Ci

N^Jsl CH2CH2OH

Clopenthixol

CF3

N N CH2CH2oh

Flupenthixol

cf3

N_NCH3

Triperoxene

Figure 11.9. Chemical structure of the thioxanthine series of neuroleptics.

Figure 11.9. Chemical structure of the thioxanthine series of neuroleptics.

compounds with aliphatic (e.g. chlorprothixene), piperazine (e.g. clopenthixol, flupenthixol) or piperidine side chains. Their potency and side effects are essentially similar to the corresponding phenothiazine neuroleptics.

The butyrophenones and diphenylbutylpiperidines differ from the phenothia-zines and thioxanthines in that they are not tricyclic structures. The first butyrophenone to be developed was haloperidol, and this is the most widely used, potent neuroleptic. Unlike many of the phenothiazines, these neuroleptics largely lack antihistaminic, anticholinergic and adrenolytic activity; they are also non-sedative in therapeutic doses. Their potent antidopaminergic activity renders them likely to cause extrapyramidal side effects. Of the various butyrophenones shown in Figure 11.10, benperidol has been selectively used to suppress asocial sexual behaviour.

The diphenylbutylpiperidines are structurally related to the butyrophe-nones and have essentially similar properties. Pimozide is the most well-established member of this series and is a potent neuroleptic that, like other potent neuroleptics, is likely to cause extrapyramidal side effects.

Figure 11.10. Chemical structure of the butyrophenone and diphenylbutylpiper-idine series of neuroleptics indicates that N has been replaced by C.

Sulpiride is a member of a series of neuroleptics, the benzamides, of which the antiemetic drug metoclopramide is another example. The benzamides have a lower propensity to cause extrapyramidal side effects, probably because they show a high degree of selectivity for the D2 dopamine receptors.

The chemical structure of sulpiride is shown in Figure 11.11.

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