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S128

Sigma-Aldrich

N-Methylspiperone hydrochloride

solid

Synonym(s):

N-Methyl-8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro-[4.5]decan-4-one hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C24H28FN3O2 · HCl
CAS Number:
87539-19-3
Molecular Weight:
445.96
MDL number:
MFCD00083200
UNSPSC Code:
12352200
PubChem Substance ID:
24899471
NACRES:
NA.77

form

solid

Quality Level

100

color

light yellow

solubility

0.1 M HCl: soluble
ethanol: soluble

SMILES string

Cl.CN1CN(c2ccccc2)C3(CCN(CCCC(=O)c4ccc(F)cc4)CC3)C1=O

InChI

1S/C24H28FN3O2.ClH/c1-26-18-28(21-6-3-2-4-7-21)24(23(26)30)13-16-27(17-14-24)15-5-8-22(29)19-9-11-20(25)12-10-19;/h2-4,6-7,9-12H,5,8,13-18H2,1H3;1H

InChI key

OGOQOKYYPNFSOL-UHFFFAOYSA-N

General description

N-Methylspiperone acts as a D2 dopamine receptor antagonist. It is an analog of spiperone. The isotope 3-N-[11C]methylspiperone ([11C]NMSP) is widely used in dopamine receptor imaging in positron emission tomography (PET).

Application

Reference standard.

Biochem/physiol Actions

D2 dopamine receptor antagonist.

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
095K4602
092K4608
081K4614
011K4606

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H D Burns et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 25(11), 1222-1227 (1984-11-01)
Carbon-11-labeled 3-N-methylspiperone, a positron-emitting dopamine-receptor antagonist with potential for use in positron emission tomography studies of human neurotransmitter receptors, was synthesized from 11CO2 in 40 min, with a radiochemical yield of approximately 20-40%. The specific activity of the (3-N-[11C]methyl)-spiperone was
O V Rice et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 25(5), 679-689 (2001-10-30)
Several studies have indicated that the in vivo binding of D(2) receptor positron emission tomography radiotracers can, under some conditions, be influenced by competition with endogenous dopamine. The present study was undertaken to compare the extent to which the in
Kiichi Ishiwata et al.
Nuclear medicine and biology, 29(3), 307-316 (2002-04-04)
With [11C]raclopride,[11C]nemonapride and [11C]N-methylspiperone, degeneration of dopamine D2-like receptors in the unilaterally quinolinic acid-lesioned rats was evaluated by positron emission tomography (PET) and ex vivo and in vitro autoradiography. PET showed a decreased uptake of [11C]raclopride in the lesioned striatum
J Logan et al.
Journal of neural transmission (Vienna, Austria : 1996), 108(3), 279-286 (2001-05-09)
Some discrepancies between experimental results with the two D2 antagonists N-methyl spiperone (NMSP) and raclopride (RAC) have been observed. Among these are the observation that MK-801 increases NMSP binding but not RAC binding: pretreatment with reserpine increases RAC binding but
Yuki Watanabe et al.
Metabolic brain disease, 23(3), 265-274 (2008-08-08)
Alterations of the brain dopamine system have been implicated in the neurological complications of chronic liver failure. The present study was aimed at the measurement of dopamine D(2) binding sites in cirrhotic patients by positron emission tomography (PET) using (11)C-N-methylspiperone
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