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| Other names | GEA-654; 4-Chloro-α,α-dimethylphenethylalaninate;para-Chloro-α,α-dimethylphenethylalaninate;DL-Alaninep-chloro-α,α-dimethylphenylethyl ester |
| Routes of administration | Oral |
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| Formula | C13H18ClNO2 |
| Molar mass | 255.74 g·mol−1 |
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Alaproclate (developmental code nameGEA-654) is adrug that was beingdeveloped as anantidepressant by theSwedishpharmaceutical companyAstra AB (nowAstraZeneca) in the 1970s.[1]
It acts as aselective serotonin reuptake inhibitor (SSRI), and along withzimelidine andindalpine, was one of the first of its kind. Development was discontinued due to the observation ofliver complications inrodent studies. In addition to its SSRI properties, alaproclate has been found to act as anon-competitiveNMDA receptor antagonist, but does not havediscriminative stimulus properties similar tophencyclidine (PCP).[2][3]
The drug is similar inchemical structure tochlorphentermine,cloforex, andcericlamine, but is not itself aphenethylamine oramphetamine as it has anoxygenatom in place of theaminenitrogen.[1]
Alaproclate was first described in thescientific literature by 1978.[1]
TheGrignard reagent,methylmagnesium iodide, reacts with methyl 4-chlorophenylacetate (1) to give thetertiary alcohol 1-(4-chlorophenyl)-2-methyl-2-propanol (2).Acylation with 2-bromopropionyl bromide (3) gives theester (4) which, when treated with ammonia, yields alaproclate.[4][5]
