Azacyclonol

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Azacyclonol
Azacyclonol.png
Systematic (IUPAC) name
Diphenyl(piperidin-4-yl)methanol
Clinical data
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 YesY
UNII 2MMR990PEM YesY
ChEMBL CHEMBL127508 YesY
Synonyms MER-17, MDL-4,829
Chemical data
Formula C18H21NO 
Mol. mass 267.37 g/mol
 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]

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.[6]

See also[edit]

References[edit]

  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. 
  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. 
  3. ^ FARRANT J (June 1963). "Interactions between cocaine, tyramine and noradrenaline at the noradrenaline store". British Journal of Pharmacology and Chemotherapy 20: 540–9. doi:10.1111/j.1476-5381.1963.tb01491.x. PMC 1703814. PMID 13944436. 
  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. 
  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. doi:10.1016/0378-4347(95)00561-7. PMID 8738042. 
  6. ^ Campen Jr Marcus G Van, Pogge Raymond C, Schumann Edward L; Wm S Merrell Co; U.S. Patent 2,804,422 (1957).