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Merck
CN

S4063

SCH-202676 hydrobromide

98%

Synonym(s):

N-(2,3-diphenyl-1,2,4-thiadiazol-5-(2H)-ylidene)methanamine hydrobromide

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About This Item

Empirical Formula (Hill Notation):
C15H16BrN3S
CAS Number:
265980-25-4
Molecular Weight:
350.28
NACRES:
NA.77
PubChem Substance ID:
24278706
UNSPSC Code:
12352200
MDL number:
MFCD06671539

Key Documents

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InChI key

YJYGOWVFDGULLL-GEEYTBSJSA-N

SMILES string

Br.C\N=C1\SN(c2ccccc2)C(=N1)c3ccccc3

InChI

1S/C15H13N3S.BrH/c1-16-15-17-14(12-8-4-2-5-9-12)18(19-15)13-10-6-3-7-11-13;/h2-11H,1H3;1H/b16-15+;

assay

98%

mp

240.0-240.8 °C (lit.)

solubility

DMSO: 40 mg/mL, H2O: insoluble

General description

Modulates radioligand binding to various GPCRs including the human μ-, δ-, and κ-opiod, α- and β-adrenergic, muscarinic M1 and M2, and dopaminergic D1 and D2 receptors.
Shown to modulate radioligand binding to various GPCRs including the human μ-, δ-, and κ-opiod, α- and β-adrenergic, muscarinic M1 and M2, and dopaminergic D1 and D2 receptors. Modulation is G-protein independent and is both selective and reversible.

Application

SCH-202676 hydrobromide may be used in G protein-coupled receptor-mediated cell signaling studies.

Biochem/physiol Actions

Allosteric agonist and antagonist of G-protein coupled receptors (GPCRs).
SCH-202676 inhibits the binding of both agonists and antagonists to G protein-coupled receptors. It also inhibits human μ-, δ-, and κ-opioid, α- and β-adrenergic, muscarinic M1 and M2, and dopaminergic D1 and D2 receptors. Some reports indicates thiol modification as the mechanism of inhibition rather than allosteric modulation.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
021K4608

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Anna M Lewandowicz et al.
British journal of pharmacology, 147(4), 422-429 (2006-01-13)
1. Previous studies suggest that the thiadiazole compound SCH-202676 (N-(2,3-diphenyl-1,2,4-thiadiazol-5-(2H)-ylidene)methanamine) acts as an allosteric modulator of a variety of structurally distinct G protein-coupled receptors (GPCRs). It was postulated that SCH-202676 would directly bind a structural motif in the receptor molecule
A B Fawzi et al.
Molecular pharmacology, 59(1), 30-37 (2000-12-23)
A novel thiadiazole compound, SCH-202676 (N-(2,3-diphenyl-1,2, 4-thiadiazol-5-(2H)-ylidene)methanamine), has been identified as an inhibitor of both agonist and antagonist binding to G protein-coupled receptors (GPCRs). SCH-202676 inhibited radioligand binding to a number of structurally distinct, heterologously expressed GPCRs, including the human

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