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MedKoo Cat#: 461828 | Name: Affinisine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Affinisine is a monoterpenoid indole alkaloid which can be isolated from plants of the genus Tabernaemontana. It may be an effective inhibitor of both acetylcholinesterase and butyrylcholinesterase based on previous research.

Chemical Structure

Affinisine
Affinisine
CAS#2912-11-0

Theoretical Analysis

MedKoo Cat#: 461828

Name: Affinisine

CAS#: 2912-11-0

Chemical Formula: C20H23N2O

Exact Mass: 307.1810

Molecular Weight: 307.41

Elemental Analysis: C, 78.14; H, 7.54; N, 9.11; O, 5.20

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Affinisine;
IUPAC/Chemical Name
((6R,6aS,9S,10R,11S,Z)-8-ethylidene-5-methyl-5,6,6a,7,8,9,10,12-octahydro-7l3-6,9-methanoindolo[3,2-g]quinolizin-10-yl)methanol
InChi Key
PCPGNZHEIQJMGI-HJWNKFQBSA-N
InChi Code
InChI=1S/C20H23N2O/c1-3-12-8-18-15-9-14(12)19(11-23)22(18)10-16-13-6-4-5-7-17(13)21(2)20(15)16/h3-8,14-15,18-19,23H,9-11H2,1-2H3/b12-3-/t14-,15+,18-,19-/m0/s1
SMILES Code
OC[C@H]1[C@]2([H])/C([CH][C@@]3([H])[C@](C2)([H])C(N(C)C4=C5C=CC=C4)=C5C[N@]13)=C\C
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 307.41 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
1: Fagundes Rosales P, Gower A, Lucia Ruiz Benitez M, Silveira Pacheco B, Vieira Segatto N, Roesch-Ely M, Collares T, Kömmling Seixas F, Moura S. Extraction, isolation and in vitro evaluation of affinisine from Tabernaemontana catharinensis in human melanoma cells. Bioorg Chem. 2019 Sep;90:103079. doi: 10.1016/j.bioorg.2019.103079. Epub 2019 Jun 19. PMID: 31255990. 2: Stephen MR, Rahman MT, Tiruveedhula VVNPB, Fonseca GO, Deschamps JR, Cook JM. Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-Na -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine. Chemistry. 2017 Nov 7;23(62):15805-15819. doi: 10.1002/chem.201703572. Epub 2017 Oct 18. PMID: 28875520; PMCID: PMC6168078. 3: Yang Z, Tan Q, Jiang Y, Yang J, Su X, Qiao Z, Zhou W, He L, Qiu H, Zhang M. Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids. Angew Chem Int Ed Engl. 2021 Jun 1;60(23):13105-13111. doi: 10.1002/anie.202102416. Epub 2021 May 5. PMID: 33783073. 4: Ebede GR, Ndongo JT, Mbing JN, Kenfack HCM, Pegnyemb DE, Bochet CG. Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae). Nat Prod Res. 2021 Jun;35(11):1757-1765. doi: 10.1080/14786419.2019.1636243. Epub 2019 Jul 5. PMID: 31274013. 5: Reis FL, Adolpho L, Ruiz ALTG, Simionatto E, Dalcol II, Mostardeiro MA, Morel AF. In vitro antiproliferative activity of alkaloids isolated from Tabernaemontana catharinensis A.DC (Apocynaceae). Nat Prod Res. 2022 Nov;36(22):5808-5812. doi: 10.1080/14786419.2021.2017928. Epub 2022 Jan 25. PMID: 35075954. 6: Rosales PF, Marinho FF, Gower A, Chiarello M, Canci B, Roesch-Ely M, Paula FR, Moura S. Bio-guided search of active indole alkaloids from Tabernaemontana catharinensis: Antitumour activity, toxicity in silico and molecular modelling studies. Bioorg Chem. 2019 Apr;85:66-74. doi: 10.1016/j.bioorg.2018.12.016. Epub 2018 Dec 15. PMID: 30599414. 7: Musquiari B, Crevelin EJ, Bertoni BW, França SC, Pereira AMS, Castello ACD, Castillo-Ordoñez WO, Giuliatti S, Lopes AA. Precursor-directed Biosynthesis in Tabernaemontana catharinensis as a New Avenue for Alzheimer's Disease-modifying Agents. Planta Med. 2021 Feb;87(1-02):136-147. doi: 10.1055/a-1315-2282. Epub 2020 Dec 15. PMID: 33321518. 8: Zhan G, Miao R, Zhang F, Chang G, Zhang L, Zhang X, Zhang H, Guo Z. Monoterpene indole alkaloids with acetylcholinesterase inhibitory activity from the leaves of Rauvolfia vomitoria. Bioorg Chem. 2020 Sep;102:104136. doi: 10.1016/j.bioorg.2020.104136. Epub 2020 Jul 24. PMID: 32738570. 9: Amelia P, Nugroho AE, Hirasawa Y, Kaneda T, Tougan T, Horii T, Morita H. Two new sarpagine-type indole alkaloids and antimalarial activity of 16-demethoxycarbonylvoacamine from Tabernaemontana macrocarpa Jack. J Nat Med. 2019 Sep;73(4):820-825. doi: 10.1007/s11418-019-01317-4. Epub 2019 May 28. PMID: 31140017. 10: Kam TS, Choo YM. Alkaloids from Alstonia angustifolia. Phytochemistry. 2004 Mar;65(5):603-8. doi: 10.1016/j.phytochem.2003.12.014. PMID: 15003424. 11: Vieira IJ, Medeiros WL, Monnerat CS, Souza JJ, Mathias L, Braz-Filho R, Pinto AC, Sousa PM, Rezende CM, Epifanio Rde A. Two fast screening methods (GC- MS and TLC-ChEI assay) for rapid evaluation of potential anticholinesterasic indole alkaloids in complex mixtures. An Acad Bras Cienc. 2008 Sep;80(3):419-26. doi: 10.1590/s0001-37652008000300003. PMID: 18797794. 12: Andrade MT, Lima JA, Pinto AC, Rezende CM, Carvalho MP, Epifanio RA. Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme. Bioorg Med Chem. 2005 Jun 2;13(12):4092-5. doi: 10.1016/j.bmc.2005.03.045. PMID: 15911323.