• N&PD Moderators: Skorpio

Organic nitrogenous compound stench’s, are they worse than sulphur Ones?

Neuroprotection

Bluelighter
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Apr 18, 2015
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firstly, sorry if this is the wrong place, i’ve no idea where such a question should go. also, chemistry isn’t my field so I know very little about it hence the type of questions I’m asking. It’s just that I’m aware that some of you on here work with reagents and could help answer, my strange and random questions so here goes.
Organosulphur compounds have the greatest reputation for having terrible odors. however, I get the feeling that nitrogenous substances are underrepresented and there’s generally much less information available regarding their odor characteristics. from the little unclear information I found, am I right to think that the short chain diamines (putrescine and cadaverine) are more revolting than most thiols.
How about indoles and in particular skatole? i’ve actually read that this smell is detectable at even lower concentrations than those of many thiols no, I can’t confirm the accuracy of that. on the topic of skatole and other indoles, is it true they don’t behave as bases like traditional amines? if that is true, does it make deodorising anything which comes into contact with indoles?
I have many more questions on this topic, but I think there’s more than enough already on this post.
 
Indole and skatole are not very volatile. Their odor at low concentration is agreeable. For high purity indole it is even pleasant. Cadaverine and putrescine's odor is not remarkably terrible. If you want an example of really bad smelling nitrogenous compounds, check out isonitriles.

Yes, indole and skatole are very weak bases. Washing with dilute acids does not remove them from contaminated sites. Try oxidizers instead.
 
Indole and skatole are not very volatile. Their odor at low concentration is agreeable. For high purity indole it is even pleasant. Cadaverine and putrescine's odor is not remarkably terrible. If you want an example of really bad smelling nitrogenous compounds, check out isonitriles.

Yes, indole and skatole are very weak bases. Washing with dilute acids does not remove them from contaminated sites. Try oxidizers instead.


Thanks for that. I know about the isonitriles also called organic isocyanides. apparently, they smell like a combination of superglue, burning, plastic, tyres and someone said they smell purely alien. I listen to a YouTube video of someone synthesising isocyanide and then smelling it with his friends. apparently, the smell doesn’t travel that far despite its terrible properties.
In regards to skatole, the same guy tried to synthesise and purify it but interestingly, unlike the isocyanides, he quickly threw away, the skatole because he said it stunk out his lab and he had to be really careful about contamination. does this mean that if concentrated skatole touches your skin, it would be difficult to remove?
 
If you read stories about thioacetone, i don't think the stink is comparable. Think buildings and small towns getting evacuated when a small amount is spilled in a fume hood due to the stench.
 
Researched MACA/ Lepidium Meyenii. Contained Nitrogen containing Amine s.
What ? This turned up: from the simplest one Ammonia/ NH3 and MethylAmine/ CH3NH2. Via Putrescine and Cadaverine to Caffeine. Which seem s about odorless.

https://chem.libretexts.org/Courses/Sacramento_City_College/SCC:_CHEM_330_-_Adventures_in_Chemistry_(Alviar-Agnew)/09:_Organic_Chemistry/9.09:_Nitrogen-Containing_Compounds-_Amines_and_Amides

Had a Cactus that flowered once in a while. Called the Cadaver Cactus.
https://en.wikipedia.org/wiki/Stapelia
 
If you read stories about thioacetone, i don't think the stink is comparable. Think buildings and small towns getting evacuated when a small amount is spilled in a fume hood due to the stench.

OK, the WORST (if that is the appropriate term) is apparently the selenium analogue of acetone.

There is a famous (possibly apocryphal) story of a chemist carrying a sample of selenoacetone (selone) onto a train. Then said chemist dropped the sample. The outcome was after the railway company instituing three deep-cleans of the carriage, that carriage was eventually burnt.

Now I have noted people suggesting that telluroacetone is even worse. But it's far less volatile and appears to be more of an organo-metallic compound given that the extra shells of electrons means that the Te=C bond is not the same as the O=C bond in acetone, the S=C bond in thioacetone and even the Se=C bond in selenoacetone.

But as always, @Skorpio is right. So many stories surround the stench of thioacetone. It's volatile and that's why it's so awful. I'm prepared to think that in the confines of a heated railway carriage, selecoacetone MAY be even worse. But the odour threshold of thioacetone combined with it's physical properties means that it can stink up not just a room, but anything and everything downwind of a sample, potentially making people miles away ask 'what on earh is THAT SMELL?'.
 
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