Alstonine

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MedKoo CAT#: 584176

CAS#: 642-18-2

Description: 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.


Chemical Structure

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Alstonine
CAS# 642-18-2

Theoretical Analysis

MedKoo Cat#: 584176
Name: Alstonine
CAS#: 642-18-2
Chemical Formula: C21H20N2O3
Exact Mass: 348.1474
Molecular Weight: 348.4
Elemental Analysis: C, 72.40; H, 5.79; N, 8.04; O, 13.78

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 47485-83-6   642-18-2    

Synonym: BG 8; BG-8; BG8; Alstonine.

IUPAC/Chemical Name: (4S,4aS,14aS)-1-(methoxycarbonyl)-4-methyl-4a,5,14,14a-tetrahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizin-6-ium-13-ide

InChi Key: WYTGDNHDOZPMIW-RCBQFDQVSA-N

InChi Code: 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/t12-,15-,16-/m0/s1

SMILES Code: C[C@@H]1OC=C(C(OC)=O)[C@]2([H])[C@@]1([H])C[N+]3=C(C([N-]C4=C5C=CC=C4)=C5C=C3)C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 348.4 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Linck VM, Ganzella M, Herrmann AP, Okunji CO, Souza DO, Antonelli MC, Elisabetsky E. Original mechanisms of antipsychotic action by the indole alkaloid alstonine (Picralima nitida). Phytomedicine. 2015 Jan 15;22(1):52-5. doi: 10.1016/j.phymed.2014.10.010. Epub 2014 Nov 6. PubMed PMID: 25636871.

2: Cachet X, Porée FH, Michel S, Lemoine P. Tetra-hydro-alstonine. Acta Crystallogr Sect E Struct Rep Online. 2013 Aug 7;69(Pt 9):o1389-90. doi: 10.1107/S1600536813021168. eCollection 2013. PubMed PMID: 24427031; PubMed Central PMCID: PMC3884471.

3: Herrmann AP, Lunardi P, Pilz LK, Tramontina AC, Linck VM, Okunji CO, Gonçalves CA, Elisabetsky E. Effects of the putative antipsychotic alstonine on glutamate uptake in acute hippocampal slices. Neurochem Int. 2012 Dec;61(7):1144-50. doi: 10.1016/j.neuint.2012.08.006. Epub 2012 Aug 25. PubMed PMID: 22940693.

4: Linck VM, Bessa MM, Herrmann AP, Iwu MM, Okunji CO, Elisabetsky E. 5-HT2A/C receptors mediate the antipsychotic-like effects of alstonine. Prog Neuropsychopharmacol Biol Psychiatry. 2012 Jan 10;36(1):29-33. doi: 10.1016/j.pnpbp.2011.08.022. Epub 2011 Sep 8. PubMed PMID: 21925231.

5: Linck VM, Herrmann AP, Piato AL, Detanico BC, Figueiró M, Flório J, Iwu MM, Okunji CO, Leal MB, Elisabetsky E. Alstonine as an antipsychotic: effects on brain amines and metabolic changes. Evid Based Complement Alternat Med. 2011;2011:418597. doi: 10.1093/ecam/nep002. Epub 2011 Jun 23. PubMed PMID: 19189988; PubMed Central PMCID: PMC3140158.

6: de Moura Linck V, Herrmann AP, Goerck GC, Iwu MM, Okunji CO, Leal MB, Elisabetsky E. The putative antipsychotic alstonine reverses social interaction withdrawal in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2008 Aug 1;32(6):1449-52. doi: 10.1016/j.pnpbp.2008.04.013. Epub 2008 Apr 29. PubMed PMID: 18539376.

7: Elisabetsky E, Costa-Campos L. The alkaloid alstonine: a review of its pharmacological properties. Evid Based Complement Alternat Med. 2006 Mar;3(1):39-48. Epub 2006 Jan 16. PubMed PMID: 16550222; PubMed Central PMCID: PMC1375234.

8: Costa-Campos L, Iwu M, Elisabetsky E. Lack of pro-convulsant activity of the antipsychotic alkaloid alstonine. J Ethnopharmacol. 2004 Aug;93(2-3):307-10. Erratum in: J Ethnopharmacol. 2005 Feb 10;97(1):165. PubMed PMID: 15234769.

9: Costa-Campos L, Dassoler SC, Rigo AP, Iwu M, Elisabetsky E. Anxiolytic properties of the antipsychotic alkaloid alstonine. Pharmacol Biochem Behav. 2004 Mar;77(3):481-9. PubMed PMID: 15006458.

10: Costa-Campos L, Elisabetsky E, Lara DR, Carlson TJ, King SR, Ubillas R, Nunes DS, Iwu MM, Nkemjika CO, Ozioko A, Agwu CO. Antipsychotic profile of alstonine: ethnopharmacology of a traditional Nigerian botanical remedy. An Acad Bras Cienc. 1999;71(2):189-201. PubMed PMID: 10412490.

11: Costa-Campos L, Lara DR, Nunes DS, Elisabetsky E. Antipsychotic-like profile of alstonine. Pharmacol Biochem Behav. 1998 May;60(1):133-41. PubMed PMID: 9610935.

12: WAKIM KG, CHEN KK. The action of alstonine. J Pharmacol Exp Ther. 1947 May;90(1):57-67. PubMed PMID: 20241896.

13: WAKIM KG, CHEN KK. The action of alstonine. Fed Proc. 1947;6(1):380. PubMed PMID: 20249625.