Azacyclonol

{{Short description|Medication which diminishes hallucinations}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 458783562

| IUPAC_name = Diphenyl(piperidin-4-yl)methanol

| image = Azacyclonol.svg

| image_class = skin-invert-image

| tradename =

| legal_AU =

| legal_BR = C1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_US =

| legal_UK =

| legal_UN =

| legal_status = Rx-only

| routes_of_administration = Oral

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 115-46-8

| CAS_supplemental =
{{CAS|1798-50-1}} (HCl)

| ATC_prefix = none

| PubChem = 15723

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 14952

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 2MMR990PEM

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 127508

| synonyms = MER-17; MDL-4829; Diphenylmethanolpiperidine

| C=18 | H=21 | N=1 | O=1

| SMILES = OC(c1ccccc1)(c2ccccc2)C3CCNCC3

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ZMISODWVFHHWNR-UHFFFAOYSA-N

}}

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.{{Cite journal | vauthors = BRAUN DL, BROWN BB, FELDMAN RG | title = The pharmacologic activity of alpha-(4-piperidyl)-benzhydrol hydrochloride (azacyclonol hydrochloride); an ataractive agent | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 118 | issue = 2 | pages = 153–61 | date = October 1956 | pmid = 13368052 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=13368052 | access-date = 2010-04-16 | archive-date = 2019-12-08 | archive-url = https://web.archive.org/web/20191208002146/http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=13368052 | url-status = dead }}{{Cite book| author = Swiss Pharmaceutical Society | title = Index Nominum 2000: International Drug Directory (Book with CD-ROM) | publisher = Medpharm Scientific Publishers | location = Boca Raton | year = 2000 | isbn = 3-88763-075-0 | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA84}} 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.{{Cite journal| author = FARRANT J | title = Interactions between cocaine, tyramine and noradrenaline at the noradrenaline store | journal = British Journal of Pharmacology and Chemotherapy | volume = 20 | issue = 3| pages = 540–9 |date=June 1963 | pmid = 13944436 | pmc = 1703814 | doi = 10.1111/j.1476-5381.1963.tb01491.x}}

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.{{Cite journal|vauthors=FORSTER W, HENDERSON AL | title = A clinical study of Frenquel (alpha (4-piperidyl) benzhydrol hydrochloride) in chronic schizophrenia | journal = Canadian Medical Association Journal | volume = 76 | issue = 2 | pages = 97–101 |date=January 1957 | pmid = 13383414 | pmc = 1823487 }} However, due to poor and mixed clinical effectiveness, 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.{{Cite journal| author = Martens J | title = Determination of the terfenadine metabolite azacyclonol in human serum using gas chromatography-mass spectrometry | journal = Journal of Chromatography B | volume = 678 | issue = 2 | pages = 349–53 |date=April 1996 | pmid = 8738042 | doi = 10.1016/0378-4347(95)00561-7}}

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.Campen Jr Marcus G Van, Pogge Raymond C, Schumann Edward L; Wm S Merrell Co; {{US patent|2804422}} (1957).