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Merck

C156

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

Key Documents

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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.

Disclaimer

Hygroscopic

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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V V Zakusov et al.
Farmakologiia i toksikologiia, 48(1), 15-19 (1985-01-01)
The physiological action of the tropan derivative troparil (2-beta-methoxycarbonyl-3-beta-phenyltropan or 2-exo-3-exo-2-carbomethoxy-aryltropan was studied. Troparil was demonstrated to be a highly active stimulant of the nervous activity according to a lot of parameters. The drug appeared more powerful than amphetamine but
P Kotian et al.
Journal of medicinal chemistry, 39(14), 2753-2763 (1996-07-05)
A set of 3 beta-(4'-substituted phenyl)-2 beta-heterocyclic tropanes was designed, synthesized, and characterized. We discovered that these compounds can function as bioisosteric replacements for the corresponding WIN 35,065-2 analogs which possess a 2 beta-carbomethoxy group. Several of the compounds showed
J W Boja et al.
European journal of pharmacology, 184(2-3), 329-332 (1990-08-10)
Two potent cocaine analogs have been developed that have the highest known affinities for the cocaine binding site in rat striatum. Both 3 beta-(4-chlorophenyl)- (RTI-COC-31) and 3 beta-(4-methylphenyl)-tropane-2-carboxylic acid methyl ester (RTI-COC-32) compete for [3H]WIN 35,428 and [3H]mazindol binding with
Chunyang Jin et al.
Journal of medicinal chemistry, 51(24), 8048-8056 (2008-12-05)
Previous studies showed that the mixed monoamine transporter inhibitor (6, RTI-112) reduced cocaine self-administration at a high level of serotonin transporter (5-HTT) occupancy with no detectable dopamine transporter (DAT) occupancy. In this study, a series of 3beta-(substituted phenyl)tropane-2beta-carboxylic acid methyl
F I Carroll et al.
Journal of medicinal chemistry, 37(18), 2865-2873 (1994-09-02)
Several new 3 beta-(4'-substituted phenyl)-, 3-beta-(3'-substituted phenyl)-, and 3 beta-(3',4'-disubstituted phenyl)tropane-2 beta-carboxylic acid methyl esters were prepared and assayed for inhibition of [3H]WIN 35,428 binding to the dopamine transporter. The 3 beta-(3',4'-dichloro) and 3 beta-(4'-chloro-3'-methyl) analogues (2w and 2y; RTI-111
View All Related Papers

Global Trade Item Number

SKUGTIN
C156-5MG04061832269825

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