n.
A volatile yellow liquid, C5H11NO2, formerly used in medicine as a vasodilator, but now replaced by other nitrates, such as nitroglycerin. It is used illicitly to induce euphoria and enhance sexual stimulation.
amyl nitrite
| Dictionary: amyl nitrite |
n.
| 5min Related Video: amyl nitrite |
| Drug Info: Amyl Nitrite |
Chemical formula:
Amyl Nitrite Inhalation vapour, solution
What is this medicine?
AMYL NITRITE is used to relieve chest pain caused by angina.
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
• anemia
• glaucoma
• head injury, recent stroke, or bleeding in the brain
• low blood pressure
• an unusual or allergic reaction to amyl nitrite, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding
How should I use this medicine?
This medicine is for inhalation. Do not take by mouth. Follow the directions on the prescription label. Use this medicine at the first sign of an angina attack (chest pain or tightness). Do not remove the woven covering on the glass ampule. Crush the ampule between the fingers and with the patient in a sitting position, pass in front of the nose several times for inhalation of the vapor. Remain in a sitting position after use. The dose may be repeated in 3 to 5 minutes if needed for pain relief. If there is still no relief after a second dose, seek medical attention. Do not use this medicine more often than directed.
Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.
Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.
What may interact with this medicine?
Do not take this medicine with any of the following medications:
• medicines used to treat erectile dysfunction like sildenafil, tadalafil, and vardenafil
This medicine may also interact with the following medications:
• alcohol
This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.
What should I watch for while using this medicine?
Check your heart rate and blood pressure regularly while you are using this medicine. Ask your doctor or health care professional what your heart rate and blood pressure should be and when you should contact him or her.
You may get drowsy or dizzy. Do not drive, use machinery, or do anything that needs mental alertness until you know how this drug affects you. Do not stand or sit up quickly, especially if you are an older patient. This reduces the risk of dizzy or fainting spells. Alcohol can make you more drowsy and dizzy. Avoid alcoholic drinks.
What side effects may I notice from receiving this medicine?
Side effects that you should report to your doctor or health care professional as soon as possible:
• bluish discoloration of lips, fingernails, or palms of hands
• fast, slow, or irregular heartbeat, palpitations, chest pain
• low blood pressure
• shortness of breath
• the feeling of extreme pressure in the head
• unusually weak or tired
Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
• dizziness
• flushing of the face and neck
• headache
This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.
Where should I keep my medicine?
Keep out of reach of children.
Store in the refrigerator between 2 and 8 degrees C (36 and 46 degrees F). The contents of the capsule are flammable. Protect from light. Keep container tightly closed. Throw away any unused medicine after the expiration date.
Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
| Medical Dictionary: amyl nitrite |
n.
A volatile yellow liquid used as a vasodilator and as an antidote in cyanide poisoning.
| Wikipedia: Amyl nitrite |
Not to be confused with amyl nitrate.
| Amyl nitrite | |
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| IUPAC name |
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| Other names | Isoamyl nitrite Nitramyl 3-methyl-1-nitrosooxybutane (3-methylbutyl) nitrite Pentyl alcohol nitrite(ambiguous) Nitrous acid, pentyl ester(ambiguous) poppers (colloquial, street slang) |
| Identifiers | |
| CAS number | [] |
| RTECS number | NT0187500 |
| SMILES |
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| Properties | |
| Molecular formula | C5H11NO2 |
| Molar mass | 117.15 g mol−1 |
| Appearance | Colourless liquid |
| Density | 0.872 g/cm3, liquid (25 °C) |
| Boiling point |
99 °C |
| Solubility in water | Low |
| Hazards | |
| Main hazards | vasodilator |
| Flash point | 21 °C |
| Related compounds | |
| Related compounds | Nitroglycerine Isopentanol Butyl nitrite Isobutyl nitrite Ethyl nitrite |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Amyl nitrite is the chemical compound with the formula C5H11ONO. A variety of isomers are known, but they all feature an amyl group attached to the nitrito functional group. The alkyl group is unreactive and the chemical and biological properties are mainly due to the nitrite group. Like other alkyl nitrites, amyl nitrite is bioactive in mammals, being a vasodilator which is the basis of its use as a prescription medicine. As an inhalant, it also has a psychoactive effect which has led to its recreational use.
Contents |
Nomenclature
The term "amyl nitrite" encompasses several isomers. For example, a common form of amyl nitrite with the formula (CH3)2CHCH2CH2ONO may be more specifically referred to as isoamyl nitrite. When the amyl group is a linear or normal (n) alkyl group, the resulting amyl nitrite would have the structural formula CH3(CH2)4ONO.
Amyl nitrite is often confused with amyl nitrate, a substance with a different chemical composition and different properties.
Synthesis and reactions
Alkyl nitrites are prepared by the reaction of alcohols with nitrous acid:[1]
- C5H11OH + HONO → C5H11ONO + H2O
The reaction is called esterification. Synthesis of alkyl nitrites is generally 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 nitrous 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.[2]
Physiological effects
Amyl nitrite, in common with other alkyl nitrites,[3] is a potent vasodilator, i.e. it expands blood vessels, resulting in lowering of the blood pressure. Alkyl nitrites function as a source of nitric oxide, which signals for relaxation of the involuntary muscles. Physical effects include decrease in blood pressure, headache, flushing of the face, increased heart 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 (vomiting), hypotension, hypoventilation, dyspnea (shortness of breath), and syncope (fainting). The effects set in very quickly, typically within a few seconds and disappearing soon after (within a minute).
It induces the formation of methemoglobin, which sequesters cyanide as non-toxic cyanomethemoglobin.[4]
Applications
Amyl nitrite is employed medically to treat heart diseases such as angina and also to treat cyanide poisoning.[5] It is also used as an inhalant drug that induces a brief euphoria; whilst already intoxicated with stimulant drugs such as cocaine or ecstasy, the euphoric state intensifies and lasts for several minutes longer. Once some stimulative drugs wear off, a common side effect is a period of depression or anxiety, colloquially called a "comedown"; amyl nitrite is sometimes used to "come up" again in order to stop these adverse effects. This drug is often used to obtain an erection with rather rapid onset. This effect, combined with its dissociative effects, makes it an attractive but risky recreational drug (see poppers).[6]
References
- ^ Noyes, W. A. “n-Butyl Nitrite” Organic Syntheses, Collected Volume 2, p.108 (1943). [1] (PDF)
- ^ Chen, Y. K.; Jeon, S.-J; Walsh, P. J.; Nugent, W. A. “(2S)-(-)-3-exo-(Morpholino)isoborneol ((-)-MIB)” Organic Syntheses, Volume 82, pp. 87 (2005). [2] (PDF)
- ^ Nickerson, Mark, John O Parker, Thomas P Lowry, and Edward W Swenson. Isobutyl Nitrite and Related Compounds. 1st ed. San Francisco: Pharmex, Ltd, 1979. [3]PDF
- ^ Vale, J. A. (2001). "Cyanide Antidotes: from Amyl Nitrite to Hydroxocobalamin - Which Antidote is Best?". Toxicology 168 (1): 37–38.
- ^ Cheng, L.; Goodwin, C. A.; Schully, M. F.; Kakkar, V. V.; Claeson, G. (1965). "The Effects of Nitroglycerin and Amyl Nitrite on Arteriolar and Venous Tone in the Human Forearm". Circulation 3 (2): 755.
- ^ AJ Giannini, AE Slaby, MC Giannini. The Handbook of Overdose and Detoxification Emergencies. New Hyde Park, NY. Medical Examination Publishing Co., 1982, pp.48-50.
External links
- 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".
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 | Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2007. Published by Houghton Mifflin Company. All rights reserved. Read more |
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| Drug Info. Gold Standard. Copyright © 2008 by Gold Standard. All rights reserved. Read more |
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| Medical Dictionary. The American Heritage® Stedman's Medical Dictionary Copyright © 2002, 2001, 1995 by Houghton Mifflin Company. Read more |
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