348.40
Percent Composition: C 72.40%, H 5.79%, N 8.04%, O 13.78%
Literature References: From Alstonia constricta F. Mull., Rauwolfia vomitoria Afzel., Rauwolfia obscura K. Schum., Vinca rosea L., and other Apocynaceae: Sharp, J. Chem. Soc. 1934, 287; Schlittler et al., Helv. Chim. Acta 35, 271 (1952); Pillay, Kumari, J. Sci. Ind. Res. 20B, 458 (1961); C.A. 56, 7425b (1962). Structure: Bader, Helv. Chim. Acta 36, 215 (1953). Stereoisomer of serpentine (alkaloid), q.v. Stereochemistry: Wenkert, Roychaudhuri, J. Am. Chem. Soc. 79, 1519 (1957); 80, 1613 (1958); Shamma, Richey, ibid. 85, 2507 (1963). Biosynthesis: Woodward, Angew. Chem. 68, 13 (1956).
Properties: Fine, yellow needles from acetone, dec above 300° (brown at 200°, black at 260°). uv max (methanol): 252, 289, 309, 336, 369 nm (log e 4.54, 4.08, 4.36, 3.39, 3.60). Quickly decomposes on standing in organic solvents, yielding red solns with blue fluorescence.
Absorption maximum: uv max (methanol): 252, 289, 309, 336, 369 nm (log e 4.54, 4.08, 4.36, 3.39, 3.60)
Derivative Type: Hydrochloride
Molecular Formula: C21H20N2O3.HCl
Molecular Weight: 384.86
Percent Composition: C 65.54%, H 5.50%, N 7.28%, O 12.47%, Cl 9.21%
Properties: Yellow plates from abs alcohol, dec 286°. [a]D +132° (c = 1.06). Sol in water.
Optical Rotation: [a]D +132° (c = 1.06)
Althea Althiazide Altretamine Aluminon Aluminum Acetate Solution

Alstonine
Alstonine2DACS3.svg
Systematic (IUPAC) name
(19α,20α)-16-(Methoxycarbonyl)-19-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium
Clinical data
Legal status  ?
Identifiers
ATC code None
PubChem CID 441979
ChemSpider 149308
Chemical data
Formula C21H21N2O3 
Mol. mass 349.402496 g/mol

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.[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] It also attenuates amfetamine-induced lethality and stereotypy as well as apomorphine-induced stereotypy.[1] It also attenuates haloperidol-induced catalepsy.[3] These effects appear to be mediated by stimulation of the 5-HT2C receptor.[4] It also, similarly to clozapine, inhibits the reuptake of glutamate in hippocampal slices.[5] Unlike clozapine, however, it lacks pro-convulsant activity in mice.[6]