Editing Amyl nitrite (section)

{{Short description|Chemical compound}}
{{Distinguish|Amyl nitrate}}
{{cs1 config|name-list-style=vanc}}
{{infobox drug
| Watchedfields      = changed
| verifiedrevid      = 451716663
| type               = 
| drug_name          = 
| image              = Amyl nitrite.svg
| image_class        = skin-invert-image
| width              = 175px
| alt                = Chemical structure of amyl nitrite
| image2             = Amyl-nitrite-3D-balls.png
| width2             = 200px
| alt2               = Ball-and-stick model of amyl nitrite
| IUPAC_name         = (3-methylbutyl) nitrite
| synonyms           = Isoamyl nitrite,<br/>Isopentyl nitrite,<br/>Nitramyl,<br/>3-methyl-1-nitrosooxybutane,<br/>Pentyl alcohol nitrite&nbsp;(ambiguous),<br/>''poppers'' (ambiguous, colloquial, slang)
| legal_AU           = [[Standard for the Uniform Scheduling of Medicines and Poisons#Schedule 3|S3]] (Pharmacist only) / [[Standard for the Uniform Scheduling of Medicines and Poisons#Schedule 4|S4]] (Prescription only)
| legal_AU_comment   = <ref>''[https://www.legislation.gov.au/F2024L01228 Therapeutic Goods (Poisons Standard—October 2024) Instrument 2024]'' (Cth). Schedule 3 "when in preparations for human therapeutic use and packaged in containers with child‑resistant closures"; schedule 4 otherwise.</ref>
| legal_UK           = [[Medicines Act 1968|Controlled Drug (Medicines Act 1968)]]
| legal_US           = Unscheduled [[Crime Control Act of 1990|(illegal under Crime Control Act of 1990)]]
| legal_DE           = Unscheduled (unauthorized sale and purchase illegal)
| legal_BR           = C1
| legal_BR_comment   = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2024-05-28 |title=RDC Nº 877 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 877 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-da-diretoria-colegiada-anvisa-n-877-de-28-de-maio-de-2024-562758149 |url-status=live |archive-url=https://web.archive.org/web/20240925040323/https://www.in.gov.br/en/web/dou/-/resolucao-da-diretoria-colegiada-anvisa-n-877-de-28-de-maio-de-2024-562758149 |archive-date=2024-09-25 |access-date=2024-09-25 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2024-05-28}}</ref>
| DrugBank_Ref       = {{drugbankcite|correct|drugbank}}
| DrugBank           = DB01612
| ChEBI_Ref          = {{ebicite|correct|EBI}}
| ChEBI              = 2691
| SMILES             = CC(C)CCON=O
| UNII_Ref           = {{fdacite|correct|FDA}}
| UNII               = 5N0U5TUC9Z
| PubChem            = 8053
| StdInChI_Ref       = {{stdinchicite|correct|chemspider}}
| StdInChI           = 1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3
| StdInChIKey_Ref    = {{stdinchicite|correct|chemspider}}
| StdInChIKey        = OWFXIOWLTKNBAP-UHFFFAOYSA-N
| CAS_number         = 110-46-3
| CAS_number_Ref     = {{cascite|correct|CAS}}
| ChemSpiderID_Ref   = {{chemspidercite|correct|chemspider}}
| ChemSpiderID       = 7762
| KEGG_Ref           = {{keggcite|correct|kegg}}
| KEGG               = D00517
| C                  = 5
| H                  = 11
| N                  = 1
| O                  = 2
| density            = 0.872
| solubility         = Slightly soluble
| melting_point      = 
| boiling_point      = 99
| ATC_prefix         = V03
| ATC_suffix         = AB22
<!-- | OtherCompounds = [[Nitroglycerine]]<br/>[[Isopentanol]]<br/>[[Butyl nitrite]]<br/>[[Isobutyl nitrite]]<br/> [[Ethyl nitrite]]<br/> [[Methyl nitrite]]<br/> [[Isopropyl nitrite]]<br/> [[Cyclohexyl nitrite]] -->}}

'''Amyl nitrite''' is a [[chemical compound]] with the [[chemical formula|formula]] C<sub>5</sub>H<sub>11</sub>ONO. A variety of isomers are known, but they all feature an [[Pentyl|amyl]] group attached to the [[nitrite]] functional group. The alkyl group (the amyl in this case) is unreactive and the chemical and biological properties are mainly due to the nitrite group. Like other [[alkyl nitrite]]s, amyl nitrite is bioactive in mammals, being a [[vasodilator]], which is the basis of its use as a prescription medicine.<ref>{{cite web |title=Amyl Nitrite (Inhalation Route) Description and Brand Names - Mayo Clinic |url=https://www.mayoclinic.org/drugs-supplements/amyl-nitrite-inhalation-route/description/drg-20061803 |access-date=2023-12-05 |website=www.mayoclinic.org}}</ref> As an inhalant, it also has a [[Psychoactive drug|psychoactive]] effect, which has led to its recreational use, with its smell being described as that of old socks or dirty feet.<ref>{{cite web|url=http://www.urban75.com/Drugs/drugamyl.html|title=Drugs - Amyl, Butyl or Isobutyl Nitrite, Nitrates, Poppers|work=urban75.com}}</ref> 
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It was first documented in 1844 and came into medical use in 1867.<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=XXX |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PAXXX |language=en}}</ref>