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Isovaleric acid - sweaty socks chemical

Posted on Poppers Guide's Forum

Topic created by Nitritespecialist
on Sun, 22 Nov 2020 at 17:58

Nitritespecialist said on Sun, 22 Nov 2020 at 17:58...

Isovaleric acid is the impurity that causes amyl nitrite to smell like sweaty socks. Wikipedia has a full description of it. I have smelled this exact smell in degraded amyl alcohol. In smaller quantities, it can smell spicey or medicinal. I have smelled this two odors in my amyl poppers.

Amyl nitrite reportedly has a fragrant, fruity odor. I have also smelled this in amyl nitrite. It's been a light fragrant, slightly fruity odor that does correspond to potent effects.

Wowza said on Mon, 23 Nov 2020 at 07:58...

So the "bowl of tropical fruit" odor is not present in fresh potent AN? Is isovaleric acid present in degraded IBN as well? Interesting, maybe it is another poppers myth that fresh IBN smells like a locker room. In the early 70's there were lots of newspaper articles about poppers - could be that this was just a smart quote for a newspaper.

Traditional wisdom (now overturned by Ns maybe) is that AN = tropical fruit odor, so Jungle Juice and IBN = old socks, so Locker Room.

Nitritespecialist said on Thu, 26 Nov 2020 at 18:24...

All poppers can have various odors depending upon impurities present.

BUT, I have purchased isopentyl nitrite, butyl nitrite and isobutyl nitrite from Tokyo Chemical and Alfa Aesar. All were 95% pure. The isopentyl had a slight tropical fruit odor when fresh, but quickly turned into a sour, fishy vinegar scent, despite my best efforts to preserve it.

The isobutyl nitrite had a pungent sweet chemical odor similar to nail polish compounds.

The butyl nitrite had a very sweet banana like odor, especially after it had degraded. When left open in a room, the BN quickly left a locker room scent, very distinct and not like the banana scent that remained in the bottle.

I have not purchased normal amyl nitrite because the mark up is huge. What I have made has a variety of odors and not sure if any of the odors I have smelled are part of the true odor or not.

The Professor said on Thu, 15 Apr 2021 at 01:35...

@Nitritespecialist : you are off base here; Isovaleric acid (3-Methylbutanoic acid) is NOT a decomposition product of any alkyl nitrite. Take a whiff of Valerian root for an example of what Isovaleric acid smells like.

Butanoic Acid (aka Butyric acid) IS a decomposition product of any Alkyl Nitrite, and it is the compound that's responsible for the banana, dirty sock/body odor aroma of a crudely produced alkyl nitrite.

If you don't want the odor, either sequester it after prep or alter your prep to avoid its production.

The fishy vinegar scent is typical of Pyridine (commonly used to stabillize alkyl nitrites; it smells like dead fish, but doesn't interfere with the legitimate uses of the nitrite.

Other decomp products of alkyl nitrites:

2-methyl propanal
the parent alcohol
formic acid
2-methyl-propyl ester
amyl/isoamyl/butyl/isobutyl/propyl/isopropyl/etc acetate,
amyl/isoamyl/butyl/isobutyl/propyl/isopropyl/etc nitrate
2-methyl propanoic acid
amyl/isoamyl/butyl/isobutyl/propyl/isopropyl/etc ester
butanoic acid
2-methylpropyl ester
I, I '[methylene bis(oxy)]bis[2-methyl propane]

most present decomp products are the parent alcohol, 2-methyl propanoic acid, and butanoic acid

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