V101
L(–)-Vesamicol hydrochloride
solid
Synonym(s):
L-(−)-2-(4-Phenylpiperidino)cyclohexanol hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C17H25NO · HCl
CAS Number:
Molecular Weight:
295.85
UNSPSC Code:
12352200
MDL number:
SMILES string
Cl.O[C@@H]1CCCC[C@H]1N2CCC(CC2)c3ccccc3
form
solid
optical activity
[α]25/D −23.2°, c = 1 in ethanol(lit.)
color
white
Biochem/physiol Actions
Potent inhibitor of vesicular acetylcholine storage; active enantiomer of vesamicol.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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B A Bahr et al.
Proceedings of the National Academy of Sciences of the United States of America, 83(7), 2267-2270 (1986-04-01)
Transport and storage of acetylcholine by purified Torpedo electric organ synaptic vesicles is blocked by the drug L-trans-2-(4-phenylpiperidino)cyclohexanol (AH-5183). This study sought evidence of a specific receptor for the drug. Highly tritiated L-trans-2-(4-phenyl [3,4-3H] piperidino)-cyclohexanol (L-[3H] AH5183) was synthesized. An
The vesicular acetylcholine transport system.
Marshall,L, et al.
Trends in Neurosciences, 10, 174-174 (1987)
C Prior et al.
General pharmacology, 23(6), 1017-1022 (1992-11-01)
1. Vesamicol (2-[4-phenylpiperidino] cyclohexanol) inhibits the transport of acetylcholine into synaptic vesicles in cholinergic nerve terminals. 2. Recent pharmacological studies of the effects of vesamicol on skeletal neuromuscular transmission have revealed a pattern of activity for the compound consistent with
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