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C156

Sigma-Aldrich

D-CPT tartrate

>94%, solid

Synonym(s):

β-CPT tartrate, (–)-2β-Carbomethoxy-3β-phenyltropane tartrate, Troparil tartrate, WIN 35,065-2

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About This Item

Empirical Formula (Hill Notation):
C16H21NO2 · C4H6O6
CAS Number:
50372-80-0
Molecular Weight:
409.43
UNSPSC Code:
12352202
PubChem Substance ID:
329774896
NACRES:
NA.77

assay

>94%

form

solid

optical activity

[α]22/D −95.9°, c = 1.1 in H2O(lit.)

drug control

USDEA Schedule II; Home Office Schedule 2; regulated under CDSA - not available from Sigma-Aldrich Canada

color

white

solubility

H2O: soluble
ethanol: soluble

storage temp.

−20°C

SMILES string

OC(C(O)C(O)=O)C(O)=O.COC(=O)[C@@H]1C2CCC(C[C@@H]1c3ccccc3)N2C

InChI

1S/C16H21NO2.C4H6O6/c1-17-12-8-9-14(17)15(16(18)19-2)13(10-12)11-6-4-3-5-7-11;5-1(3(7)8)2(6)4(9)10/h3-7,12-15H,8-10H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t12-,13+,14+,15-;/m0./s1

InChI key

WYGLYLVLBCZESH-PEVLCXCCSA-N

Biochem/physiol Actions

Binds to the cocaine receptor site on the dopamine transporter and blocks dopamine uptake.

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.

Caution

Hygroscopic

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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M C Ritz et al.
Journal of neurochemistry, 55(5), 1556-1562 (1990-11-01)
[3H]WIN 35,065-2 binding to striatal membranes was characterized, primarily by centrifugation assay. Like [3H]cocaine, [3H]WIN 35,065-2 binds to both high- and low-affinity sites. [3H]WIN 35,065-2, however, exhibits consistently higher affinities than [3H]cocaine. Saturation experiments indicate a low-affinity binding site with
S A Lomenzo et al.
Journal of medicinal chemistry, 40(26), 4406-4414 (1998-01-22)
A series of 6-alkyl-3 beta-benzyl-2-[(methoxycarbonyl)methyl]tropane analogues were synthesized and evaluated as cocaine binding site ligands at the dopamine transporter (DAT). The in vitro affinity (Ki) for the DAT of the 6-alkyl-3 beta-benzyl-2-[(methoxycarbonyl) methyl]tropane analogues was determined by inhibition of [3H]WIN
U Schäfer et al.
Neuroreport, 6(14), 1833-1836 (1995-10-02)
The effect of intraventricular fetal mesencephalic grafts placed in the previously 6-hydroxydopamine (6-OHDA) lesioned striatum on the kinetics of [3H]dopamine (DA) uptake into striatal synaptosomes prepared from the non-lesioned (contralateral) striatum was studied in rats. Using WIN 35,065 as specific
T U Järbe
British journal of pharmacology, 73(4), 843-852 (1981-08-01)
1 Pigeons trained to discriminate between the presence or absence of effects induced by cocaine hydrochloride (5.6 mg/kg) were tested for generalization with norcocaine and two phenyltropane analogues (WIN 35,428 and WIN 35,065-2). Separate dose-effect curves were obtained at different
Emily M Jutkiewicz et al.
Annals of emergency medicine, 54(3), 409-420 (2008-11-18)
Cocaine toxicity results in cardiovascular complications, seizures, and death and accounts for approximately 20% of drug-related emergency department visits every year. Presently, there are no treatments to eliminate the toxic effects of cocaine. The present study hypothesizes that a bacterial
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