Isopropyl nitrite

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Isopropyl nitrite
Isopropyl-nitrite-2D-skeletal.png
Isopropyl nitrite 3d structure.png
Clinical data
Other namesIsopropyl alcohol nitrite; nitrous acid, isopropyl ester; 1-methylethyl nitrite; 2-propyl nitrite
ATC code
  • None
Legal status
Legal status
Identifiers
  • 2-propyl nitrite
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.007.982 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C3H7NO2
Molar mass 89.094 g·mol−1
3D model (JSmol)
Density 0.8684 g/cm3
Boiling point 40 °C (104 °F)
  • O=NOC(C)C
  • InChI=1S/C3H7NO2/c1-3(2)6-4-5/h3H,1-2H3 Yes check.svgY
  • Key:SKRDXYBATCVEMS-UHFFFAOYSA-N Yes check.svgY
   (verify)

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. [3]

Contents

Isopropyl nitrite in a glass bottle Isopropyl nitrite compound.jpg
Isopropyl nitrite in a glass bottle

Applications

Isopropyl nitrite is one of the compounds used as poppers, an inhalant drug that induces a brief euphoria.

Safety

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, [4] which may be reversible. [5]

Related Research Articles

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Amyl nitrite is a chemical compound with the formula C5H11ONO. A variety of isomers are known, but they all feature an 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 nitrites, amyl nitrite is bioactive in mammals, being a vasodilator, which is the basis of its use as a prescription medicine. As an inhalant, it also has a psychoactive effect, which has led to its recreational use, with its smell being described as that of old socks or dirty feet. It was first documented in 1844 and came into medical use in 1867.

<span class="mw-page-title-main">Nitrate</span> Polyatomic ion (NO₃, charge –1) found in explosives and fertilisers

Nitrate is a polyatomic ion with the chemical formula NO
3
. Salts containing this ion are called nitrates. Nitrates are common components of fertilizers and explosives. Almost all inorganic nitrates are soluble in water. An example of an insoluble nitrate is bismuth oxynitrate.

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

Sodium nitrate is the chemical compound with the formula NaNO
3
. This alkali metal nitrate salt is also known as Chile saltpeter to distinguish it from ordinary saltpeter, potassium nitrate. The mineral form is also known as nitratine, nitratite or soda niter.

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

Silver nitrate is an inorganic compound with chemical formula AgNO
3
. It is a versatile precursor to many other silver compounds, such as those used in photography. It is far less sensitive to light than the halides. It was once called lunar caustic because silver was called luna by ancient alchemists who associated silver with the moon. In solid silver nitrate, the silver ions are three-coordinated in a trigonal planar arrangement.

The nitrite ion has the chemical formula NO
2
. Nitrite is widely used throughout chemical and pharmaceutical industries. The nitrite anion is a pervasive intermediate in the nitrogen cycle in nature. The name nitrite also refers to organic compounds having the –ONO group, which are esters of nitrous acid.

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

Sodium nitrite is an inorganic compound with the chemical formula NaNO2. It is a white to slightly yellowish crystalline powder that is very soluble in water and is hygroscopic. From an industrial perspective, it is the most important nitrite salt. It is a precursor to a variety of organic compounds, such as pharmaceuticals, dyes, and pesticides, but it is probably best known as a food additive used in processed meats and in fish products.

<span class="mw-page-title-main">Nitrosamine</span> Organic compounds of the form >N–N=O

In organic chemistry, nitrosamines are organic compounds with the chemical structure R2N−N=O, where R is usually an alkyl group. They feature a nitroso group bonded to a deprotonated amine. Most nitrosamines are carcinogenic in nonhuman animals. A 2006 systematic review supports a "positive association between nitrite and nitrosamine intake and gastric cancer, between meat and processed meat intake and gastric cancer and oesophageal cancer, and between preserved fish, vegetable and smoked food intake and gastric cancer, but is not conclusive".

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

Butyl nitrite is the organic compound with the formula CH3(CH2)3ONO. It is an alkyl nitrite made from n-butanol. Butyl nitrite is used recreationally as poppers. Synonyms include 1-butyl nitrite, n-butyl nitrite and nitrous acid butyl ester.

Poppers is a slang term referring to recreational drugs belonging to the alkyl nitrite family of chemical compounds. When fumes from these substances are inhaled, they act as potent vasodilators, producing mild euphoria, warmth, and dizziness. Most effects have a rapid onset and are short-acting. Its recreational use is believed to be potentially dangerous for people with heart problems, anaemia, or glaucoma. Reported adverse effects include fainting, retinal toxicity, and vision loss.

<span class="mw-page-title-main">Processed meat</span> Type of meat

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

Potassium nitrite (distinct from potassium nitrate) is the inorganic compound with the chemical formula KNO2. It is an ionic salt of potassium ions K+ and nitrite ions NO2, which forms a white or slightly yellow, hygroscopic crystalline powder that is soluble in water.

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

<span class="mw-page-title-main">Nitroso</span> Class of functional groups with a –N=O group attached

In organic chemistry, nitroso refers to a functional group in which the nitric oxide group is attached to an organic moiety. As such, various nitroso groups can be categorized as C-nitroso compounds, S-nitroso compounds, N-nitroso compounds, and O-nitroso compounds.

<span class="mw-page-title-main">Alkyl nitrite</span> Organic compounds of the form R–O–N=O

In organic chemistry, alkyl nitrites are a group of organic compounds based upon the molecular structure R−O−N=O, where R represents an alkyl group. Formally they are alkyl esters of nitrous acid. They are distinct from nitro compounds.

Isopropyl alcohol is a colorless, flammable, organic compound with a pungent alcoholic odor.

<span class="mw-page-title-main">Chloroquine retinopathy</span> Medical condition

Chloroquine retinopathy is a form of toxic retinopathy caused by the drugs chloroquine or hydroxychloroquine, which are sometimes used in the treatment of autoimmune disorders such as rheumatoid arthritis and systemic lupus erythematosus. This eye toxicity limits long-term use of the drugs.

<span class="mw-page-title-main">Flunitrazolam</span> Triazolobenzodiazepine drug

Flunitrazolam is a triazolobenzodiazepine (TBZD), which are benzodiazepine (BZD) derivatives, that has been sold online as a designer drug, and is a potent hypnotic and sedative drug similar to related compounds such as flunitrazepam, clonazolam and flubromazolam. It was first definitively identified and reported to the EMCDDA Early Warning System, by an analytical laboratory in Germany in October 2016, and had not been described in the scientific or patent literature before this. It is the triazole analogue of Flunitrazepam (Rohypnol). The addition of the triazole ring to the scaffold increases potency significantly, this is evident as flunitrazolam is reported anecdotally to be active in the microgram level. It is active at 0.1 mg.

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Hexyl nitrite has the formula C6H13NO2 and is a nitrite and more specifically, an alkyl nitrite. It is an ester of hexanol and nitrous acid. It has the structural formula of: CH3(CH2)5ONO The CAS Registry Number is 638-51-7 and the European Community number 680-102-5. It is REACH and TSCA registered. It is also known as nitrous acid, hexyl ester. It is the aliphatic analogue of cyclohexyl nitrite.

References

  1. Therapeutic Goods (Poisons Standard—October 2024) Instrument 2024 (Cth)
  2. Anvisa (2024-05-28). "RDC Nº 877 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 877 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União. Archived from the original on 2024-09-25. Retrieved 2024-09-25.
  3. Lide DR, ed. (2004). Handbook of Chemistry and Physics (85th ed.). CRC Press. ISBN   978-0-8493-0485-9.
  4. Davies AJ, Kelly SP, Naylor SG, Bhatt PR, Mathews JP, Sahni J, et al. (November 2012). "Adverse ophthalmic reaction in poppers users: case series of 'poppers maculopathy'". Eye. 26 (11): 1479–1486. doi:10.1038/eye.2012.191. PMC   3496104 . PMID   23079752.
  5. Vignal-Clermont C, Audo I, Sahel JA, Paques M (October 2010). "Poppers-associated retinal toxicity". The New England Journal of Medicine. 363 (16): 1583–5. doi: 10.1056/NEJMc1005118 . PMID   20942681.