V104

D-(+)-Vesamicol hydrochloride

solid

• 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

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302 + H312 + H332
• Precautionary Statements: P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312
• 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