Sciencemadness Discussion Board

Isobutyl Nitrite

Maja - 4-4-2006 at 10:05

Hi,

Making Isobutyl Nitrite is just like with other alcohols ?
R-OH =NaNO2/H2SO4=> R-ONO + NaSO4 + H2O
Would This work ? From MSDS : Stability
Stable. Incompatible with acids, alcohols, strong bases. Decomposes slowly in Water. Flammable - incompatible with strong oxidizing agents. Note wide explosion limits. May be light and moisture sensitive. Oxidizer. May explode if heated.

If you have some refs on this...Or some other information on Isobutyl Nitrite. It would be great. Thank you.

chemoleo - 4-4-2006 at 16:19

May I ask what your interest is in this? Possibly because its similarity to amylnitrite?
Regardless, it's a very easy prep - simple stoichiometric titration of HNO2 (from NaNO2 and HCl) into the alcohol, or rather, a mix of ROH/NaNO2 where HCl is titrated into. Yes it works fine with all primary alcohols, just beware some are quite volatile, particulalrly methylnitrite (gas) and ethylnitrite.
They start to stink of NOx upon storage at RT - even after washing with NaHCO3 and the like. Not the most stable of all things.

BromicAcid - 4-4-2006 at 20:25

Wow, that sounds considerably more simple then I would have imagined, I thought NaNO<sub>2</sub> was more sensitive to acid then that and that such a reaction would not be allowed (I thought it decomposed readily in acid, then again I've never had the pleasure of working with sodium nitrite). I did use Isopropyl nitrite though some time ago for a diazotization reaction for which it is particularly useful, though it really doesn't matter what you want it for, I might want this chemical some day because I like the combination of letters that make up its name.

[Edited on 4/5/2006 by BromicAcid]

Maja - 5-4-2006 at 04:22

Quote:
Originally posted by chemoleo
May I ask what your interest is in this? Possibly because its similarity to amylnitrite?


I was interested to Amyl/Isobutyl/... other nitrites because they are so expensive (10ml for 10EU). And i thought that isobutyl nitrite synthese is very hard... But I can see it's quite simple. Isobutyl Nitrite boils at 67C. So it wouldn't be released as a gas... Thanks.

Douchermann - 5-4-2006 at 18:17

I have done this synthesis once, along with amyl nitrite. Make a solution of NaNO2, using 95mls of water and 24 grams of NaNO2. Cool this in a salt/ice bath to about 0C. Make another solution by first mixing 7ml water, 9ml H2SO4, then add about 29ml of your butyl alcohol. Just add these two solutions together very slowly. Use a seperatory funnel or burette to drip a small ammount in at a time. I have gotten about 27ml (never measured it, just eyeballed it) using these ammounts. You have to keep the temperatures really low though. Dry it with MgSO4 once you've seperated it. Its insoluble and less dense than water by the way. Also, don't sniff the reaction vessel while you are making it. We all know what butyl nitrite is used for, and you'll get plenty of that just from making it. Butyl nitrite will slightly decompose during distilation if you choose to distil it, so use reduced pressure.

[Edited on 6-4-2006 by Douchermann]

Maja - 7-4-2006 at 01:36

Thanks Douchermann !

Maja - 12-5-2006 at 09:49

I have one more question... There is some stabilizer for R-Nitrites ? I have googled a little bit ,but did not find anything. Please share your knowledge.

chemoleo - 12-5-2006 at 18:31

It's a good question, I was wondering the same. Testing some amylnitrite, even prolonged shaking in NaHCO3 did not prevent decomposition, as evidenced by a strong smell of nitric/ous oxides after a few days. Since base doesn't seem to help I was wondering whether a tiny amount of i.e. H2SO4 would help, although I'd doubt that very much (from a mechanistic perspective).
Maybe distillation really is the clue to this, making sure to use a non-volatile acid (i.e. H2SO4) for the synthesis, rather than HCl.

Maja - 13-5-2006 at 00:31

Actually I have used a few times H2SO4 and HCl. With H2SO4 you will get a lot of precipicate(Na2SO4) and it's hard to stir with magnetic stirrer. So I have used over head. It solved problem. Did not tried to distill isobutyl nitrite ,but shaked a few times with Soda in separatory funnel, then with water, add a few more times with dH2O. Tested for pH.... Almost neutral. But noticed a strange thing. When a drop of R-Nitrite is dropped onto water you can see it DECOMPOSING ! It's bubbling and then pH decreases <7... But this happens only with a few drops. I think it happens all the time when nitrite isn't dry, but I cant see it at higher amounts. So then I dried it with MgSO4 for a few hours and filtered. Now after three days it's still fresh and no pH change noticed and no smell/red fumes. I keep it in a brown glass bottle away from light/sunlight. And also I'm getting pretty good yield from H2SO4. From 116ml of isobutyl alcohol I was able to get 110ml of Nitrite ! I will try adding a drop of H2SO4. Chemoleo, I think we need to search what stabilizers used in commercial Nitrites ,but I didn't found anything named.

[Edited on 13-5-2006 by Maja]

dobka - 26-5-2006 at 01:11

Maybe you know the literature, where I could read the full infirmation about synthesis of isobutyl nitrite?
Would be very nice.

Nicodem - 26-5-2006 at 07:11

The general procedure for the esterification of alcohols with HNO2 is described in the most obvious place to check out before asking questions like that, in the "Vogel's textbook of Practical Organic Chemistry, 5th edition", pages 413-414.

[Edited on 26-5-2006 by Nicodem]

Isobutyl nitrite

SHOT - 29-7-2006 at 16:28

So I was on this trip to London, England and I was walking on the street with two more "guys". So we were walking and then we entered this creepy looking store. They sell opiums in there, so the "guys" with me bought something called "Poppers" which was actually isobutyl nitrite. When inhalated isobutyl nitrite decreases blood pressure which lately makes you laugh a lot. Its not compleatly non-toxic. I would like to know how can I make this stuff. I will really be greatfull if you guys help me. Thanks

[Edited on 30-7-2006 by SHOT]

Vitus_Verdegast - 29-7-2006 at 18:22

Most of us are in the know that London is the capital of England. Opium is illegal there. "Poppers", which is either isoamyl or isobutyl nitrite, is mainly used by "the guys" to relax the rectum sphincter as to easily allow penetration. It is certainly not completely non-toxic. Furthermore is it easily made from the corresponding alcohol, an slight molar excess of NaNO2 and a mineral acid. You better not try this because you'll easily end up harming yourself, due to the volatility of the substance.

R-OH + NaNO2 + H2SO4 ==> R-ONO + NaHSO4 + H2O

Better study some chemistry first before attempting this...:D

http://en.wikipedia.org/wiki/Nitrite_inhalants



[Edited on 30-7-2006 by Vitus_Verdegast]

Nicodem - 29-7-2006 at 23:55

I wander why new members post questions that were already answered thoroughly in other threads? And why do they like to open new threads so much? Can't you, dear new members, use the forum's search function before posting? (it is the first damn link on the top left side of every page!)

I miss those beautiful times from another forum when we could just reply with "UTFSE!" so much!:D

Nostalgia, I guess, but I feel better now.:P

SHOT - 30-7-2006 at 09:23

Quote:
Originally posted by Vitus_Verdegast
Most of us are in the know that London is the capital of England. Opium is illegal there. "Poppers", which is either isoamyl or isobutyl nitrite, is mainly used by "the guys" to relax the rectum sphincter as to easily allow penetration. It is certainly not completely non-toxic. Furthermore is it easily made from the corresponding alcohol, an slight molar excess of NaNO2 and a mineral acid. You better not try this because you'll easily end up harming yourself, due to the volatility of the substance.

R-OH + NaNO2 + H2SO4 ==> R-ONO + NaHSO4 + H2O

Better study some chemistry first before attempting this...:D

http://en.wikipedia.org/wiki/Nitrite_inhalants



[Edited on 30-7-2006 by Vitus_Verdegast]



Oh. Ive studied chemistry enough. I just wanted to know another way of making this. Those guys with me told me that they inhale this gas which evaporates from the liquid nitrite. And this makes 'em laugh.

EDIT: I am not so dumb! I know that London is the capital of England WTF?

[Edited on 30-7-2006 by SHOT]

Vitus_Verdegast - 30-7-2006 at 10:02

I feel exceptionally kind today, so I thought what the heck I'll spoonfeed our Bulgarian friend here by using the f#&!king search engine in his place.

After searching for 1.2 sec, look what I came up with:
https://sciencemadness.org/talk/viewthread.php?tid=5598#pid6...

But I'm all for installing the UTFSE rule ! :):)


(Btw, dear SHOT, you've stated "So I was on this trip to London, England" --> What I meant is, if you had stated "So I was on this trip to London," most of us would know that you mean the capital of England instead of the backward hick town of London, Alabama.)

[Edited on 30-7-2006 by Vitus_Verdegast]

dry?

hvinh - 3-8-2011 at 07:37

Quote: Originally posted by Douchermann  
I have done this synthesis once, along with amyl nitrite. Make a solution of NaNO2, using 95mls of water and 24 grams of NaNO2. Cool this in a salt/ice bath to about 0C. Make another solution by first mixing 7ml water, 9ml H2SO4, then add about 29ml of your butyl alcohol. Just add these two solutions together very slowly. Use a seperatory funnel or burette to drip a small ammount in at a time. I have gotten about 27ml (never measured it, just eyeballed it) using these ammounts. You have to keep the temperatures really low though. Dry it with MgSO4 once you've seperated it. Its insoluble and less dense than water by the way. Also, don't sniff the reaction vessel while you are making it. We all know what butyl nitrite is used for, and you'll get plenty of that just from making it. Butyl nitrite will slightly decompose during distilation if you choose to distil it, so use reduced pressure.

[Edited on 6-4-2006 by Douchermann]



hi Douchermann:
I have a question.. amylnitrate are so expensive nowsaday.. i like to make them myself..
1. Is there a website that you recommend me to buy the ingredients?

Thanks for help!
Vincent H.

[Edited on 3-8-2011 by hvinh]

[Edited on 3-8-2011 by hvinh]

redox - 3-8-2011 at 08:00

I hate to spoonfeed, but:

All the reactants can be found on Ebay.
Sodium Nitrite: $15-20 for one pound
Sulfuric Acid: $20-25 for 500 mL
Isobutyl (isoamyl shows on Ebay once in a while): $25 for 500 mL




I would recommend learning some chemistry before you try this synthesis.

[Edited on 3-8-2011 by redox]

woelen - 4-8-2011 at 00:02

Don't try this yourself if you don't have any chemistry background. You will most likely poison yourself. As you can read here it is quite difficult to get and keep the material free of nitrogen oxides. Nitrogen oxides are VERY poisonous when inhaled!

hvinh - 4-8-2011 at 17:34

Redox and Woelen,

Thanks, guys, I will try to make a very small portion at a time, and not to inhale the nitrogen oxides during the process. I had a couple courses of chemistry in college and aware of the danger of acid... Just i have never tried to synthesize it.. You two might have done it so in the past...

Any more suggestions or recommendations!

I'd appreciate your valuable advice !

redox - 4-8-2011 at 18:42

When I performed the butyl nitrite synthesis, I noticed that the colder the reaction temperature, the less NOx fumes were effervesced. Keep it cold, use a salted ice bath.

Also, its already been mentioned, but the alkyl nitrites degrade significantly over time. Wash your sample with sodium or potassium carbonate solution once in a while. It smells a lot better when its not NOx'ed.

In addition, when you perform the synthesis, add the the acid (or alcohol) dropwise to the rest of the solution. Its much less dangerous and higher yielding when done this way.

Best regards and good luck,

Redox

hvinh - 5-8-2011 at 16:53

Redox,

At this time, i have the acid sulfuric that I purchased at Orchard Supply Hardware. It said concentrated.. and the color is "dark". The acid that is sold on the website is clear. I wonder if it is okay to use it.

Thanks for help!

Bot0nist - 5-8-2011 at 17:07

Probably contaminated with Fe and or carbon. There are many threads here that deal with the cleaning of sub standard H<sub>2</sub>SO<sub>4</sub> (Drain cleaners).

Dilution and filtering, and H<sub>2</sub>O<sub>2</sub> oxidation are a few ways to purify it, short of distillation. (which I don't recommend)

I am not sure what the contaminates are or what effect they will have on the synthesis, But if you plan on exposing your lungs to the finished product please strive to use the cleanest reagents and the neatest procedures you can. Lungs are precious and the damage they take is cumulative.

redox - 5-8-2011 at 17:29

It should be all right as long as you distill your final product. Do you have a distillation apparatus?

Is the sulfuric "dark" as in pitch black? Is it colloidal? Was it marketed as drain cleaner?

Details!

Also, a new lot on ebay for isopentyl alcohol just popped up, you might want to utilize this rare occurrence.

http://cgi.ebay.com/Isoamyl-alcohol-1-Liter-/390336380379?pt...

Panache - 6-8-2011 at 07:14

it works fine with isopropanol also, making the secondary nitrite obviously, i adaptated it from whatever the vogel ref. was making, i think the secondary, for a male friend of mine who was using it in the function spelt out by Vitus. I couldn't believe the prices he was paying otherwise. Stores fine in the freezer. He seemed pleased by it, keeps nagging me for more.

hvinh - 6-8-2011 at 20:28

yes, the acid sulfuric that i have is marketed as "drain cleaner". I should not use it then, since my lungs are precious!

Thanks

redox - 10-8-2011 at 04:56

Good choice, the "fixers and corrosion inhibitors" could easily contaminate the alkyl nitrite. 98% sulfuric acid can easily be obtained from ebay, elemental scientific, biodiesel companies, etc.

Good luck! :cool:

hvinh - 10-8-2011 at 05:21

Hi Redox

I would like to ask you one more question.. Is the fume going to be very bad.. I know that ventilation is necessary and will keep the reactions at a low temperature as I can and will only do synthesis with a small amount of chemicals..

Thanks for helping :)

redox - 10-8-2011 at 15:43

Quote: Originally posted by hvinh  
Hi Redox

I would like to ask you one more question.. Is the fume going to be very bad.. I know that ventilation is necessary and will keep the reactions at a low temperature as I can and will only do synthesis with a small amount of chemicals..

Thanks for helping :)


I performed the synthesis in a fume hood, but it probably wasn't really necessary. As long as the reaction is run at ICE COLD temperatures, you'll be fine. Also, you may want to do it outside, just so you aren't overwhelmed in case you add the acid (or alcohol) too quickly.

What scale were you considering? 10 grams? 1000 grams?
The higher the scale, the more careful you need to be in cooling and addition.

bahamuth - 11-8-2011 at 14:08

Quote: Originally posted by Maja  
I have one more question... There is some stabilizer for R-Nitrites ? I have googled a little bit ,but did not find anything. Please share your knowledge.


http://www.sciencemadness.org/talk/viewthread.php?tid=15605#...

Quote: Originally posted by Maja  
I think we need to search what stabilizers used in commercial Nitrites ,but I didn't found anything named.

[Edited on 13-5-2006 by Maja]


http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en...


And by god, I feel ashamed for feeding this tread, since there is a existing one with virtually the same name.

Perhaps they should be merged....

redox - 11-8-2011 at 15:03

Maja posted that question before the other isobutyl nitrite thread was conceived.



[Edited on 11-8-2011 by redox]

bahamuth - 11-8-2011 at 15:46

My bad for not noticing that.., now I really feel ashamed.....

redox - 11-8-2011 at 15:54

No worries mate! Maja's last post was 5 months ago, he'll probably never see your little blunder.

hvinh - 13-8-2011 at 20:17

Hi Redox

Ok. I will do it in the back yard then. And I will do it just a little bit at a time.. may be 10 gram.. not 1000 :-)

I will start ordering the ingredient sometimes next month.. after all the research.

Thanks, bro!

sonottawa - 16-8-2011 at 13:37

Quote: Originally posted by Maja  
Thanks Douchermann !


I just made the solution of Amyl Nitrite (I hope so) by using your formula above:

Beaker A:
-95 mls of d-H2O
-24 grs of NaNO2
Beaker B:
-7 mls of d-H2O
-9 mls of H2SO4
-29 mls of IPA

After using a separatory funnel to get the top layer, I’ve dried the solution with hot – dried bicarbonate and then store it in a dark glass container.

I also took a little bit of the solution and ignition it to see the blue-white fire as the final test. But I’d like to know if there is any other test of impurity of Amyl Nitrite ? Because I’ve never use poppers before, so I can’t tell if I really get the real Amyl nitrite or not.



497 - 16-8-2011 at 14:03

You're definitely not going to get amyl nitrite by using IPA... they get much crappier as you go to fewer carbons. Even the amyl chain makes an only mildly interesting compound.
Isopropyl nitrite will show you very quickly how fun methemoglobinemia is.

redox - 16-8-2011 at 14:09

Quote: Originally posted by 497  
You're definitely not going to get amyl nitrite by using IPA... they get much crappier as you go to fewer carbons. Even the amyl chain makes an only mildly interesting compound.
Isopropyl nitrite will show you very quickly how fun methemoglobinemia is.


I think he may be referring to IsoPentyl Alcohol.

sonottawa- IPA is usually reserved for isopropyl alcohol.

sonottawa - 23-8-2011 at 22:42

Quote: Originally posted by redox  
Quote: Originally posted by 497  
You're definitely not going to get amyl nitrite by using IPA... they get much crappier as you go to fewer carbons. Even the amyl chain makes an only mildly interesting compound.
Isopropyl nitrite will show you very quickly how fun methemoglobinemia is.


I think he may be referring to IsoPentyl Alcohol.

sonottawa- IPA is usually reserved for isopropyl alcohol.


Yes, I did used the IPA - Isopropyl Alcohol: (CH3)2CHOH to perform the reaction following the synthesis found on Google.

As I'm kinda newbie in this underground chemist level, so I have few questions about it:

1. I didn't realize that there is a different between the 2 solvents. Please give me more advices !

2. So what is the solution that I've got after all ?

3. To make a real QUICK RUSH poppers, which is the right solvent that I need to have (isopropyl alcohol/isobutyl alcohol/...) ?

Thanks for all

watson.fawkes - 24-8-2011 at 05:35

Quote: Originally posted by sonottawa  
3. To make a real QUICK RUSH poppers
This forum frowns upon handing out recipes to drug cooks, even when the drugs are legal in jurisdiction, more because this forum is about science. Do you have a scientific question here? Do you have any scientific interest here, even? Everybody starts somewhere, and you're right at the beginning.

redox - 24-8-2011 at 05:42

Quote: Originally posted by sonottawa  
Quote: Originally posted by redox  
Quote: Originally posted by 497  
You're definitely not going to get amyl nitrite by using IPA... they get much crappier as you go to fewer carbons. Even the amyl chain makes an only mildly interesting compound.
Isopropyl nitrite will show you very quickly how fun methemoglobinemia is.


I think he may be referring to IsoPentyl Alcohol.

sonottawa- IPA is usually reserved for isopropyl alcohol.


Yes, I did used the IPA - Isopropyl Alcohol: (CH3)2CHOH to perform the reaction following the synthesis found on Google.

As I'm kinda newbie in this underground chemist level, so I have few questions about it:

1. I didn't realize that there is a different between the 2 solvents. Please give me more advices !

2. So what is the solution that I've got after all ?

3. To make a real QUICK RUSH poppers, which is the right solvent that I need to have (isopropyl alcohol/isobutyl alcohol/...) ?

Thanks for all


1. Isopropyl alcohol is CH3CH3CHOH. Isopentyl (isoamyl) alcohol is CH3CH3CHCH2CH2OH.

2. If you used IPA (referring to isopropyl alcohol), then your product was isopropyl nitrite.

3. I would assume a more volatile alkyl nitrite would be more potent, so for a quick rush popper use isopropyl alcohol.

Don't hurt yourself.

[Edited on 24-8-2011 by redox]

Thanks a lot, Redox...

sonottawa - 24-8-2011 at 10:18

Thanks for your quick reply.

In conclusion, I've confused between the 2 solvents which is has similar name (tomato / potato, hehe, for me, anyways). And I end up with Isopropyl nitrite, not related to any of the Alkyl nitrite's (QUICK Rush) family, even it does have the same last name "Alcohol" .

But still, I'm curious about it and need more explanations, 'cause I don't have a teacher or anyone nearby that I can get answer from, so thanks in advance to whom will spend time to read & answer to this new student pain-in-tha-ass

1. Could anyone give me a reason why they don't use Isopropyl nitrite as a drug recreation as Alkyl's ?

2. If ppl consume my product, what could it be the feeling or it's just like a poisonous solution ?

3. Can we use it in another reason, different than "drug recreation" purpose ?

4. What is the real role of Isobutyl alcohol/Methanol (if we can call them all as a "denatured alcohol") in the whole process of the synthesis ?

5. If we couldn't find any of the solvents named above, what will it be the replacement ? (just thinking if we can use the Vodka with the flavor to replace it, it will give a different odor, for example)

6. How could we test the final solution, just to make sure that is exactly what we're looking for ?


Thanks,

[Edited on 24-8-2011 by sonottawa]

Bot0nist - 24-8-2011 at 10:28

Quote: Originally posted by sonottawa  


2. If ppl consume my product, what could it be the feeling or it's just like a poisonous solution ?

[Edited on 24-8-2011 by sonottawa]


More than likely this is what will happen. Oxides of nitrogen are not good for return business.

Making chemicals in your lab for 'ppl' to consume is not a good idea unless you have experience, proper technique, and the ability to assure the safety of your product. I don't want to sound mean, but I don't think you have any of these.

Quote:
sonottawa says; "I ain't a chemist and just have a limited background of chemistry stuff"


Good luck in your endeavor, and please be safe.:)

[Edited on 24-8-2011 by Bot0nist]

sonottawa - 24-8-2011 at 21:12

I really appreciate for ur advices.

In the other hand, I did realize how is the important of safety and healthy for someone whom will uses my product.

But one thing for sure, myself will be the 1st one to try my own product before give it away to my friends. That's why I keep searching and try to get more experiences from others in this 4room.

But I really really need to success this time & as ppl says:"There’s a will, there’s a way" so I ain't sad or intend to "retreat" 'cause of the judgments after all.

One of the reasons why I decided to put my feet deep in this "career of chemist",

- I'm curious and really enjoy working in my mini home lab, to see how cool are the chemicals react, and get so excited while getting the correct solution as the final answer.

- And of course for making money by my way, even thought I could easily obtain the all-ready-made stuffs and sale it to other dealers. So it's more for my survivor things than just having fun + free time to play around with my safety short life.

Thanks for all,

help?

spyentist - 1-10-2011 at 10:28

as 'sonottawa' had posted, stumbled on a similar recipe:
Beaker A:
-95 mls of d-H2O
-24 grs of NaNO2
Beaker B:
-7 mls of d-H2O
-9 mls of H2SO4
-29 mls of IPA (except i am planning on using iso butyl alcohol)

the questions i have are related to process. i don't have much equipment so i don't have a burette or separator funnel.
can i do this by simply pouring it in slowly and stirring continuously?

also, i was told to 'dry' it with MgSO4 and i assume that means mix together and drain off? is that right? most humbly, when in the process and what exactly am i looking for as the desired product to separate from the solution? i assume the 'drying' occurs after separating the isobutyle nitrite form solution.

lastly, how volatile is this process and what would be the danger in doubling the quantities? is it the nox gases that are the risks and not some explosive reaction?

i apologize in advance for my naivete but if not here, where, right? -grin.

Steve_hi - 1-10-2011 at 13:14



Quote: Originally posted by Maja



I think we need to search what stabilizers used in commercial Nitrites ,but I didn't found anything named.

[Edited on 13-5-2006 by Maja]


http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en...

this product is no longer available
but i see that 2% sodium carbonate was used in it as a stabilizer does that mean it can be used in the synthesis of the product to which this thread is dedicated to as a stabalizer as well since this to is a nitrite?



Steve_hi - 1-10-2011 at 16:43

Just found a youtube video
http://www.youtube.com/watch?v=ygAxh81WaWg
http://www.erowid.org/archive/rhodium/chemistry/eleusis/nitr...

[Edited on 2-10-2011 by Steve_hi]


MAKING POPPERS

Iso-amyl nitrite is the ester formed from the chemical reaction of isoamyl alcohol and nitrous acid. The chemical synthesis is as follows:

Commercial grade isoamyl alcohol is combined with an aqueous solution of sodium nitrate sufficient to produce about 20% excess nitrous acid. While stirring slowly, a 1:3 aqueous dilution of sulfuric acid is gradually added to the mixture. The sulfuric acid reacts with the sodium nitrate to generate nitrous acid. The distinct odor of amyl alcohol disappears when the chemical reaction has proceeded to completion. As long as any odor lingers, there remains some unreacted amyl alcohol, and some more sodium nitrate and sulfuric acid should be added. After allowing the liquid phases to separate, the upper, non-aqueous layer of amyl nitrite is washed with a cold solution of sodium carbonate to absorb the water held by the ester. The portion which distills over 95° and 100°C is medicinally pure isoamyl nitrite.

Adapted from Remington's Practice of Pharmacy, Third Edition, 1894

Isobutyl nitrite is produced following the indentical procedure, substituting isobutyl alcohol for the isoamyl alcohol.


[Edited on 2-10-2011 by Steve_hi]
http://pediaview.com/openpedia/Amyl_nitrite

[Edited on 2-10-2011 by Steve_hi]

Bitburger - 26-10-2011 at 06:17

Is this actually a esterification or rather a substitution reaction, where the hydrogen of the -OH function is replaced by the nitrosyl group?

I think that butyl nitrite (or (oxy)nitrosobutane in the case of substitution) is a useful reagent to make a variety of nitroso-compounds. I think that it can decompose in the stomache since HCl is present there. Carcinogenic nitrosoamines are thus formed in the presence of secundairy amines. I know that amyl nitrite is popular in the gay scene to open your ass and make bottom sex less painful. But it's just mess and may cause cancer.

Maybe other nitroso compounds might be formed, like the reaction between R-MgX + R'-ONO which might give rise to nitrosobutane?

scorpio4191 - 27-11-2013 at 08:00

I have a quick question, can Methyl Alcohol be used in this case?

Nicodem - 27-11-2013 at 08:37

No, the O-nitrosation of methanol cannot give isobutyl nitrite. Isobutanol is a reactant, not a reagent, so you cannot just change it for something else.

woelen - 27-11-2013 at 09:30

Quote: Originally posted by Steve_hi  


Commercial grade isoamyl alcohol is combined with an aqueous solution of sodium nitrate sufficient to produce about 20% excess nitrous acid. While stirring slowly, a 1:3 aqueous dilution of sulfuric acid is gradually added to the mixture. The sulfuric acid reacts with the sodium nitrate to generate nitrous acid. The distinct odor of amyl alcohol disappears when the chemical reaction has proceeded to completion. As long as any odor lingers, there remains some unreacted amyl alcohol, and some more sodium nitrate and sulfuric acid should be added. After allowing the liquid phases to separate, the upper, non-aqueous layer of amyl nitrite is washed with a cold solution of sodium carbonate to absorb the water held by the ester. The portion which distills over 95° and 100°C is medicinally pure isoamyl nitrite.


Where did you find this non-information? It is wrong! The person who wrote this most likely did not make a typo, because he is very consistent in providing wrong information. Everywhere, where you read sodium nitrate, you should substitute sodium nitrite. With sodium nitrate you will not have any reaction at all in aqueous solution.

bfesser - 27-11-2013 at 09:52

Quote: Originally posted by Steve_hi  
Adapted from Remington's Practice of Pharmacy, Third Edition, 1894

woelen - 27-11-2013 at 11:12

I do not think that this is the direct source of that information, but that some intermediate person without much knowledge of chemistry (someone who does not know the difference between nitrite and nitrate) has copied the info.

bfesser - 27-11-2013 at 12:17

I'd guess that it was "adapted from" the original by <strong>Steve_hi</strong>. I'm working on tracking down a copy of the original, out of curiosity.

Random - 28-11-2013 at 09:14

This is dangerously wrong information. One member here had an accident with nitric acid and ethanol if I remember correctly.

JAVA - 30-1-2014 at 12:42

The yellow colour is typical for this nitroso compound, I think...

Don't use H3PO4 since much NO2 comes free. What's the scientific reason?

What does dissolve and 37%HCl and the amylalcohol and sodium nitrite to get a homogenisation?

butyl nitrite is a alternative: if you sniff it be (stay) very carefull. It's used in the gay world - not a hard drug. But if you sniff way too much you get the same symptoms as a HCN poisoning. But this goes over, luckily. Not that dangerous.

This is just to show the product, that is washed with sodium bicarbonate, KOH, 2 times destillated. Dry it over MgSO4 and redestill.




butyl nitrite.jpg - 32kB

Ester's of Alachol.

one2rock - 14-6-2015 at 12:43

Hello, ok, I am new to this, but let me share some history. way back in 1850 ish, esters of Alcohol were being discovered, and never has any real negative effects been reported in all that time until we get to the baby killing, whore, nancy Reagan, and her illegal war on drugs. until then poppers were so called because when you opened them, there was so much pressure, and audible "PPSSSSSTTTTT" was created, and if you tried to cover the little brown bottle with your thumb, it took almost all your might, due to the pressure, and it turned your thumb brown, and yes at first was used as a medicine for angina, because it made your heart beat faster, but it is also a first class laxative due to its vasco whatever properties, and most importantly, it caused an intense euphoric state, for a min or so, I was lucky enough to experience the original 1970-1980ish products, before the afore mentioned traitor's reign, and I want to find the original formula, once again, this iso amyl, butyl, and propel garbage they offer at gay bookstores is criminal, and a very harmfull and toxic substitute to the original medication. sure everything causes cancer eventually, thankfully THC oil destroys tumors and cells. im just tired of being forced to go to gay bookstores to get the crap they "never Fake it" and have decided to re create the original to the best of my ability. I do thank all of you who have posted, because it is for the same basic reasons, give us our euphoria back. so I have made several batches experimenting with different alcohols and acids, but nothing in coming near the old formula. please help if anyone knows the "secret" I am missing. what caused the original to evaporate so quickly, and cause such euphoria?? I have also decided to test other alcohols, like moonshine or barcardi 151, please help. sorry for bad grammer and sp. and thanks in advance if you have a legit answer.:(:(:(:(:(:(:(
I know you guys are excellent at your craft, and I will probably find the answers if I read all posts, im just time constrained, and not hip to all scientific jargon as of yet, but use all possible safty precautions, goggles, gloves vents, jackets ext... but I also have to experiment more, I know the 5th edition textbook, I was able to download it, and all it says is use a 3 prong beaker thingy, but after a few attempts I began to question the pressure, I tried to put a rubber stopper in the open hole, but it pops off eventually, then I wonder how will I slowly add the second mixture without depressurizing the whole thing, or does it even matter? I noticed if I hold the stopper in place, even then its too much, and if I remove it, immediately that brown gas forms, is maintaining pressure important? or just let it breathe??? I am a layman, so simple explinations please.

[Edited on 14-6-2015 by one2rock]

Hawkguy - 14-6-2015 at 12:58

One2rock: There are supposed to be negative effects caused by some poppers, as pressure can build inside the eyeballs causing eventual damage, similar to how type 2 diabetes leads to vision loss... Also, I'm very sure the 'good ol stuff' was Amyl Nitrite. The only difference is that today it is usually something else, or when you make it, you are also inhaling a ton of Nitrogen Dioxide.

[Edited on 14-6-2015 by Hawkguy]

one2rock - 14-6-2015 at 13:00

that's never been proven.

Hawkguy - 14-6-2015 at 13:02

It might depend on the specific ester. I know FOR SURE that that happens with 2 - Propyl Nitrite. I think it also might cause nerve damage? As it might mess with Vitamin B12 once Nitrogen Oxides get into the body.

[Edited on 14-6-2015 by Hawkguy]

Hawkguy - 14-6-2015 at 13:06

I think you'll be safe with Amyl Nitrite though, if you clean it and purify it/ etc...