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Isoamyl nitrite (aka isopentyl nitrite or, incorrectly, amyl nitrite) is an alkyl nitrite ester that has several uses in medicine and chemical synthesis. The term “amyl nitrite” is also used to denote a mixture of mostly isoamyl nitrite with other C5 nitrites. Amyl nitrite is used here to refer to the mixture.
Amyl nitrite was known in the 19th century for several purposes. An early description of a medicinal use for amyl nitrite was in 1867, when Scottish physician Thomas Lauder Brunton used amyl nitrate as a vasodilator to treat patients with angina pectoris. Since then, the substance has been developed primarily as a vasodilator that is given by inhalation to lower blood pressure and to treat various heart conditions.
In 1878, German chemist Otto N. Witt used amyl nitrite in the synthesis of aromatic nitrosamines. The next year, Witt included amyl nitrite in a report on coloring materials derived from diazo compounds.
In 1967,J. A. Kruuv, W. R. Inch, and J. A. McCredie at the University of Western Ontario (London) allowed mice with implanted mammary C3H tumors to breathe the compound along with oxygen. Blood flow decreased in the tumors, whereas it increased in adjacent normal tissues. Disappointingly, however, the treatment protected the tumors from radiation rather than making them more radiosensitive.
Amyl nitrite is psychoactive; it is used recreationally as “poppers” to induce a euphoric state. Ironically, it is also used to combat depression or anxiety when users come down after their highs. Users variously describe its strong, pungent odor as fruity or like banana oil, old socks, or dirty feet. As shown in the hazard information table, it must be handled carefully, especially in large amounts.
Other medicinal uses for amyl nitrite include treatment for cyanide poisoning. For further reading on its pharmaceutical uses, see the ScienceDirect topics page.
Finally, isoamyl nitrite has been widely used as a reagent in chemical synthesis. See another ScienceDirect topics page for several of these applications.
Isoamyl nitrite hazard information*
| Hazard class** | GHS code and hazard statement | |
|---|---|---|
| Flammable liquids, category 2 | H225—Highly flammable liquid and vapor |  |
| Acute toxicity, oral, category 4 | H302—Harmful if swallowed |  |
| Skin corrosion/irritation, category 1B | H314—Causes severe skin burns and eye damage |  |
| Skin sensitization, category 1 | H317—May cause an allergic skin reaction | |
| Serious eye damage/eye irritation, category 1 | H318—Causes serious eye damage | |
| Acute toxicity, inhalation, category 3 | H331—Toxic if inhaled |  |
| Germ cell mutagenicity, category 2 | H341—Suspected of causing genetic defects |  |
| Specific target organ toxicity, single exposure, category 1 | H370—Causes damage to organs (blood, nervous system, cardiovascular system) | |
*Compilation of multiple safety data sheets.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals. Explanation of pictograms.
Molecule in the News
Protonitazene1 is a benzimidazole2 derivative that has strong opioid effects. It was first described in 1959 German patent 1,057,123 to Karl Hoffmann and co-inventors at Ciba-Geigy (Basel, Switzerland; now Novartis) on analgesically active benzimidazoles. The following year, the inventors reported the synthesis of a series of 1-aminoalkyl-2-benzyl-nitro-benzimidazole analgesics, including one that was 1000 times as potent as morphine3; it eventually became known as protonitazene.
Protonitazene was developed as an alternative to morphine, but development ceased when it exhibited serious side effects. The US Food and Drug Administration declined to approve its use and classified it as a Schedule I drug. In the past decade it has appeared as a designer drug responsible for numerous overdoses.
In late November, the Los Angeles Times reported that protonitazene, described as 3 times stronger than fentanyl4, was responsible for the first reported death from the drug. A known drug dealer was arrested and charged with distributing a substance that resulted in death.
1. CAS Reg. No. 95958-84-2.
2. CAS Reg. No. 51-17-2.
3. CAS Reg. No. 57-27-2.
4. CAS Reg. No. 437-38-7.
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Isoamyl nitrite fast facts
| CAS Reg. No. | 110-46-3 |
| SciFindern name | Nitrous acid, 3-methylbutyl ester |
| Empirical formula | C5H11NO2 |
| Molar mass | 117.15 g/mol |
| Appearance | Colorless to yellow liquid |
| Boiling point | 99 °C |
| Water solubility | 380 mg/L (25 ºC) |
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