| Stereochemistry | RACEMIC |
| Molecular Formula | C17H25NO.ClH |
| Molecular Weight | 295.847 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.O[C@@H]1CCCC[C@H]1N2CCC(CC2)C3=CC=CC=C3
InChI
InChIKey=XJNUHVMJVWOYCW-GBNZRNLASA-N
InChI=1S/C17H25NO.ClH/c19-17-9-5-4-8-16(17)18-12-10-15(11-13-18)14-6-2-1-3-7-14;/h1-3,6-7,15-17,19H,4-5,8-13H2;1H/t16-,17-;/m1./s1
(-)-vesamicol is an active enantiomer of vesamicol (AH5183 or [(-)-trans-2-(4-phenylpiperidino)cyclohexanol]). It inhibits the uptake of acetylcholine into cholinergic neuronal storage vesicles. Vesicular acetylcholine transporter (VAChT) is inhibited by (-)-vesamicol, which binds tightly to an allosteric site.
CNS Activity
Originator
Approval Year
PubMed
Sample Use Guides
Mice: male nude mice were fed a diet
containing 50 mg vesamicol/kg food (10 mg vesamicol/kg
body weight) per day. The administration of vesamicol decreased the tumor growth rate of A549 human BAC tumors. The administration of 50 mg vesamicol/kg food in
the diet was well tolerated and caused no discomfort or weight loss in mice.
Route of Administration:
Oral
The effects of vesamicol (AH5183), a blocker of acetylcholine transport, on the voltage-clamped neuromuscular junction of the frog were studied. Vesamicol (15-30 uM) reduced the peak height of the ionophoretically applied acetylcholine-induced current. The amplitude of the evoked endplate current was also decreased in the presence of vesamicol (30 uM).
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
