Azacyclonol
- none
- BR: Class C1 (Other controlled substances)[1]
- In general: ℞ (Prescription only)
- Diphenyl(piperidin-4-yl)methanol
- 115-46-8
N
1798-50-1 (HCl)
- 15723
- 14952
Y
- 2MMR990PEM
- ChEMBL127508
Y
- DTXSID2045280
![Edit this at Wikidata](http://upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png)
- Interactive image
- OC(c1ccccc1)(c2ccccc2)C3CCNCC3
- InChI=1S/C18H21NO/c20-18(15-7-3-1-4-8-15,16-9-5-2-6-10-16)17-11-13-19-14-12-17/h1-10,17,19-20H,11-14H2
Y
- Key:ZMISODWVFHHWNR-UHFFFAOYSA-N
Y
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![check](http://upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png)
Azacyclonol (trade names Ataractan, Calmeran, Frenoton, Frenquel, Psychosan), also known as γ-pipradrol, is a drug which is an ataractive; an agent which diminishes hallucinations in psychotic individuals.[2][3] It has also been called a tranquilizer and antipsychotic, though these definitions are not accurate as it does not actually possess such properties. Despite being a positional isomer of pipradrol, it is not a psychostimulant, and instead has mild depressant effects.[2][4]
The drug was introduced in Europe in the mid-1950s for the treatment of schizophrenia likely because it was found to attenuate the subjective psychedelic effects of LSD and mescaline 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 as diphenylmethanolpiperidine and is the parent structure of the antihistamines fexofenadine and terfenadine. Terfenadine produces azacyclonol as a major active metabolite.[6]
It is made by the organometallic addition of 4-bromopyridine to benzophenone, followed by catalytic hydrogenation of the pyridine heteroaromatic ring system to the corresponding piperidine.[7]
References
- ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
- ^ a b c BRAUN DL, BROWN BB, FELDMAN RG (October 1956). "The pharmacologic activity of alpha-(4-piperidyl)-benzhydrol hydrochloride (azacyclonol hydrochloride); an ataractive agent". The Journal of Pharmacology and Experimental Therapeutics. 118 (2): 153–61. PMID 13368052. Archived from the original on 2019-12-08. Retrieved 2010-04-16.
- ^ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.
- ^ FARRANT J (June 1963). "Interactions between cocaine, tyramine and noradrenaline at the noradrenaline store". British Journal of Pharmacology and Chemotherapy. 20 (3): 540–9. doi:10.1111/j.1476-5381.1963.tb01491.x. PMC 1703814. PMID 13944436.
- ^ a b FORSTER W, HENDERSON AL (January 1957). "A clinical study of Frenquel (alpha (4-piperidyl) benzhydrol hydrochloride) in chronic schizophrenia". Canadian Medical Association Journal. 76 (2): 97–101. PMC 1823487. PMID 13383414.
- ^ Martens J (April 1996). "Determination of the terfenadine metabolite azacyclonol in human serum using gas chromatography-mass spectrometry". Journal of Chromatography B. 678 (2): 349–53. doi:10.1016/0378-4347(95)00561-7. PMID 8738042.
- ^ Campen Jr Marcus G Van, Pogge Raymond C, Schumann Edward L; Wm S Merrell Co; U.S. patent 2,804,422 (1957).
- v
- t
- e
- Butyrophenones: Benperidol
- Bromperidol
- Droperidol
- Haloperidol#
- Moperone
- Pipamperone
- Spiperone
- Timiperone
- Trifluperidol
- Phenothiazines: Acepromazine
- Acetophenazine
- Butaperazine
- Carphenazine (carfenazine)‡
- Chlorpromazine
- Cyamemazine
- Dixyrazine
- Fluphenazine
- Levomepromazine (methotrimeprazine)
- Mesoridazine
- Perazine
- Periciazine
- Perphenazine
- Piperacetazine
- Pipotiazine
- Prochlorperazine
- Promazine
- Sulforidazine
- Thiopropazate
- Thioproperazine
- Thioridazine
- Trifluoperazine
- Triflupromazine
- Others/unknown: Azacyclonol
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III