| Identification | Back Directory | [Name]
koumine | [CAS]
1358-76-5 | [Synonyms]
koumine
(3R,7alpha,20alpha)-1,2,18,19-Tetradehydro-3,17-epoxy-7,20(2H,19H)cyclovobasan
7,20(2H,19H)-Cyclovobasan, 1,2,18,19-tetradehydro-3,17-epoxy-, (3R,7alpha,20alpha)-
6,4-(Epoxymethano)-3,11b-methano-11bH-pyrido[4,3-c]carbazole, 11c-ethenyl-1,2,3,4,4a,5,6,11c-octahydro-2-methyl-, (3S,4S,4aR,6R,11bS,11cS)- | [Molecular Formula]
C20H22N2O | [MDL Number]
MFCD11111448 | [MOL File]
1358-76-5.mol | [Molecular Weight]
306.407 |
| Chemical Properties | Back Directory | [Occurrence]
Koumine is an alkaloid isolated from Gelsemium elegans Benth. | [Melting point ]
168℃ | [Boiling point ]
436.5±45.0 °C(Predicted) | [density ]
1.42 | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO : 31.25 mg/mL (101.99 mM; Need ultrasonic) | [form ]
powder | [pka]
8.67±0.40(Predicted) | [color ]
Yellow-brown | [Optical Rotation]
[α]/D 295 to 245° | [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+/s3 | [InChIKey]
VTLYEMHGPMGUOT-KWZROIJWNA-N | [SMILES]
C1C=CC2N=C3[C@]4([H])OC[C@@]5([H])[C@]([H])([C@]6(C=C)CN(C)[C@]5(C[C@@]36C=2C=1)[H])C4 |&1:6,10,12,14,20,22,r| |
| Safety Data | Back Directory | [WGK Germany ]
WGK 3 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 2 Inhalation
Acute Tox. 2 Oral |
| Hazard Information | Back Directory | [Description]
The Chinese drug 'Kou-wen', said to be derived from Gelsemium elegans Benth.,
is stated to contain this alkaloid which forms rhombic prisms from Me2 CO. It
has [α]23D - 265° (EtOH) and forms a crystalline hydrochloride, m.p. 255°C
(dec.) and a hydrobromide, m.p. 269°C (dec.). | [Chemical Properties]
It is soluble in organic solvents such as acetone, chloroform, ether, and benzene, but poorly soluble in water. It is derived from the Gelsemium elegans (Gardn. et Champ.) Benth, a plant of the Cucurbitaceae family. | [Uses]
Koumine is known to attenuate the lipopolysaccharide-stimulated inflammation in RAW264.7 macrophages. | [in vivo]
Koumine is less toxic, with the median lethal dose (LD50) of 300.0 mg/kg on Wistar rats. Koumine (0.6, 3, or 15 mg/kg/per, p.o.) exhibits antirheumatic properties in rats with adjuvant-induced arthritis (AIA) and collagen-induced arthritis (CIA)[2].
Koumine inhibits the increase in cytokines in joint tissue and TNF-α level in serum at 15 mg/kg, and suppresses the increase in the serum level of IL-1β at 3 and 15 mg/kg[2].
Koumine (0.28, 7 mg/kg, s.c.) significantly reduces neuropathic pain after nerve injury. Koumine suppresses the increased Iba-1 protein level[3]. | [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) |
|
|