Sciencemadness Discussion Board - Chemicals from Urine? Anything useful?

Chemicals from Urine? Anything useful?

PickledPackratParalysis - 12-6-2013 at 15:31

I just noticed that some of my bottled pee had evaporated, and the sides of the container were coated with whitish-yellow 'salt'. In another container there were also about 1 mm diameter orangeish specks with the whitish-yellow 'salt'. I don't think the salt is NaCl (or however you say sodium chloride), but it struck me that there might be a use for the stuff left over once pee evaporates.
Sorry if this is considered unduly gross!

I was just curious!

BCNOFNe - 12-6-2013 at 16:12

How old is this urine experiment of yours? Was the urine pretreated with anything to prevent bacteria growth?

chemcam - 12-6-2013 at 16:18

I am sure all chemists have pondered this at least once in their life. Well just think of all the compounds that get expelled from your urine, too many to know them all, but urea would be present and is useful but not much would be there, many dissolved solids would crystallize out like iron and sodium salts.
You would have to know your target compound and do an extraction, or you could distill the urine as well but I would think that is a smelly process, ammonia from decomposing organics... Oh, if you are a heavy drinker it could be a source of Acetaldehyde, maybe?

But the question really is...why do you have bottled urine? Perhaps, checking for certain metabolites?

If you work up some turds maybe you can get a thiol or 2..lol

DraconicAcid - 12-6-2013 at 16:19

Urine luck! I happen to have a book handy that gives loads of information on that subject!

Practical Physiological Chemistry (Hawk, 1916) has several chapters on urine, including the table "Composition of a normal urine (1500 cc)":
Water: 1440 g
Solids: 60 g
Urea: 35 g
Uric acid: 0.75 g
Hippuric Acid: 0.7 g
Oxalic Acid: 0.015 g
Aromatic oxyacids: 0.06 g
Creatinine: 1.0 g
Thiocyanic acid (as KSCN): 0.15 g
Indican: 0.01 g
Ammonia: 0.65 g
Sodium Chloride: 16.5 g
Phosphoric Acid: 2.5 g
...And other sulphates, calcium, potassium, and magnesium.

The salt is probably mostly sodium chloride, although there's probably a good deal of ammonium chloride mixed in with it (urea hydrolyzes to ammonia upon standing in solution).

The same book gives a procedure for isolating urea from urine- mix 800 mL urine with 250 mL "baryta mixture" (composed of 1 volume saturated aqueous barium nitrate and two volumes saturated barium hydroxide solution), stir thoroughly, filter out the precipitates, evaporate down to a syrup on a steam bath (good ventilation required!), extract with warm 95% ethanol. Boil the extract with charcoal to decolorize it, filter hot, and stand the filtrate in a cold place for crystallization.

Uric acid may be isolated from 200 mL of filtered urine by acidifying it with 2-10 mL of conc. hydrochloric acid and allowing to stand in a cold place for 24 hours.

It gives a procedure for isolating creatinine, but it involves 10 L of urine and 180 g of picric acid- I'm not sure which I'd like to avoid more.

Hippuric acid may be isolated from horse or cow urine (500 - 1000 mL urine, add calcium hydroxide until it's basic, filter out any precipitate, concentrate the filtrate over a Bunsen burner lame to a small volume, acidify strongly with conc. HCl, allow to stand 24 hours in the cold to crystallize. Recrystallize from hot water, decolorizing with carbon. OR, mix 500 mL horse urine with 125 g ammonium sulphate and 7.5 mL of conc. sulphuric acid, allow to stand for 24 hours, collect the crystals and recrystallize as above). If horse/cow urine is not available, then you can use your own if you consume 2 grams of ammonium/sodium benzoate before bed, and collect the urine first thing in the morning.

neptunium - 12-6-2013 at 16:24

need I mentioned the 1669 isolation of Phosphorus from gallons of urine?

PickledPackratParalysis - 12-6-2013 at 17:32

Sounds like some awesome stuff! No, it was not sterilized...
Now the question is, is there anything I can do without a chemistry lab. I'm just getting started here... I have a centrifuge, mortar and pestle, and household products that I can press gang into chemical use, but no Hydrochloric acid, barium nitrate, picric acid... etc etc...
I guess to have any fun I need to get some real chemicals, but what about doing it 'old school' like the medieval physicians who mixed up plants or rocks and maybe boiled something in a pot?

BCNOFNe - 12-6-2013 at 17:49

I have a pdf of a NASA report that talks about all the fun stuff that they did with urine, it is pretty interesting and I would attach it to this post but the file is too large. BUT if you do a google search for "nasa cr-1802" it should be the first listing.

Random - 13-6-2013 at 14:27

Thiocyanate from urine sounds tempting. I would need 10L urine for 1g though.

[Edited on 13-6-2013 by Random]

unionised - 14-6-2013 at 08:37

I wondered about the thiocyanate.
It's not mentioned in the NASA document.
At that concentration, would it give an obvious red colour with Fe+++?

I think this report gives more realistic figures for [SCN]-
http://link.springer.com/article/10.1007%2FBF01088426#page-1

something like 0.003 to 0.01g/l

Random - 14-6-2013 at 10:29

Quote: Originally posted by unionised

I wondered about the thiocyanate.
It's not mentioned in the NASA document.
At that concentration, would it give an obvious red colour with Fe+++?

I think this report gives more realistic figures for [SCN]-
http://link.springer.com/article/10.1007%2FBF01088426#page-1

something like 0.003 to 0.01g/l

That seems more realistic. Maybe we could eat apple seeds and apricot kernels for higher concentration but I think it could increase amount of ingested HCN to dangerous levels if big amounts are eaten on purpose.

Adas - 14-6-2013 at 12:42

I mixed some urine and a small amount of 37% H2SO4. The liquid turned somewhat orangeish and there was some orange-brown percipitate at the bottom. But it stinked too much so I ended the experiment.

platedish29 - 14-6-2013 at 17:34

Never, ever boil urine off at standard open ventilated regions any close to the population. Even chimmeys may risk your status to that which mostly transcends the nature of a suffering corpse... thats an horrendous smell. furthermore you never gonna syrup up the urea the way down: it explodes way too much.
A big deal is to prepare nitrates through straws and wood ash baths. Besides, I could never find the procedures to this but keeping things mostly neutral, tapped, away from sunlight and urine-moist would be the proper chase to go if you pee a lot!
Oh yeah another good deal for the miserable drunk chemist: to have free nitric in hands

PickledPackratParalysis - 26-6-2013 at 06:47

I took a look at the NASA report... It seems that using electrolysis on the urine would 'convert' most of the organic molecules to C, O2, H2, Nitrogen... forgot the symbol for that! But anyway, it then talks about straining the inorganic salts from the water using electrodialysis. I looked that up on wikipedia, and saw that it is somehow using electric current to make a 'unnaturally' high salt concentration by forcing salt into one side of the container. It doesn't really explain the 'do it at home' version though... I was wondering if something like a crude electrolysis cell could be modified for electrodialysis.

I successfully split water into hydrogen and oxygen with a homemade electrolysis cell and saltwater (probably baby stuff for you guys... I got it out of a chemistry book). The problem for me of using this configuration, is that the positive was hooked up to an aluminum foil (anion?) which slowly disintegrated into little flecks of aluminum in the salt water during the experiment. I don't think that kind of solution contamination would be acceptable for experiments where it's the solution you want rather than gas released from the solution.

Any ideas for how to make a 'clean' electrodialysis cell?

Adas - 26-6-2013 at 09:00

I once tried urine electrolysis. I only remember some kind of bad smell.

PickledPackratParalysis - 26-6-2013 at 13:54

Maybe I should try it...in a well ventilated area of course.

pneumatician - 23-7-2013 at 19:12

hi, I get this salt from urine. no electrolysis, no chems added... so before I read a lot of chem literature... can someone tell me what the hell is this ?

http://verdaguer.com/391/pneumatician/microsal/

you can see some grains stuck to glass but this is by, I think, static electri.

bfesser - 23-7-2013 at 19:14

Yes, it's a nondescript white powder.

zed - 24-7-2013 at 14:27

Now, if a fella were commercially minded, he could trade clean schoolboy urine, for junkie urine. First, some junkies might be willing to pay well for the clean urine....So they could pass their mandatory court-ordered UAs. Next, the junkie urine would be full of Morphine metabolites, that could probably be converted back into Morphine.

In the early days of antibiotic therapy, Penicillin was damned hard to come by. The urine of some patients receiving Penicillin therapy, was processed to recover the Penicillin, so it could be re-used. It was a matter of life and death. Patients considered hopeless, recovered from deadly infections when the "Miracle Drug" was given.

Might be small amounts of really valuable stuff even in average urine. Antigen-Antibody complexes, and whatnot.

testimento - 24-7-2013 at 14:41

One could take a piss on a shallow pan to evaporate the liquids and minimize the amount of urea and other compounds being decomposed. Urea slowly decomposes with moisture, AFAIK. So sad one person would only generate some 10kg of urea in a year.

Pulverulescent - 25-7-2013 at 05:20

Pure urea is stable in solution below ~30°C, IIRC . . .

Morphine Metabolites

chemcam - 25-7-2013 at 09:36

Quote: Originally posted by zed

Next, the junkie urine would be full of Morphine metabolites, that could probably be converted back into Morphine.

Back when I was a junkie, I had this exact thought! I wasn't studying chemistry though so I had no idea what to do. I still don't really, but the main metabolites are morphine-3-glucuronide (M3G), morphine-6-glucuronide (M6G), normorphine, codeine, and morphine-3-sulfate.
The most present metabolite is M3G (55% to 75%).

These metabolites haven't been studied all that well by big pharma but they believe M3G is responsible for the addiction and pain killing potential while M6G is responsible for the overdose effects; shallow breathing, etc...
Normorphine is the N-demethylated derivative of morphine and is a weak opiate.
Codeine is 3-methylmorphine an isomer of methylated morphine.
Morphine-3-sulfate? If it is the same thing as 'morphine sulfate' then what, it must just be unreacted?

I no longer use opiates but I am still interested in the chemistry behind them.

-------
Journal of Pharmaceutical Sciences
Volume 66, Issue 9, pages 1288–1293, September 1977
DOI: 10.1002/jps.2600660921
Reference Link: Abstract

Isolation and identification of morphine 3- and 6-glucuronides, morphine 3,6-diglucuronide, morphine 3-ethereal sulfate, normorphine, and normorphine 6-glucuronide as morphine metabolites in humans
S. Y. Yeh
C. W. Gorodetzky
H. A. Krebs

Maybe someone can attach a digital copy of this reference in the following posts? Thanks in advance, I have a hard copy but its in very, VERY bad shape. Coffee spilled on it, pages ripped... Basically, I tried to scan but it looks like shat.

Edit: Thanks for the move bfesser, I hope this gets some attention
Edit 2: Thanks also to solo for providing the requested reference.

[Edited on 7-26-2013 by chemcam]

solo - 25-7-2013 at 12:48

Reference Information

Isolation and identification of morphine 3- and 6-glucuronides, morphine 3,6-diglucuronide, morphine 3-ethereal sulfate, normorphine, and normorphine 6-glucuronide as morphine metabolites in humans
S. Y. Yeh C. W. Gorodetzky H. A. Krebs
Journal of Pharmaceutical Sciences
Volume 66, Issue 9, pages 1288–1293, September 1977
DOI: 10.1002/jps.2600660921

Attachment: Isolation and identification of morphine 3- and 6-glucuronides, morphine 3,6-diglucuronide, morphine 3-ethereal sulfate, (713kB)
This file has been downloaded 1076 times

mayko - 19-8-2013 at 06:53

If you check out Experiments in Organic Chemistry by Louis Fieser, 1941 (available from the forum library), there is a chapter on isolating urea from urine, as well as a chapter on eating sodium benzoate to increase the hippuric acid content of urine before isolation.

The latter in particular sounds like an interesting experiment that would never be done in a modern university.

Edit: This book also suggests adding a bit of toluene as a preservative.

[Edited on 19-8-2013 by mayko]

confused - 19-8-2013 at 07:59

autoclave the urine in a presure cooker, removing mibrobes
hook it up to a vaccum pump, with a cold finger trap to remove water.
then analyse/purify whatever compounds you want to extract

phlogiston - 8-9-2013 at 14:18

So, it turns out that current state-of-the-art metabolomics techniques can identify 3000 compounds in urine:

http://www.plosone.org/article/info%3Adoi%2F10.1371%2Fjourna...

Regarding the benzoate, people suffering from certain inheritable metabolic disorders take it regularly in quite large amounts to reduce their plasma glycine levels. It is also a common food preservative.

[Edited on 9-9-2013 by phlogiston]

DraconicAcid - 9-9-2013 at 08:05

Quote: Originally posted by mayko

If you check out Experiments in Organic Chemistry by Louis Fieser, 1941 (available from the forum library), there is a chapter on isolating urea from urine, as well as a chapter on eating sodium benzoate to increase the hippuric acid content of urine before isolation.

The latter in particular sounds like an interesting experiment that would never be done in a modern university.

It was still in the lab manual in 1991 at the University of Alberta.

ElectroWin - 9-9-2013 at 14:38

Quote: Originally posted by PickledPackratParalysis

I just noticed that some of my bottled pee had evaporated, and the sides of the container were coated with whitish-yellow 'salt'.

check for: sodium bicabonate, and urea nitrate

fresh urine has virtually no nitrates, but after it has fermented awhile in air, (especially in the dark), bacteria make nitrates. and urea nitrate is sparingly soluble so i think you should find it in there. Naquet, 1855: principles of chemistry gives a method for preparing pure urea from urine. If you want to try this I suggest evaporating at reduced pressure, to speed the process without creating biuret.

the bicarbonate will be in there if there has been enough time to absorb CO2 from the atmosphere.

phlogiston - 10-9-2013 at 00:42

Quote: Originally posted by zed

Might be small amounts of really valuable stuff even in average urine. Antigen-Antibody complexes, and whatnot.

In the Netherlands, urine from pregnant women is collected on a very large scale (about 30000 liters a week) and used to isolate Human Chorionic Gonadotropin (HCG), a hormone. It is used to prepare a drug to treat infertility problems. I have been told this is the only country where this is done.

On a side note, for those interested in the history of discoveries, the last author in the ref posted by solo:

Quote: Originally posted by solo

Reference Information
Isolation and identification of morphine 3- and 6-glucuronides, morphine 3,6-diglucuronide, morphine 3-ethereal sulfate, normorphine, and normorphine 6-glucuronide as morphine metabolites in humans
S. Y. Yeh C. W. Gorodetzky H. A. Krebs
Journal of Pharmaceutical Sciences
Volume 66, Issue 9, pages 1288–1293, September 1977
DOI: 10.1002/jps.2600660921

is the famous Hans Krebs, best known for his discovery of several very important metabolic pathways in the early 30's, including the citric acid cycle (or 'Krebs cycle') and the urea cycle and winning the nobel prize in medicine in 1953.

[Edited on 10-9-2013 by phlogiston]

kt5000 - 2-12-2013 at 22:59

Quote: Originally posted by PickledPackratParalysis

I just noticed that some of my bottled pee

You bottle pee??

Urea, man, lots of urea. Good for fertilizing lawns and damn near anything else, iirc.

UnintentionalChaos - 2-12-2013 at 23:24

It is really odd that this thread surfaces again...I was just considering doing the prep of hippuric acid...

thebean - 3-12-2013 at 08:58

I few months back I was told that adding NaCl to urine could produce ammonia over a few months. Being inquisitive I did so and discovered after about five months that there was no NaCl, but a deep green insoluble. Could anyone tell me what this green insoluble might be?

eidolonicaurum - 2-1-2014 at 05:41

You can get urea from urine, and white phosphorus. Much else is usually so low in concentration as not to be worth it. Unless you're really desperate.........

Urea can be extracted like this:
Boil down urine so smaller volume to deal with (you are going to need litres of raw material)
Add calcium chloride (chalk + hcl) -> precipitates calcium cyanate because urea <--> ammonium cyanate
Filter off, and powder up.
Boil with ammonium sulphate solution to form precipitate of calcium sulphate and urea solution.
Filter off calcium sulphate, and boil down. Urea will come out of solution.

Phosphorus:
Boil down urine to solid, and keep heating until no more change occurs. Grind up the white solid (chuck the black stuff) with sand and aluminium powder, then heat in a retort to the highest temperature you can reach. The hotter the better. Condense all vapours under water. Hopefully, you will have some (impure) white phosphorus.

Good luck! Let me know if the phosphorus one works, if you ever do it.

[Edited on 2-1-2014 by eidolonicaurum]

eidolonicaurum - 2-1-2014 at 05:57

I just saw an earlier post of yours, and it looks like you are going to need to get some more chemicals from somewhere if you want to do the interesting things. I mean, theres a suprising amount you can get OTCwise, but you just have to know where to look. Its also quite ridiculous how much you can get on ebay/amazon etc. Another place is sites where schools get their chemicals from, like philip harris, though they can be more/quite expensive.