Stereochemistry | ABSOLUTE |
Molecular Formula | C20H22N2O2 |
Molecular Weight | 322.4009 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@H]3OC[C@@H]1[C@@]4([H])N(C)C[C@]2(C=C)[C@@]4([H])[C@@]35C(=O)NC6=CC=CC=C56
InChI
InChIKey=NFYYATWFXNPTRM-QJICHLCESA-N
InChI=1S/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11-,13+,15+,16+,17-,19-,20-/m0/s1
Gelsemine is the principal alkaloid in Gelsemium sempervirens Ait. A single intrathecal injection of gelsemine produced potent and specific antinociception in formalin-induced tonic pain, bone cancer-induced mechanical allodynia, and spinal nerve ligation-induced painful neuropathy. Gelsemine exhibits potent and specific antinociception in chronic pain by acting at spinal α3 glycine receptors. Gelsemine is an effective agent for treatment of both neuropathic pain and sleep disturbance in PSNL mice; anterior cingulate cortex might play a role in the hypnotic effects of gelsemine.
CNS Activity
Originator
Approval Year
PubMed
Patents
Sample Use Guides
In PSNL mice, gelsemine (2 and 4 mg/kg) increased the mechanical threshold for 4 h and prolonged the thermal latencies for 3 h. Furthermore, gelsemine (4 mg/kg, administered at 6:30 AM) increased non-rapid eye movement (non-REM, NREM) sleep, decreased wakefulness, but did not affect REM sleep during the first 3 h in PSNL mice.
Route of Administration:
Intraperitoneal
Differential concentrations of gelsemine (1, 3, 10,
30, 100, 300, and 1000 uM) or glycine (3, 10, 30, 100, 300, and
1000 uM) were added to H3
-strychnine and the rat crude membrane.
Both gelsemine and glycine concentration-dependently
displaced H3
-strychnine binding by a maximum displacement
of 100%. The IC50 values of gelsemine and glycine were
43.8 and 82.1 uM, and their Ki values were 21.9 and 41.0 uM,
respectively.