Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Adatanserin: Difference between pages

{{Short description|Chemical compound}}

| image = Adatanserin.svg

| tradename =

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| routes_of_administration =

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 127266-56-2

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

| ChEMBL = 2107510

| C=21 | H=31 | N=5 | O=1

'''Adatanserin''' ('''WY-50,324''', '''SEB-324''') is a mixed [[5-HT1A receptor|5-HT_1A receptor]] [[partial agonist]] and [[5-HT2A receptor|5-HT_2A]] and [[5-HT2C receptor|5-HT_2C receptor]] [[receptor antagonist|antagonist]].<ref name="pmid8497336">{{cite journal |vauthors=Singh A, Lucki I | title = Antidepressant-like activity of compounds with varying efficacy at 5-HT1A receptors | journal = Neuropharmacology | volume = 32 | issue = 4 | pages = 331–40 |date=April 1993| pmid = 8497336 | doi = 10.1016/0028-3908(93)90153-T| s2cid = 38611829 }}</ref><ref name="pmid8632301">{{cite journal |vauthors=Kleven MS, Koek W | title = Pharmacological characterization of in vivo properties of putative mixed 5-HT1A agonist/5-HT2A/2C antagonist anxiolytics. I. Antipunishment effects in the pigeon | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 276 | issue = 2 | pages = 388–97 |date=February 1996| pmid = 8632301 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8632301}}</ref><ref name="pmid10602693">{{cite journal |vauthors=Abou-Gharbia MA, Childers WE, Fletcher H | title = Synthesis and SAR of adatanserin: novel adamantyl aryl- and heteroarylpiperazines with dual serotonin 5-HT(1A) and 5-HT(2) activity as potential anxiolytic and antidepressant agents | journal = Journal of Medicinal Chemistry | volume = 42 | issue = 25 | pages = 5077–94 |date=December 1999| pmid = 10602693 | doi = 10.1021/jm9806704|display-authors=etal}}</ref> It was under development by [[Wyeth]] as an [[antidepressant]] but was ultimately not pursued.<ref name="pmid10602693"/><ref name="isbn0-521-64615-4">{{cite book | author = Stahl, S. M. | title = Essential psychopharmacology: neuroscientific basis and practical application | publisher = Cambridge University Press | location = Cambridge, UK | year = 2000 | isbn = 0-521-64615-4 | url = https://archive.org/details/essentialpsychop00step| url-access = registration | page = [https://archive.org/details/essentialpsychop00step/page/262 262] | quote = adatanserin. }}</ref>

Adantaserin has been shown to be [[neuroprotective]] against [[ischemia]]-induced [[glutamatergic]] [[excitotoxicity]], an effect which appears to be mediated by blockade of the 5-HT_2A receptor.<ref name="pmid11741003">{{cite journal |vauthors=Dawson LA, Galandak J, Djali S | title = Attenuation of ischemic efflux of endogenous amino acids by the novel 5-HT(1A)/5-HT(2) receptor ligand adatanserin | journal = Neurochemistry International | volume = 40 | issue = 3 | pages = 203–9 |date=March 2002| pmid = 11741003 | doi = 10.1016/S0197-0186(01)00082-1| s2cid = 24104458 }}</ref>

==Synthesis==

:[[File:Adatanserin synthesis.svg|upright=2]]

2-Chloropyrimidine (1) reacts with [[piperazine]] (2), forming 2-(1-piperazinyl)pyrimidine (3). Treatment with the [[phthalimide]] derivative N-(2-bromoethyl)phthalimide (4) in an [[alkylation]] reaction produces (5), which is [[protecting group|deprotected]] using [[hydrazine]] to give the [[primary amine]] (6). [[Amide]] formation with the [[acid chloride]] of [[1-Adamantanecarboxylic acid|1-adamantanecarboxylic acid]] yields adatanserin.<ref>{{cite patent |country=US |number=5482940 |inventor=Magid A.-M., et al. |title=Use of aryl- and heteroaryl piperazinyl carboxamides in the treatment of various central nervous system disorders |status=patent |gdate=1996-01-09 |fdate=1993-04-19 |pridate=1990-03-14 |assign1=American Home Products Corp}}</ref><ref name="pmid10602693"/>

==See also==

* [[Flibanserin]]

==References==

{{Reflist}}

{{Serotonergics}}

{{Piperazines}}

[[Category:5-HT1A agonists]]

[[Category:5-HT2A antagonists]]

[[Category:5-HT2C antagonists]]

[[Category:Abandoned drugs]]

[[Category:Adamantanes]]

[[Category:Carboxamides]]

[[Category:Piperazines]]

[[Category:Aminopyrimidines]]

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