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Details

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
Structure of GELSEMINE

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

HIDE SMILES / InChI

Description

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.