amyl nitrite

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Chemical formula:

Espa�ol:
• Nitrito de amilo, Vapor para inhalación, solución

Amyl Nitrite Inhalation vapour, solution

What is this medicine?

AMYL NITRITE (AM il  NYE trate) 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.

A volatile yellow liquid used as a vasodilator and as an antidote in cyanide poisoning.

• PHARMACOLOGY - amyl nitrite: rapidly absorbed inhalant that causes rapid drop in blood pressure, faintness, and flushing
• Drug Names and Forms - amyl nitrite: pharmaceutical drug that dilates blood vessels, producing brief exhilaration

Not to be confused with amyl nitrate.

Amyl nitrite
IUPAC name (3-methylbutyl) nitrite
Other names Isoamyl nitrite Nitramyl 3-methyl-1-nitrosooxybutane Pentyl alcohol nitrite(ambiguous) Nitrous acid, pentyl ester(ambiguous) poppers (colloquial, street slang)
Identifiers
CAS number	110-46-3 Y
PubChem	10026
ChemSpider	9632 Y
UNII	5N0U5TUC9Z Y
DrugBank	DB01612
KEGG	D00517 Y
ChEBI	CHEBI:55344 Y
RTECS number	NT0187500
ATC code	V03AB22
Jmol-3D images	Image 1
SMILES O=NOCCCCC
InChI InChI=1S/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3 Y Key: CSDTZUBPSYWZDX-UHFFFAOYSA-N Y InChI=1/C5H11NO2/c1-2-3-4-5-8-6-7/h2-5H2,1H3 Key: CSDTZUBPSYWZDX-UHFFFAOYAT
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, 372 K, 210 °F
Solubility in water	Low
Hazards
Main hazards	vasodilator
Flash point	21 °C
Related compounds
Related compounds	Nitroglycerine Isopentanol Butyl nitrite Isobutyl nitrite Ethyl nitrite Methyl nitrite Isopropyl nitrite Cyclohexyl nitrite
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 1 Nomenclature 2 Synthesis and reactions 3 Physiological effects 4 Applications 5 References 6 External links

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.

Despite a very similar name to amyl nitrite, amyl nitrate has 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, in general, 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]

Amyl nitrites are also useful as reagents in a modification of the Sandmeyer reaction. The reaction of the alkyl nitrite with an aromatic amine in a halogenated solvent produces a radical aromatic species, this then abstracts a halogen atom from the solvent. For the synthesis of aryl iodides diiodomethane is used,^[3][4] whereas bromoform is the solvent of choice for the synthesis of aryl bromides.^[5]

Physiological effects

Amyl nitrite, in common with other alkyl nitrites,^[6] 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 disappear soon after (within minutes).

Applications

Amyl nitrite is employed medically to treat heart diseases such as angina and also to treat cyanide poisoning.^[7] It is also used as an inhalant drug that induces a brief euphoric state, and when combined with other intoxicant stimulant drugs such as cocaine or ecstasy (see MDMA), the euphoric state intensifies and is prolonged. Once some stimulative drugs wear off, a common side effect is a period of depression or anxiety, colloquially called a "come down"; amyl nitrite is sometimes used to combat these negative after-effects. This effect, combined with its dissociative effects, have led to its use as a recreational drug (see poppers).^[8]

Amyl nitrite is also sometimes used as an antidote for cyanide poisoning. It can act as an oxidant, to induce the formation of methemoglobin. Methemoglobin in turn can sequester cyanide as cyanomethemoglobin.^[9]

References

1. ^ Noyes, W. A. (1943), "n-Butyl Nitrite", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV2P0108 ; Coll. Vol. 2: 108 
2. ^ Chen, Y. K.; Jeon, S.-J; Walsh, P. J.; Nugent, W. A. (2005), "(2S)-(-)-3-exo-(Morpholino)isoborneol ((-)-MIB)", Org. Synth. 82: 87, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=v82p0087 
3. ^ Smith, William B.; Ho, Oliver Chenpu (1990). "Application of the isoamyl nitrite-diiodomethane route to aryl iodides". The Journal of Organic Chemistry 55 (8): 2543. DOI:10.1021/jo00295a056. 
4. ^ Cornforth, John; Kumar, Ashok; Stuart, Alan S. (1987). "Synthesis of substituted dibenzophospholes. Part 6. Preparation of symmetrical and non-symmetrical quaterphenyl intermediates". Journal of the Chemical Society, Perkin Transactions 1: 859. DOI:10.1039/P19870000859. 
5. ^ Cadogan, J. I. G.; Roy, D. A.; Smith, D. M. (1966). "An alternative to the Sandmeyer reaction". Journal of the Chemical Society C: Organic: 1249. DOI:10.1039/J39660001249. 
6. ^ Nickerson, Mark, John O Parker, Thomas P Lowry, and Edward W Swenson. Isobutyl Nitrite and Related Compounds, 1st ed. San Francisco: Pharmex, Ltd, 1979.
7. ^ 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): 755–66. PMID 4954412. 
8. ^ 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.
9. ^ Vale, J. A. (2001). "Cyanide Antidotes: from Amyl Nitrite to Hydroxocobalamin - Which Antidote is Best?". Toxicology 168 (1): 37–38. 

External links

• Kjonaas, Richard A. (1996). "Amyl: A Misunderstood Word". Journal of Chemical Education 73 (12): 1127. DOI:10.1021/ed073p1127.  Editorial on the use of the word "amyl".

v t e Alkyl nitrites ("Poppers") Amyl nitrite (isoamyl nitrite, isopentyl nitrite) Butyl nitriteP Cyclohexyl nitrite Ethyl nitrite Hexyl nitrite Isobutyl nitrite (2-methylpropyl nitrite) Isopropyl nitrite Methyl nitrite

v t e Antidotes (V03AB) Nervous system Nerve agent / Organophosphate poisoning Atropine# Biperiden Diazepam# Oximes (Pralidoxime Obidoxime) see also Cholinesterase Opioid overdose Diprenorphine Doxapram Nalorphine Naloxone# Naltrexone Nalmefene Barbiturate overdose Bemegride Ethamivan Benzodiazepine overdose Cyprodenate Flumazenil GHB overdose Physostigmine SCH-50911 Reversal of neuromuscular blockade Sugammadex Cardiovascular Heparin Protamine# Digoxin toxicity Digoxin Immune Fab Beta blocker Glucagon Other Methanol / Ethylene glycol poisoning Ethanol Fomepizole Paracetamol toxicity (Acetaminophen) Acetylcysteine# Glutathione Methionine# Arsenic poisoning Dimercaprol# Succimer Cyanide poisoning nitrite (Amyl nitrite Sodium nitrite#) Sodium thiosulfate# 4-Dimethylaminophenol Hydroxocobalamin Toxic metals (cadmium mercury lead thallium) Edetates Dimercaprol# Prussian blue# Hydrofluoric acid Calcium gluconate# Other Prednisolone/promethazine oxidizing agent (potassium permanganate) iodine-131 (Potassium iodide) Methylthioninium chloride# Emetic Ipecacuanha (Syrup of ipecac) Copper sulfate #WHO-EM ‡Withdrawn from market Clinical trials: †Phase III §Never to phase III M: TOX gen / txn pto ant

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