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{{refimprove|date=September 2017}}
{{chembox
{{chembox
| verifiedrevid = 443882998
| verifiedrevid = 443882998
| Reference=<ref>''[[Merck Index]]'', 11th Edition, '''5032'''.</ref>
| Reference=<ref>''[[Merck Index]]'', 11th Edition, '''5032'''.</ref>
| ImageFileL1 = Isobutyl-nitrite-2D-skeletal.png
| ImageFileL1 = Isobutyl nitrite Structural Formula V1.svg
| ImageFileR1= Isobutyl_nitrite_3d_structure.png
| ImageFileR1= Isobutyl_nitrite_3d_structure.png
| IUPACName=2-Methylpropyl nitrite
| PIN=2-Methylpropyl nitrite
| OtherNames=
| OtherNames=Isobutyl nitrite
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=542-56-3
| CASNo=542-56-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = GW9WAB6QOM
| PubChem=10958
| PubChem=10958
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
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| MolarMass=103.11976
| MolarMass=103.11976
| Appearance=Colorless liquid
| Appearance=Colorless liquid
| Odor=Almond-like<ref>[http://www.cdc.gov/niosh/npg/npgd0353.html CDC - NIOSH Pocket Guide to Chemical Hazards]</ref>
| Odor=Almond-like<ref>[https://www.cdc.gov/niosh/npg/npgd0353.html CDC - NIOSH Pocket Guide to Chemical Hazards]</ref>
| Density=0.87 g/mL
| Density=0.87 g/mL
| MeltingPt=
| MeltingPt=
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| AutoignitionPt =
| AutoignitionPt =
}}
}}
|Section4={{Chembox Legal status
| legal_AU = S4
| legal_AU_comment = <ref>''[https://www.legislation.gov.au/F2024L01228 Therapeutic Goods (Poisons Standard—October 2024) Instrument 2024]'' (Cth)</ref>
| legal_BR = C1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_US =
| legal_UK =
| legal_UN =
}}
}}
}}


'''Isobutyl nitrite''', C<sub>4</sub>H<sub>9</sub>NO<sub>2</sub>, is an [[alkyl nitrite]], an [[ester]] of [[isobutanol]] and [[nitrous acid]]. Its chemical structure is ([[methyl|CH<sub>3</sub>]])<sub>2</sub>CH-[[Methylene bridge|CH<sub>2</sub>]]-[[nitrite|ONO]].
'''Isobutyl nitrite''', C<sub>4</sub>H<sub>9</sub>NO<sub>2</sub>, is an [[alkyl nitrite]], an [[ester]] of [[isobutanol]] and [[nitrous acid]]. Its chemical structure is ([[methyl|CH<sub>3</sub>]])<sub>2</sub>CH-[[Methylene bridge|CH<sub>2</sub>]]-[[nitrite|ONO]].


Isobutyl nitrite is a pungent colorless liquid. It acts as a [[vasodilator]], and is used as an [[inhalant]] [[recreational drug]], [[poppers]].
Isobutyl nitrite is a pungent colorless liquid. It acts as a [[vasodilator]], and is used as an [[inhalant]] [[recreational drug]], [[poppers]].


==Applications==
==Applications==
Isobutyl nitrite is one of the compounds used as [[poppers]], an [[inhalant]] drug that induces a brief [[euphoria]]. It is also used as part of the antidote package for [[cyanide poisoning]].{{medcn|date=April 2014}}
Isobutyl nitrite is one of the compounds used as [[poppers]], an [[inhalant]] drug that induces a brief [[euphoria]]. Also, it is used as part of the antidote package for [[cyanide poisoning]].{{medcn|date=April 2014}}


==Safety==
==Safety==
May cause [[Headache|headaches]], [[dizziness]] and [[Syncope (medicine)|fainting]]. Isobutyl nitrite is poisonous to people with [[glucose-6-phosphate dehydrogenase deficiency]].<ref>{{Cite journal |last1=Bubp |first1=Jeff |last2=Jen |first2=Marilyn |last3=Matuszewski |first3=Karl |date=September 2015 |title=Caring for Glucose-6-Phosphate Dehydrogenase (G6PD)–Deficient Patients: Implications for Pharmacy |journal=Pharmacy and Therapeutics |volume=40 |issue=9 |pages=572–574 |issn=1052-1372 |pmc=4571844 |pmid=26417175}}</ref>
Isobutyl nitrite is poisonous to people with [[glucose-6-phosphate dehydrogenase deficiency]].{{medcn|date=March 2013}}


==References==
==References==
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[[Category:Alkyl nitrites]]
[[Category:Alkyl nitrites]]
[[Category:Antianginals]]
[[Category:Antianginals]]
[[Category:Isobutyl esters]]




Latest revision as of 12:23, 17 December 2024

Isobutyl nitrite[1]
Names
Preferred IUPAC name
2-Methylpropyl nitrite
Other names
Isobutyl nitrite
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.018 Edit this at Wikidata
UNII
  • InChI=1S/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3 checkY
    Key: APNSGVMLAYLYCT-UHFFFAOYSA-N checkY
  • InChI=1/C4H9NO2/c1-4(2)3-7-5-6/h4H,3H2,1-2H3
    Key: APNSGVMLAYLYCT-UHFFFAOYAF
  • O=NOCC(C)C
Properties
C4H9NO2
Molar mass 103.11976
Appearance Colorless liquid
Odor Almond-like[2]
Density 0.87 g/mL
Boiling point 67 °C (153 °F; 340 K)
Slightly soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly flammable
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Isobutyl nitrite, C4H9NO2, is an alkyl nitrite, an ester of isobutanol and nitrous acid. Its chemical structure is (CH3)2CH-CH2-ONO.

Isobutyl nitrite is a pungent colorless liquid. It acts as a vasodilator, and is used as an inhalant recreational drug, poppers.

Applications

[edit]

Isobutyl nitrite is one of the compounds used as poppers, an inhalant drug that induces a brief euphoria. Also, it is used as part of the antidote package for cyanide poisoning.[medical citation needed]

Safety

[edit]

May cause headaches, dizziness and fainting. Isobutyl nitrite is poisonous to people with glucose-6-phosphate dehydrogenase deficiency.[5]

References

[edit]
  1. ^ Merck Index, 11th Edition, 5032.
  2. ^ CDC - NIOSH Pocket Guide to Chemical Hazards
  3. ^ Therapeutic Goods (Poisons Standard—October 2024) Instrument 2024 (Cth)
  4. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  5. ^ Bubp, Jeff; Jen, Marilyn; Matuszewski, Karl (September 2015). "Caring for Glucose-6-Phosphate Dehydrogenase (G6PD)–Deficient Patients: Implications for Pharmacy". Pharmacy and Therapeutics. 40 (9): 572–574. ISSN 1052-1372. PMC 4571844. PMID 26417175.


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