:Isopropyl nitrite
{{short description|Chemical compound}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 447190201
| IUPAC_name = 2-propyl nitrite
| image = Isopropyl-nitrite-2D-skeletal.png
| image_class = skin-invert-image
| width = 150
| image2 = Isopropyl nitrite 3d structure.png
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU = S10
| legal_AU_comment = [https://www.legislation.gov.au/F2024L01228 Therapeutic Goods (Poisons Standard—October 2024) Instrument 2024] (Cth)
| legal_BR = C1
| legal_BR_comment = {{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}}
| legal_CA =
| legal_UK = Controlled Drug (Medicines Act 1968)
| legal_US = Unscheduled (illegal under Crime Control Act of 1990)
| legal_status =
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 541-42-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2T3Y2PS0ZE
| ATC_prefix = None
| ATC_suffix =
| PubChem = 10929
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10466
| synonyms = Isopropyl alcohol nitrite; nitrous acid, isopropyl ester; 1-methylethyl nitrite; 2-propyl nitrite
| chemical_formula =
| C=3 | H=7 | N=1 | O=2
| smiles = O=NOC(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C3H7NO2/c1-3(2)6-4-5/h3H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SKRDXYBATCVEMS-UHFFFAOYSA-N
| density = 0.8684
| boiling_point = 40
}}
The chemical compound isopropyl nitrite (or 2-propyl nitrite) is an alkyl nitrite made from isopropanol. It is a clear pale yellow oil that is insoluble in water.{{Cite book | veditors = Lide DR |title=Handbook of Chemistry and Physics |publisher= CRC Press |edition= 85th |year=2004 |isbn=978-0-8493-0485-9 }}
Applications
Safety
{{Further|Poppers}}
Isopropyl nitrite has been associated with eye maculopathy, visual impairment with central scotomata, bilateral foveal yellow spots, and inner segment/outer segment (IS/OS) junction disruption,{{cite journal | vauthors = Davies AJ, Kelly SP, Naylor SG, Bhatt PR, Mathews JP, Sahni J, Haslett R, McKibbin M | display-authors = 6 | title = Adverse ophthalmic reaction in poppers users: case series of 'poppers maculopathy' | journal = Eye | volume = 26 | issue = 11 | pages = 1479–1486 | date = November 2012 | pmid = 23079752 | pmc = 3496104 | doi = 10.1038/eye.2012.191 }} which may be reversible.{{cite journal | vauthors = Vignal-Clermont C, Audo I, Sahel JA, Paques M | title = Poppers-associated retinal toxicity | journal = The New England Journal of Medicine | volume = 363 | issue = 16 | pages = 1583–5 | date = October 2010 | pmid = 20942681 | doi = 10.1056/NEJMc1005118 | doi-access = free }}
References
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{{Nitric oxide signaling}}