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V100

Sigma-Aldrich

(±)-Vesamicol hydrochloride

>98%, solid

Synonym(s):

(±)-2-(4-Phenylpiperidino)cyclohexanol hydrochloride, AH-5183 hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C17H25NO · HCl
CAS Number:
120447-62-3
Molecular Weight:
295.85
MDL number:
MFCD00055231
UNSPSC Code:
12352200
PubChem Substance ID:
24277880

Assay

>98%

form

solid

color

white

solubility

aqueous buffers below pH 8: 1 mM
DMSO: soluble
ethanol: soluble

SMILES string

Cl.OC1CCCCC1N2CCC(CC2)c3ccccc3

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

InChI key

XJNUHVMJVWOYCW-UHFFFAOYSA-N

Gene Information

human ... SLC18A3(6572)

Biochem/physiol Actions

Potent inhibitor of vesicular acetylcholine storage.

Certificates of Analysis (COA)

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Mee-Rye Park et al.
ChemSusChem, 13(17), 4455-4467 (2020-03-12)
There is strong interest in the valorization of lignin to produce valuable products; however, its structural complexity has been a conversion bottleneck. Chemical pretreatment liberates lignin-derived soluble fractions that may be upgraded by bioconversion. Cholinium ionic liquid pretreatment of sorghum
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
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)
Phedias Diamandis et al.
Nature chemical biology, 3(5), 268-273 (2007-04-10)
The identification of self-renewing and multipotent neural stem cells (NSCs) in the mammalian brain holds promise for the treatment of neurological diseases and has yielded new insight into brain cancer. However, the complete repertoire of signaling pathways that governs the

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