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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:
Molecular Weight:
409.43
UNSPSC Code:
12352202
PubChem Substance ID:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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R D Spealman et al.
The Journal of pharmacology and experimental therapeutics, 225(3), 509-514 (1983-06-01)
Intramuscular injections of the stereoisomers of cocaine and of its phenyltropane analog were compared for their effects on schedule-controlled behavior of squirrel monkeys. Monkeys responded by pressing a lever under a multiple schedule with alternating fixed-interval and fixed-ratio components; responding
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
Cocaine receptors: in vivo labeling with 3H-(-)cocaine, 3H-WIN 35,065-2, and 3H-WIN 35,428.
U Scheffel et al.
Synapse (New York, N.Y.), 4(4), 390-392 (1989-01-01)
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
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

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