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COO/COA

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C156

D-CPT tartrate

Name: <SC>D</SC>-CPT tartrate
Brand: SIGMA

>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

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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.

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)

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Synthesis, ligand binding, and quantitative structure-activity relationship study of 3 beta-(4'-substituted phenyl)-2 beta-heterocyclic tropanes: evidence for an electrostatic interaction at the 2 beta-position.

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

Development of 3-phenyltropane analogues with high affinity for the dopamine and serotonin transporters and low affinity for the norepinephrine transporter.

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

[Pharmacology of troparil].

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

Synthesis, ligand binding, and QSAR (CoMFA and classical) study of 3 beta-(3'-substituted phenyl)-, 3 beta-(4'-substituted phenyl)-, and 3 beta-(3',4'-disubstituted phenyl)tropane-2 beta-carboxylic acid methyl esters.

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

Synthesis and transporter binding properties of 2,3-diphenyltropane stereoisomers. Comparison to 3beta-phenyltropane-2beta-carboxylic acid esters.

A C Chang et al.

Journal of medicinal chemistry, 40(8), 1247-1251 (1997-04-11)

2beta,3beta-Diphenyl-(5), 2alpha,3alpha-diphenyl-(6), and 2alpha,3beta-diphenyltropane (3) as well as 2,3-diphenyltrop-2-ene (4) were prepared in racemic form and assayed for inhibition of radioligand binding at the dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporters. Among all three transporters, compounds 4-6 bound the

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