Basic information
- CAS
76778-22-8- Standard SMILES
c1ccc(CCCN2CCN(CCOC(c3ccccc3)c3ccccc3)CC2)cc1- InChIKey
RAQPOZGWANIDQT-UHFFFAOYSA-N- Molecular formula
- C28H34N2O
- Average molar mass
- 414.6 g/mol
- Monoisotopic mass
- 414.26711371
Overview
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+).
Names & identifiers
- Preferred name
- 1-(2-(Diphenylmethoxy)ethyl)-4-(3-phenylpropyl)piperazine
- IUPAC
- 1-(2-benzhydryloxyethyl)-4-(3-phenylpropyl)piperazine
- English name
- 1-(2-Diphenylmethoxyethyl)-4-(3-phenylpropyl)piperazinedihydrochloride
- Molecular formula
- C28H34N2O
- Molecular weight
- 414.58
Names & synonyms
Show more names
Database identifiers
- CAS
76778-22-8- PubChem CID
- 3456
- DTXSID
DTXSID2043743- ChEMBL
CHEMBL26320- ChEBI
CHEBI:64093- UNII
- 9J9974WIBA
- Nikkaji
- J227.604F
Properties
Computed structural properties
- XLogP
- 5.4
- Topological polar surface area
- 15.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 10
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 440
Experimental & physicochemical properties
Ionization Efficiency
Positive
4.61
2.7
Agilent XCT
Electrospray ionization
formic acid (5.3nM)
Physicochemical properties
- Boiling point
- 540.6 · 540.6±50.0 °C(Predicted)
- Density
- 1.067 · 1.067±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Desiccate at -20°C
- solubility
- Soluble in DMSO
- form
- Powder
- pka
- 7.55 · 7.55±0.10(Predicted)
- FDA UNII
- 9 J9974WIBA · 9J9974WIBA
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 280 · P280-P305+P351+P338
Safety & regulation
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Applications
UsesGBR 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].
Suppliers45 total
Additional notes
DefinitionChEBI: 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 stria al membranes).
Related reactions
No reaction records under the current filter.
Compound notes
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