CAS 67469-81-2|GBR 12935 dihydrochloride

Introduction：Basic information about CAS 67469-81-2|GBR 12935 dihydrochloride, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. GBR 12935 dihydrochloride BiologicalActivity
3. Chemical & Physical Properties
4. Safety Information
5. Articles5
6. Synonyms

Common Name	GBR 12935 dihydrochloride
CAS Number	67469-81-2	Molecular Weight	487.504
Density	/	Boiling Point	564ºC at 760 mmHg
Molecular Formula	C₂₈H₃₆Cl₂N₂O	Melting Point	/
MSDS	USA	Flash Point	294.9ºC

Names

Name	1-(2-benzhydryloxyethyl)-4-(3-phenylpropyl)piperazine,dihydrochloride
Synonym	More Synonyms

GBR 12935 dihydrochloride BiologicalActivity

Description	GBR 12935 2Hcl is a potent, and selective dopamine reuptake inhibitor.IC50 value: Target: dopamine reuptake inhibitorin vitro: The calculated Kd of [3H]GBR-12935 binding to CYP2D6 was 42.2 nM, indicating that GBR-12935 has a high affinity for CYP2D6. The binding of [3H]GBR-12935 to CYP2D6 was decreased partially by substrates or inhibitors of CYP2D isoforms (quinine, quinidine, propranolol, bufuralol, imipramine, and desipramine) [1]. Co-perfusion of 100 microM GBR 12909 or GBR 12935 with either 100 microM sulpiride or raclopride produced a significant reduction in the GBR 12909 or GBR 12935 induced increase in the extracellular levels of dopamine to basal levels. In vitro, GBR 12909 (1-9 nM) dose-dependently inhibited active uptake of [3H]dopamine in homogenates of the nucleus accumbens [2].in vivo: GBR 12935 elevated locomotion to a greater extent in C57BL/6J mice at the maximally active dose of 10 mg/kg. Locomotor stimulation by GBR 12935 remained consistent in both strains with repeated injections. DBA/2J mice became sensitized to cocaine-induced stereotypy with repeated injections. Cocaine induced no stereotypy in C57BL/6J mice on any test day. No stereotypies were induced by GBR 12935 in either strain on any test day [3].
Related Catalog	Signaling Pathways >>Neuronal Signaling >>Dopamine TransporterResearch Areas >>Neurological Disease
References	[1]. Hiroi T, et al. Specific binding of 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenyl propyl) piperazine (GBR-12935), an inhibitor of the dopamine transporter, to human CYP2D6. Biochem Pharmacol. 1997 Jun 15;53(12):1937-9. [2]. Rahman S, et al. Negative interaction of dopamine D2 receptor antagonists and GBR 12909 and GBR 12935 dopamine uptake inhibitors in the nucleus accumbens. Eur J Pharmacol. 2001 Feb 23;414(1):37-44. [3]. Tolliver BK, et al. Comparison of cocaine and GBR 12935: effects on locomotor activity and stereotypy in two inbred mouse strains. Pharmacol Biochem Behav. 1994 Jul;48(3):733-9.

Description

GBR 12935 2Hcl is a potent, and selective dopamine reuptake inhibitor.IC50 value: Target: dopamine reuptake inhibitorin vitro: The calculated Kd of [3H]GBR-12935 binding to CYP2D6 was 42.2 nM, indicating that GBR-12935 has a high affinity for CYP2D6. The binding of [3H]GBR-12935 to CYP2D6 was decreased partially by substrates or inhibitors of CYP2D isoforms (quinine, quinidine, propranolol, bufuralol, imipramine, and desipramine) [1]. Co-perfusion of 100 microM GBR 12909 or GBR 12935 with either 100 microM sulpiride or raclopride produced a significant reduction in the GBR 12909 or GBR 12935 induced increase in the extracellular levels of dopamine to basal levels. In vitro, GBR 12909 (1-9 nM) dose-dependently inhibited active uptake of [3H]dopamine in homogenates of the nucleus accumbens [2].in vivo: GBR 12935 elevated locomotion to a greater extent in C57BL/6J mice at the maximally active dose of 10 mg/kg. Locomotor stimulation by GBR 12935 remained consistent in both strains with repeated injections. DBA/2J mice became sensitized to cocaine-induced stereotypy with repeated injections. Cocaine induced no stereotypy in C57BL/6J mice on any test day. No stereotypies were induced by GBR 12935 in either strain on any test day [3].

Related Catalog

Signaling Pathways >>Neuronal Signaling >>Dopamine TransporterResearch Areas >>Neurological Disease

References

[1]. Hiroi T, et al. Specific binding of 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenyl propyl) piperazine (GBR-12935), an inhibitor of the dopamine transporter, to human CYP2D6. Biochem Pharmacol. 1997 Jun 15;53(12):1937-9.

[2]. Rahman S, et al. Negative interaction of dopamine D2 receptor antagonists and GBR 12909 and GBR 12935 dopamine uptake inhibitors in the nucleus accumbens. Eur J Pharmacol. 2001 Feb 23;414(1):37-44.

[3]. Tolliver BK, et al. Comparison of cocaine and GBR 12935: effects on locomotor activity and stereotypy in two inbred mouse strains. Pharmacol Biochem Behav. 1994 Jul;48(3):733-9.

Chemical & Physical Properties

Boiling Point	564ºC at 760 mmHg
Molecular Formula	C₂₈H₃₆Cl₂N₂O
Molecular Weight	487.504
Flash Point	294.9ºC
Exact Mass	486.220459
PSA	15.71000
LogP	6.52280
Appearance of Characters	white solid
InChIKey	NQWRSILGEXNJIT-UHFFFAOYSA-N
SMILES	Cl.Cl.c1ccc(CCCN2CCN(CCOC(c3ccccc3)c3ccccc3)CC2)cc1
Storage condition	-20℃

Safety Information

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR	NONH for all modes of transport

Articles5

Plasma membrane monoamine transporters: structure, regulation and function.

Nat. Rev. Neurosci. 4 , 13-25, (2003)

Studies of the biogenic amine transporters. III. Demonstration of two binding sites for [3H]GBR12935 and [3H]BTCP in rat caudate membranes.

J. Pharmacol. Exp. Ther. 268 , 1462-1475, (1994)

The present study addressed the hypothesis that there exist multiple sites/states associated with the dopamine (DA) transporter ligands. The authors used [3H](1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylp...

[3H]GBR-12935 binding to cytochrome P450 in the human brain.

J. Neurochem. 62 , 342-348, (1994)

The presence of multiple [3H]GBR-12935 binding sites in the human brain has been revealed in several recent studies. One site represents the dopamine uptake site. In rat brain it was demonstrated that...

Synonyms

1-[2-(benzhydryloxy)ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride

1-[2-(Diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine dihydrochloride

Piperazine, 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)-, hydrochloride (1:2)

1-(2-DIPHENYLMETHOXYETHYL)-4-(3-PHENYLPROPYL)PIPERAZINE DIHYDROCHLORIDE

GBR 12935 dihydrochloride

GBR 12935 (dihydrochloride)

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