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C124

Sigma-Aldrich

β-CFT naphthalenedisulfonate monohydrate

solid

Synonym(s):

(−)-2-β-Carbomethoxy-3-β-(4-fluorophenyl)tropane 1,5-naphthalenedisulfonate monohydrate, WIN 35,428 naphthalenedisulfonate monohydrate

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About This Item

Empirical Formula (Hill Notation):
C16H20FNO2 · C10H8O6S2 · H2O
CAS Number:
77210-32-3
Molecular Weight:
583.65
MDL number:
MFCD11044874
UNSPSC Code:
12352200
PubChem Substance ID:
24892389
NACRES:
NA.77

form

solid

optical activity

[α]25/D −62.5°, c = 1.0 in H2O(lit.)

drug control

USDEA Schedule II

color

white

solubility

H2O: soluble

storage temp.

2-8°C

SMILES string

O.OS(=O)(=O)c1cccc2c(cccc12)S(O)(=O)=O.COC(=O)[C@@H]3C4CCC(C[C@@H]3c5ccc(F)cc5)N4C

InChI

1S/C16H20FNO2.C10H8O6S2.H2O/c1-18-12-7-8-14(18)15(16(19)20-2)13(9-12)10-3-5-11(17)6-4-10;11-17(12,13)9-5-1-3-7-8(9)4-2-6-10(7)18(14,15)16;/h3-6,12-15H,7-9H2,1-2H3;1-6H,(H,11,12,13)(H,14,15,16);1H2/t12-,13+,14+,15-;;/m0../s1

InChI key

XSJPWVYASBDEJI-YEVYTSHMSA-N

Biochem/physiol Actions

Cocaine analog that inhibits the dopamine, norepinephrine, and serotonin transporters with Kis of 26.1 nM, 31.9 nM, and 127 nM, respectively. [11C]-β-CFT and [18F]-β-CFT are ligands for PET imaging of the dopamine transporter in vivo.

Features and Benefits

This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Repr. 2 - Skin Sens. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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M Haaparanta et al.
Synapse (New York, N.Y.), 23(4), 321-327 (1996-08-01)
We describe the 18F-radiolabelling synthesis (18F; T(1/2) = 109.8 min) of 2-beta-carbomethoxy-3 beta-(4-fluorophenyl)tropane (also known as CFT or WIN 35,428) and the biodistribution of this compound in rats. 18F-labelled CFT has high chemical and radiochemical purity and relatively high specific
Imaging striatal dopaminergic function in phospholipase A2 group VI-related parkinsonism.
Pankaj Agarwal et al.
Movement disorders : official journal of the Movement Disorder Society, 27(13), 1698-1699 (2012-11-30)
Yan-Fen Zhang et al.
Nuclear medicine and biology, 38(8), 1205-1212 (2011-07-12)
Alterations of dopamine in striatal presynaptic terminals play an important role in the hypoxic-ischemic (HI) brain injury. Quantification of DAT levels in the presynaptic site using (11)C-N-2-carbomethoxy-3-(4-fluorophenyl)-tropane ((11)C-CFT) with positron emission tomography (PET) was applied in studies for Parkinson's disease.
U Scheffel et al.
Synapse (New York, N.Y.), 23(2), 61-69 (1996-06-01)
[11C]WIN 35,428 (also designated [11C]CFT) is now being used in several positron emission tomography (PET) centers to image dopamine (DA) transporter sites in the mammalian brain. Whether and to what extent in vivo WIN 35,428 binding is influenced by intra-
Thomas E Wooters et al.
Behavioural brain research, 219(1), 98-107 (2011-01-12)
Rats raised in an enriched condition (EC) are less sensitive to the locomotor effects of stimulant drugs than rats raised in an impoverished condition (IC). Methylphenidate (MPD), a primary pharmacotherapy for attention-deficit/hyperactivity disorder, has abuse potential. This study determined whether
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