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Sticky Yopo Alkaloid Trouble

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69ron

69ron

Rising Star
SWIM has just tried extracting some yopo and did a very thorough job of purifying the alkaloids as usual, but this time the outcome is sticky and will not dry to a hard crystalline substance like it usually does.

The Yopo extract is very active but causes more side effects than usual.

The sticky nature of the alkaloid extract is annoying. SWIM has had this problem before, but it’s rare. It seems to have something to do with the strain of seeds used in the extraction.

His extraction was extremely thorough and he even did an A/B on it 3 times and it’s still sticky!!! He used all the normal extraction chemicals and tools (DCM, citric acid, sodium carbonate, water, IPA, Soxhlet, etc.) he always uses. Nothing changed, but still the outcome is very sticky.

SWIM is attempting to find out just what exactly is causing this sticky result and the excessive side effects. This is one of his most unpleasant experiences with Yopo’s side effects. Usually they are mild, but with this batch they are quite strong. SWIM believes the sticky material is causing the side effects.

He dissolved the triple A/B purified alkaloid extract in water made pH 1.8 with 10% HCl solution in water. Then using 10% sodium carbonate solution, he brought the pH up to 6.6, then 7.6, 8.6, 9.6, and finally 10.6. At each pH interval he extracted 7 times with DCM.

He’s already evaporated the pH 6.6 and pH 8.6 batches.

He’s still working with the other batches and won’t have results from them for a while.

All of the extracts are amber in color, but only pH batches 6.6 and 8.6 are nearly dried. He’s planning to test the activity of all 5 different pH extracts.

The batch from pH 6.6 smells and tastes like peanuts and is only slightly sticky and it seems like it’s not going to be sticky once it’s completely dry. The batch from pH 6.6 should not contain any DMT or bufotenine, but possibly some beta-carbolines. DMT has a pKa of 8.68, and at pH 6.6 99% should be protonated and insoluble in DCM. Bufotenine is said to have a pKa of 9.67, and at pH 6.6 99.9% should be protonated and insoluble in DCM.

The batch from pH 7.6 should have 50% or more of the DMT present, if any is present.

The batch from pH 8.6 is very sticky and tastes very bitter. This batch should normally be more than 50% of the bufotenine, and some of the DMT that wasn’t extracted at pH 7.6.

The batch from pH 9.6 should have some of the bufotenine that wasn’t extracted at pH 8.6.

The batch from pH 10.6 should have no alkaloids. There are about a dozen alkaloids in the seeds, and most are barely known, so I don’t really know which pH batches most of these other alkaloids will be present in. This batch could actually be active, but I doubt it. Very few alkaloids would extract at this pH after the exhaustive extracts at the lower pH levels.
 
So, SWIM’s experiment is getting a little more interesting.

As suspected, the pH 6.6 extracts dried to a solid crystalline substance.

The pH 7.6 extracts dried to a slightly sticky substance.

The pH 8.6 extracts dried to a very sticky substance.

The pH 9.6 and pH 10.6 extracts are currently drying.

All of the extracts are various shades of amber.



Activity tests

Now for the more interesting part of this test.

He’s done three activity tests with the extracts at pH 6.6, pH 7.6, and pH 8.6. He did them in that order, once every hour.

Activity test for the pH 6.6 DCM extract

10 mg of pH 6.6 extracts was vaporized and inhaled in two inhalations. The smell and taste of the vapor was like toasted peanuts. The effects started with an immediate prickling sensation in the head and tension in the head. After about 3 minutes this became a tingling sensation in the face and the tension in the head started to subside. The effects peaked after about 15 minutes where the tingling became more pleasant and spread through the rest of the body. There was slight euphoria but no visual or auditory effects at all. This is NOT BUFOTENINE, and doesn’t feel like DMT either. But it’s effective. So some alkaloid is extracted at pH 6.6. The tingling reminds SWIM of beta-carboline effects. The seeds are known to contain beta-carbolines in small amounts.

Activity test for the pH 7.6 DCM extract

One hour later he vaporized 10 mg of the pH 7.6 portion and inhaled in two inhalations. The smell and taste was not like peanuts. It was medicinal and made his mouth feel a tiny bit numb. The effects were pretty much identical to the effects from pH 6.6 but lacking the tension in the head. He thought he noticed a very slight hint of DMT in it, but wasn’t sure.

Activity test for the pH 8.6 DCM extract

The following hour he vaporized 10 mg of the pH 8.6 portion and inhaled in two inhalations. The taste was bitter, almost like very strong coffee. The smoke was a little harsher than the previous two tests. He immediately felt a little nausea after the second inhalation. Some tingling was felt in the head as before, but weaker, and about 30 seconds after the second inhalation, very strong visual effects started. After about 1 minute, the nausea was gone and the visual effects were becoming quite strong. At about 5 minutes into it, there were imaginary sounds all around him, mostly music and voices, and the visuals were extremely swirly. He relaxed, closed his eyes and immediately had very strong visions. It was extremely colorful with bursting firework like colors of every kind shooting all over the place over a pulsating red background that looked like lava pouring from a volcano. It was very exciting and festive and soon he started seeing outlines of people dancing. These were very clear and sharply defined. It was like watching a rock video. The dancers were transparent and superimposed over the background lava. Sparkly multicolored glowing rocks were flying all around. After a while he opened his eyes and started wringing down the experience on his computer. The effects were clearly that of bufotenine, and were cleaner and cleaner than a usual extract and more like pure bufotenine. After 1 hour when the effects were almost gone, he tried 20 mg of tetrahydroharmine citrate sublingually. After about 30 minutes there was a definite increase in potency of the bufotenine with an added “smoothness” to the experience, and visuals were again pretty strong, and the tingling sensation was VERY INTENSE.



What was learned in this experiment?

So, from this experiment we learn a few things. First, there are some alkaloids that can be extracted at pH 6.6 and pH 7.6 that are active but not hallucinogenic at the doses tested. The alkaloid mix extracted at pH 6.6 produces tension in the head, as well as tingling sensations. The alkaloid mix extracted at pH 7.6 produces only tingling sensations. The alkaloid mix extracted at pH 8.6 was clearly mostly bufotenine. This was the largest portion of all the extracts so far.

Ok, so the extract at pH 8.6 was by far the most sticky of them all. This is not because of the bufotenine. Bufotenine is not sticky, but a dry off-white or slightly amber crystal.

So this test unfortunately has not yet gotten rid of the sticky material. It unfortunately extracts at the same pH that bufotenine extracts at. This sticky material is causing the nausea, but isn’t the source of the head tension felt from the seeds. The unpleasant head and body tension causing alkaloid gets extracted at pH 6.7.

From this test we’ve learned that we can remove the tension causing alkaloid from the seeds by extracting it at pH 6.7. This is good news. So if we pre-extract with DCM at pH 6.7, we can get rid of the alkaloid(s) responsible for causing tension in the head. We can then further purify the bufotenine by removing other non hallucinogenic (at least at 10 mg they are non hallucinogenic) alkaloids at pH 7.6.



How to remove the sticky material causing the nausea?

The sticky material causing the nausea is unfortunately extracted along with bufotenine at pH 8.6. So how do we get rid of the sticky material causing the nausea?

He is going to try backwashing the pH 8.6 extract to get rid of the sticky material. To backwash, he’ll dissolve the alkaloids in DCM, and wash using pH 10.6 water (made pH 10.6 with sodium carbonate). Bufotenine is degraded in high pH values, but pH 10.6 seems to be OK. He will wash it about 7 times. He believes that this sticky material is not an alkaloid but instead something that is attracted to the bufotenine, and is simply coming out along with it. It’s possible that this sticky material could be removed with activated charcoal, but SWIM will try that in a different test. First, he’ll backwash the DCM and see if that works.
 
swims got the incredibly frustrating non-drying sticky substance too, he can't scrape anything up to try it... even after 5 days, heating, cold, tried everything.... should he add something to it maybe bit of lime or baking soda or powdered salvia leaf to make it more solid?
 
Kemist, the seeds were from BBB, but he's got great seeds from them before. They are always different.

The best method to get the sticky nauseating toxins out is by column chromatography. You run a standard column with silica and elute with a 3:1 mix of ethyl acetate to methanol. Only the good stuff elutes (DMT, DMT N-Oxide, bufotenine), the sticky nausea causing toxins stay on the silica. It works really well.

You don't need a REAL column. You can do it ghetto style with a funnel and some silica gel.
 
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