Ethyl nitrite
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| Names | |||
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| Preferred IUPAC name Ethyl nitrite | |||
| Other names 1-Nitrosooxyethane Ethyl alcohol nitrite Nitrous acid Nitrous ether Ethyl ester Nitrethyl | |||
| Identifiers | |||
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3D model (JSmol) |
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| ChEMBL |
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| ChemSpider |
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| ECHA InfoCard | 100.003.385  | ||
PubChem CID |
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CompTox Dashboard (EPA) |
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InChI
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| Properties | |||
Chemical formula | C2H5NO2 | ||
| Molar mass | 75.067 g·mol−1 | ||
| Boiling point | 17 °C (63 °F; 290 K) | ||
Solubility in water | 5.07 g/100 ml | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | [1] | ||
| NFPA 704 (fire diamond) |  2 4 4 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).  N verify (what is  Y N ?) Infobox references | |||
Chemical compound
The chemical compound ethyl nitrite is an alkyl nitrite with a chemical formula C2H5NO2. It may be prepared from ethanol.[2]
Uses
It is used as a reagent with butanone to yield the dimethylglyoxime end product.
Ethyl nitrite is the main ingredient in a traditional ethanol-based South African remedy for colds and flu known as Witdulsies, which is sold in pharmacies. It is known as a traditional Afrikaans remedy; the same remedy is apparently made by the Amish in the US. However, FDA has blocked over-the-counter sales of this same remedy, known in the US as sweet nitrite or sweet spirit of nitre, since 1980.[3] Its use has been associated with fatal methemoglobinemia.[4]
Methemoglobinemia is the primary toxic effect of ethyl nitrite.[5] Due to ethyl nitrite's high volatility and faint smell, in the presence of ethyl nitrite vapors, it is easy to breath a high dose of it without realizing, resulting in methemoglobinemia,[6] which may or may not be severe, or even fatal.
References
- ^ "NFPA 704 Ratings for Common Chemicals".
- ^ Semon, W. L.; Damerell, V. R. (1943). "Dimethylglyoxime". Organic Syntheses; Collected Volumes, vol. 2, p. 204.
- ^ "Rulemaking History for OTC Sweet Spirits of Nitre Drug Products". fda.gov. Retrieved 2016-12-26.
- ^ "ETHYL NITRITE - National Library of Medicine HSDB Database". toxnet.nlm.nih.gov. Retrieved 2017-11-18. "Archived copy". Archived from the original on 2017-12-01. Retrieved 2017-11-18.
{{cite web}}: CS1 maint: archived copy as title (link) CS1 maint: bot: original URL status unknown (link) - ^ "Ethyl nitrite". Haz-Map. Retrieved 2020-08-08.
- ^ Titov, V Yu; Petrenko, Yu M (2005). "Proposed mechanism of nitrite-induced methemoglobinemia". Biochemistry (Moscow). 70 (4): 473–83. doi:10.1007/s10541-005-0139-7. PMID 15892615. S2CID 22906218.
External links
- WebBook page for ethyl nitrite
- v
- t
- e
- Nitroxyl anion (NO−; oxonitrate(1-), hyponitrite anion)
- Nitric oxide (NO⋅; nitrogen monoxide)
- Nitrosonium (NO+; nitrosyl cation)
| sGC |
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(prodrugs)
- Nitrates: Diethylene glycol dinitrate (DEGDN)
- Erythritol tetranitrate (ETN)
- Ethylene glycol dinitrate (EGDN; nitroglycol)
- Isosorbide mononitrate (ISMN)
- Isosorbide dinitrate (ISDN)
- Itramin tosilate
- Mannitol hexanitrate
- Naproxcinod (nitronaproxen; AZD-3582, HCT-3012)
- NCX-466
- NCX-2216
- NCX-4016
- NCX 4040
- NCX-4215
- Nicorandil
- Nipradilol (K-351)
- Nitrate (NO−
3) - Nitroatorvastatin (NCX-6560)
- Nitroflurbiprofen (HCT-1026)
- Nitrofluvastatin
- Nitroglycerin (glyceryl trinitrate (GTN))
- Nitropravastatin (NCX-6550)
- Pentaerithrityl tetranitrate (PETN)
- Propatylnitrate
- Propylene glycol dinitrate (PGDN)
- Sodium trioxodinitrate (Angeli's salt)
- Tenitramine
- Trolnitrate
- Nitroso compounds/nitrites: Nitrite (NO−
2); O-Nitroso compounds (alkyl nitrites): Amyl nitrite (isoamyl nitrite, isopentyl nitrite) - Cyclohexyl nitrite
- Ethyl nitrite
- Hexyl nitrite
- Isobutyl nitrite (2-methylpropyl nitrite)
- Isopropyl nitrite
- Methyl nitrite
- n-Butyl nitrite
- Pentyl nitrite
- tert-Butyl nitrite; S-Nitroso compounds (thionitrites): LA810
- S-Nitrosoalbumin (SNALB)
- S-Nitrosated AR545C
- S-Nitroso-N-acetylcysteine (SNAC)
- S-Nitroso-N-acetylpenicillamine (SNAP)
- S-Nitroso-N-valerylpenicillamine (SNVP)
- S-Nitrosocaptopril (SNO-Cap)
- S-Nitrosocysteine (SNC, CysNO, SNO-Cys)
- S-Nitrosodiclofenac
- S-Nitrosoglutathione (GSNO, SNOG)
- SNO-t-PA
- SNO-vWF; N-Nitroso compounds (e.g., nitrosamines): SIN-1A
- Nitrosyl compounds: Metal nitrosyl complexes: Roussin's black salt
- Roussin's red salt
- Sodium nitroprusside (SNP)
- NONOates (diazeniumdiolates): Diethylamine/NO (DEA/NO)
- Diethylenetriamine/NO (DETA/NO)
- GLO/NO
- JS-K
- Methylamine hexamethylene methylamine/NO (MAHMA/NO)
- PROLI/NO
- Spermine/NO (SPER/NO)
- V-PYRRO/NO
- Heterocyclic compounds: Furoxans: Furoxan
- REC15/2739; Sydnonimines: Feprosidnine
- Linsidomine (SIN-1)
- Molsidomine (SIN-10)
- Sydnonimine
- Unsorted: Cimlanod
- FK-409
- FR144220
- FR146881
- N-Acetyl-N-acetoxy-4-chlorobenzenesulfonamide
(inhibitors)
| NOS |
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| Arginase |
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| CAMK |
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- Precursors: L-Arginine
- Nω-Hydroxy-L-arginine (NOHA)
- Indirect/downstream NO modulators: ACE inhibitors/AT-II receptor antagonists (e.g., captopril, losartan)
- ETB receptor antagonists (e.g., bosentan)
- L-Type calcium channel blockers (e.g., dihydropyridines: nifedipine)
- Nebivolol (beta blocker)
- PDE5 inhibitors (e.g., sildenafil)
- non-selective PDE inhibitors (e.g., caffeine)
- PDE9 inhibitors (e.g., paraxanthine)
- cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil)
- Statins (e.g., simvastatin)
See also: Receptor/signaling modulators
