Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H21NO |
Molecular Weight | 267.3654 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(C1CCNCC1)(C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=ZMISODWVFHHWNR-UHFFFAOYSA-N
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
Azacyclonol (aka gamma-pipradrol) is an ataractive agent; a compound which diminished hallucinations in psychotic individuals. It is sometimes referred to as a tranquilizer or antipsychotic, though it does not actually possess these properties. It was used in Europe during the 1950's for treatment of schizophrenia; likely to reduce the psychedelic effects of LSD and mescaline. However, it had mixed clinical effectiveness and did not gain widespread adoption and was eventually discontinued. Azacyclonol was sold under several trade names: Ataractan, Calmeran, Frenoton, Frenquel and Psychosan.
CNS Activity
Approval Year
PubMed
Title | Date | PubMed |
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Azacyclonol (frenquel) hydrochloride in the treatment of chronic schizophrenia; a double-blind, controlled study. | 1957 Sep 28 |
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Intravenous use of azacyclonol. | 1958 May |
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Azacyclonol in chronic schizophrenia. | 1959 Sep 1 |
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[Azacyclonol (Frenquel). Uses and results]. | 1960 Oct |
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THE HYPOGLYCAEMIC EFFECT OF AZACYCLONOL AND ITS MECHANISM. | 1963 Oct 1 |
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Interplay between CYP3A-mediated metabolism and polarized efflux of terfenadine and its metabolites in intestinal epithelial Caco-2 (TC7) cell monolayers. | 1999 May |
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The effect of rifampin administration on the disposition of fexofenadine. | 2001 Mar |
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Hepatobiliary disposition of a drug/metabolite pair: Comprehensive pharmacokinetic modeling in sandwich-cultured rat hepatocytes. | 2006 Aug |
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The effect of short- and long-term administration of verapamil on the disposition of cytochrome P450 3A and P-glycoprotein substrates. | 2006 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13383414
Chronic Schizophrenics were treated for four weeks with daily oral doses of 20 mg Frenquel to control the hallucinogenic effects of LSD. Twenty-one of thirty-eight patients showed definite improvements, while seven more showed doubtful-improvement. Frenquel was also used in oral doses of up to 400 mg daily.
Route of Administration:
Oral
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NCI_THESAURUS |
C28197
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m575
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3680
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SUB05628MIG
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15723
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C100095
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AZACYCLONOL
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204-092-5
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CHEMBL127508
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C76502
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ACTIVE MOIETY
PARENT (METABOLITE)
SALT/SOLVATE (PARENT)