Alkyl Nitrites are a group

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 muscles are relaxed. As a recreational drug, they are primarily used to enhance the sexual experience.
Contents
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1 Basics
2 Usage
3 Chemistry
4 Health hazards
5 Medical uses
6 Street names
7 External links
8 References
9 Further reading
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Basics

Cyclohexyl nitrite, butyl nitrite, isobutyl nitrite, and other light alkyl nitrites can be found as the primary ingredient in so-called 'room odorizers', 'video head cleaners', and 'leather cleaners', despite the malodorous nature of some of these compounds. Traditionally marketed in small glass bottles, they are, like amyl nitrite capsules, 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. Some manufacturers include qualifying statements on their web sites such as: "All our nitrite based products are sold as room odorants, liquid incense, liquid aromas, or video head cleaner only. Although research indicates it is generally safe to do so, we do not encourage the misuse of our products as poppers. We are not responsible for the media claims that liquid aromas or poppers are said to be aphrodisiacs or sex drugs, and we do not endorse such claims. Our products do not contain amyl nitrite or butyl nitrite. They contain highly pure isobutyl nitrite, alkyl nitrites, cyclohexyl nitrite or hexyl nitrites only." Some web site dealers provide disclaimers on their sites as well.
The alkyl nitrite which has been used medicinally, amyl 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 or allowed to permeate the room. 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 many more doses.
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Usage

Inhaling nitrites relaxes smooth muscles throughout the body, including the sphincter muscles of the anus and the vagina. This causes the blood vessels to dilate (which causes a sudden drop in blood pressure), increases heart rate, and produces a sensation of heat and excitement that can last for several minutes.
The recreational use of alkyl nitrites is typically an attempt to enhance a sexual experience. The head rush, euphoria, and sensations of relaxation that result from the blood pressure drop are often felt to increase sexual arousal and desire. At the same time, the relaxation of the sphincters of the anus and vagina can make penetration easier. Similarly, a temporary reduction in the stiffness of the erection can also make penetration easier or more comfortable, so long as an adequate degree of stiffness is retained. Some people find poppers can also moderate their gag reflex, facilitating fellatio. Others report that poppers can enhance and prolong orgasms.
While anecdotal evidence reveals that both men and women can find the experience of using poppers pleasurable, this experience is not universal. Some people report that the smell of second-hand poppers (which delivers a relatively small dose) can cause head-aches and nausea. Others feel the reduction in erection stiffness can interfere with sexual performance. Some men find that poppers can interfere with their ability to attain or maintain an erection. These undesirable effects occur for most people as exposure increases, reducing the likelihood of a dangerous overdose.
The use of poppers was popularized in Radley Metzger's 1972 cult classic film Score. 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 often wrote about poppers with stories similar to this front page Wall Street Journal article. They were discussed again in the mainstream news at the turn of the century when the danger of combining nitrites with sildenafil (Viagra) or other impotence drugs became known. (e.g. Viagra May Cause Heart Attack Deaths In Younger Men With No Heart Problems, Study Finds), and again on the anniversary of the first quarter century of the AIDS epidemic, in a feature article in the June 5, 2006 edition of New York magazine (AIDS in New York: A Biography).
Alkyl nitrites are sometimes assumed to be used exlusively or primarily by homosexual men, but usage is reportedly popular among heterosexual men and women as well.
Nitrite users tend to be adults rather than adolescents.
Some nitrite users combine them with other recreational drugs to enhance the effects. For example, combining Ecstasy with poppers reportedly produces an intense rush of euphoria and physical pleasure. Since the rise of Disco in the mid-1970s and of Acid House music in the late 1980s, nitrite inhalants have been a large part of the disco scene and rave culture, used on the dance floor to heighten the experience of music and lights.
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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 [+ CuCl2 or amine ] ==> MDP2P
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Health hazards

Some of the information in this article or section has not been verified and might not be reliable. It should be checked for inaccuracies and modified as needed, citing sources.
The possible hazards of nitrite use have been a contentious issue since the mid-1970’s. Over the next decade, however, no allegation would be more hotly debated, or more serious, than that of a possible link between nitrites and AIDS, or AIDS-related illnesses such as Kaposi's sarcoma.
After a 1983 meeting between the Center for Disease Control's principal AIDS investigator, James Curran, and Joseph Miller, the president of Great Lakes Products, Inc. (a then-major manufacturer of popular nitrite brands such as RUSH®, who sought the meeting with Dr. Curran in order to discuss a possible poppers-AIDS connection -- before the HIV virus was discovered), Miller reported in a press release that poppers had been exonerated by the Center for Disease Control. Dr. Curran later pointed out in a September 27, 1983 letter to Miller that he had been misinterpreted in the press release. Curran stated that: “Other health hazards 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.”
Two years later, in 1985, after a demand from Hank Wilson, creator of the 'Committee to Monitor Poppers', that Dr. Curran take an anti-poppers stand, Dr. Curran responded to the one-man committee by telling Wilson that "Current data does not warrant an anti-poppers campaign". -- May 6,1985 letter to the Committee to Monitor Poppers
Upon the discovery of the HIV virus and research that showed HIV to be the cause of AIDS, poppers were eliminated as the cause of AIDS. The role of popper use as a risk factor in HIV infection continues to be explored. The immunosuppressive effect of poppers may increase susceptibility to HIV infection and also HHV-8 infection. Use may also affect sexual behavior increasing risk for infection.
Kaposi's sarcoma occurred 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 were suggested as a candidate for that cofactor, especially in view of the fact that they had been shown to be carcinogenic (it should be noted that the results of those studies were never repeated by other scientists, and that there were contradictory results both by the same researcher and between different researchers; see the reference section).
The large MACS study in 1987 concluded that no such connection with poppers existed. However, a later 1993 MACS publication PMID 8356966 found nitrite inhalant use a significant risk factor for KS. In 2002, Casper PMID 11920325, found that poppers use was an independent risk factor for HHV-8 seroconversion. In 2000, Pauk et al. PMID 11070101 found amyl nitrite use an independent risk factor for HHV-8 infection.In 2006,Casper et al. found a strong and dose dependent relation between popper use and HHV-8 infection in the EXPLORE study.(Casper et al.,"HIV Serodiscordant sex partners and the prevalence of HHV-8 infection among HIV negative men who have sex with men:Baseline data from the EXPLORE Study." Sexually Transmitted Infections June 1 2006 Vol. 82 Issue 3: 229-235. It is now generally accepted that HHV-8, a member of the herpes family, is a co-factor for or the cause of Kaposi's sarcoma. Research continues to explore risks for the transmission of HHV-8 and the progression to Kaposi's sarcoma. Research findings have been inconsistent, Haverkos and Drotman, PMID 7744258 cite 5 published studies finding a correlation between KS and poppers use and point out that differences in research methodologies may account for some of the discrepancies.
An argument continues today that, there are a number of possible negative health effects caused by poppers. For example, that high doses of Nitrites may cause methemoglobinemia, particularly in individuals predisposed towards such a condition.[1]. However, as the authors point out, it would take 'excessively high doses of poppers, administered chronically', to possibly cause methemogtlobinaemia (and that methemogtlobinaemia is readily reversible with the administration of methylene blue). Or that use with Viagra can cause heart failure (though there is no indication in the literature that such heart failure has ever occurred), and individuals with anaemia or heart, breathing or blood pressure conditions may be at risk of complications[citation needed]. It’s also suggested that since pressure in the eye and cranium is increased, individuals with glaucoma or traumatic head injuries may have an added risk of negative short or long term effects[citation needed].
According to the National Institute on Drug Abuse, use of poppers is associated with unsafe sexual practices that increase the risk of contracting and spreading infectious diseases such as HIV/AIDS and hepatitis.[2], though it's notable that nitrites are not alone in being associated with unsafe sexual practices. Included along with nitrite use would be alcohol use, marijuana use, among other drug use, and that use of nitrites may only be a marker for high-risk behavior in general[citation needed].
Impure alkyl nitrites can burn the skin on contact. All alkyl nitrites can be fatal if swallowed or injected. It has also been reported by some users of an association with mild to extreme headaches.
There has also been significant input from researchers and governmental officials in the USA and other countries, that poppers do not pose a significant hazard to users [3]. Some experts, including Thomas P Lowry, MD, went even further. In a research paper published in the Journal of Psychoactive Drugs; Jan-Jun, 1982; Vol. 14(2): 77-79, Dr. Lowry not only addressed the issue of potential hazards of poppers, but also discussed their use as aphrodisiacs, thereby combining a discussion of effects and sociological aspects.
Over the past quarter century, prominent AIDS researchers and activists, such as Paul Varnell and Bruce Voeller (the scientist who gave AIDS its name) made their concerns known about what they believed to be misrepresentations about poppers.
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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. Most Certified first responders and Emergency departments in the United States maintain a supply of Amyl Nitrite for such use.
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Street names

(NOTE: Street names for these products include names that are actual brand names. For example, RUSH® and Locker Room®, the original nitrite aromas, and Liquid Gold™, a brand from England, are all registered trade names of actual popper brands.)
Poppers
Amyls
Snappers
Locker Room®
RUSH®
Liquid Gold™
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External links

Toronto Canada Harm Reduction -- expert advice on poppers
DanceSafe UK
DrugScope - DrugSearch
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References

The neutrality of this section is disputed.
Please see discussion on the talk page.
Alkyl nitrites were shown to be immunosuppressive, mutagenic and carcinogenic in animals (but only when administered in doses greatly exceeding those of typical use). These results cannot be reasonably extrapolated to human beings.

"A Critical Review of the Bibliography/References listed above regarding Anti-Popper Research" -- Lisa Ringold, PhD pharmacology
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Further reading

Elf Sternberg's Guide to Poppers
Psychosexual Aspects of the Volatile Nitrites
The Libra Project amyl nitrite page
Fact Sheet -- Inhalants from the Missouri Dept. of Mental Health, Division of Alcohol and Drug Abuse
HIV & AIDS - Poppers
The AZ of Drugs
Sex Talk -- Queer Lesbian Gay Sexuality -- Gay.com
Poppers: www.addaction.org.uk
Duesberg on AIDS- The Poppers Story
The Poppers Story -- the History of Nitrite Odorants
Are Poppers Safe: IN A SERIES OF ONGOING PROJECTS FOR EDUCATING THE PUBLIC ABOUT "MAKING SEX SAFE" AND "SENSIBLE SEX."
Paul Varnell: "The controversy over poppers"
Guide to Alkyl Nitrites - Poppers Statements
The Art of Scientific Scrutiny: Investigating the Poppers-AIDS Hypothesis By Christine Weber, B.Sc.
The Pink Paper Issue 67 8 April 1989: Poppers in perspective
Amazon.com: Death Rush: Poppers and AIDS: Books: John Lauritsen
Poppers Bibliography John Lauritsen, author of "The AIDS War"
Duesberg on AIDS- John Lauritsen Bibliography
Confusion Between Nitrites & Nitrates by Erowid & Torsten v 1.0, March 2001
Ask Dr. Shulgin Online
Harper's Magazine Publishes AIDS Denialist
Index Home About Steve Harris M.D.: HIV/AIDS, Poppers, from the web...
Drugs: A Guide for Addicts, Youths and Parents Alike
Amyl Nitrate & Butyl Nitrate www2.potsdam.edu

Alkyl nitrites edit
{Amyl nitrite} {Butyl nitrite} {Ethyl nitrite} {Methyl nitrite} {Isopropyl nitrite} {Isobutyl nitrite} {Cyclohexyl nitrite}