21087-98-9

Basic information

• Product Name: KOENIMBINE
• Synonyms: KOENIMBINE;3,11-Dihydro-8-methoxy-3,3,5-trimethylpyrano[3,2-a]carbazole;Kenimbine;Koenimbin;NSC 127152;8-Methoxy-3,3,5-trimethyl-3,11-dihydro-chromeno[5,6-b]indole
• CAS NO: 21087-98-9
• Molecular Formula: C₁₉H₁₉NO₂
• Molecular Weight: 293.3597
• Mol File: 21087-98-9.mol

Chemical Properties

• Melting Point: 194-195℃
• Boiling Point: 482.1°Cat760mmHg
• Flash Point: 171.8°C
• Appearance: /
• Density: 1.193
• Vapor Pressure: 5.5E-09mmHg at 25°C
• Refractive Index: 1.658
• PKA: 17.02±0.40(Predicted)
• CAS DataBase Reference: KOENIMBINE(CAS DataBase Reference)
• NIST Chemistry Reference: KOENIMBINE(21087-98-9)
• EPA Substance Registry System: KOENIMBINE(21087-98-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36-53
• Safety Statements: 26
• Hazardous Substances Data: 21087-98-9(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
KOENIMBINE is used as a bioactive compound for its potential therapeutic applications. The compound's unique structure and properties make it a promising candidate for the development of new drugs and treatments.
2. Used in Chemical Research:
KOENIMBINE serves as a valuable subject for chemical research, particularly in the study of alkaloids and their derivatives. Its unique properties, such as the double bond in the pyrone ring, provide opportunities for further exploration and understanding of its chemical behavior.
3. Used in Drug Synthesis:
KOENIMBINE can be utilized as a starting material or intermediate in the synthesis of other pharmaceutical compounds. Its reactivity and structural features make it a useful building block for creating new drugs with potential therapeutic benefits.
4. Used in Analytical Chemistry:
The unique ultraviolet spectrum of KOENIMBINE, with absorption maxima at specific wavelengths, can be employed in analytical chemistry for the identification and quantification of the compound in various samples. This can be particularly useful in quality control and purity assessment of pharmaceutical products containing KOENIMBINE.
5. Used in Natural Product Chemistry:
KOENIMBINE's isolation from the fruit of Murraya koenigii Spreng highlights its importance in the field of natural product chemistry. Researchers can study the compound to better understand the chemical diversity found in nature and potentially discover new bioactive compounds with therapeutic potential.

References

Narasimhan, Paradkar, Chitguppi., Tetrahedron Lett., 5501 (I968)

InChI:InChI=1/C19H19NO2/c1-11-9-15-14-10-12(21-4)5-6-16(14)20-17(15)13-7-8-19(2,3)22-18(11)13/h5-10,20H,1-4H3

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Downstream Products

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Relevant articles and documents

Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo

A series of pyrano[3,2-a]carbazole alkaloids were designed and synthesized as analogues of Claulansine F (Clau F, 10a) isolated from Clausena lansium. Some of compounds showed strong neuroprotective effects and were promising agents against ischemic stroke. Among these compounds, 7c was the most active in inhibiting the programmed death of PC12 cells and primary cortical neurons. This compound induced neuroprotection following ischemic reperfusion and decreased neurological deficit scores in treated animals. Furthermore, 7c could penetrate the blood-brain barrier (BBB) in rats, and its exposure in the brain was 4.3-fold higher than that in plasma. More importantly, compared to edaravone, 7c exhibited stronger free radical scavenging activity. Our findings suggest that 7c may be promising for further evaluation as an intervention for ischemic stroke.

Synthesis of the Pyrano[3,2- a ]carbazole Alkaloids Koenine, Koenimbine, Koenigine, Koenigicine, and Structural Reassignment of Mukonicine

Using the palladium(II)-catalyzed oxidative cyclization of a diarylamine and the annulation of a dimethylpyran ring by Lewis acid promoted reaction with prenal as key steps, the total syntheses of the 6-oxygenated pyrano[3,2-a]carbazole alkaloids koenine and koenimbine, and of the 6,7-dioxygenated pyrano[3,2-a]carbazole alkaloids koenigine and koenigicine (koenimbidine, koenidine) were achieved. Moreover, these studies led to an improved synthetic route to the 2,6-dioxygenated carbazole alkaloid glycozolidol. Mukonicine, originally published as 6,8-dimethoxypyrano[3,2-a]carbazole, was found to be identical with koenigicine.