Clinical data | |
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Trade names | Devryl, Olaxin, [1] Develar [2] [3] |
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CompTox Dashboard ( EPA) | |
Chemical and physical data | |
Formula | C18H21ClN2 |
Molar mass | 300.83 g·mol−1 |
3D model ( JSmol) | |
Density | 1.120 g/cm3 [1] |
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Clomacran is an antipsychotic drug of the dihydro acridine class, developed in the 1970s [2] by the pharmaceutical company Smith, Kline & French (now GlaxoSmithKline) under the brand names Devryl and Olaxin. [1]
It was used to treat schizophrenia in the 70s. [6] It was withdrawn from the market in the UK, due to liver toxicity, in 1982. [4] [7] [8]
The first step involves FGI of 3-chloro-N,N-dimethylpropylamine Fb: [109-54-6] (2) into the Grignard reagent, i.e. (3-(Dimethylamino)propyl)magnesium chloride [19070-16-7] ([154034-91-0]). The Grignard reaction with 2-chloroacridone [7497-52-1] (1) affords the tertiary carbinol (3). Dehydration by means of acid or simply heat gives the corresponding olefin (4). Catalytic reduction completes the synthesis of (5).
Clinical data | |
---|---|
Trade names | Devryl, Olaxin, [1] Develar [2] [3] |
ATC code | |
Legal status | |
Legal status | |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
ChEBI | |
ChEMBL | |
CompTox Dashboard ( EPA) | |
Chemical and physical data | |
Formula | C18H21ClN2 |
Molar mass | 300.83 g·mol−1 |
3D model ( JSmol) | |
Density | 1.120 g/cm3 [1] |
| |
|
Clomacran is an antipsychotic drug of the dihydro acridine class, developed in the 1970s [2] by the pharmaceutical company Smith, Kline & French (now GlaxoSmithKline) under the brand names Devryl and Olaxin. [1]
It was used to treat schizophrenia in the 70s. [6] It was withdrawn from the market in the UK, due to liver toxicity, in 1982. [4] [7] [8]
The first step involves FGI of 3-chloro-N,N-dimethylpropylamine Fb: [109-54-6] (2) into the Grignard reagent, i.e. (3-(Dimethylamino)propyl)magnesium chloride [19070-16-7] ([154034-91-0]). The Grignard reaction with 2-chloroacridone [7497-52-1] (1) affords the tertiary carbinol (3). Dehydration by means of acid or simply heat gives the corresponding olefin (4). Catalytic reduction completes the synthesis of (5).