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Alkyl nitrites are a group of organic compounds with the general formula R-O-N=O, where R is any organic group. Amyl nitrite has historically been used for the treatment of angina, among other legitimate medicinal uses. Other alkyl nitrites, including butyl nitrite, isobutyl nitrite, isopropyl nitrite, ethyl nitrite, methyl nitrite as well as the disputed cyclohexyl nitrite, have been widely used for 40 years as the primary ingredients in room odorizer products and as recreational drug. The vapours of the alkyl nitrite are inhaled directly from the bottle, inducing an almost-instant, euphoric head rush; the body's smooth muscle, such as the sphincter, is relaxed. As a recreational drug, they are primarily used to enhance the sexual experience.

Basics

Cyclohexyl nitrite, butyl nitrite, isobutyl nitrite, and other light alkyl nitrites can be found as the primary ingredient in so-called 'room odorizers,' despite the malodorous nature of some of these compounds. These products are traditionally marketed in small glass bottles that, like amyl nitrite capsules, are referred to as poppers. Nitrite-based odorizers are available in adult bookstores and shops and over the Internet, and are regulated by a variety of federal and local regulations and legal restrictions, though the status of cyclohexyl nitrite — technically not a member of the class of alkyl nitrites encompassed by the law — remains in question in the United States, as a result of the controversial Federal Analog Act.

The alkyl nitrite which has been used medicinally, amyl nitrite (pentyl nitrite), was popularized in Hunter S. Thompson's Fear and Loathing in Las Vegas. Other popular nitrites include isopropyl nitrite, isobutyl nitrite, butyl nitrite and cyclohexyl nitrite.

The two main vessels for alkyl nitrites are small glass vials/bottles ("freshness jars"), or small ampules which are popped or snapped in order to release the vapors. The name snappers is sometimes used. The vials are simply uncapped, and the vapours are inhaled. The ampules contain small amounts of the alkyl nitrite, and are enough for only a few doses; while the vials contain enough of the alkyl nitrite for hundreds of doses.

Users

Poppers are often found in usage by homosexual men, but usage is reportedly popular among straight men and women as well. These products are generally used in an attempt to enhance the sexual experience. The existence of poppers became more widely known to the layman when they appeared in Radley Metzger's cult classic film Score (1972). In the film, a bisexual woman glides them under the nose of a heterosexual woman in an attempt to loosen her vagina for seduction. During the 1970's and 1980's, the mainstream media widely reported on the use of nitrite odorizers.

The alkly nitrites relax smooth muscle, which is what the sphincter muscles of the body are comprised of (Included in the sphincter muslce group are the anus and the vagina). Anectdotal evidence reveals that men and women, both, often find the experience of using poppers pleasurable. Homosexual men are a marketing target for "Poppers," since the alkyl nitrites help relax the muscles of the anus, allowing easier penetration and enhanced sensation. In addition, they are widely reported to greatly enhance and prolong orgasms. Ironically, some men find that poppers interfere with the ability to maintain an erection.

Nitrite users — who tend to be adults rather than adolescents as are most other inhalant users — seek to enhance the sexual experience. Inhaled nitrites dilate blood vessels, increase heart rate, and produce a sensation of heat and excitement that can last for several minutes.

They are also inhaled by users of other recreational drugs to enhance the effects, for example Ecstasy, the effects of which combine with those of Nitrites to produce an extremely intense rush of euphoria and physical pleasure. Since the rise of Acid House in the late 1980s Nitrites are a large part of rave culture, used on the dance floor to heighten the experience of music and lights.

Chemistry

Alkyl nitrites can be synthesized from primary alcohols according to the following reaction process:

R-OH + NaNO₂ + H₂SO₄ ==> R-ONO + NaHSO₄ + H₂O

It has been reported (US Patent 4,638,094) that alkyl nitrites are also a precursor for MDP2P, a phenylacetone used in the production of MDMA, more commonly known as "ecstasy." The basic reaction process is shown below:

MeONO in corresponding alcohol + safrole + PdCl₂ ==> MDP2P

Health hazards

The possible hazards of nitrite use has been a contentious issue since their introduction; in particular, a possible link between nitrites and AIDS and AIDS related illnesses such as Kaposi's sarcoma has been hotly disputed. At the time the AIDS crisis began to unfold, the poppers industry was making over $50 million a year and was the main financial support of the gay press through advertising. Joseph Miller, president of Great Lakes Products, the manufacturers of popular nitrite brands such as RUSH, claimed in 1983 that poppers had been exonerated by the Center for Disease Control; James Curran of the CDC was quick to reply that he had been misinterpreted by Miller, but the gay press failed to publicize his response. He also stated that:

Other health hazards (than AIDS) from misuse of these drugs have been documented. Your press release and advertisements in the Advocate are misleading and misrepresent the CDC findings and their implications... While it is unlikely that nitrites will be implicated as the primary cause of AIDS, their role as a co-factor in some of the illnesses found in this syndrome has not been ruled out. I must insist that you discontinue the misuse and misinterpretation of CDC findings.

Letter from James Curran to Joseph Miller, September 27, 1983

In particular, an argument is often made connecting Kaposi's sarcoma, a rare form of cancer, with poppers use. Some scientists, including Peter Duesberg, suggest the existence of a link between the two. These scientists argue that Kaposi's sarcoma occurs in homosexual AIDS-patients 20 times more often than in non-homosexual AIDS-patients, and that therefore some cofactor must be involved beyond the virus HIV itself. Poppers have been suggested as a candidate for that cofactor, especially in view of the fact that they have been shown to be carcinogenic. However, despite their carcinogenic and mutagenic properties, poppers have not been concretely linked as a cofactor in either the AIDS virus itself or Kaposi's sarcoma.

Apart from the AIDS controversy, there are a number of negative health effects caused by poppers that are not still being debated. High doses of Nitrites may cause methemoglobinemia, particularly in individuals predisposed towards such a condition.. Use with viagra can cause heart failure, and individuals with anaemia or heart, breathing or blood pressure conditions may be at risk of complications. Since pressure in the eye and cranium is increased, individuals with glaucoma or traumatic head injuries may be have an added risk of negative short term and long term effects.

According to the National Institute on Drug Abuse, use of these drugs is associated with unsafe sexual practices that greatly increase the risk of contracting and spreading infectious diseases such as HIV/AIDS and hepatitis. A short-term immunosuppressive effect has been observed in mice as well as in humans -- which has been shown to quickly reverse itself after discontinued exposure; regular use of the drug over years may lead to an irreversible suppression of the immune system. -- however this is speculation, and no evidence of long term immune suppression has been seen.

Poppers users also run the risk of developing a psychological dependence to the drug, and tolerance has been shown to increase with use.

Alkyl nitrites can burn the skin on contact, and may be fatal if swallowed or injected.

Medical uses

Alkyl nitrites are clinically utilized as a vasodilator in order to treat angina, and as part of the treatment regimen for cyanide poisoning.

Street names

• Poppers
• Amyls
• Snappers
• Locker Room
• Rush

External links

• The Poppers Story - Exploring the possible connection between AIDS and Poppers
• - Toronto Canada Harm Reduction -- expert advice on poppers
• - ©GQ Magazine -- another prespective on Duesberg
• DanceSafe UK
• DrugScope - DrugSearch
• Duesberg/Lauritsen on poppers causing some of the AIDS-defining symptoms

References

Limited studies have shown Alkyl nitrites to be both mutagenic and carcinogenic in animals and humans. This has not been proven, however, and other studies have produced different results.

• Hersh E.M., Reuben J.M., Bogerd H., Rosenblum M., Bielski M., Mansell P.W.A., Rios A., Newell G.R., Sonnenfeld G. (1983), Effect of the recreational agent isobutyl nitrite on human peripheral blood leukocyte and on in vitro interferon production. Cancer Res 43, 1365
• Jorgensen K.A., Lawesson S.O. (1982), Amyl nitrite and Kaposi's sarcoma in homosexual men. N. Engl. J. Med. 307, 893
• Mirvish S.S., Ramm M.D., Bobcock D.M. (1988), Indications from animal and chemical experiments of a carcinogenic role for isobutyl nitrite. In: Health Hazards of Nitrite Inhalants (Haverkos H.W. Dougherty J.A., eds.) NIDA Res Monogr 83, National Institute on Drug Abuse, Washington DC, P 39
• Newell G.R., Mansell P.W., Spitz M.R., Reuben J.M., Hersh E.M. Volatile Nitrites Use and Adverse Effects Related to the Current Epidemic of the Acquired Immune Deficiency Syndrome. Am. J. Med. 78:811,1985.
• Harry Haverkos et al., "Disease manifestation among homosexual men with acquired immunodeficiency syndrome: A possible role of nitrites in Kaposi's sarcoma, Sexually Transmitted Diseases, October-December 1985. Harry Haverkos and John Dougherty, editors; Health Hazards of Nitrite Inhalants, NIDA Research Monograph 83, 1988
• I. Quinto, "The Mutagenicity of Alkylnitrites in the Salmonella Test" (translation from the Italian), Bolletino Societa Italiana Biologia Sperimentale, 56:816-820, 1980.
• Sidney Mirvish et al., "Mutagenicity of Iso-Butyl Nitrite Vapor in Ames Test and Some Relevant Chemical Properties, Including the Reaction of Iso-Butyl Nitrite with Phosphate", Environmental and Molecular Mutagenesis, 1993;21:247-252.

• Antianginals
• Antidotes
• Alkyl nitrites
• Schedule VI controlled substances