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M120

Sigma-Aldrich

Metaphit methanesulfonate salt

≥98% (HPLC), solid

Synonym(s):

1-[1-(3-Isothiocyanato)phenyl]cyclohexylpiperidine methanesulfonate salt

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About This Item

Linear Formula:
C18H24N2S · CH3SO3H
CAS Number:
99287-12-4
Molecular Weight:
396.57
MDL number:
MFCD00069307
UNSPSC Code:
12352200
PubChem Substance ID:
24278579

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

color

white

solubility

H2O: >20 mg/mL

storage temp.

−20°C

SMILES string

CS(O)(=O)=O.S=C=Nc1cccc(c1)C2(CCCCC2)N3CCCCC3

InChI

1S/C18H24N2S.CH4O3S/c21-15-19-17-9-7-8-16(14-17)18(10-3-1-4-11-18)20-12-5-2-6-13-20;1-5(2,3)4/h7-9,14H,1-6,10-13H2;1H3,(H,2,3,4)

InChI key

ZASHKPXYYPYQRI-UHFFFAOYSA-N

Gene Information

human ... OPRS1(10280)

Biochem/physiol Actions

Metaphit methanesulfonate salt is an irreversible, non-competitive antagonist at the phencyclidine site on the NMDA receptor; sigma receptor irreversible, competitive antagonist.

Caution

Hygroscopic

Storage Class Code

13 - Non 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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I Zimányi et al.
Synapse (New York, N.Y.), 3(3), 239-245 (1989-01-01)
[3H]Mazindol was used to label the dopamine uptake complex in mouse striatum in vitro in the presence and absence of metaphit, an isothiocyanate derivative of phencyclidine. In some experiments, metaphit was present in the incubation fluid throughout the procedure; in
L S Bluth et al.
European journal of pharmacology, 161(2-3), 273-277 (1989-02-28)
Pretreatment of guinea pig brain membranes with 1-[1-(3-isothiocyanatophenyl)cyclohexyl]piperidine (Metaphit) caused irreversible and differential inhibition of ligand binding to sigma (sigma) receptors. The concentration of Metaphit required to produce 50% inhibition of binding of [3H]1,3-di-o-tolylguanidine ([3H]DTG), [3H](+)-3-(3-hydroxy-phenyl)-N-(1-propyl)piperidine ([3H](+)-3-PPP), and [3H](+)-N-allylnormetazocine ([3H](+)-SKF
E D French et al.
European journal of pharmacology, 140(3), 267-274 (1987-08-21)
Metaphit, a derivative of phencyclidine (PCP) which irreversibly binds to a population of PCP receptor sites in rat brain, has been considered as a potentially specific PCP antagonist. In whole animal studies, however, metaphit has been shown to have either

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