Azacyclonol

Medication which diminishes hallucinations From Wikipedia, the free encyclopedia

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]

Other namesMER-17; MDL-4829; Diphenylmethanolpiperidine
Routes of
administrationOral
ATC code
  • none
Legal status
  • BR: Class C1 (Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Quick facts Clinical data, Other names ...
Azacyclonol
Clinical data
Other namesMER-17; MDL-4829; Diphenylmethanolpiperidine
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • BR: Class C1 (Other controlled substances)[1]
  • In general: ℞ (Prescription only)
Identifiers
  • Diphenyl(piperidin-4-yl)methanol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.003.720 Edit this at Wikidata
Chemical and physical data
FormulaC18H21NO
Molar mass267.372 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:ZMISODWVFHHWNR-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)
Close

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]

See also

References

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