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Merck

V104

D-(+)-Vesamicol hydrochloride

solid

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10 MG

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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

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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

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This Item
513100551850138001
D-(+)-Vesamicol hydrochloride solid

Sigma-Aldrich

V104

D-(+)-Vesamicol hydrochloride

DL-threo-PDMP, Hydrochloride PDMP closely resembles the natural sphingolipid substrate of brain glucosyltransferase and acts as a potent and competitive inhibitor of this enzyme.

Sigma-Aldrich

513100

DL-threo-PDMP, Hydrochloride

Quinacrine dihydrochloride A non-specific phospholipase A2 (PLA2) inhibitor.

Sigma-Aldrich

551850

Quinacrine dihydrochloride

D-Amino Acid Oxidase Inhibitor II, CBIO The D-Amino Acid Oxidase Inhibitor II, CBIO, also referenced under CAS 61977-29-5, controls the biological activity of D-Amino Acid Oxidase.

Sigma-Aldrich

138001

D-Amino Acid Oxidase Inhibitor II, CBIO

solubility

DMSO: soluble, ethanol: soluble

solubility

DMSO: soluble, ethanol: soluble, methanol: soluble

solubility

water: soluble

solubility

DMSO: 50 mg/mL

form

solid

form

solid

form

solid

form

powder

color

white

color

white

color

yellow

color

off-white

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

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.[1]

Application

D-(+)-Vesamicol hydrochloride can be used as a reactant to prepare:
  • Trialkylstannyl vesamicol analogs as potent vesicular acetylcholine transporters (VAChTs) and sigma receptors.[2]
  • Vesamicol analog, (+)-2-[4-(4-iodophenyl)piperidino] cyclohexanol as a possible tumor imaging agent.[3]

Biochem/physiol Actions

Less active enantiomer of vesamicol

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

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

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Certificates of Analysis (COA)

Lot/Batch Number
028H4698
089H4613

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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)
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)
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)

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