Sciencemadness Discussion Board

2,4 Dinitrophenol

SupaVillain - 25-3-2015 at 08:33

Dinitrophenol is available on ebay!?

http://www.ebay.com/itm/111629714904?ssPageName=STRK:MESELX:...

Anybody ever try something like this? Thoughts?

Loptr - 25-3-2015 at 09:11

Apparently it is used as a weight loss aid?? (google search)

I was under the impression it was explosive if not kept wet. I am confused.

Molecular Manipulations - 25-3-2015 at 09:43

If you use a very powerful blasting cap you could probably get it to detonate. But it's a very, very lousy explosive, and has a very low oxygen balance.
It's used as a dieting drug because it prevents or slows ATP (adenosine triphosphate) production which is where all biological energy is stored. The energy that may have turned into fat is thus waisted as heat.
From Wikipedia:
Quote:

DNP acts as a protonophore, allowing protons to leak across the inner mitochondrial membrane and thus bypass ATP synthase. This makes ATP energy production less efficient. In effect, part of the energy that is normally produced from cellular respiration is wasted as heat.


[Edited on 25-3-2015 by Molecular Manipulations]

Loptr - 25-3-2015 at 09:54

2,4-Dinitrophenol (DNP) is reported to cause rapid loss of weight, but unfortunately is associated with an unacceptably high rate of significant adverse effects. DNP is sold mostly over the internet under a number of different names as a weight loss/slimming aid. It causes uncoupling of oxidative phosphorylation; the classic symptom complex associated with toxicity of phenol-based products such as DNP is a combination of hyperthermia, tachycardia, diaphoresis and tachypnoea, eventually leading to death. Fatalities related to exposure to DNP have been reported since the turn of the twentieth century. To date, there have been 62 published deaths in the medical literature attributed to DNP. In this review, we will describe the pattern and pathophysiology of DNP toxicity and summarise the previous fatalities associated with exposure to DNP.

http://www.ncbi.nlm.nih.gov/pubmed/21739343

Bert - 25-3-2015 at 09:56

http://www.shape.com/blogs/shape-your-life/dnp-weight-loss-d...

If you don't mind cataracts, brain dammage or death as a side effect...

Banned for such use in USA since 1938. Plenty of legitimate other uses , so not banned from commerce.

There was a wave of quick buck wannabee cooks coming here interested in the synthesis a while back.

SupaVillain - 25-3-2015 at 10:18

You do realize that the FDA is considering to approve it soon right? Let me find the link here, not that it clearly isnt meant to be ingested

SupaVillain - 25-3-2015 at 10:38

Here is the link,

http://www.iflscience.com/health-and-medicine/reinvented-ban...

Im surprised all that any of you have to say about it is about illegal ingestion but it anything related to death with DNP is not DNP related, it's called overdose. That's a word that has been around a long time.

Bert - 25-3-2015 at 11:01

If you decide to eat DNP, please keep good notes & report your first hand experience-

Chemosynthesis - 25-3-2015 at 11:53

Quote: Originally posted by SupaVillain  
You do realize that the FDA is considering to approve it soon right? Let me find the link here, not that it clearly isnt meant to be ingested

That's funny, I didn't see any clinical trials, which happen before approval. Now, it's common knowledge to those in the field that clinical trial results aren't always posted on time, but what I see is rat data from this year. Not even non-human primate data.
This is hardly being close to FDA approved for human ingestion in a medical treatmeant capacity.
http://www.sciencemag.org/content/347/6227/1253
Iflscience is kind of a joke, in my opinion. No offense if you like it.

Now if DNP is on the approval list as a slow release or pH formulation, I would like to know, because I had people asking for consulting on it a couple years ago, and I declined. It is possible to have some formulations diminish incidents of side effects, such as 5-ASA drugs and sulfa pyridine (ex. Sulfa pyridine and mesalazine, despite the availability of less toxic alternatives).
Quote: Originally posted by SupaVillain  
Here is the link,

http://www.iflscience.com/health-and-medicine/reinvented-ban...

Im surprised all that any of you have to say about it is about illegal ingestion but it anything related to death with DNP is not DNP related, it's called overdose. That's a word that has been around a long time.

Arguably any toxicity is an overdose, but a specific toxicity is intrinsic to a substance as it is part of the dose-response curve.
I am surprised your only question was a vague "anyone ever try something like this?" and you want more of a response. Please clarify. You are asking about ingestion for weight loss by uncoupling the electron transport chain as a thermogenic agent?
Edit: because there was one mention about poor explosive properties due to negative oxygen balance you may have skipped. It was a small mention, but not all the response is on ingestion.

[Edited on 25-3-2015 by Chemosynthesis]

Dr.Bob - 25-3-2015 at 12:02

Apparently the key is to have a slow, steady release, in order to keep the blood levels low and consistent, as high amounts are what really cause severe side effects. So using a slow release system, they can keep a much lower, but steady amount in the blood, which does cause the liver and other tissues, to a lesser degree, burning glucose and fat in a moderately safe level. There are some mononitrophenols which might be even safer, that are also being investigated for weight loss/obesity/diabetes.

Chemosynthesis - 25-3-2015 at 12:30

It is definitely feasible. That is one of the major paradigms behind Pentasa and Asacol formulations of mesalamine, as well as ensuring a more targeted drug localization for IBD patients. Sulfa sensitive patients tolerate the lower maximal concentration better, though drugs such as olsalazine which lack the sulfa pyridine moiety tend to have more favorable toxicity profiles. The reverse is why extended release formulations don't exchange for normal/uncoated drugs at the pharmacy.
I am pretty skeptical that DNP is nearly that close to approval (for what? Weight loss?) without a citation, though.
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3048933/
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3550200/
I have used it in a synthetic capacity, if that is what the OP is asking. Relatively common reagent. Even got a small drop on a finger while cleaning out glassware, which stained my skin.

DraconicAcid - 25-3-2015 at 12:42

Quote: Originally posted by Bert  
If you decide to eat DNP, please keep good notes & report your first hand experience-

Better yet, have a friend nearby to take dictation.

"It tastes like aaargh?" What does that mean?

SupaVillain - 25-3-2015 at 12:50

By "anyone ever try something like this?", I meant has anyone had experience buying this type of chemical off of ebay, like did you have a good experience in the sense that it was actually lab grade or such. It would have been nice had you discussed the chemical further than ingestion. Ingestion isnt my intention and neither is the seller's I believe.

Chemosynthesis - 25-3-2015 at 13:01

Ah, thanks for clarifying. I haven't purchased it off eBay. I forget where it was purchased from, but it was a reagent grade material. I have used it for a diazo coupling before, in some derivative or another. It is possible that gut microbiota could cleave that diazo bond for colonic absorption, but I wasn't using it for that purpose. I forget exactly what I was making.

As for ingestion, that type of thing is a large part of my professional background, so it is going to be a focus in most of my activities both on and off the board. Well over a decade has passed since I was involved in any licensed pyrotechnics groups, and I never did anything with DNP in that regard.
It is worth noting that DNP has caused toxicities inhalation ally and through cutaneous absorption, if you work with it. Staining can be interesting. I made Brady's reagent for kicks using DNP. That is a worthwhile experiment. If you try it, store appropriately (preferably use at once). See Synthesis, 2005, 547-550 and various sources in this thread for ideas on how to proceed with an intermediate for that if interested: http://www.sciencemadness.org/talk/viewthread.php?tid=8898

[Edited on 25-3-2015 by Chemosynthesis]

SupaVillain - 25-3-2015 at 13:14

Well whats listed on ebay is a crystalline powder but I've seen non-crystalline powder before, and it is darker in that other form than what is pictured. People who have taken it have reported a difference in strength of effects and the different times that it heats the body up. I think in this powdered form it is possible to poison by inhalation or if you are around large amounts of it, however whenever I've seen it it's been totally safe in handful amounts.

Chemosynthesis - 25-3-2015 at 14:41

Ingestion bioavailability profile can depend on the polymorph of active pharmaceutical compounds, more than other routes of administration. This is due to inactive conformers and altered absorption/solubility of crystalline states and densities. Surface area can also play a role.

I would not comment on the safety of "handful amounts." This is anecdotal at best. Not only is this not quantifiable, but no mention of dosing regimen is made, which is important. Data on biological half lives of DNP appears conflicting, but a maintenance dose schedule can dramatically affect plasma concentration up to a certain steady state limit. This has both chronic and acute toxicity implications. Duration of use at a dose is also very important from a toxicological perspective.

Some examples are drug induced chronic pancreatitis (ex. Valproate, both acute and chronic risk), and and chronic nephrotoxicity (ex. Cyclosporine), and chronic hepatotoxicity (ex. methotrexate). Often the chronic toxicity dose is much lower than acute.

ni3rtap - 8-4-2015 at 21:55

The mechanism of it's toxicity is really interesting. I was surprised that the body doesnt actually have trouble producing so much more ATP and that its dangerous, almost entirely from the heat you produce. Though, it's all about the calories.

It would be really interesting if someone started supplying it to arctic fisherman "deadliest catch" to augment the survival suits. It might be difficult to get it to work quickly enough.

Marvin - 9-4-2015 at 08:01

Quote: Originally posted by ni3rtap  
The mechanism of it's toxicity is really interesting. I was surprised that the body doesnt actually have trouble producing so much more ATP ... .


Wikipedia is not always right, but it says exactly the opposite.
Quote:

It defeats the proton gradient across mitochondria and chloroplast membranes, collapsing the proton motive force that the cell uses to produce most of its ATP chemical energy. Instead of producing ATP, the energy of the proton gradient is lost as heat.

macckone - 9-4-2015 at 20:12

On a side note and back to actual chemistry,
Does anyone have a good way to convert 2,4 Dinitrophenol to 1-chloro-2,4-dinitrobenzene? The later being a very useful intermediate.

Chemosynthesis - 9-4-2015 at 21:15

Really interesting glutathione alkylating agent for liver cultures, among other things.
Wikipedia claims "DNCB is produced commercially by the nitration of p-nitrochlorobenzene with a mixture of nitric and sulfuric acids. Other methods afford the compound less efficiently include the chlorination of dinitrobenzene, nitration of o-nitrochlorobenzene and the dinitration of chlorobenzene."
Here is a link to a kinetics paper on this reaction, with some reaction parameters:
http://link.springer.com/article/10.1023%2FA%3A1013408229563...

Additional copied and pasted various details with other possibilities and citations follows, which more directly answers your question:
Chlorination of dinitrobenzene.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 280

Obtained by nitrating o-nitrochlorobenzene.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 353

Dinitration of chlorobenzene in sulfuric acid.
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V17 (1996) 144

Although chlorobenzene can be dinitrated directly, this results in unnecessary isomer problems. 4-Chloronitrobenzene is usually nitrated with mixed acid (35/65) at 60 deg C to give the pure dinitro isomer. However, 2-chloronitrobenzene can be nitrated to produce 1-chloro-2,4-dinitrobenzene, together with ca. 10 wt% of the isomeric 2-chloro-1,3-dinitrobenzene. This may be separated for disposal, but the mixed isomers are preferably used directly if tolerated by the end product (e.g., sulfur dyes).
Booth G; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (1999-2012). New York, NY: John Wiley & Sons; Nitro Compounds, Aromatic. Online Posting Date: June 15, 2000

kecskesajt - 18-6-2015 at 00:43

Daaamn peoples.Why u do this.All you have to do is to not eat as much as an elephant.I weighted 65 kg when I was 10 y/o and now all weight 60kg as a 15 y/o.If somebody cant loose weight, contact with a doctor and beg for a Thyroid test.

Pumukli - 18-6-2015 at 03:08

macckone: Using PCl5 or POCl3 may convert the DNP to DNCB. At least POCl3 works in converting picric acid into picryl chloride.

(R. Boyer, E.V. Spencer, G.F.Wright, Can. J. Res, 24 B 200 (1946))

byko3y - 18-6-2015 at 13:26

kecskesajt, gays love to have attractive body with muscles but without any fat. A healthy human always have some fat in his body.
When you want to have big muscles - you need to eat a lot. But when you eat a lot - you get a lot of fat. But if you starve - you will lose a lot of muscles in fact. To become a fat-less gay-standard you need to artificially adjust your fat-muscle balance.

kecskesajt - 19-6-2015 at 01:16

Quote: Originally posted by byko3y  
kecskesajt, gays love to have attractive body with muscles but without any fat. A healthy human always have some fat in his body.
When you want to have big muscles - you need to eat a lot. But when you eat a lot - you get a lot of fat. But if you starve - you will lose a lot of muscles in fact. To become a fat-less gay-standard you need to artificially adjust your fat-muscle balance.

Im never said that I'm fatless, and full of muscles.I said that dont take this shit.And as elephant, I meant carbonhydrates.
Alright,Im out.

nebotmo - 23-6-2015 at 17:32

Has anyone ever discussed the synthesis of this compound on the forum (a search turned nothing up)? It seems rather interesting, especially when starting from phenol. How is the selective nitration achieved? I found this procedure/write-up (see "Procedure") from
http://www.researchgate.net/publication/257861451_Synthesis_...
Sourced from the Russian Journal of Applied Chemistry.
Is it just a matter of the nitration medium?
<a href="http://s000.tinyupload.com/index.php?file_id=02241846839006779788">Procedure</a>

SupaVillain - 4-7-2015 at 22:09

Lol i posted this because I was the seller. Sold strictly for legal purposes only and no longer sold due to humanity's sloppiness of their own perception of situations in the case that someone is hurt, for example, being dumb enough to think it my fault that someone hurts themselves with this when retardation is required, since the chemical is inanimate and comes with words of warning and was never advertised for consumption. I dont think the interweb gods of this site want you discussing ingestion, neither do the ingesters because you lack even the basics of an understanding of how other people can have thoughts, lives, and perspectives that are completely different than your own. In place of that value you have the ability to criticize yet never achieve something as good as you criticize.

Now as far as the encouraged discussion of 2,4-Dinitrophenol via this site, if you want to learn more on preparing DNP you should look up the preparatory manual for explosives. It's not hard to do and is pretty simple if I remember correctly. I dont advise you actually make it though. If you dont have a couple hundred dollars of safety equipment and experience you'll not survive the synthesis.

It may have great fat loss power but I can assure you youll get the same effects from a PSMF or low carb diet and drinking lots of water all day. I could just not say any of this but I'd rather do so and be able to post where to find the synthesis for the good chemists here without feeling like I've handed something dangerous to a wild roaring pack of retards

kecskesajt - 5-7-2015 at 00:26

Well,I dont know if it is a good book( I heard bad thing about this book),But there is syntesis of DNP from NaOH,Phenol,HNO3 and NaNO2.

Boffis - 5-7-2015 at 06:53

@nebotmo

Some years ago I started a thread on preparing this and other compounds from 2,4-dinitrochlorobenzene because there was an ebay seller selling this stuff by the bucket full at that time, in spite of the hazards associated with it. I intended to post a whole series of syntheses that could be easily performed on this material, the first was 2,4-dinitrophenol but I abandoned the thread because it became choked with drivel (search for dinitrochlorobenzene). In addition to my thread there is also a very nice thread on the synthesis of 2,4-dinitrobromobenzene which can be used as an alternative to the chloro-compound

The post above requesting details on how to turn 2,4-dinitrophenol back to the "more useful" 2,4-dinitrochlorobenzene brought a smile to my face:)

macckone - 5-7-2015 at 08:21

More useful, is always in the eye of the beholder. I have uses for 2,4 dinitrochlorobenzene in identifying ketones and determining if they are pure.

*edit* Surely you have used 2,4 DNPH (aka brady's reagent) to identify ketones? The stuff isn't really available to home chemists.


[Edited on 5-7-2015 by macckone]

Boffis - 6-7-2015 at 11:02

@macckone My point was that if people had bothered to check out the seller on ebay (US) rather than post irrelevant drivel they wouldn't now need to try and make it from dinitrophenol. Besides that's a ridiculous route, if you can buy PCl5, thionyl chloride etc you should be able to buy dinitrochlorobenzene or at least a halobenzene and nitrate it.



[Edited on 6-7-2015 by Boffis]

macckone - 6-7-2015 at 14:20

I was looking for an easier route.
Nitrating chlorobenzene seems a lot easier
than obtaining PCl5.
I would have to make it as well and
frankly that is a nasty process even if
it relatively straight forward.
ie. burn phosophorus in a total
dry chlorine atmosphere and collect
the pentachloride. Of course that requires
phosphorus which is a control chemical
but is relatively straight forward to make
from aluminum and phosphoric acid.
Of course that goes back to the pentachloride
being a nasty chemical to work with.

Of course obtaining DNPH in a good purity
is the goal, because if it isn't pure then
the ketone MP tests are not accurate.

Marvin - 6-7-2015 at 14:49

Quote: Originally posted by SupaVillain  
...if you want to learn more on preparing DNP you should look up the preparatory manual for explosives.


Ledgard is a fantasist.

nebotmo - 6-7-2015 at 14:56

Quote: Originally posted by Boffis  
@nebotmo

Some years ago I started a thread on preparing this and other compounds from 2,4-dinitrochlorobenzene because there was an ebay seller selling this stuff by the bucket full at that time, in spite of the hazards associated with it. I intended to post a whole series of syntheses that could be easily performed on this material, the first was 2,4-dinitrophenol but I abandoned the thread because it became choked with drivel (search for dinitrochlorobenzene). In addition to my thread there is also a very nice thread on the synthesis of 2,4-dinitrobromobenzene which can be used as an alternative to the chloro-compound

The post above requesting details on how to turn 2,4-dinitrophenol back to the "more useful" 2,4-dinitrochlorobenzene brought a smile to my face:)


Yeah I am aware of the hydrolysis of the mentioned compound. I was merely curious of alternate routes to it's synthesis starting from phenol.

@kecskesajt, do you have a source for that?

kecskesajt - 6-7-2015 at 23:30

http://www.google.hu/search?redir_esc=&redir_esc=&hl...

[Edited on 7-7-2015 by kecskesajt]

SupaVillain - 9-7-2015 at 10:16

I dont care about Ledgard or the book if the synthesis in that book is wrong then correct me otherwise i make no effort to further discuss

Marvin - 9-7-2015 at 18:08

Specifically for 2,4DNP his method, and I think I'm looking at a second edition, is a corrupt version of Example 1 in US Patent 3,933,926. This is normal procedure for him.

Ignoring the book and considering the patent, it's clever, plausible and well written but we've seen a lot of patents like that. Some produce highly toxic by products, some are wildly unsafe to do for other reasons and a lot just don't seem to work at all no matter how carefully they are followed. Patents are some of the least reliable sources we have, but if someone can try it safely that is the version to try.

Bottom line - only a fool trusts Ledgard.

SupaVillain - 15-7-2015 at 02:01

You know, I still have a load of the stuff but i've never got around to selling more because i dont care about that crap. The money i got from it was directly spent on scientific apparatus. The more i learn about science and the more I build for my ability to experiment, the more i find my love for the hobby, the more i love myself, the less i feel like i want someone else in my life, and the less I care about what others think of my actions. I live more freely. Not all of us youngins are governed mentally by the pressures of the failed society around us. Being a thug is not as entertaining or fulfilling as even the basics of the sciences.