(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)


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)

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)

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)

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)


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!


(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

Thank you Analogue!
Piperine is interesting, although besides enjoying by spicing my food, I have no experience. Do you have any experience with it as a MAOI or potentiator of another substance? I would love to hear first hand reportage.
L

Nice work Analogue, not many piperine -if any- pictorials are around. I was wondering ,do you have brown resin precipitate at the water stage?The resins seem to be the most difficult issue to deal with. I happened to come across them and they can make the material difficult to work with: for example there is this nugging suspicion that propably they hold quite some piperine in them.

A modification for better yields would be to microwave the pepper for a minute or two at the highest setting before adding the alcohol.This would help with the yields and also propably shorten extraction times. One could also microwave with the solvent added but i CANNOT and WILL NOT advice that in a home setting without proper training since explosions can ensue.

The only limiting factor for multiple passages of solvent is the price of alcohols, in some countries its expensive (yes even IPA). In this case water can be used if a surfactant is added such as odium dodecyl sulfate (wikipedia has info about it) which is not THAT exotic and can solubilise piperine in water. Check this paper : http://www.informaworld.com/smpp/content~db=all~content=a901841281 . It seems to work reasonably well even without the hydrotrope, just the surfactant.

Oh and also: piperine is not just a P450 inhibitor...I think its most interesting action is that it is a p-glycoprotein inhibitor! Look into that also and you might be amazed

That is really cool! I'll be trying this out soon. I do have to ask though, since it's actually the piperine in pepper that makes one sneeze, how bad would the sneeze attack be if one inhaled this pure product? I'm not willing to bioassay.

Thanks for writing this up. I think I'll give this a try in the near future.

Thankyou all for the replies, questions, and help! Will be updating the pictorial and answer questions when SWIM has time. Also going to do a side by side extraction to see if/how much microwaving increases yields.

Out of all the psychoactive molecules you could have made why did you choose piperine? What do you intend to do with your piperine?

Very cool! Piperine always finds its way into my mimosaroo but I use store bought, I've never tried to extract it before.

Very interesting. I dont think you will have any problem working your way out of the nursery.

Is the face of the man in your avatar a mandrake plant?

Ljosalfar:

Unfortunately no, all that SWIM has used piperine so far for has been mainly as a cheap way to enhance turmeric supplementation, although SWIM would love to combine it with shrooms, mescaline, or any other psychedelics it may increase absorption with. SWIM also hasnt used piperine solely by itself, however, when paired with sublingual curcumin/ethanol tincture, swim notices a more pronounced "buzz", tingly legs and slight giddiness (i know some may say it must be placebo, but if it is, its a rather strong/enjoyable placebo affect)

Crystalito:

SWIM has never noticed a "brown resin" precipitate out of the diluted solution, in his (limited) experience, it seems to just stay cloudy, as if it were yellow tinted milk, one would never even notice the crystals forming, unless they stick to the container's sides while tilting the solution. Everytime SWIM extracts, he just lets it sit for a few days and runs the diluted solution through the strainer. It looks like a yellow sludge while wet, but dries into a nice yellow cotton candy-like netting of crystals. (always had relatively good yields compared to storebought so never bothered trying to increase efficiency.)

also, would there be any difference in microwaving the pepper before/after grinding to a powder to increase yields? SWIM thinks it probably wont matter, but wants to get a second opinion before he tests this

Morbiddoctor:

hahaha, well SWIM wasnt expecting anything when he first noticed the airborne piperine/iso and was kind of shocked. Basically it doesnt make you want to sneeze as much as coughing, which isnt too bad actually, you just may need to leave the room to let it settle down or open a window. (SWIM sprayed a bit on the concentrated iso extract in a forceful stream into the sink and instantly felt as if tear gas was unleashed upon the kitchenette and had to vacate for a minute, haha)

Seraph:

Basically the ease of extraction and the amazing properties! No one would suspect that table pepper has the ability to increase bioavailability of such a wide range of substances (namely curcumin which has strong lab evidence (with animals) to be a good tool for fighting cancer and Alzheimer's, and is also good for fighting depression and is thought to be a RIMA, but no evidence that it supports oral dmt) and possibly various psychedelics

OpeningPandorasBox:

Well.. actually its a man's face made from naked women, haha
Matins de Barros paints tons of them, which is very unusual, but ive always found them interesting (as far as portraits go)

Is there a specific paper that has a list of substances increased be P-gp's? SWIM briefly looked over a research paper that sites Loperamide (opiate) is able to cross the blood-brain barrier through the help of P-gp inhibitors (piperine). So SWIM assumes it allows multiple drugs (several opiates specifically?) access through the BBB. SWIM was unaware of this aspect of piperine (JUST SPECULATIONS AT THIS MOMENT)
Any information will be added to the pictorial - Thanks for your help!

http://www.erowid.org/ar...2002.41.10_2521-2528.pdf

The attached link might be of utmost interest. You could spread thinly small batches (this might be of importance since the paper proposes it works better this way) of pepper at a time on a plate and microwave full power 600/750 watts for a minute or two. I would say microwave after grinding so as to be sure that microwaves irradiate your mass to depth. Another nice "trick" is presoaking the pepper in water (so you increase their water content) before microwaving -this is done without the water of course.This will a) remove water soluble molecules b)rupture cells even better before extraction with alcohol. A further step in this direction could be after the soak and the straining to freeze the pepper powder and use the microwave to thaw/irradiate it since this might promote further cell rupture.

Also, note that microwaving might also remove volatiles from your sample which can be a blessing: less undesirables in your solvent.



Heheh, loperamide is every opiophile's wet dream although im not that interested in this class of psychoactive agents. P-gps usually control the efflux of many substances from the cellular compartments to their enviroment. I assume you read the wikipedia article, it seems that...many xenobiotics, lipids, peptides etc are their "substrate".

I am afraid i cant access these papers but you might find them interesting should you be able to acquire them...

http://www.springerlink....ection=614776&page=1

http://www.ncbi.nlm.nih.gov/pubmed/20645922

Should you wish to experiment with piperine keep in mind that piperine use can upregulate p-gp. Think of it as ...umm...tolerance or even better resistance so its better not to "stack" experiments together, give them a week or so in between. Im not too sure on that bit, maybe it can be researched further but keep in mind that it has been reported as a phenomenon.


Your work is very interesting all in all, keep it up!

Anything new on the topic? It looks very promising only to be lost/forgoten...

hey Analogue, i recently finished doing this tek, woohoo!
but my final product looks very different from yours. Mine looks like a greenish yellow waxy substance, whereas yours looks like a white powder. you said in the OP that the final product ends up looking like cotton candy, but mine doesn't look like this at all. Why is this, and why does mine have more impurities? I used whole black pepper and ground it up, and followed the exact instructions.

Also, after filtering the water+ethanol solution thru the coffee filter to acquire the piperine, the solution still remained white. Howcome?? Because when i poured the ethanol into the water, white precipitate formed immediately like you described in the OP; however, upon filtration, the solution still remained milky white.

The pics are below of my final extracted product, and the filtered milky white water+ethanol solution. Thanks! <3



edit*

Try cleaning that further, by dissolving it in a minimum amount of hot acetone and letting it cool..

How long did you let it sit and in what temperatures after you diluted the ethanolic fraction in water?

since i will be consuming this, i'd rather just consume it impure without the use of Acetone, cuz its very toxic.
but i will do an acetone wash on a small seperate batch, just to see if it clears out impurities.


I let the ground pepper sit in the ethanol for 2 days. A second pull is currently still sitting in the black pepper.
everything was done at room temperature (~23C here). After i filtered the ethanol+water solution, the solution still remained milky white, like i mentioned; so then, i added 2 ice cubes to the solution to lower the temperature and make the piperine more insoluble in water; however, the solution still remained milky white upon re-filtering

it should be pure enough as is, did you let it dry all the way from liquid in a bowl? swim lets it dry on the filter and always ends up like golden threads..
and did you use ethanol alcohol? swims always used isopropanol, maybe its more selective then ethanol?
and the solution once filtered remains opaque, just less so
also, how long did you let it sit for the xtals to grow? (never tempered with the temps here, just waited about 3 days)
goodluck

(also, will be continuing this when swim has time, hes been kinda swamped lately)

ohh ok i see! i just checked the OP again, and just took notice of this step: "Shake the watered down solution briefly and then let it sit for several days (two or three) " lol I just filtered the water+IPA solution after about 15-30 mins, instead of letting it sit for 2-3 days. I used 91% IPA btw, not ethanol; so my bad for the wrong terminology. I also let the filtered final product dry on the coffee filter for 1 day.

I'll filter my solution again (since it has been 2-3 days now), and see what comes up! thanks for the help bro

Might try this extraction later this week as I have everything I need already.
I don't drink coffee so is there anything I can use apart from coffee filters that will suffice or should I just pick up a pack next time I'm at the shops?

Wow very interesting post i will have to try this! I wonder how it would work as an ayhuasca admixture? I am trying to make a mixture that uses the least amount of harmaline possible, so maybe by using some piperine in the mix i could increase the absorbtion of both maoi and dmt. Also, i saw codeine on the list so i would assume this could increase the absorbtion of most opiates?