7248-28-4

Usage

Uses

Used in Pharmaceutical Industry:
STRYCHINE-N-OXIDE is used as a research compound for understanding the metabolic pathways and effects of strychnine. Its study can contribute to the development of new drugs or therapies targeting specific conditions or diseases.
Used in Chemical Research:
STRYCHINE-N-OXIDE serves as a valuable compound in chemical research, particularly in the field of organic chemistry. It can be used to explore the reactivity and properties of N-oxides, as well as their potential applications in the synthesis of other compounds.
Used in Toxicology Studies:
As a metabolite of strychnine, STRYCHINE-N-OXIDE can be utilized in toxicology studies to investigate the effects of strychnine poisoning and develop potential antidotes or treatments for strychnine toxicity.

InChI:InChI=1/C21H22N2O3/c24-18-10-16-19-13-9-17-21(6-7-23(17,25)11-12(13)5-8-26-16)14-3-1-2-4-15(14)22(18)20(19)21/h1-5,13,16-17,19-20H,6-11H2/t13-,16-,17-,19-,20-,21+,23+/m0/s1

Upstream product

• 57-24-9 strychnidin-10-one 

Downstream Products

• 27239-48-1 18-Oxostrychnin 
• 57-24-9 strychnidin-10-one 
• 6882-90-2 Strychninonsaeure 
• 465-62-3 (-)-pseudostrychnine 
• 125-15-5 strychnicine 
• 5525-31-5 icajine 

Relevant academic research and scientific papers

Natural Product Diversification by One-Step Biocatalysis using Human P450 3A4

Efficient synthetic techniques for the diversification of natural products are incremental for drug discovery processes of the pharmaceutical industry because these complex bioactive compounds often require an adjustment of properties. Human liver P450 3A4, key player of the body's detoxification system and decisive factor of a drug's metabolic fate, is renowned for its broad substrate scope including many natural products. In this study, we investigated the synthetic potential of human P450 3A4 for the diversification of natural product classes and isolated the produced metabolites of six selected natural products at a preparative 100-mg scale. Aided by efficient expression levels in P. pastoris, this whole-cell biocatalyst was found to be highly effective at the intended job allowing the identification of a total of 31 authentic human metabolites, many of them for the first time. By revealing an unprecedented degree of diversification, this study extends the synthetic repertoire for efficient enzymatic natural product modification in a one-step fashion and adds a completely new view to an old enzyme traditionally used for inhibition and toxicology studies.

Synthesis of bis-strychnos alkaloids (–)-sungucine, (–)-isosungucine, and (–)-strychnogucine B from (–)-strychnine

It was developed a concise synthetic route resulting in the first syntheses of bis-Strychnos alkaloids (–)-sungucine, (–)-isosungucine, and (–)-strychnogucine B from commercially available (–)-strychnine. Employing a highly convergent synthetic strategy, it was demonstrated that both Strychnos monomers could be efficiently prepared from commercially available (–)-strychnine. The venerable Mannich reaction was enlisted to join the two Strychnos monomers in a biomimetic fashion. Subsequent epimerization and olefin isomerization yielded (–)-strychnogucine B. Functional group manipulation transformed (–)-strychnogucine B into (–)-sungucine and (–)-isosungucine. Computational chemistry was employed to rationalize the regiochemical course of key steps en route to the bis-Strychnos targets.

Concise Syntheses of bis-Strychnos Alkaloids (?)-Sungucine, (?)-Isosungucine, and (?)-Strychnogucine B from (?)-Strychnine

The first chemical syntheses of complex, bis-Strychnos alkaloids (?)-sungucine (1), (?)-isosungucine (2), and (?)-strychnogucine B (3) from (?)-strychnine (4) is reported. Key steps included (1) the Polonovski–Potier activation of strychnine N-oxide; (2) a biomimetic Mannich coupling to forge the signature C23?C5’ bond that joins two monoterpene indole monomers; and (3) a sequential HBr/NaBH3CN-mediated reduction to fashion the ethylidene moieties in 1–3. DFT calculations were employed to rationalize the regiochemical course of reactions involving strychnine congeners.

Effects of N-oxidation on the 15N chemical shifts in the Strychnos alkaloids strychnine and brucine

The effects of N-oxidation on the 15N chemical shifts of the Strychnos alkaloids strychnine and brucine are discussed. The 15N shifts were determined using the inverse-detected, long-range GHMBC experiment at natural abundance. Following N-oxidation, the N-19 resonance shifted downfield from 35.0 ppm in strychnine to 136.3 ppm in the N-19-oxide. The N-19 resonance of brucine shifted downfield from 35.9 to 135.5 ppm in the N-19-oxide. Small upfield shifts were observed for the N-9 resonances of both N-oxides. The 1H and 13C shifts of both N-oxides were assigned using inverse-detected 2D NMR methods to ensure proper assignments of the long-range 1H-15N couplings. Copyright