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| Other names | MER-17; MDL-4829; Diphenylmethanolpiperidine |
| Routes of administration | Oral |
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| ECHA InfoCard | 100.003.720 |
| Chemical and physical data | |
| Formula | C18H21NO |
| Molar mass | 267.372 g·mol−1 |
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Azacyclonol (trade namesAtaractan,Calmeran,Frenoton,Frenquel,Psychosan), also known asγ-pipradrol, is adrug which is anataractive; an agent which diminisheshallucinations inpsychotic individuals.[2][3] It has also been called atranquilizer andantipsychotic, though these definitions are not accurate as it does not actually possess such properties. Despite being apositional isomer ofpipradrol, it is not apsychostimulant, and instead has milddepressant effects.[2][4]
The drug was introduced inEurope in the mid-1950s for the treatment ofschizophrenia likely because it was found to attenuate the subjectivepsychedelic effects ofLSD andmescaline in humans.[2][5] However, due to poor and mixed clinical effectiveness,[5] it never gained widespread acceptance and was eventually discontinued.
Azacyclonol is also known asdiphenylmethanolpiperidine and is theparent structure of theantihistaminesfexofenadine andterfenadine. Terfenadine produces azacyclonol as a majoractive metabolite.[6]
It is made by the organometallic addition of 4-bromopyridine tobenzophenone, followed by catalytic hydrogenation of the pyridine heteroaromatic ring system to the corresponding piperidine.[7]