V104
D-(+)-Vesamicol hydrochloride
solid
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About This Item
Empirical Formula (Hill Notation):
C17H25NO · HCl
CAS Number:
Molecular Weight:
295.85
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Form:
solid
Product Name
D-(+)-Vesamicol hydrochloride, solid
InChI key
XJNUHVMJVWOYCW-QJHJCNPRSA-N
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
form
solid
color
white
solubility
DMSO: soluble
ethanol: soluble
Quality Level
Related Categories
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
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
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)
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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