Ethyl nitrite

Last updated
Ethyl nitrite
Ethyl-nitrite-2D-skeletal.png
Ethyl nitrite 3d structure.png
Names
Preferred IUPAC name
Ethyl nitrite
Other names
1-Nitrosooxyethane
Ethyl alcohol nitrite
Nitrous acid
Nitrous ether
Ethyl ester
Nitrethyl
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.385 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C2H5NO2/c1-2-5-3-4/h2H2,1H3 Yes check.svgY
    Key: QQZWEECEMNQSTG-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H5NO2/c1-2-5-3-4/h2H2,1H3
    Key: QQZWEECEMNQSTG-UHFFFAOYAU
  • O=NOCC
Properties
C2H5NO2
Molar mass 75.067 g·mol−1
Boiling point 17 °C (63 °F; 290 K)
5.07 g/100 ml
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
[1]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
2
4
4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

The chemical compound ethyl nitrite is an alkyl nitrite with a chemical formula C2H5NO2. It may be prepared from ethanol. [2]

Contents

Preparation of ethyl nitrite.png

Uses

It is used as a reagent with butanone to yield the dimethylglyoxime end product.

Preparation of dimethylglyoxime.png

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.

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<span class="mw-page-title-main">Butanone</span> Chemical compound

Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

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<span class="mw-page-title-main">Chloroethane</span> Chemical compound commonly known as ethyl chloride

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Diethyl ether, or simply ether, is an organic compound in the ether class with the formula C4H10O, (CH3CH2)2O or (C2H5)2O, sometimes abbreviated as Et2O. It is a colourless, highly volatile, sweet-smelling, extremely flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication.

<span class="mw-page-title-main">Methemoglobin</span> Type of hemoglobin

Methemoglobin (British: methaemoglobin, shortened MetHb) (pronounced "met-hemoglobin") is a hemoglobin in the form of metalloprotein, in which the iron in the heme group is in the Fe3+ (ferric) state, not the Fe2+ (ferrous) of normal hemoglobin. Sometimes, it is also referred to as ferrihemoglobin. Methemoglobin cannot bind oxygen, which means it cannot carry oxygen to tissues. It is bluish chocolate-brown in color. In human blood a trace amount of methemoglobin is normally produced spontaneously, but when present in excess the blood becomes abnormally dark bluish brown. The NADH-dependent enzyme methemoglobin reductase (a type of diaphorase) is responsible for converting methemoglobin back to hemoglobin.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

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<span class="mw-page-title-main">Methyl nitrite</span> Chemical compound

Methyl nitrite is an organic compound with the chemical formula CH
3
ONO
. It is a gas, and is the simplest alkyl nitrite.

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<span class="mw-page-title-main">Ethyl acrylate</span> Chemical compound

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Cetacaine is a topical anesthetic that contains the active ingredients benzocaine (14%), butamben (2%), and tetracaine hydrochloride (2%). Cetacaine also contains small amounts of benzalkonium chloride at 0.5% and 0.005% of cetyl dimethyl ethyl ammonium bromide all in a bland water-soluble base. Although Cetacaine has been widely used in the medical and dental fields, it has yet to be officially approved by the FDA. Cetacaine is produced by the company Cetylite Industries, Inc. and they provide Cetacaine in three forms: liquid, gel, and spray.

References

  1. "NFPA 704 Ratings for Common Chemicals".
  2. Semon, W. L.; Damerell, V. R. (1943). "Dimethylglyoxime". Organic Syntheses .; Collective Volume, vol. 2, p. 204
  3. "Rulemaking History for OTC Sweet Spirits of Nitre Drug Products". fda.gov. Retrieved 2016-12-26.
  4. "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)
  5. "Ethyl nitrite". Haz-Map. Retrieved 2020-08-08.
  6. 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.