Names | |
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Preferred IUPAC name
(Piperidin-1-yl){3-[(4-{2-[(propan-2-yl)oxy]phenyl}piperazin-1-yl)methyl]phenyl}methanone | |
Other names
RWJ-37796
| |
Identifiers | |
3D model (
JSmol)
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ChEMBL | |
ChemSpider | |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C26H35N3O2 | |
Molar mass | 421.585 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Mazapertine (RWJ-37796) is an antipsychotic agent that was developed by Johnson & Johnson but never marketed. It exerts its pharmacological effect through affinity for dopamine D2, serotonin 5-HT1A, and α1-adrenergic receptors. [1]
Mazapertine is safe and well tolerated when administered orally. [2]
Analogs of mazapertine with conformational restriction have been prepared and have greater affinity for the 5-HT1A receptor. [3]
The laboratory synthesis of mazapertine has been reported. [4] [5] [6] It begins with alkylation of 2-nitrophenol (1) with isopropyl bromide to give 2-isopropoxynitrobenzene (2). Catalytic hydrogenation of nitro group gives 2-isopropoxyaniline (3). Intermolecular ring formation of this aniline with bis(2-chloroethyl)amine yields 1-(2-isopropoxyphenyl)piperazine (4). Separately, amide formation of 3-(chloromethyl)benzoyl chloride (5) with piperidine gives 1-[3-(chloromethyl)benzoyl]piperidine (6). The last step is the convergent synthesis between the above two arms of the synthesis to afford the alkylation product mazapertine (7).
Names | |
---|---|
Preferred IUPAC name
(Piperidin-1-yl){3-[(4-{2-[(propan-2-yl)oxy]phenyl}piperazin-1-yl)methyl]phenyl}methanone | |
Other names
RWJ-37796
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEMBL | |
ChemSpider | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C26H35N3O2 | |
Molar mass | 421.585 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Mazapertine (RWJ-37796) is an antipsychotic agent that was developed by Johnson & Johnson but never marketed. It exerts its pharmacological effect through affinity for dopamine D2, serotonin 5-HT1A, and α1-adrenergic receptors. [1]
Mazapertine is safe and well tolerated when administered orally. [2]
Analogs of mazapertine with conformational restriction have been prepared and have greater affinity for the 5-HT1A receptor. [3]
The laboratory synthesis of mazapertine has been reported. [4] [5] [6] It begins with alkylation of 2-nitrophenol (1) with isopropyl bromide to give 2-isopropoxynitrobenzene (2). Catalytic hydrogenation of nitro group gives 2-isopropoxyaniline (3). Intermolecular ring formation of this aniline with bis(2-chloroethyl)amine yields 1-(2-isopropoxyphenyl)piperazine (4). Separately, amide formation of 3-(chloromethyl)benzoyl chloride (5) with piperidine gives 1-[3-(chloromethyl)benzoyl]piperidine (6). The last step is the convergent synthesis between the above two arms of the synthesis to afford the alkylation product mazapertine (7).