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Easy Piperine Extraction Pictorial

Migrated topic.

Analogue

Rising Star
(This proceedure is very simple and can be explained in a few sentences, but seeing as how there isn't a pictorial for it out there/several unnecessarily complex teks out there I thought i would add this)

What is Piperine??
Piperine is one of the main actives in common black and white pepper (usually 5-9% by weight) and used both in synthesis, as well as a potentiator of many compounds, in that it inhibits certain enzymes that break down various actives, increasing bioavailability. (Meaning it increases the % of a substance that your body can absorb)

(Specifically, Piperine is a P450 inhibitor, as well as a p-glycoprotein inhibitor)

NOTES: Gloved are a good idea to use to avoid getting piperine onto sensitive areas (burns similar to capsaicin)
While the pepper/alcohol solution is still concentrated, it can evaporate/easy to inhale which can be irritating, but
relatively harmless


Step 1:
Grind/pulverize black pepper (Piper nigrum)
grind1.jpg


I just used a regular bladed coffee grinder

Step 1.5:
It may be possible to increase yield of piperine and shorten duration of extraction time by microwaving the pepper for a minute or two on high (spread the coarsely ground pepper evenly on a plate), prior to adding to your solvent. (may want to add a mug of water while microwaving to protect the magnetron)
-Credit to Crystalito
(no personal experience yet)


Step 2:
Soak/Shake pepper in a jar with 91% or higher isopropanol (rubbing) alcohol for a day or two
(the ratio for pepper to alcohol isn't exact, but its good to have the alcohol level decently higher then the pepper level when settled to make decanting easier)
soake.jpg

this picture is after i already decanted some with a syringe

NOTE: May be possible to substitute ISO with water and the addition of a surfacent (odium dodecyl sulfate) for those of you who dont have easy/cheap access to rubbing alcohol.
Credit to Crystalito
(no firsthand experience)

Step 3:
Dilute the alcohol you decanted off with water.
(again, the proportions aren't precise, just dilute the alcohol solution enough to make it cloudy, you cant really add too much water, it just means you'll just need to filter more solution)
precip.jpg

as soon as you add the solution to water the piperine should precipitate as it is insoluble in water

Step 4:
Shake the watered down solution briefly and then let it sit for several days (two or three)
cloudy.jpg

should look about like this

Step 5:
Filter out your crystals! (while you cant see them since they're suspended in the solution, the crystals have separated and grown large enough to not pass through he coffee filter (I used the top portion of a 2-liter bottle with just one regular circular coffee filter, no need to double up)
filterv.jpg


Step 6:
Let dry and scrape up (its ready to go!) it looks like yellow cotton candy in person.. also can be re-crystalized if you want to try to grow beautiful crystals, however they are ready to use now!
dryd.jpg


(I suggest those who are interested/dont know yet to also look up curcumin, as piperine increases absorption by up to 2000%)

List of Piperine affected substances
(taken from Observant's post here in the nexus)

"Table 1. Substances for which piperine has been directly shown to increase bioavailability.
barbiturates
beta-carotene
coenzyme Q10 (CoQ10)
curcumin (extract from turmeric)
dapsone
ethambutol isoniazid
nalorphine
phenytoin
propranolol
pyrazinamide
rifampicin selenium (from selenomethionine)
sulfadiazene
theophylline
vitamin B-6 (pyridoxine)
glucose (absorption increased)
amino acids (absorption increased)

A far larger list could be compiled of substances (including drugs and dietary substances) whose bioavailability is assumed to be altered by piperine due to the known effects of piperine on proteins that metabolize or transport these substances.


Table 2 lists some of the drugs that fall into this category. It would be useful to have an analogous list for dietary substances, but in most cases the data do not exist.
Table 2. Metabolizing enzymes inhibited or induced by piperine, and a few of the substances whose bioavailability is affected by these enzymes. Metabolizing Enzymes: CYP1A1, CYP1B1, CYP1B2, CYP2E1, CYP3A4


Drugs: acetaminophen, alfentanyl, amiodarone, amlodipine, astemizole, atorvastatin, barbiturates, benzodiazepines, buspirone, Cafergot, caffeine, carbamazepine, cerivastatin, chlorpheniramine, chlorzoxazone, cimetidine, ciprofloxacin, cisapride, clarithromycin, cocaine, codeine, cyclosporine, dapsone, dextromethorphan, diethyl-dithiocarbamate, diltiazem, disulfiram, efavirenz, enflurane, eplerenone, erythromycin, estradiol, ethanol, felodipine, fentanyl, finasteride, fluconazole, fluvoxamine, gestodene, Gleevec, glucocorticoids, haloperidol, halothane, hydrocortisone, indinavir, irinotecan, isoflurane, isoniazid, itraconazole, ketoconazole, LAAM, lercanidipine, lidocaine, lovastatin, methadone, methoxyflurane, mibefradil, mifepristone, modafinil, nefazodone, nelfinavir, nevirapine, nifedipine, nisoldipine, nitrendipine, norfloxacin, norfluoxetine, odanestron, phenobarbital, phenytoin, pimozide, pioglitazone, progesterone, propranolol, quinidine, quinine, rifabutin, rifampin, ritonavir, salmeterol, saquinavir, sevoflurane, sildenafil (Viagra), simvastatin, sirolimus, St. John’s wort, tamoxifen, taxol, terfenadine, testosterone, theophylline, trazodone, troglitazone, verapamil, vincristine, zaleplon, zolpidem


Other actions of piperine

Aside from its effects on bioavailability, piperine has a number of other actions in the body. (It is suspected, but not proven, that some of these actions result from piperine’s effects on the bioavailability of other substances.) These actions include:

* Increasing the brain’s production of beta-endorphins
* Pain relief
* Increasing the brain’s production of serotonin
* Anticonvulsant, anti-epileptic action
* Increasing the adrenal glands’ production of epinephrine (adrenaline)
* Altering contractions in the upper and lower digestive tract
* Reducing the stomach’s production of acid (for about 1 hour)
* Decreasing ulceration of the stomach
* Increasing the pancreas’s production of digestive enzymes (amylase, lipase, trypsin and chymotrypsin)
* Stimulating production of melanin
* Reducing inflammation due to irritation or allergy
* Relieving asthma symptoms

These actions have been deduced from lab experiments, not clinical studies, and so the dosages required to achieve them are not known."

Piperine ALSO acts as a p-glycoprotein inhibitor
 
I hope someone is still reading this post and can help me, as I'm very interested in the topic.
Can anyone tell me why you would go through all this trouble instead of just buying piperine as "Bioperine"?
Bioperine is usually labeled as 95% Piperine, which is a little fishy; why not just call it Piperine?
The reason I ask is cause supposedly you can use Piperine to create Piperic Acid, then on to other things.

Maybe make some boss perfume 😉

N E idea why you would not start with Bioperine? It's OTC and you're 95% there.
 
harryboberries said:
I hope someone is still reading this post and can help me, as I'm very interested in the topic.
Can anyone tell me why you would go through all this trouble instead of just buying piperine as "Bioperine"?
Bioperine is usually labeled as 95% Piperine, which is a little fishy; why not just call it Piperine?
The reason I ask is cause supposedly you can use Piperine to create Piperic Acid, then on to heliotropin.

Then you could make some boss perfume 😉

N E idea why you would not start with Bioperine? It's OTC and you're 95% there.

We will have none of that talk here. Im no mod... so i wont warn you.
No synthesis talk.
 
Did not mean to do anything wrong. I mean that is far from a synthesis.
Am I confused or is this not exactly what the site is for?
Maybe it's because I didn't talk about the correct Tryptamine.

So back to the question at hand. Is the Piperine being made, the same thing that can be bought OTC as Bioperine?
 
More or less yes, but why buy it when you can extract grams of it easily? I think half of it is the fun and the achievment of doing it yourself...plus you know what you isolate rather than take bioperine's claims at face value (i do not know what the rest 5% is plus i think it can be cheaper if you do it yourself).


I do not think its a matter of "correct tryptamine", i think most people in many places are ...fed up of people looking towards easy precursors -by the way practically its more complicated if you look at experiments done on its hydrolysis and further use. I think the most interesting part of it lies solely on piperine, unhydrolysed :).

If though you want to experiment with bioperine please feel free. Maybe you could also use bioperine pills to see solubilty of piperine in different solvents (that could help extractions). Nothing is lost in such procedures ;) One could also use bioperine to grow piperine crystals which can be amazing! An idea here would be to dissolve them in hot/boiling alcohol and let it cool gradually undisturbed.
 
^^^ Thanks so much for the clarification.
Honestly, I would like to try my hand doing both.
1. I would like to purify the Bioperine to maybe remove that 5%.
2. I would love to extract from pepper. One day, no more Bioperine.

I really enjoyed reading this thread, especially because of the pictures.
My hope is to be educated and to educate; that is my reason for pointing this out.
 
first off to everyone, sorry swim was gone so long, got really busy with finals and of course parties and such, ontop of the nexus going down.

swim performed a side-by-side comparison of freeze/microwaved vs. the first method and did find differences,
the freeze/microwaved formed vey needle-like crystals that were somewhat shiny, but dull - also had more yeild
the grind and soak method formed very shiny platelet crystals and slightly less yeild

unfortunately, due to spring cleaning and forgetfulness, swim's exact yielding measurements have been recycled into toilet paper by now.. (weights were approx. .350 mg per 70ml of extract from a solution of 300ml iso and 68g pulverized pepper, meaning both methods yielded approx. 2.2% by weight)
also, it was noted that the frozen/microwaved method smelled different after being microwaved, got darker faster and remained darker, and needle-like crystal structures may imply higher purity?

swim can conduct teh experiment again if swiy needs to, but wont otherwise as swim doesnt see much point to

1.2g per 5$
5g per 5$ and approx 4$ or less for the alcohol (where swim lives)

soo, just from what 2 secs of google shopping tells me, costs are approximately
homemade - $1.8 per g purity ?
storebought - $4.17-8.77 per g purity 95%

that being said, usually piperine wouldnt be needed in bulk and swim personally does this for the fun of it and only uses it with curcumin supplementation or curries with curcumin
 
Jason 77 said:
Regarding use of alcohol. Can a high alcohol vodka or grain alcohol be used instead of the rubbing alcohol? Thank you for the great information.
Yes, something like Everclear would work. This is experiment #80 in Harwood & Moody's 'Experimental Organic Chemistry', for example, using 95% ethanol as the solvent at 15mL per gram of peppercorns.

After the initial Soxhlet extraction of peppercorns, the liquid extract is cleaned by hot filtering. After evaporating down to 0.1mL per gram of peppercorns, ethanolic potassium hydroxide is added at the rate of 1mL per gram of peppercorns and the liquid is separated from any precipitate by decanting or suction filtration. Freezing the solution allows recovery of piperine crystals. A good first crop should present a yield of around 2%.
 
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