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Other names | Millipertine; WIN18935; WIN-18,935; Win-18935 |
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Chemical and physical data | |
Formula | C24H31N3O3 |
Molar mass | 409.530 g·mol−1 |
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Milipertine (INN , USAN ; developmental code name WIN-18935) is a drug of the pertine group described as an antipsychotic, neuroleptic, and tranquilizer which was under development for the treatment of schizophrenia but was never marketed. [1] [2] [3] [4]
Structurally, it is a substituted tryptamine and a piperazinylethylindole. [5] [6] [7] The drug is closely structurally related to other "pertines" including alpertine, oxypertine, and solypertine, which are also tryptamines and piperazinylethylindoles. [5] [6] [8]
The related drug oxypertine shows high affinity for the serotonin 5-HT2 and dopamine D2 receptors (Ki = 8.6 nM and 30 nM, respectively) and is also known to act as a catecholamine depleting agent. [9] [10] Oxypertine, milipertine, and solypertine all antagonize the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals. [9] [11] ortho-Methoxyphenylpiperazine (oMeOPP) has been said to be a metabolite of milipertine, as well as of oxypertine and several other drugs. [12] [13]
Milipertine produced troublesome side effects in clinical studies including orthostatic hypotension, drowsiness, extrapyramidal symptoms, elevated liver enzymes, and weight loss. [14] [15] [4] The side effects of milipertine occurred too frequently and at doses well below those producing antipsychotic effects and its development was abandoned. [14] [15] [4]
Milipertine was first described in the scientific literature by 1968. [1]
Pertines (class 7; Table 5.12) The pertines oxypertine, solypertine, milipertine, and alpertine are piperazinylethylindoles.
Furthermore, oMeOPP is a metabolite of some prescribed drugs: enciprazione, milipertine, urapidil, dropropizine and oxypertine.[1,47]