isomers

Topic created by Cornholio
on Mon, 6 Dec 2021 at 22:46

Cornholio said on Mon, 6 Dec 2021 at 22:46...

Just stocked up on what little remains on pa.eu (that doesn't have the isopropyl substitution warnings) and it got me thinking about how some products are marketed as amyl and some as pentyl.
I'm in no way a chemist (so feel free to tell me I'm completely wrong) but from what I can tell amyl and pentyl are directly interchangeable terms. Pentyl is the more logical name, following on from the base hydrocarbon pentane (butane, propane, etc.) whilst amyl is just an alternative name derived from the word for starch (which oddly has six carbon atoms???). They both equally refer to hydrocarbon groups with five carbon atoms in any isomeric arrangement.

A quick look on Wikipedia shows the following isomers available for the amyl/pentyl group and the respective alcohols that they form.

n-amyl 1-pentanol
a-amyl 2-methyl-1-butanol
isoamyl 3-methyl-1-butanol

neopentyl 2,2-dimethyl-1-propanol
sec-amyl 2-pentanol
sec-isoamyl 3-methyl-2-butanol
tert-amyl 2-methyl-2-butanol

I've separated the top group as those seem to be the ones that are currently used as poppers. The bottom four isomers are ones that I don't appear to have come across before.
To compare to the list above I've had a look at some labels on bottles. A few that I have bought recently and some that are empty old ones that were bought a little while ago.
This is what they claim is in the bottles:

LR JJ Plat pentyl nitrite 2-methyl-1-butyl nitrite
LR JJ Gold pentyl nitrite 2-methyl-1-butyl nitrite
LR JJ Black pentyl nitrite 2-methyl-1-butyl nitrite
Gate isoamyl nitrite 3-methyl-1-butyl nitrite
Everest Brutal isoamyl nitrite 3-methyl-1-butyl nitrite
LR Blue Boy pentyl nitrite 2-methyl-1-butyl nitrite
BlackOut isoamyl nitrite 3-methyl-1-butyl nitrite
JJ Lockeroom pentyl nitrite 2-methyl-1-butyl nitrite
Everest Prem. isoamyl nitrite 3-methyl-1-butyl nitrite
AMYL isoamyl nitrite 3-methyl-1-butyl nitrite
HardWare pentyl nitrite 2-methyl-1-butyl nitrite
Eagle pentyl nitrite

The last one is a little harder to identify. EU manufacturers are kindly forced to put CAS numbers on bottles and list the full actual ingredients so you will often see the nitrites paired with their respective alcohols on these products.
Locker Room being manufactured in Canada (yet seemingly not actually sold in Canada) do not have to be so detailed. They separately list (as the only two ingredients) the common name of the nitrite and then the detailed chemical name (as listed above).
There is not usually a single mention that there could be any alcohol impurities in there. The bottle of Eagle breaks this mould and does indeed list two alcohols alongside the pentyl nitrite. Di-Sec Butylcarbinol which, from what I can tell, is just another name for 2-methyl-1-butanol. This hints that it is the same as the other pentyl nitrites. However, it also lists 1-pentanol which leads me to think that the product is possibly a mixture of a-amyl (pentyl?) and n-amyl (amyl?) nitrites?

n-Amyl nitrite does seem to be lacking amongst the commercial vendors (yes I know GoldenCock offer some n-amyl products but they are more of a specialised boutique supplier). I'm also aware that amyl nitrite is controlled in the UK by the Medicines Act 1997 as a prescription only drug and I think plenty of other countries also have similar restrictions banning it's use as an inhalant (hence the leather cleaning thing). Although I did quickly check the Medicines Act 1997 and it does indeed just list it as amyl nitrite with no specific isomer which pretty much covers everything on the list above which are already universally for sale (from France at least - absolutely nothing illegal about importing nitrites to the UK :-)

Despite all that, I was under the impression that the only nitrite banned in France was butyl nitrite so how come we don't we see more n-amyl (1-pentyl nitrite) products from French brands like Everest, Men's or Jolt? Does anyone know of any other n-amyl offerings beyond the potential mix in the bottle of Eagle? Not that I'm chasing the next big hit (or tying to get back to the good old days before 2010 when Joe Miller...) . Well maybe I am a little bit but am just curious as well.

Also regarding the secondary and tertiary alcohols above, perhaps someone with a little more chemistry knowledge could reason why these don't exist (as poppers). Do they not form nitrites well? Don't work good? Are toxic? Or perhaps just plain too expensive to make with no better benefits than the primaries in use.

Cornholio said on Mon, 6 Dec 2021 at 22:55...

Sorry it killed my makeshift table, better one maybe?

LR JJ Plat -------- pentyl nitrite ---- 2-methyl-1-butyl nitrite
LR JJ Gold ------ pentyl nitrite ---- 2-methyl-1-butyl nitrite
LR JJ Black ----- pentyl nitrite ---- 2-methyl-1-butyl nitrite
Gate -------------- isoamyl nitrite -- 3-methyl-1-butyl nitrite
Everest Brutal -- isoamyl nitrite -- 3-methyl-1-butyl nitrite
LR Blue Boy ---- pentyl nitrite ---- 2-methyl-1-butyl nitrite
BlackOut -------- isoamyl nitrite -- 3-methyl-1-butyl nitrite
JJ Lockeroom -- pentyl nitrite ---- 2-methyl-1-butyl nitrite
Everest Prem -- isoamyl nitrite -- 3-methyl-1-butyl nitrite
AMYL ------------- isoamyl nitrite -- 3-methyl-1-butyl nitrite
HardWare ------- pentyl nitrite ---- 2-methyl-1-butyl nitrite
Eagle ------------- pentyl nitrite ---- ???

The Professor said on Mon, 6 Dec 2021 at 23:19...

Amyl is latin slang for 'of meal'. Originally, Amyl alcohol was only available as fusel oil (a byproduct of the fermentation of ethanol). Another word for ethanol is grain alcohol. These grains were ground at the 'mill' and the result was 'Meal'

A roundabout way of saying the Amyl alcohol was derived form meal.

The modern name for that liquid is Pentanol, meaning 5 (Pentanol has 5 carbons)

n_Amyl alcohol and 1-Pentanol are identical

Back when Amyl nitrite was first made in prescription, glass sealed ampoules, the product was called 'Amyl nitrite' but was a mixture of isomers of Amyl nitrite.

Any primary alcohol can be nitrosated into an Alky nitrite. Most secondary, and some tertiary alcohols can also be nitrosated.

The difference between the various alcohols when nitrosated is in the reactivity of the popper. the Amyls are lower potency than the Butyls, which are lower than the Propyls.

People's preferences are all over the map, but the reason that many of the alcohols are not used probably comes down to cost to manufacture.

e.g.
Normalized for 100% NO
n-Amyl Nitrite: 71.9%
isoAmyl Nitrite: 75.2%
n-Butyl nitrite: 81.1%
isoButyl nitrite: 90.9%
tert-Butyl nitrite: 98.6%
100% Nitric Oxide (NO) gas: 100%
n-Propyl nitrite: 103.6%
isoPropyl nitrite: 115.8% [104 f (40C) boiling point]
Ethyl nitrite: 162.2%

that's a chart of reactivity by alcohol. A secondary Amyl would fit somewhere between isoamyl and n-Butyl. The difference in reactivity between an often used alcohol (isoAmyl or n-Butyl) and a not often use3d alcohol (sec-Amyl) wouldn't be noticeable to a human, so they might as well make it with the least expensive alcohol

Nitritespecialist said on Wed, 8 Dec 2021 at 02:00...

@Cornhole....one of the first things you learn in Chemistry 101 is that chemicals have lots of synonyms. The CAS-number however is more precise and should only connote one compound.

n-amyl, n-pentyl are the same exact compound. Still you cannot be sure what is in OTC poppers. I asked LRM if they used only pentyl nitrite in JJ Black and sure enough....I didn't get an answer. Austrailian authorities did tests on EVerett Premium and determined it was as it stated...isoamyl nitrite. I bought one EP and it did smell of isoamyl nitrite, which acquires a funky off odor rather quickly. I didn't like it even though it had some effect.

LRM JJ Black seems to have ample active ingredient in it, presumably pentyl nitrite because none of mine of acquired that funky odor, BUT I've had to wash some of mine due to high acid, which stings the skin and blunts effects. There's amazing ass effects to be had with pentyl nitrite, but it all depends on what exactly is in the bottle.

Cornholio said on Wed, 8 Dec 2021 at 16:46...

Thanks for the replies all.
@prof so there is nothing to be gained from other amyl isomers. They would be almost the same as what is already available and definitely not commercially viable. One question I still have is how come you never see n-propyl? It’s reactivity seems a lot different to isopropyl yet I’ve never seen it available. I’m aware that ethyl nitrite is toxic (too reactive). But n-propyl is less reactive than ipn so would be less toxic surely?
@nitritespecialist yes I also bought some Everest Premium (as you can see in the list above) and was also not particularly happy with it. I couldn’t be sure on smells but I would say it’s effects were certainly similar to some of my older degraded bottles (as in it makes your head spin but gives you a very uneasy feeling). I suspect that it’s high purity has left it with a shorter shelf life (you chemists will probably tell me that’s a load of bull). Maybe if they had included some kcarb and AA then it might have been a very nice product. The Everest brutal was my favourite of the above. It is also isoamyl but nothing like the premium. Although maybe the extremely wide neck on the large bottle meant I was just sniffing more of it than the others (don’t normally do it straight from the bottle but with the brutal it just seemed right)

When you mention pentyl nitrite above what do actually mean? A-amyl nitrite? My understanding is that they can all be correctly named pentyl nitrite (n-amyl, a-amyl & isoamyl), or indeed amyl nitrite as that is a broader term for all the isomers.

Have just received my first batch of butyls from Artisanal and first impressions are good. Thought they were going to smell all fruity (like bananas) from what I’ve read on here but it was more like nail polish remover (which I do kinda like in a weird way). Although, only tried the one bottle so far, maybe the others are different. They all come with a modest amount of AA (definitely not half the bottle) and smidge of what I assume is kcarb. However I was slightly disappointed as it got me so horny I shot my load really quick (and that wasn’t even the kaboom!). Nice problem to have I suppose.

The Professor said on Wed, 8 Dec 2021 at 17:23...

The confusion on the Santo arena comes from the ampoules that were sold in the sixties. The label said amyl nitrite, the ingredients were a mixture of amyl nitrite isomers.

Some manufacturers continue to take the liberty of calling anything that's an amyl isomer 'Amyl'

Butyl should not smell sweet like bananas; that aroma comes from Butyl acetate, a decomposition product. Without acetates, Butyl Angela very wealthy of ginger ale.

I've made n-Propyl nitrite before. It's extremely reactive and sorry lived. I've tried it was a tower in a mix of Butyl and isobutyl, and it was still too strong for me.

Poppers should be a pleasant and comfortable experience. Pepto is just a rush above the reactivity of nitric oxide itself (the active ingredient In a popper), and the increase on heart rate is more than it should be to accommodate the increase in blood vessel diameter, so the body alerts that 'something is amiss' when your heart starts to try to leap out of your chest.

Isopropyl is much cheaper, and already over the top, so it is used commercially for cost reasons.

Personally, tert-Butyl is our cake icing (at 98.6% reactivity of doesn't unleash hell on your heart.

Nitritespecialist said on Wed, 8 Dec 2021 at 22:30...

@Cornhole....that nail polish scent is indicative of isobutyl nitrite. I bought 100 mls of 95% isobutyl nitrite from TCI and it smelled exactly like a very sweet nail polish compound.

People have said Artisanal sells mixed nitrites, so it might not be pure IBN. Think "locker room" when you think Butyl Nitrite. Locker Room was one of the first brand names of poppers and it's no doubt because when pure BN is left open in a room, the room acquires a very very distinct odor of a freshly deodorized Locker Room; hence, it is sometimes described as a room deodorizer. The 95% Butyl Nitrite I bought from Sigma Aldrich degraded in the bottle and left a very very distinct sweet banana smell, probably indicating that the original liquid was highly pure BN.