| Identification | Back Directory | [Name]
GELSEMINE | [CAS]
509-15-9 | [Synonyms]
Gelsemin
GESEMINE
GELSAMINE
GELSEMINE
gelsemine free base
3h)indol)-2’(1’,h)-one
8abeta,9s*,10s*))-8alph
Gelsemine, 98%, from Gelsemium elegans (Gardner & Chapm.) Benth.
ne,5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-,(3r-(3alpha,4abeta,5alpha,
-octahydro-7-methylspiro(3,5,8-ethanylylidene-1h-pyrano(3,4-c)pyridine-10,3’-(
spiro(3,5,8-ethanylylidene-1h-pyrano(3,4-c)pyridine-10,3’-(3h)indol)-2’(1’h)-o
(3r-(3alpha,4abeta,5alpha,8alpha,8abeta,9s*,10s*))-5-ethenyl-3,4,4a,5,6,7,8,8a
Spiro[3,5,8-ethanylylidene-1H-pyrano[3,4-c]pyridine-10,3'-[3H]indole] , gelsemine deriv.
Spiro[3,5,8-ethanylylidene-1H-pyrano[3,4-c]pyridine-10,3'-[3H]indol]-2'(1'H)-one, 5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-
(3S,3aS,3'S,8S,8aS)-1-methyl-3-vinyl-1,2,3,3a,5,7,8,8a-octahydrospiro[3,8,5-(epiethane[1,1,2]triyl)oxepino[4,5-b]pyrrole-4,3'-indolin]-2'-one
(3S,3aS,3'S,5R,8aS,9R)-1-Methyl-3-vinyl-1,2,3,3a,5,7,8,8a-octahydrospiro[3,8,5-(epiethane[1,1,2]triyl)oxepino[4,5-b]pyrrole-4,3'-indolin]-2'-one
Spiro[3,5,8-ethanylylidene-1H-pyrano[3,4-c]pyridine-10,3'-[3H]indol]-2'(1'H)-one,5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-Methyl-, (3R,3'S,4aR,5S,8S,8aS,9S)-
[3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*)]-5-Etheny l-3,4,4a,5,6,7,8,8a-octahydro-7-methylspiro[3,5,8-ethanylylidene-1H-p yrano[3,4-c]pyridine-10,3'-[3H]indol]-2'(1'H)-one
Spiro[3,5,8-ethanylylidene-1H-pyrano[3,4-c]pyridine-10,3'-[3H]indol]-2'(1'H)-one, 5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-, [3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S,10S)]-
Spiro[3,5,8-ethanylylidene-1H-pyrano[3,4-c]pyridine-10,3'-[3H]indol]-2'(1'H)-one, 5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-, [3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*)]- | [EINECS(EC#)]
208-095-2 | [Molecular Formula]
C20H22N2O2 | [MDL Number]
MFCD00082347 | [MOL File]
509-15-9.mol | [Molecular Weight]
322.4 |
| Chemical Properties | Back Directory | [Melting point ]
181-183°C | [alpha ]
D20 +13° (c = 1.2 in chloroform) | [Boiling point ]
461.02°C (rough estimate) | [density ]
1.1478 (rough estimate) | [refractive index ]
1.5700 (estimate) | [storage temp. ]
2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
powder | [pka]
7.75 in 80% methylcellosolve | [color ]
White | [InChIKey]
NFYYATWFXNPTRM-ZFBNGESUNA-N | [SMILES]
[C@]12(C(=O)NC3C=CC=CC1=3)[C@]1([H])OC[C@@]3([H])[C@@]([H])(C1)[C@]1(C=C)CN(C)[C@@]3([H])[C@]21[H] |&1:0,10,14,16,19,25,27,r| | [LogP]
3.080 (est) | [Uses]
Medicine, as a CNS stimulant |
| Hazard Information | Back Directory | [Hazard]
A toxic plant alkaloid | [Chemical Properties]
It is a white crystal, soluble in organic solvents such as methanol, ethanol, and DMSO. It comes from Gelsemium elegans and Gelsemium elegans of the Cucurbitaceae family. | [in vivo]
Gelsemine is an effective agent for treatment of both neuropathic pain and sleep disturbance in partial sciatic nerve ligation (PSNL) mice. Gelsemine (4 mg/kg) exerts analgesic effects on PSNL-induced mechanical allodynia and thermal hyperalgesia. In PSNL mice, Gelsemine (2 and 4 mg/kg) increases the mechanical threshold for 4 h and prolonged the thermal latencies for 3 h. Furthermore, Gelsemine (4 mg/kg, administered at 6:30 AM) increases non-rapid eye movement (non-REM, NREM) sleep, decreases wakefulness, but does not affect rapid eye movement (REM) sleep during the first 3 h in PSNL mice[1].
Immunohistochemical study shows that PSNL increases c-Fos expression in the neurons of the anterior cingulate cortex, and Gelsemine (4 mg/kg) decreases c-Fos expression by 58%[1]. |
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