Azacyclonol

Azacyclonol
Systematic (IUPAC) name
Diphenyl(piperidin-4-yl)methanol
Clinical data
Pregnancy cat.  ?
Legal status Prescription only
Routes Oral
Identifiers
CAS number 115-46-8 N
1798-50-1 (HCl)
ATC code None
PubChem CID 15723
ChemSpider 14952 Y
UNII 2MMR990PEM Y
ChEMBL CHEMBL127508 Y
Synonyms MER-17, MDL-4,829
Chemical data
Formula C18H21NO 
Mol. mass 267.37 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

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

  1. ^ 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. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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.