Butaclamol
Chemical compound
From Wikipedia, the free encyclopedia
Butaclamol (AY-23,028) is a type of antipsychotic which was never marketed.[1] Sold as the hydrochloride salt for use in research, the compound acts as a dopamine receptor antagonist.[2]
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| Formula | C25H31NO |
| Molar mass | 361.529 g·mol−1 |
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Discussion
pKa = 7.15 (uncorrected for ionic strength)[3]
McN-4171 is an analog of butaclamol.[3][4] McN-4612-Y is also described in the attached article. This is similar to McN 4612-z except it is the opposite optical antipode. It is therefore supposedly an antipsychotic.
Synthesis
The synthesis has been reported:[5][6][7] Patent:[8]
- The starting material is made by a Favorskii reaction of dibenzosuberone with acetylene followed by a Meyer–Schuster rearrangement to the aldehyde and oxidation to the acid. Another method is Reformatsky reaction with bromoethylacetate and catalytic hydrogenation of the olefin in the ester that follows dehydration.
- The starting material is called 10,11-Dihydro-5H-dibenzo-[a,d]cycloheptene-5-acetic acid, PC12669091 (1). FGI by any of a number of methods to the isocyanate (NCO) gives (2). Addition of one equivalent of water gives N-formyl-10,11-dihydro-5H-dibenzo(a,d)cycloheptene-5-methylamine (3). Cyclization gives 1,7,8,12b-tetrahydrobenzo(6,7)cyclohept(1,2,3-de)isoquinoline [7574-72-3] (4). A modified Robinson annulation with methylvinylketone gave PC21397166 (5).
