Amyl nitrite

Source: Wikipedia, the free encyclopedia.
Not to be confused with Amyl nitrate.
Amyl nitrite
Chemical structure of amyl nitrite
Ball-and-stick model of amyl nitrite
Clinical data
Other namesIsoamyl nitrite,
Isopentyl nitrite,
Nitramyl,
3-methyl-1-nitrosooxybutane,
Pentyl alcohol nitrite (ambiguous),
poppers (ambiguous, colloquial, slang)
ATC code
Legal status
Legal status
Identifiers
  • (3-methylbutyl) nitrite
JSmol)
Density0.872 g/cm3
Boiling point99 °C (210 °F)
Solubility in waterSlightly soluble mg/mL (20 °C)
  • CC(C)CCON=O
  • InChI=1S/C5H11NO2/c1-5(2)3-4-8-6-7/h5H,3-4H2,1-2H3 checkY
  • Key:OWFXIOWLTKNBAP-UHFFFAOYSA-N checkY
  (verify)

Amyl nitrite is a

vasodilator, which is the basis of its use as a prescription medicine.[1] 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.[2]
It was first documented in 1844 and came into medical use in 1867.[3]

Uses

Nomenclature

The term "amyl nitrite" encompasses several

alkyl
group, and the resulting amyl nitrite would have the structural formula CH3(CH2)3CH2ONO, also referred to as n-amyl nitrite.

A common form of amyl nitrite is the isomer with the formula (CH3)2CHCH2CH2ONO, which may be more specifically referred to as isoamyl nitrite.

The similarly named amyl nitrate has very different properties. At the same time, isopropyl nitrite has a similar structure and similar uses (also called 'poppers') but with worse side-effects. [11]

Amyl nitrite is sometimes referred to colloquially as banapple gas.[12]

Synthesis and reactions

Alkyl nitrites are prepared by the reaction of alcohols with nitrous acid:[13]

ROH + HONO → RONO + H2O, where R = alkyl group

The reaction is called

esterification. Synthesis of alkyl nitrites is, in general, straightforward and can be accomplished in home laboratories. A common procedure includes the dropwise addition of concentrated sulfuric acid to a cooled mixture of an aqueous sodium nitrite solution and an alcohol. The intermediately-formed stoichiometric mixture of nitrogen dioxide and nitric oxide then converts the alcohol to the alkyl nitrite, which, due to its low density, will form an upper layer that can be easily decanted
from the reaction mixture.

Isoamyl nitrite decomposes in the presence of base to give nitrite salts and the isoamyl alcohol:

C5H11ONO + NaOH → C5H11OH + NaNO2

Amyl nitrite, like other alkyl nitrites, reacts with carbanions to give oximes.[14]

Amyl nitrites are also useful as reagents in a modification of the

aryl bromides.[17]

Physiological effects

An early container of amyl nitrite, Hunterian Museum, Glasgow

Amyl nitrite, in common with other

fainting. The effects set in very quickly, typically within a few seconds and disappear within a few minutes. Amyl nitrite may also intensify the experience of synesthesia.[19]
Amyl nitrite, when given as a medication for patients with angina, can also be administered as an ampule. The ampule is put in a gauze pad and then inhaled by the patient during an angina attack and repeated every fifteen minutes. However, oral dosing of amyl nitrite is ineffective due to poor absorption and extensive hepatic metabolism. Amyl nitrite has been widely replaced by nitroglycerin for the treatment of acute angina.

Toxicity

Although there are case reports of life-threatening toxicity involving unusually large amounts,[20] typical inhaled doses of amyl nitrite are considered relatively safe.[21][22] However, liquid amyl nitrite is highly toxic when ingested because of the unsafely high concentration it causes in blood.[23] Regardless of the form or route of administration, acute toxicity principally results when the nitrite oxidizes a significant proportion of hemoglobin in the blood without oxygen, forming methemoglobin, which cannot carry oxygen. Severe poisoning cases will progress to methemoglobinemia, characterized by a blue-brown discoloration under the skin which could be mistaken for cyanosis.[20][23] Treatment with oxygen and intravenous methylene blue frustrates visual confirmation further as methylene blue itself is, as its name suggests, a blue dye; the patient's changes in different shades of blue notwithstanding, it is an effective antidote by way of catalyzing the production of the enzyme responsible for reducing the methemoglobin in the blood back to hemoglobin.

The discoloration does mean that regular near-infrared–based pulse oximetry becomes useless. More fundamentally, blood gas analysis on the whole has limited effectiveness, as the increased methemoglobin level increases the oxygen binding affinity of regular hemoglobin.[20] Therefore, the measurement of actual ratios and levels of methemoglobin and hemoglobin must accompany any blood gas partial pressure sample in these cases.

In popular culture

The

Troubled Waters" (1974-1975) features amyl nitrite inhaled by the antagonist Hayden Danziger – played by Robert Vaughn – to help him feign a heart attack for his alibi. However, the episode consistently refers to the substance incorrectly as amyl nitrate.[24]

The 1978 Derek Jarman film Jubilee features a character named Amyl Nitrate (a misspelled reference to amyl nitrite).

The punk band Amyl and the Sniffers reference recreational use of amyl nitrite in their name.[25]

References

  1. ^ "Amyl Nitrite (Inhalation Route) Description and Brand Names - Mayo Clinic". www.mayoclinic.org. Retrieved 2023-12-05.
  2. ^ "Drugs - Amyl, Butyl or Isobutyl Nitrite, Nitrates, Poppers". urban75.com.
  3. ISBN 9783527607495
    .
  4. ^ a b Giannini AJ, Slaby AE, Giannini MC (1982). The Handbook of Overdose and Detoxification Emergencies. New Hyde Park, NY.: Medical Examination Publishing Co. pp. 48–50.
  5. PMID 4954412
    .
  6. ^ Vale JA (2001). "Cyanide Antidotes: from Amyl Nitrite to Hydroxocobalamin – Which Antidote is Best?". Toxicology. 168 (1): 37–38.
  7. PMID 19650716
    .
  8. PMID 20653465
    .
  9. ^ "Dichlorodifluoromethane". LearnChemistry. Royal Society of Chemistry.
  10. ^ "Amyl Nitrite Use and Manufacturing". PubChem. U.S. National Library of Medicine.
  11. ISBN 9780123864550
    .
  12. ISBN 158112404X
    . Retrieved 5 February 2017.
  13. ^ Noyes WA (1943). "n-Butyl Nitrite". Organic Syntheses; Collected Volumes, vol. 2, p. 108.
  14. ^ Chen YK, Jeon SJ, Walsh PJ, Nugent WA (2005). "(2S)-(−)-3-exo-(Morpholino)isoborneol ((−)-MIB)". Organic Syntheses. 82: 87.
  15. doi:10.1021/jo00295a056
    .
  16. doi:10.1039/P19870000859
    .
  17. doi:10.1039/J39660001249
    .
  18. ^ Nickerson M, Parker JO, Lowry TP, Swenson EW (1979). Isobutyl Nitrite and Related Compounds (PDF) (1st ed.). San Francisco California: PHARMEX. Archived from the original (PDF) on 2007-09-27.
  19. ISBN 978-0-262-53255-6
    .
  20. ^
    PMID 11971852
    .
  21. S2CID 5903121
    .
  22. ^ O'Malley MF, O'Malley R (May 2020). "Volatile Nitrites". MSD Manual. 2023 Merck & Co., Inc.
  23. ^ a b "Amyl Nitrite". Toxbase. UK National Poisons Information Service. December 2018. Retrieved September 29, 2020.
  24. ^ "Episode review: Columbo Troubled Waters". Columbophile blog. 29 September 2018. Retrieved 8 April 2023.
  25. ^ "Amyl and The Sniffers: 'It's just charmingly violent powerful fun'". 2019-05-14. Retrieved 2023-12-02.

Further reading
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