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GBR 12935

CAT: 0804-HY-12242ASize: 1 EachDry Ice: NoHazardous: No
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Description
GBR 12935 is a potent, and selective dopamine reuptake inhibitor, with the binding constant (Kd) of 1.08 nM in COS-7 cells. GBR 12935 stimulates the locomotion activity in different mice strains but fails to induce stereotypy. Thus, GBR 12935 also prevents the d-Fenfluramine-induced head-twitch response in mice[1][2][3][4].
CAS Number
76778-22-8
UNSPSC
12352005
Hazard Statement
H302-H315-H319-H335
Target
Dopamine Transporter
Type
Reference compound
Related Pathways
Neuronal Signaling
Applications
Neuroscience-Neuromodulation
Field of Research
Neurological Disease
Assay Protocol
https://www.medchemexpress.com/gbr-12935.html
Solubility
10 mM in DMSO
Smiles
N1(CCOC(C2=CC=CC=C2)C3=CC=CC=C3)CCN(CCCC4=CC=CC=C4)CC1
Molecular Formula
C28H34N2O
Molecular Weight
414.58
Precautions
P261-P280-P302+P352
References & Citations
[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.|[4]Darmani NA. Cocaine and selective monoamine uptake blockers (sertraline, nisoxetine, and GBR 12935) prevent the d-fenfluramine-induced head-twitch response in mice. Pharmacol Biochem Behav. 1998 May;60 (1) :83-90.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

1-(2-(Diphenylmethoxy)ethyl)-4-(3-phenylpropyl)piperazine

1-[2-(benzhydryloxy)ethyl]-4-(3-phenylpropyl)piperazine is an N-alkylpiperazine that consists of piperazine bearing 2-(benzhydryloxy)ethyl and 3-phenylpropyl groups at positions 1 and 4 respectively. Potent and selective inhibitor of dopamine uptake (KD = 5.5 nM in rat striatal membranes). It has a role as a dopamine uptake inhibitor. It is an ether, a N-alkylpiperazine and a tertiary amino compound. It is a conjugate base of a 1-[2-(benzhydryloxy)ethyl]-4-(3-phenylpropyl)piperazinediium(2+).

CAS Number76778-22-8
PubChem CID3456
IUPAC Name1-(2-benzhydryloxyethyl)-4-(3-phenylpropyl)piperazine
Molecular FormulaC28H34N2O
Molecular Weight414.6
XLogP5.4
Topological Polar Surface Area15.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count10
Heavy Atom Count31
Formal Charge0
Complexity440
SMILES
C1CN(CCN1CCCC2=CC=CC=C2)CCOC(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChI=1S/C28H34N2O/c1-4-11-25(12-5-1)13-10-18-29-19-21-30(22-20-29)23-24-31-28(26-14-6-2-7-15-26)27-16-8-3-9-17-27/h1-9,11-12,14-17,28H,10,13,18-24H2
InChIKey
RAQPOZGWANIDQT-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 1-(2-(Diphenylmethoxy)ethyl)-4-(3-phenylpropyl)piperazine
CAS: 76778-22-8
CID: 3456
Formula: C28H34N2O
MW: 414.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight414.6
XLogP35.4
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count10
Exact Mass414.267113712
Monoisotopic Mass414.267113712
Topological Polar Surface Area15.7 Ų
Heavy Atom Count31
Formal Charge0
Complexity440
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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