Vesamicol

Vesamicol

File:Vesamicol.png
Systematic (IUPAC) name
2-(4-phenyl-1-piperidyl)cyclohexan-1-ol
Identifiers
CAS Number	22232-64-0
PubChem	CID: 5662
IUPHAR/BPS	4759
ChemSpider	5460
ChEMBL	CHEMBL20730
Chemical data
Formula	C17H25NO
Molecular mass	259.39 g/mol
SMILES OC1CCCCC1N2CCC(CC2)c3ccccc3

Vesamicol is an experimental drug, acting presynaptically by inhibiting acetylcholine (ACh) uptake into synaptic vesicles and reducing its release. Vesamicol may have applications in BAC therapy. It has been described as a hydroxylated phencyclidine regioisomer.

Mechanism of action

Vesamicol can be broadly categorized as a cholinergic physiological antagonist, because it reduces the apparent activity of cholinergic neurons, but does not act at the postsynaptic ACh receptor. Vesamicol causes a non-competitive and reversible block of the intracellular transporter VAChT responsible for carrying newly synthesized ACh into secretory vesicles in the presynaptic nerve terminal. This transport process is driven by a proton gradient between cell organelles and the cytoplasm. Blocking of acetylcholine loading leads to empty vesicles fusing with neuron membranes, decreasing ACh release.