Kopsinine | CAS#559-51-3 | alkaloid

MedKoo Cat#: 558577 | Name: Kopsinine

Description:

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

Kopsinine is a plant alkaloid with anti-cholinergic activity.

Chemical Structure

Kopsinine

CAS#559-51-3

Theoretical Analysis

MedKoo Cat#: 558577

Name: Kopsinine

CAS#: 559-51-3

Chemical Formula: C21H26N2O2

Exact Mass: 338.2000

Molecular Weight: 338.45

Elemental Analysis: C, 74.53; H, 7.74; N, 8.28; O, 9.45

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

Kopsinine;

IUPAC/Chemical Name

methyl (3aS,3a1R,5R,5aR,10bS)-2,3,4,5,11,12-hexahydro-1H,3a1H,6H-3a,5a-ethanoindolizino[8,1-cd]carbazole-5-carboxylate

InChi Key

IYLRRIUNGGQRTN-KDJJVYBXSA-N

InChi Code

InChI=1S/C21H26N2O2/c1-25-17(24)15-13-19-7-4-11-23-12-10-20(18(19)23)14-5-2-3-6-16(14)22-21(15,20)9-8-19/h2-3,5-6,15,18,22H,4,7-13H2,1H3/t15-,18+,19-,20-,21+/m0/s1

SMILES Code

O=C([C@H]1[C@@]2(CC3)NC4=C(C=CC=C4)[C@@]2(CCN5CCC6)[C@@]5([H])[C@@]63C1)OC

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 338.45 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.

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: Xie J, Wolfe AL, Boger DL. Total synthesis of kopsinine. Org Lett. 2013 Feb 15;15(4):868-70. doi: 10.1021/ol303573f. Epub 2013 Feb 7. PubMed PMID: 23391149; PubMed Central PMCID: PMC3578506. 2: Lee K, Boger DL. Total synthesis of (-)-kopsinine and ent-(+)-kopsinine. Tetrahedron. 2015 Jun 3;71(22):3741-3746. PubMed PMID: 26074629; PubMed Central PMCID: PMC4461145. 3: Harada S, Sakai T, Takasu K, Yamada K, Yamamoto Y, Tomioka K. Total synthesis of (-)-kopsinine by an asymmetric one-pot [n+2+3] cyclization. Chem Asian J. 2012 Oct;7(10):2196-8. doi: 10.1002/asia.201200575. Epub 2012 Aug 21. PubMed PMID: 22907720. 4: Huang WY, Liu GT. [Mechanism of the protective action of kopsinine against hepatotoxicity of carbon tetrachloride]. Zhongguo Yao Li Xue Bao. 1989 Sep;10(5):461-4. Chinese. PubMed PMID: 2618736. 5: Huang WY, Liu GT. [Protective action of kopsinine against experimental liver injuries in mice]. Zhongguo Yao Li Xue Bao. 1989 Jan;10(1):65-8. Chinese. PubMed PMID: 2816405. 6: Cheenpracha S, Raksat A, Ritthiwigrom T, Laphookhieo S. Monoterpene indole alkaloids from the twigs of Kopsia arborea. Nat Prod Commun. 2014 Oct;9(10):1441-3. PubMed PMID: 25522533. 7: Huang WY, Liu GT. [Induction by kopsinine of hepatic mixed-function oxidase in mice]. Zhongguo Yao Li Xue Bao. 1990 May;11(3):264-8. Chinese. PubMed PMID: 2088003. 8: Zhang J, Liu GT. [Protective action of kopsinine F against experimental liver injury in mice]. Yao Xue Xue Bao. 1989;24(3):165-9. Chinese. PubMed PMID: 2816370. 9: Tan MJ, Yin C, Tang CP, Ke CQ, Lin G, Ye Y. Antitussive indole alkaloids from Kopsia hainanensis. Planta Med. 2011 Jun;77(9):939-44. doi: 10.1055/s-0030-1250631. Epub 2010 Dec 16. PubMed PMID: 21165819. 10: Sears JE, Boger DL. Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition Cascade of 1,3,4-Oxadiazoles: Initial Scope and Applications. Acc Chem Res. 2016 Feb 16;49(2):241-51. doi: 10.1021/acs.accounts.5b00510. Epub 2016 Jan 27. PubMed PMID: 26813287; PubMed Central PMCID: PMC4755904. 11: Jones SB, Simmons B, Mastracchio A, MacMillan DW. Collective synthesis of natural products by means of organocascade catalysis. Nature. 2011 Jul 13;475(7355):183-8. doi: 10.1038/nature10232. PubMed PMID: 21753848; PubMed Central PMCID: PMC3439143. 12: Mitaine AC, Mesbah K, Richard B, Petermann C, Arrazola S, Moretti C, Zèches-Hanrot M, Men-Olivier LL. Alkaloids from Aspidosperma species from Bolivia. Planta Med. 1996 Oct;62(5):458-61. PubMed PMID: 17252481. 13: Harada S. [Asymmetric syntheses of azacycloalkanes by one-pot [1+2+n] cyclization]. Yakugaku Zasshi. 2013;133(9):975-82. Review. Japanese. PubMed PMID: 23995805. 14: Naaz H, Singh S, Pandey VP, Singh P, Dwivedi UN. Anti-cholinergic alkaloids as potential therapeutic agents for Alzheimer's disease: an in silico approach. Indian J Biochem Biophys. 2013 Apr;50(2):120-5. PubMed PMID: 23720886. 15: Kam TS, Subramaniam G, Sim KM, Yoganathan K, Koyano T, Toyoshima M, Rho MC, Hayashi M, Komiyama K. Reversal of multidrug resistance (MDR) by aspidofractinine-type indole alkaloids. Bioorg Med Chem Lett. 1998 Oct 6;8(19):2769-72. PubMed PMID: 9873619. 16: Feng XZ, Kan C, Potier P, Kan SK, Lounasmaa M. [Monomeric Indole Alkaloids from Kopsia officinalis.]. Planta Med. 1983 Aug;48(8):280-2. German. PubMed PMID: 17404997. 17: Mehri H, Rochat C, Baassou S, Sevenet T, Plat M. [Plant from New-Caledonia. Alkaloids of Melodinus reticulatus]. Planta Med. 1983 Jun;48(2):72-6. German. PubMed PMID: 17404953. 18: Lee K, Boger DL. Total syntheses of (-)-kopsifoline D and (-)-deoxoapodine: divergent total synthesis via late-stage key strategic bond formation. J Am Chem Soc. 2014 Feb 26;136(8):3312-7. doi: 10.1021/ja500548e. Epub 2014 Feb 17. PubMed PMID: 24499015; PubMed Central PMCID: PMC3985950. 19: Addae-Kyereme J, Croft SL, Kendrick H, Wright CW. Antiplasmodial activities of some Ghanaian plants traditionally used for fever/malaria treatment and of some alkaloids isolated from Pleiocarpa mutica; in vivo antimalarial activity of pleiocarpine. J Ethnopharmacol. 2001 Jun;76(1):99-103. PubMed PMID: 11378289.