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Key Documents

V104

Sigma-Aldrich

D-(+)-Vesamicol hydrochloride

solid

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About This Item

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

form

solid

Quality Level

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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