Azacyclonol
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Azacyclonol
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|---|---|
| Systematic (IUPAC) name | |
| Diphenyl(piperidin-4-yl)methanol | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ℞ Prescription only |
| Routes | Oral |
| Identifiers | |
| CAS number | 115-46-8  1798-50-1 (HCl) |
| ATC code | None |
| PubChem | CID 15723 |
| ChemSpider | 14952  |
| UNII | 2MMR990PEM |
| ChEMBL | CHEMBL127508 |
| Synonyms | MER-17, MDL-4,829 |
| Chemical data | |
| Formula | C18H21NO |
| Mol. mass | 267.37 g/mol |
| SMILES | eMolecules & PubChem |
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Azacyclonol (trade names Ataractan, Calmeran, Frenoton, Frenquel, Psychosan), also known as γ-pipradol, is a drug which is a so-called ataractive, or agent which diminishes hallucinations in psychotic individuals.[1][2] 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.[1][3]
The drug was introduced in Europe in the mid 1950s for the treatment of schizophrenia likely on account of the fact that it was found to attenuate the subjective psychedelic effects of LSD and mescaline in humans.[1][4] However, due to poor and mixed clinical effectiveness[4] it never gained widespread acceptance and was eventually discontinued.
The antihistamine agent terfenadine produces azacyclonol as an active major metabolite.[5]
See also
References
- ^ 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. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=13368052.
- ^ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0. http://books.google.com/books?id=5GpcTQD_L2oC&lpg=PA84&as_brr=3&pg=PA84#v=onepage&q&f=false.
- ^ FARRANT J (June 1963). "Interactions between cocaine, tyramine and noradrenaline at the noradrenaline store". British Journal of Pharmacology and Chemotherapy 20: 540–9. PMC 1703814. PMID 13944436. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1703814.
- ^ 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. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1823487.
- ^ 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. PMID 8738042.
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