Amyl nitrite

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IUPAC name: 3-methyl-1-nitrosooxybutane
CAS number 463-04-7	ATC code V03AB22
Chemical formula	C₅H₁₁N O₂
Molecular weight	117.15 g/mol
Bioavailability	?
Metabolism	?
Elimination half life	?
Excretion	?
Pregnancy category	?
Legal status	Schedule VI
Delivery	?

The chemical compound amyl nitrite (here referring to isoamyl nitrite) is an alkyl nitrite. It has a characteristic penetrating odour, and produces marked effects on the human body when its vapour is inhaled. It acts as a vasodilator (expanding blood vessels and thus lowering blood pressure) and finds applications in medicine in the treatment of heart disease such as angina. Amyl nitrite is also used to treat cyanide poisoning. It induces the formation of methemoglobin which binds cyanide into non-toxic cyanomethemoglobin.

Amyl nitrite capsules were created by Alton J. Parker. They are used recreationally, and are often called poppers. It can also be used recreationally as an inhalant (See Nitrite inhalants).The effects of amyl nitrite are thought to be due to the action of nitric oxide in the body.

Nitramyl is another name for isoamyl nitrite. The name "amyl nitrite" is actually ambiguous as it can refer not only to 3-methyl-1-nitrosooxybutane, but also its isomers 2-methyl-1-nitrosooxybutane, 3-nitrosooxypentane, 2-nitrosooxypentane, and most commonly 1-nitrosooxypentane-n-amyl nitrite. Other synonyms for amyl nitrite, which may refer to any isomer, include Pentyl Alcohol Nitrite and Nitrous acid, pentyl ester. The name "amyl nitrate" is commonly mistaken for amyl nitrite; they are two different chemicals.

1 Chemistry
2 Physiological effects
3 Amyl Nitrite in Popular Culture
4 See also
5 External links

[edit] Chemistry

Isoamyl nitrite is a clear liquid of specific gravity 0.872, boiling at about 95 to 96 degrees Celsius. It has a solubility in water of about .01 g/100 mL, but dissolves readily in alcohol, ether, glacial acetic acid, chloroform, and benzene. It is prepared by passing nitrous fumes (from starch and concentrated nitric acid) into warm isoamyl alcohol, or by distilling a mixture of 26 parts of potassium nitrite in 15 parts of water with 30 parts of isoamyl alcohol in 30 parts of sulfuric acid. On heating with methanol, it is converted into isoamyl alcohol and methyl nitrite; a similar reaction takes place with ethanol, but the change is less complete. It is readily decomposed by nascent hydrogen, with the formation of ammonia and isoamyl alcohol; and in alkaline hydrolysis it forms isoamyl alcohol.

n-amyl nitrite is a yellow-coloured liquid of specific gravity 0.853, boiling at 104 degrees Celsius. It decomposes in water. When the liquid is dropped onto fused caustic potash (liquid KOH), it forms potassium valerate.

[edit] Physiological effects

Amyl nitrite, along with other alkyl nitrites, is a potent vasodilator that functions in-situ via the nitric oxide pathway. Physical effects include decrease in blood pressure, headache, flushing of the face, increase in pulse rate, dizziness and relaxation of involuntary muscles, especially the blood vessel walls and the anal sphincter. There are no withdrawal symptoms. Overdose symptoms include nausea, emesis, hypotension, hypoventilation, dyspnea and syncope. Clinically, amyl nitrite is prescribed for unstable angina.

[edit] Amyl Nitrite in Popular Culture

Amyl Nitrite is used recreationally in Fear and Loathing in Las Vegas.

It was also mentioned in the movie Fight Club during one of the group therapy sessions.

"Narrator: Oh, yeah, Chloe... Chloe looked the way Meryl Streep's skeleton would look if you made it smile and walk around the party being extra nice to everybody.

Chloe: Well, I'm still here. But I don't know for how long. That's as much certainty as anyone can give me. But I've got some good news: I no longer have any fear of death. But... I am in a pretty lonely place. No-one will have sex with me. I'm so close to the end and all I want is to get laid for the last time. I have pornographic movies in my apartment, and lubricants, and amyl nitrate... [the group leader takes the mic] Group Leader: Thank you, Chloe... everyone, let's thank Chloe."

[edit] See also

[edit] External links

Links to external chemical sources.
Abstract for an article in the Journal of Chemical Education (1996, volume 73, page 1127) by Richard A. Kjonaas on the use of the word "amyl".