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Author: Subject: 2,4 Dinitrophenol
SupaVillain
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[*] posted on 25-3-2015 at 08:33
2,4 Dinitrophenol


Dinitrophenol is available on ebay!?

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

Anybody ever try something like this? Thoughts?

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Loptr
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[*] posted on 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.
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[*] posted on 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]




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Loptr
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[*] posted on 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
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[*] posted on 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.




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[*] posted on 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
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[*] posted on 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.
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[*] posted on 25-3-2015 at 11:01


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




Rapopart’s Rules for critical commentary:

1. Attempt to re-express your target’s position so clearly, vividly and fairly that your target says: “Thanks, I wish I’d thought of putting it that way.”
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Anatol Rapoport was a Russian-born American mathematical psychologist (1911-2007).

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Chemosynthesis
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[*] posted on 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]
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Dr.Bob
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[*] posted on 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.
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Chemosynthesis
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[*] posted on 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.
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[*] posted on 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?




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SupaVillain
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[*] posted on 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.
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Chemosynthesis
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[*] posted on 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]
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[*] posted on 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.
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[*] posted on 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.
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[*] posted on 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.
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[*] posted on 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.
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[*] posted on 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.
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Chemosynthesis
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[*] posted on 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
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[*] posted on 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.
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[*] posted on 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))
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[*] posted on 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.
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[*] posted on 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.
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[*] posted on 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>
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