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Alstonine

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Alstonine
alstonine 2D skeletal
alstonine 3D BS
Clinical data
ATC code
  • none
Identifiers
  • (19α,20α)-16-(Methoxycarbonyl)-19-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H21N2O3
Molar mass349.410 g·mol−1
3D model (JSmol)
  • O=C(OC)\C1=C\O[C@H]([C@H]5[C@@H]1Cc3[n+](ccc4c2ccccc2[nH]c34)C5)C
  • 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-HT2C 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-HT2A and 5-HT2C 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]

See also

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References

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  1. ^ a b c Elisabetsky E, Costa-Campos L (March 2006). "The alkaloid alstonine: a review of its pharmacological properties". Evidence-Based Complementary and Alternative Medicine. 3 (1): 39–48. doi:10.1093/ecam/nek011. PMC 1375234. PMID 16550222.
  2. ^ Linck VM, Bessa MM, Herrmann AP, Iwu MM, Okunji CO, Elisabetsky E (January 2012). "5-HT2A/C receptors mediate the antipsychotic-like effects of alstonine". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 36 (1): 29–33. doi:10.1016/j.pnpbp.2011.08.022. PMID 21925231. S2CID 3236174.
  3. ^ Linck VM, Herrmann AP, Piato AL, Detanico BC, Figueiró M, Flório J, et al. (July 2011). "Alstonine as an antipsychotic: effects on brain amines and metabolic changes". Evidence-Based Complementary and Alternative Medicine. 2011 (418597): 418597. doi:10.1093/ecam/nep002. PMC 3140158. PMID 19189988.
  4. ^ Meltzer HY (2012). "Serotonergic Mechanisms as Targets for Existing and Novel Antipsychotics". In Gross G, Geyer MA (eds.). Current Antipsychotics. Handbook of Experimental Pharmacology. Vol. 212. Berlin Heidelberg: Springer. pp. 87–124. doi:10.1007/978-3-642-25761-2_4. ISBN 978-3-642-25761-2. PMID 23129329.
  5. ^ Herrmann AP, Lunardi P, Pilz LK, Tramontina AC, Linck VM, Okunji CO, et al. (December 2012). "Effects of the putative antipsychotic alstonine on glutamate uptake in acute hippocampal slices". Neurochemistry International. 61 (7): 1144–1150. doi:10.1016/j.neuint.2012.08.006. PMID 22940693. S2CID 14234269.
  6. ^ Costa-Campos L, Iwu M, Elisabetsky E (August 2004). "Lack of pro-convulsant activity of the antipsychotic alkaloid alstonine". Journal of Ethnopharmacology. 93 (2–3): 307–310. doi:10.1016/j.jep.2004.03.056. PMID 15234769.
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