Azacyclonol: Difference between revisions

| image = Azacyclonol.png

| tradename =

| routes_of_administration = Oral

| CAS_number = <!-- blanked - oldvalue: 115-46-8 -->

| synonyms = MER-17, MDL-4,829

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

| molecular_weight = 267.37 g/mol

| smiles = OC(c1ccccc1)(c2ccccc2)C3CCNCC3

'''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 [[hallucination]]s in [[psychotic]] individuals.<ref name="pmid13368052">{{Cite journal| author = 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 | year = 1956 | month = October | pmid = 13368052 | doi = | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=13368052}}</ref><ref name="isbn3-88763-075-0">{{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 | pages = | isbn = 3-88763-075-0 | oclc = | doi = | url = http://books.google.com/books?id=5GpcTQD_L2oC&lpg=PA84&as_brr=3&pg=PA84#v=onepage&q&f=false}}</ref> 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.<ref name="pmid13368052"/><ref name="pmid13944436">{{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 = | pages = 540–9 | year = 1963 | month = June | pmid = 13944436 | pmc = 1703814 | doi = | url = }}</ref>

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 drug|psychedelic]] effects of [[lysergic acid diethylamide|LSD]] and [[mescaline]] in humans.<ref name="pmid13368052"/><ref name="pmid13383414">{{Cite journal| author = 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 | year = 1957 | month = January | pmid = 13383414 | pmc = 1823487 | doi = | url = }}</ref> However, due to poor and mixed clinical effectiveness<ref name="pmid13383414"/> it never gained widespread acceptance and was eventually discontinued.

The [[antihistamine]] agent [[terfenadine]] produces azacyclonol as an [[activity (chemistry)|active]] major [[metabolite]].<ref name="pmid8738042">{{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 | year = 1996 | month = April | pmid = 8738042 | doi = | url = }}</ref>

==See also==

* [[Pipradrol]]

* [[Terfenadine]]

* [[Fexofenadine]]

[[Category:Piperidines]]

[[Category:Alcohols]]