||It has been suggested that this article be merged into Alkyl nitrites. (Discuss) Proposed since January 2013.|
Most widely sold concentrated products include the original compound amyl nitrite (isoamyl nitrite, isopentyl nitrite), cyclohexyl nitrite, isobutyl nitrite (2-methylpropyl nitrite), and isopropyl nitrite (2-propyl nitrite). Isopropyl nitrite became popular due to a ban on isobutyl nitrite in the EU in 2007. More rarely sold is the compound butyl nitrite.
- 1 History
- 2 Chemistry
- 3 Medical use
- 4 Recreational drug use
- 5 Health issues
- 6 Legal status
- 7 See also
- 8 References
|Sir Thomas Lauder Brunton|
|Known for||Treatment of angina pectoris|
In 1844, the French chemist Antoine Jérôme Balard synthesized amyl nitrite. Sir Thomas Lauder Brunton (1844–1916), a Scottish physician, famously pioneered the use of amyl nitrite to treat angina pectoris (now treated with nitroglycerin). Brunton's clinical use of amyl nitrite to treat angina was inspired by earlier work with the same reagent by Arthur Gamgee and Benjamin Ward Richardson. Brunton reasoned that the pain and discomfort of angina could be reduced by administering amyl nitrite to dilate the coronary arteries of patients, thus improving blood flow to the heart muscle.
Time and the Wall Street Journal reported that the popper fad began among homosexual men as a way to enhance sexual pleasure, but "quickly spread to avant-garde heterosexuals" as a result of aggressive marketing. A series of interviews conducted in the late 1970s revealed a wide spectrum of users."
The first few members of the series are volatile liquids; methyl nitrite and ethyl nitrite are gaseous at room temperature and pressure. Organic nitrites are prepared from alcohols and sodium nitrite in sulfuric acid solution. They decompose slowly on standing, the decomposition products being oxides of nitrogen, water, the alcohol, and polymerization products of the aldehyde.
Physical and chemical properties
(Sutton, 1963 for amyl nitrite, butyl nitrite, isobutyl nitrite):
|Alkyl nitrite||CAS||Formula||Molecular weight (g·mol−1)||Physical state||Boiling point (°C)||Specific gravity|
|Amyl nitrite (isoamyl nitrite, isopentyl nitrite)||110-46-3||(CH3)2CHCH2CH2ONO||117.15||Transparent liquid||97–99||0.872|
|Butyl nitrite||544-16-1||CH3(CH2)2CH2ONO||103.12||Oily liquid||78.2||0.9144 (0/4 °C)|
|Isobutyl nitrite (2-methylpropyl nitrite)||542-56-3||(CH3)2CHCH2ONO||103.12||Colorless liquid||67||0.8702 (20/20 °C)|
|Isopropyl nitrite (2-propyl nitrite)||541-42-4||(CH3)2CHONO||89.09||Clear pale yellow oil||39 °C at 760 mmHg|
Antidote to cyanide poisoning
Amyl nitrite is used medically as an antidote to cyanide poisoning, The light alkyl nitrites cause the formation of methemoglobin wherein, as an effective antidote to cyanide poisoning, the methemoglobin combines with the cyanide to form nontoxic cyanmethemoglobin. First responders typically carry a cyanide poison kit containing amyl nitrite.
Recreational drug use
The dose administered can easily be determined by subtracting the weight of a small vial after inhalation from its weight before inhalation, using an accurate scale. Two-cm vial openings, now being more common, are broad enough to cover the nostrils; smaller vial necks distribute lower doses.
- Effects are instantaneous and brief, but intense. These effects are caused by a sudden surge of blood to the heart and brain
- Light-headedness, giddiness, heat flush or heightened sensual awareness may also result. This is known as a headrush
- Some users may also experience the impression of time slowing down
- The effects fade two to five minutes after use
- Users are often left with a headache.
Inhaling nitrites relaxes smooth muscles throughout the body  Smooth muscle surrounds the body's blood vessels and when relaxed causes these vessels to dilate resulting in an immediate decrease in blood pressure.
User surveys are hard to come by, but a 1988 study found that 69% of men who had sex with men in the Baltimore/Washington DC area reported they had used poppers, with 21% having done so in the prior year. The survey also found that 11% of recreational drug users in the area reported using poppers, increasing to 22% among "heavy abusers," with an average age of first use of 25.6 years old. Both survey groups used poppers to "get high. It was reported that this group reduced usage following the AIDS epidemic, while the drug-users had not. A 1987 study commissioned by the US Senate and conducted by the Department of Health and Human Services found that less than 3% of the overall population had ever used poppers.
Use by minors is historically minimal due, in part, to the ban on sales to minors by major manufacturers for public relations reasons and because some jurisdictions regulate sales to minors by statute. A paper published in 2005 examined use of poppers self-reported by adolescents aged 12–17 in the (American) 2000 and 2001 National Household Surveys on Drug Abuse. In all, 1.5% of the respondents in this age group reported having used poppers. This figure rose to 1.8% in those over 14. Living in nonmetropolitan areas, having used mental health services in the past year (for purposes unconnected with substance use treatment), the presence of delinquent behaviours, past year alcohol and drug abuse and dependence, and multi-drug use were all associated with reporting the use of poppers.
The Merck Manual of Diagnosis and Therapy reports that there is little evidence of significant hazard associated with inhalation of alkyl nitrites. A study and ranking of drugs for harmfulness devised by British-government advisers and based upon scientific evidence of harm to both individuals and society placed alkyl nitrites among the less harmful substances when compared to other recreational drugs including alcohol and tobacco.
Alkyl nitrites are interactive with other vasodilators like sildenafil (Viagra), vardenafil (Levitra), and tadalafil (Cialis), to cause a serious decrease in blood pressure, leading to fainting, stroke, or heart attack.
Route of administration
An overdose via ingestion (rather than inhalation) may result in cyanosis, unconsciousness, coma and even death. Methylene blue is a treatment for methemoglobinemia associated with popper use. Accidental aspiration of amyl or butyl nitrites may lead to the development of lipoid pneumonia.
Habitual use and temporary symptoms
Poppers are a possible and rare cause of concern of in a small number of cases of maculopathy (eye damage) in recent case reports from UK and France. Some studies have concluded that there may be increased risk for at least temporary retinal damage with habitual popper use in certain users; In a letter to the New England Journal of Medicine, an ophthalmologist described four cases in which recreational users of poppers experienced temporary changes in vision. Another study described foveal (daylight vision) damage in six habitual poppers users.
Route of administration
The only route of administration used with poppers is inhalation, since any other route is potentially fatal.
The sale of poppers in any formulation has been banned in Canada. Although not considered a narcotic and not illegal to possess or use, they are considered a drug. Sales that are not authorized can now be punished with fines and prison.
In France, the sale of products containing butyl nitrite, pentyl nitrite, or isomers thereof, has been prohibited since 1990 on grounds of danger to consumers. In 2007, the government extended this prohibition to all alkyl nitrites that were not authorized for sale as drugs. After litigation by sex shop owners, this extension was quashed by the Council of State on the grounds that the government had failed to justify such a blanket prohibition: according to the court, the risks cited, concerning rare accidents often following abnormal usage, rather justified compulsory warnings on the packaging.
In the United Kingdom, poppers are widely available and frequently (legally) sold in gay clubs/bars, sex shops, drug paraphernalia head shops, over the Internet and on markets. It is illegal under Medicines Act 1968 to sell them advertised for human consumption, and in order to bypass this, they are usually sold as odorizers.
In the U.S., originally marketed as a prescription drug in 1937, amyl nitrite remained so until 1960, when the Food and Drug Administration removed the prescription requirement due to its safety record. This requirement was reinstated in 1969, after observation of an increase in recreational use.
Other alkyl nitrites were outlawed in the U.S. by Congress through the Anti-Drug Abuse Act of 1988. The law includes an exception for commercial purposes. The term commercial purpose is defined to mean any use other than for the production of consumer products containing volatile alkyl nitrites meant for inhaling or otherwise introducing volatile alkyl nitrites into the human body for euphoric or physical effects. The law came into effect in 1990. Visits to retail outlets selling these products reveal that some manufacturers have since reformulated their products to abide by the regulations, through the use of the legal cyclohexyl nitrite as the primary ingredient in their products, which are sold as video head cleaners, polish removers, or room odorants.
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- Kennedy, Edward, U.S. Senate, Chair Committee on Labor and Human Resources. "REPORT of the Committee on Labor and Human Resources."Comprehensive Alcohol Abuse, Drug Abuse, and Mental Health Amendments of 1988. Section 4015. 1988.
- Nickerson, Mark, John Parker, Thomas Lowry, and Edward Swenson.Isobutyl Nitrite and Related Compounds; chapter on "Sociology and Behavioral Effects" . 1st ed. San Francisco: Pharmex, Ltd, 1979. 
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- "Decree 90–274 of 26 March 1990" (in (French)). Legifrance.gouv.fr. 2009-05-15. Retrieved 2012-07-26.
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- Council of State, Ruling 312449, 15 May 2009
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- Anti-Drug Abuse Act of 1988 (Public Law 1QO-690,section 2404) (15 U.S.C. 2d57a(e)(2)).