Amyl nitrites

Amyl nitrite ( -mil NYE-trite) commonly occurs in two isomeric forms n-amyl nitrite and isoamyl nitrite (3-methy-lamyl nitrite or 3-methylpentyl nitrite). In common usage, the term amyl nitrite most commonly refers to the isoamyl form. Both isomers occur as yellowish liquids with a distinctive sweet odor and a pungent taste. They are unstable and break down when exposed to air, light, or water. Both isomers are probably best known as vasodilators, substances that cause blood vessels to relax and expand, allowing an increased flow of blood through the body. Because of its widespread use as a hazardous recreational drug, isoamyl nitrite has been banned, except for specified medical uses. 

Isoamyl nitrite is prepared in a straightforward synthesis in the reaction between isoamyl alcohol (CH3)2CHCH2CH20H) and nitrous acid (HN02). The usual method of preparation is 

Amyl nitrite. Red atoms are oxygen black atoms are carbon white atoms are hydrogen and the blue atom is nitrogen. Gray sticks indicate double bonds. PUBLISHERS RESOURCE CROUP 

law permits the sale of amyl nitrites as additives to perfumes and for other odorizing purposes. For example, they may be sold as room deodorizers, to eliminate the 

Although isoamyl nitrite has legitimate industrial and medical uses, it is probably best known as a recreational drug called poppers. The name comes from a popping sound that occurs when a bottle of the liquid is opened. The health consequences of using poppers are such 

The amyl alcohol and sodium nitrite are mixed in a flask (500 C.C.), and whilst the mixture is cooled in ice-water, the cone, sulphuric acid is added drop by drop from a funnel with constant shaking. Towards the end of the process a more vigorous reaction sets in, when care must be taken to add the sulphuric acid more slowly. When the whole of the acid has been added, the top layer of amyl nitrite is decanted into a separating-funnel. A little water is then added to the residue and, after shaking, a further quantity of amyl nitrite separates and is decanted as before. The whole of the amyl nitrite is then separated from water, dehydrated over calcium chloride and distilled. The liquid boiling at 95—100° is collected separately. Yield, 30—35 grams. 

Properties.—Yellow-green liquid with a peculiar penetrating and sweet smell, which, on inhaling, causes a rush of blood to the head, b. p. 96° sp. gr. 0 902. See Appc77tUx. p. 240. 

Equip a 1-litre three-necked flask with a powerful mechanical stirrer, a separatory funnel with stem extending to the bottom of the flask, and a thermometer. Cool the flask in a mixture of ice and salt. Place a solution of 95 g. of A.R. sodium nitrite in 375 ml. of water in the flask and stir. When the temperature has fallen to 0° (or slightly below) introduce slowly from the separatory funnel a mixture of 25 ml. of water, 62 5 g. (34 ml.) of concentrated sulphuric acid and 110 g. (135 ml.) of n-amyl alcohol, which has previously been cooled to 0°. The rate of addition must be controlled so that the temperature is maintained at 1° the addition takes 45-60 minutes. AUow the mixture to stand for 1 5 hours and then filter from the precipitated sodium sulphate (1). Separate the upper yellow n-amyl nitrite layer, wash it with a solution containing 1 g. of sodium bicarbonate and 12 5 g. of sodium chloride in 50 ml. of water, and dry it with 5-7 g. of anhydrous magnesium sulphate. The resulting crude n-amyl nitrite (107 g.) is satisfactory for many purposes (2). Upon distillation, it passes over largely at 104° with negligible decomposition. The b.p. under reduced pressure is 29°/40 mm. 

In a 200 ml. distilling flask place 64 g. (50 ml.) of dry n-butyl bromide and 80 g. of dry silver nitrite (1). Insert a reflux condenser, carrying a cotton wool (or calcium chloride) guard tube, into the mouth of the flask and close the side arm with a small stopper. Allow the mixture to stand for 2 hours heat on a steam bath for 4 hours (some brown fumes are evolved), followed by 8 hours in an oil bath at 110°. Distil the mixture and collect the fraction of b.p. 149-151° as pure 1-nitro-n-butane (18 g.). A further small quantity may be obtained by distilling the fractions of low boihng point from a Widmer flask. 

1-Nitro-n-hexane. Use 41 g. of dry silver nitrite, 51 g. of n-hexyl iodide (35-5 ml.) and 100 ml. of sodium dried ether. Reflux on a water bath for 8 hours decant the ethereal solution and wash the sohd well with sodium dried ether. Distil the residue, after the removal of the ether from the combined extracts, from 5 g. of dry silver nitrite, and collect the fraction of b.p. 190-192° (13 g.) as 1-nitro -hexane. The pure compound is obtained by distilling under diminished pressure b.p. 81 6°/15 mm. 

Much has been said about the positive effects of vitamin E (a-tocopherol) on sexual performance and ability in humans. Unfortunately, there is little scientific rationale to substantiate such claims. The primary reasons for attributing a positive role in sexual performance to vitamin E come from experiments on vitamin E deficiency in laboratory animals. In such experiments the principal manifestation of this deficiency is infertility, although the reasons for this condition differ in males and females. In female rats there is no loss in ability to produce apparently healthy ova, nor is there any defect in the placenta or uterus. However, fetal death occurs shortly after the first week of embryonic life, and fetuses are reabsorbed. This situation can be prevented if vitamin E is administered any time up to day 5 or 6 of embryonic life. In the male rat the earliest observable effect of vitamin E deficiency is immobility of spermatozoa, with subsequent degeneration of the germinal epithelium. Secondary sex organs are not altered and sexual vigor is not diminished, but vigor may decrease if the deficiency continues. 

Because of experimental results such as these, vitamin E has been conjectured to restore potency or to preserve fertility, sexual interest, and endurance in humans. No evidence supports these contentions, but because sexual performance is often influenced by mental attitude, a person who believes vitamin E may improve sexual prowess may actually find improvement. The only established therapeutic use for vitamin E is for the prevention or treatment of vitamin E deficiency, a condition that is rare in humans. 

This section considers other constituents that may cause adverse interactions when 

It is known that foods have the potential to affect in particular the pharmacokinetics 

Some mechanisms by which foods affect the pharmacokinetics of drugs are  

For interactions of MAOIs, see Drugs Acting on the Nervous System, Antidepressants 

Drugs and nutrients share similar characteristics, including sites of absorption in 

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Hydrogen cyanide (inhaled) or alkali oanides (taken by mouth, rf. p. IQ2) inhale amyl nitrite from freshly opened capsules. Obtain medical attention urgently. 

To prepare the solid phenyldlazonlum chloride or sulphate, the reaction is conducted in the absence of water as far as possible. Thus the source of nitrous acid is one of its organic esters (e.g., amyl nitrite) and a solution of hydrogen chloride gas in absolute alcohol upon the addition of ether only the diazonium salt is precipitated as a crystalline solid, for example ... 

Dissolve 3-5 g. of aniline hydrochloride in 20 ml. of absolute ethyl alcohol contained in a 50 ml. conical flask, and add 0-5 ml. of a saturate solution of hydrogen chloride in absolute ethyl alcohol. Cool in ice and add 4 g. (4 -6 ml.) of iso-amyl nitrite (compare Section 111,53) gradually. Allow the mixture to stand for 5-10 minutes at the room temperature, and precipitate the diazonium salt by the gradual addition of ether. Filter ofiF the crystals at the pump on a small Buchner funnel, wash it with 5 ml. of alcohol - ether (1 1), and then with 10 ml. of ether. Keep... 

Methyl ethyl ketone is allowed to react with n-butyl or iso-amyl nitrite in the presence of hydrochloric acid to yield diacetyl monoxime (nitrosomethyl ethyl ketone) ... 

III.2.C). The deamination of 2-aminothiazoles could be performed alternatively by refluxing them with amyl nitrite in tetrahydrofuran (604),... 

By reaction of a corresponding quaternary salt in the presence of a condensation agent such as amyl nitrite or with a heterocycioammonium salt possessing a labile group, such as Cl, I. or SR (6. 11) in the 2-position, cyanine dyes are obtained (Scheme 52). 

Diazoaminobenzene has been prepared by the action of sodium nitrite on aniline sulfate by the action of sodium nitrite on aniline hydrochloride by the action of sodium nitrite and sodium acetate on aniline hydrochloride by the action of ammonium nitrate and hydrogen sulfide on aniline hydrochloride in the presence of iron and by the action of amyl nitrite on aniline. ... 

Bromopyridine has been made by direct bromination of pyridine - from N-methyl-2-pyridone with phosphorus penta-bromide and phosphorus oxybromide from 2-aminopyridine by diazotization with amyl nitrite in 20% hydrobromic acid from sodium 2-pyridinediazotate by solution in concentrated hydrobromic acid and from 2-aminopyridinc by diazotization in the presence of bromine and concentrated hydrobromic acidd The method described here is essentially that of Craig. 

Pentyl amine, see n-Amylamine Iso-Pentyl nitrite, see Amyl nitrite Peracetic acid (40% acetic acid solution)... 

Solanidine contains at least three CMe groups, and since it yields dihydrosolanidine, m.p. 219-220°, must contain one ethylenic linkage. When solanidine is heated with copper powder at 160-300°/ll mm., it is converted into solanidone, C27H41ON, m.p. 218°, which yields an oxime, m.p. 228°, and condenses with benzaldehyde or amyl nitrite to give compounds indicating the existence in solanidone of the group —CHj—CO—CH — and therefore in solanidine of —CHjj—CHOH—CHa—... 

The initial observation that menthone reacts with amyl nitrite in the presence of base to give a good yield of an open-chain oximino ester was not expanded for synthetic purposes until Woodward almost forty years later utilized this reaction for the cleavage of a 7-keto-decahydroisoquinoline in the course of his total synthesis of quinine. 

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