| Revision as of 18:07, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456503475 of page 4-Aminoquinoline for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 14:54, 26 February 2024 edit Maxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers30,619 edits Added bibcode. | Use this tool. Report bugs. | #UCB_Gadget |
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{{cs1 config|name-list-style=vanc}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 456502257 |
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| verifiedrevid = 477221021 |
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| Name = |
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| ImageFile = 4-aminoquinoline.svg |
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| ImageFile = 4-aminoquinoline.svg |
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| ImageSize = 150px |
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| ImageSize = 130px |
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| ImageAlt = Structural formula of 4-aminoquinoline |
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| IUPACName = quinolin-4-amine |
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| ImageFile1 = 4-Aminoquinoline 3D spacefill.png |
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| ImageSize1 = 160 |
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| ImageAlt1 = Space-filling model of the 4-aminoquinoline molecule |
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| PIN = Quinolin-4-amine |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| CASNo = <!-- blanked - oldvalue: 578-68-7 --> |
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| CASNo = 578-68-7 |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo_Ref = {{cascite|changed|??}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 58146 |
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| ChEMBL = 58146 |
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| PubChem = 68476 |
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| PubChem = 68476 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 61751 |
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| ChemSpiderID = 61751 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = GTE5P5L97N |
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| UNII = GTE5P5L97N |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = FQYRLEXKXQRZDH-UHFFFAOYSA-N |
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| StdInChIKey = FQYRLEXKXQRZDH-UHFFFAOYSA-N |
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| SMILES = n1ccc(c2ccccc12)N |
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| SMILES = n1ccc(c2ccccc12)N |
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| InChI = InChI=1S/C9H8N2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H,(H2,10,11) |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=9|H=8|N=2 |
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| C = 9 | H = 8 | N = 2 |
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| Appearance = |
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| Appearance = Powder to crystalline, White/Yellow/Orange |
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| Density = |
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| Density = |
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| MeltingPt = |
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| MeltingPt = 151.0 to 155.0 °C |
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| Section3 = {{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| MainHazards = Causes skin and serious eye irritation |
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{{See also|8-Aminoquinoline}} |
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'''4-Aminoquinoline''' is a form of ] with the ] group at the 4-position of the ]. The compound has been used as a precursor for the synthesis of its derivatives.<ref name=":0">{{cite journal|last1=Al-Ahmary|first1=Khairia M.|last2=Alenezi|first2=Maha S.|last3=Habeeb|first3=Moustafa M.|date=2016-08-01|title=Synthesis, spectroscopic and DFT theoretical studies on the hydrogen bonded charge transfer complex of 4-aminoquinoline with chloranilic acid|journal=Journal of Molecular Liquids|language=en|volume=220|pages=166–182|doi=10.1016/j.molliq.2016.04.074|issn=0167-7322}}</ref> |
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A variety of derivatives of 4-aminoquinoline are ] useful in treating ] plasmodial infections.<ref>{{cite journal|last1=Bosak|first1=Anita|last2=Opsenica|first2=Dejan M.|last3=Šinko|first3=Goran|last4=Zlatar|first4=Matija|last5=Kovarik|first5=Zrinka|date=2019-08-01|title=Structural aspects of 4-aminoquinolines as reversible inhibitors of human acetylcholinesterase and butyrylcholinesterase|journal=Chemico-Biological Interactions|language=en|volume=308|pages=101–109|doi=10.1016/j.cbi.2019.05.024|pmid=31100281|bibcode=2019CBI...308..101B |s2cid=157067252 |issn=0009-2797|url=http://cer.ihtm.bg.ac.rs/handle/123456789/2905}}</ref> Examples include ], ], and ].<ref name="pmid8967977">{{cite journal |vauthors =Bray PG, Hawley SR, Ward SA |title=4-Aminoquinoline resistance of Plasmodium falciparum: insights from the study of amodiaquine uptake |journal=Mol. Pharmacol. |volume=50 |issue=6 |pages=1551–8 |year=1996 |pmid=8967977 |url=http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8967977}}</ref> Other uses for the derivatives are: anti-asthmatic, antibacterial, anti-fungal, anti-malarial, antiviral and anti-inflammatory agents. <ref name=":0" /> |
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A patent application for 4-aminoquinoline compounds was filed in 2002 and published in 2005.<ref>{{cite news|last1=DeVita|first1=Robert|url=https://patentimages.storage.googleapis.com/e6/5d/88/41b41326ea88f8/US20050009815A1.pdf|title=4-Aminoquinoline Compounds|work=United States Patent Application Publication|last2=Chang|first2=Lehua|date=13 January 2005}}</ref> |
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<gallery> |
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Image:Amodiaquine.svg|] |
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Image:Chloroquine.svg|] |
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Image:Hydroxychloroquine.svg|] |
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</gallery> |
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==See also== |
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* ] |
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* ] |
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* ] |
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==References== |
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{{reflist}} |
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==External links== |
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* {{cite journal |vauthors =Bourne SA, De Villiers K, Egan TJ |title=Three 4-aminoquinolines of antimalarial interest |journal=Acta Crystallogr C |volume=62 |issue=Pt 2 |pages=o53–7 |year=2006 |pmid=16456284 |doi=10.1107/S0108270105041235 |bibcode=2006AcCrC..62O..53B }} |
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*"4-Aminoquinoline 578-68-7 | TCI America". ''www.tcichemicals.com''. Retrieved 2020-03-06. |
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{{Antimalarials}} |
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{{DEFAULTSORT:Aminoquinoline, 4-}} |
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] |
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{{heterocyclic-stub}} |