1358-76-5 Usage
Description
Koumine, an alkaloid derived from Gelsemium elegans Benth, is a component of the Chinese drug 'Kou-wen.' It forms rhombic prisms from Me2 CO and has a specific optical rotation of [α]23D 265° (EtOH). Koumine also forms a crystalline hydrochloride with a melting point of 255°C (dec.) and a hydrobromide with a melting point of 269°C (dec.).
Uses
Used in Anti-Inflammatory Applications:
Koumine is used as an anti-inflammatory agent for attenuating lipopolysaccharide-stimulated inflammation in RAW264.7 macrophages. This application is particularly relevant in the context of inflammatory diseases and conditions where reducing inflammation is a key therapeutic goal.
Used in Pharmaceutical Industry:
Koumine is used as a pharmaceutical compound for its potential therapeutic applications. As an alkaloid with anti-inflammatory properties, it may be further researched and developed for use in the treatment of various diseases and conditions where inflammation plays a significant role.
Used in Research and Development:
Koumine is used as a research compound for studying its chemical properties, structural characteristics, and potential applications in various fields, including pharmaceuticals, biotechnology, and material science. Its unique properties and structural features make it an interesting subject for scientific investigation and potential development of new drugs or materials.
References
Chou, Pak, Hou., Chin. 1. Physiol., 5, 345 (1931)
Chou, Wang, Chen., ibid, 8,40 (1934)
Chi, Kao, Huang., 1. Amer. Chem. Soc., 60, 1723 (1938)
Check Digit Verification of cas no
The CAS Registry Mumber 1358-76-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,3,5 and 8 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1358-76:
(6*1)+(5*3)+(4*5)+(3*8)+(2*7)+(1*6)=85
85 % 10 = 5
So 1358-76-5 is a valid CAS Registry Number.
InChI:InChI=1/C20H22N2O/c1-3-19-11-22(2)16-9-20(19)13-6-4-5-7-15(13)21-18(20)17-8-14(19)12(16)10-23-17/h3-7,12,14,16-17H,1,8-11H2,2H3/t12?,14-,16?,17-,19+,20?/m1/s1
1358-76-5Relevant articles and documents
Asymmetric Total Synthesis of Sarpagine-Related Indole Alkaloids Hydroxygardnerine, Hydroxygardnutine, Gardnerine, (E)-16-epi-Normacusine B, and Koumine
Kitajima, Mariko,Watanabe, Keisuke,Maeda, Hiroyuki,Kogure, Noriyuki,Takayama, Hiromitsu
supporting information, p. 1912 - 1915 (2016/05/19)
Sarpagine-related indole alkaloids (-)-hydroxygardnerine, (+)-hydroxygardnutine, (-)-gardnerine, (+)-(E)-16-epi-normacusine B, and (-)-koumine were divergently synthesized via a common intermediate possessing a piperidine ring with an exocyclic (E)-ethylidene side chain, which was constructed by a gold(I)-catalyzed 6-exo-dig cyclization strategy.
BIOMIMETIC SYNTHESIS OF KOUMINE BY THE PALLADIUM-CATALYZED INTRAMOLECULAR COUPLING REACTION OF 18-HYDROXYTABERPSYCHINE (18-HYDROXYANHYDROVOBASINEDIOL)
Takayama, Hiromitsu,Kitajima, Mariko,Sakai, Shin-ichiro
, p. 325 - 327 (2007/10/02)
A principal Gelsemium alkaloid, koumine (1) was synthesized from 18-hydroxygardnutine (3) via the demethoxylation from the indole ring and the palladium-catalyzed cyclization between C7 and C20 of the hypothetical biogenetic intermediate, 18-hydroxytaberpsychine (2).