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V104

Sigma-Aldrich

D-(+)-Vesamicol hydrochloride

solid

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About This Item

Empirical Formula (Hill Notation):
C17H25NO · HCl
CAS Number:
112709-60-1
Molecular Weight:
295.85
MDL number:
MFCD00069370
UNSPSC Code:
12352005
PubChem Substance ID:
57654723
NACRES:
NA.22

form

solid

color

white

solubility

DMSO: soluble
ethanol: soluble

SMILES string

Cl.O[C@H]1CCCC[C@@H]1N2CCC(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/t16-,17-;/m0./s1

InChI key

XJNUHVMJVWOYCW-QJHJCNPRSA-N

General description

D-(+)-Vesamicol is a potent inhibitor of acetycholine transport into the synaptic vesicles in cholinergic nerve terminals. It is 25-times less potent than the L-form.

Application

D-(+)-Vesamicol hydrochloride can be used as a reactant to prepare:
  • Trialkylstannyl vesamicol analogs as potent vesicular acetylcholine transporters (VAChTs) and sigma receptors.
  • Vesamicol analog, (+)-2-[4-(4-iodophenyl)piperidino] cyclohexanol as a possible tumor imaging agent.

Biochem/physiol Actions

Less active enantiomer of vesamicol

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Development and evaluation of a novel radioiodinated vesamicol analog as a sigma receptor imaging agent
Ogawa K, et al.
EJNMMI Research, 2(1), 54-54 (2012)
Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor
Shiba K, et al.
Bioorganic & Medicinal Chemistry, 14(8), 2620-2626 (2006)
A validated LC method for the determination of vesamicol enantiomers in human plasma using vancomycin chiral stationary phase and solid phase extraction.
Hefnawy MM and Aboul-Enein HY.
Journal of Pharmaceutical and Biomedical Analysis, 35(3), 535-543 (2004)

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