Update this afternoon:

The conversion of the 4-aco-dmt to 4-ho-dmt most definately worked!!!

I drank the solution mixed into a bit of diet coke, and within 15 minutes i could feel it coming on, by 30 minutes I was tripping and there were no side effects! no sedation and no flu symptoms, this was much more stimulating, fully psychedelic, and had the intensity of mushrooms, very nice indeed!

I love it in the 4-ho-dmt form, NO side effects for me. In a week, i'll convert a larger dose (15mg) and take about a 10mg dose of it, this stuff is about double the strength of 4-aco-dmt, but the best part I feel so alive and magical, this is awesome, music sounds really good and colors and images are amazing even at 5mg.

I feel amazing!!! and zero side effects, this is what I was looking for!   I'm gonna enjoy the trip and listen to this heavenly music the rest of the afternoon.

More on 4-ho-dmt (the big and dandy mega-thread):
hxxp://www.bluelight.ru/vb/threads/318367-The-Big-and-Dandy-4-HO-DMT-Thread

Hypothetical dream, all the below is a dream and none of it is real:

It works, takes no longer than 10 minutes.

I decided to dream this dream because all my last 3 4-aco-dmt experiences were causing me extreme sedation, nausea, dizziness at times, loss of muscular control, my nasal passags would also clog up (in short I was allergic to the stuff)...and it was not as visual or divine as I had liked, more "wow factor and intensity needed" I needed something more stimulating, potent, and free of side effects...4-ho-dmt was the answer I was searching form, my most favorite psychedelic for sure, ranks right up there with acid. A beautiful psilocin trip.

extraction of 4-ho from 4-aco over timeframe due to extraction hydrolysis:

1. 30ml vial sat on table with screw cap
2. added 4ml distilled H20
3. microwaved on hi for 7 seconds, temp of water = 175 degree F (water could be seen boiling up into middle of vial) Let it sit and cool for several minutes.
4. added 10mg of Lye (a few very tiny granules, water sputtered and hissed a bit (but there was no bubbling up) when it was added, it dissolved right away since the water was allready warm, eye protection and gloves worn for safety anyways)
5. allowed vial to cool down to 101 degree F, stuck electronic hand-held thermometer tip in vial to measure the temp of solution, also stuck ph paper into vial to measure ph, read ph=14 (very alkaline)
6. added 10mg of 4-aco-dmt to vial, put screw cap on, and shook it vigorously, stopped shaking once it was all dissolved.
7. held vial under hot sink faucet running water (temp =133 degree F) to warm it up even more....for 6 minutes, with swirling of vial the whole time, pulling it from out under the running water every now and then to check the color of solution.
8. color of solution in vial when held under running hot water progressed slowly from clear to light green to a few minutes later (about 6 to 7 minutes in) to dark blue with twinges of brown.
9. that's when i immediately added 1/4 of a 500mg crushed white vitamin C table (ascorbic acid), measured ph again, it was neutral after addition, ie ph=7.
10. solution immediately turned a very light tan color when 1/4 of a 500mg white vitamin c ascorbic acid crushed tablet was added
11. stuck in freezer to keep vial cold.
12. drank all of solution at 10pm, had an acidic + bitter taste, any extra naoh in the solution converts to health food version of "sodium ascorbate" (vitamin c mineral) + water

10:20 could feel it come on
10:40 Remember I have an extreme tolerance to having taken something a couple days ago, so my reaction will be less at a normal high dose. tripping allready, began laughing at scenes in movie even though it wasn't funny, feel giddy, euphoric, feel a very nice body high as if I had taken 50mg of mdma, I have a huge tolerance so I shouldn't have even taken anything, so now I'll wait a good 2 weeks before consuming again. The walls are no longer white but pink in color, no sedation or side effects, energizing, absolutely love it, very psychedelic. In the meantime, i'm going to do some more time experiments and watch the slow progress from clear to colors over a 10 minute period. Even with my extreme tolerance, i found this more visual than 4-aco-dmt, afterimages persisted a good 10 seconds, and with closed eyes, saw bright colors that changed into other colors repeatedly, music was outstanding.

The color change is clear--->very light green--->green---->dark blue (bluish/brown) color----->black.

Page 49 of Magic Mushrooms by Peter Stafford:

Pure psilocybin or psilocin when placed in pure water and left at room temp discolors the water to a bluish-brown.

Stop at the dark blue/brown color and immediately add vitamin c and drink or store in freezer. If you let it react too long and it turns black, then it has all decomposed into in-actives (this happened in my first experiment, and 10mg had no effect even after 1 hour). If you stop the extraction at the "green color", it is still in the 4-aco form, it has to get to the dark blue stage for it to extract in 4-ho form.

The 4-ho-dmt is a very different animal from 4-aco-dmt, i find 4-ho-dmt to be stimulating with an amphetamine-like energy, highly visual and more psychedelic at an even lower dose...ie 15mg of 4-aco-dmt = 10mg of 4-ho-dmt. No sedation side effects, A++++ material all the way.

I prepared a 7mg dose of 4-ho-dmt (5mg) and took that about 1 hour to overcome the tolerance for a bit.

I stopped at the time when the vial solution changed to dark blue/brownish, and added vitamin C which immediately turned it a light tan color,

drank it.

It came on fast, in 15 minutes i was going up, i saw shifting images and lots of OEV,s,looking into shadows, i saw creatures come alive, it had a sexual feel to it, and it was just like i had taken 80mg of mdma, but still had an appetite. (just as Shulgin remarks on 4-ho-dmt in tihkal)....looking into wood grain, all sorts of faces,very deep, very enjoyable, just like an acid trip to me, only shorter. Amazing perfect material,no side effects, no sedation.

If you look at what happens with aspirin (Salicylic acid) when it is hydrolyzed by a base (a common University Chemistry lab experiment too), it is identical to what is happening with this stuff, check out wikipedia on "aspirin" and "hydrolysis". The difference is like night and day to me, i love this 4-ho-dmt.

base catalyzed hydrolysis is non-reversable whereas acid catalyzed hydrolysis is reversible.

See Erowid TIHKAL #19 to see all of Shulgin's experiences with 6 to 15mg of 4-ho-dmt.

See Wikipedia article on "hydrolysis" to understand how hydrolysis occurs in this extraction.

See Wikipedia article on "aspirin" mid-way through to understand hydrolysis some more:

The synthesis of aspirin is classified as an esterification reaction. Salicylic acid is treated with acetic anhydride, an acid derivative, causing a chemical reaction that turns salicylic acid's hydroxyl group into an ester group (R-OH ? R-OCOCH3). This process yields aspirin and acetic acid, which is considered a byproduct of this reaction. Small amounts of sulfuric acid (and occasionally phosphoric acid) are almost always used as a catalyst. This method is commonly employed in undergraduate teaching labs.[114]

Formulations containing high concentrations of aspirin often smell like vinegar[115] because aspirin can decompose through hydrolysis in moist conditions, yielding salicylic acid and acetic acid.[116]

The acid dissociation constant (pKa) for acetylsalicylic acid is 3.5 at 25 °C (77 °F).[117]
Good read on 4-ho-dmt from Shulgin (see Erowid TIHKAL #19 4-ho-dmt)

You don't want to stop at the green color, trust me, you want to stop at the dark blue color, then drink it, it is amazing, so simple too. more potent than 4-aco.


Shulgin on 4-ho-dmt:
http://www.erowid.org/library/books_online/tihkal/tihkal18.shtml

I didn't post experiment 1 here, but i went too far with it (let it color until it was black), and it had no effect at 10mg. Trust me, you don't want to stop at green either, you want to add vitamin c to the vial and drink it (or store in freezer) when it turns dark blue with twinges of brown, simply amazing, this 4-ho-dmt is.

Closed eye visuals were stunning while I laid in bed, neon colors begot very detailed Mayan artwork and scenes, the images were unlike anything I've ever seen with closed eyes before, rich in detail, and every color represented. I saw rock carvings with visual Aztec and Mayan writings, photo-realistic down to immaculate detail, before the scenes there were geometrics spinning wildly with sparks shooting off and changing directions, pulsating colors and electric/alive, wild.

Stafford: "Pure psilocybin or psilocin when placed in pure water and left at room temp discolors the water to a bluish-brown."

That's the same color I saw when the 4-aco converted into 4-ho-dmt (psilocin) on three seperate occasions (experiments). There is 5-stage progression for the colors----clear--->light green--->green----->dark blue w/twinges of brown---->too many minutes beyond last stage it turns black and no longer works.

From TIHKAL #18 4-ho-dmt:

DOSAGE : 10 - 20 mg, orally (as the indolol, the acetate or the phosphate)

DURATION : 3 - 6 hrs

QUALITATIVE COMMENTS : (with 6.6 mg phosphate ester, orally) "Something has started but I decide to join in a full dinner anyway. The effects develop right through the meal, with some hints of animal faces in the pork-chop bones. No movement, nothing flows, but it probably wouldn't take much effort. Another hour and I am dropping off already. The food? Somehow I doubt it. I would be completely unable to tell this from, say, 80 milligrams of MDMA except that I had a good appetite."

(with 7 mg, orally) "Basically I am not in a pleasant place -- quite neurotic -- inwardly turned -- a touch of despair -- considerable visual activity and if I were with someone I might find some sort of reinforcement. The apathy and unpleasantness is ebbing now. My mood might have been negative, and the psilocybin simply amplified everything. There was some intensification of the lights and darks around me."

(with 10 mg, orally) "Approximately forty minutes after the start, there was a flutter and a very high, stimulated feeling, and gradually things began to move very rapidly. It was astounding. When I closed my eyes I saw so many fantastically beautiful patterns, textures, colors. Everywhere I looked, eyes open, the colors were brilliant. The house looked absolutely gorgeous and nature was simply spectacular. It was a little frightening, almost too exciting, after the gentleness of other substances. I could not believe that I was doing it, and that I had the power within myself to see such beauty. I don't know how long this went on but the motion was so rapid that I felt a sort of motion sickness. Then I became quite nauseated and remained nauseated the rest of the day, until things quieted down in the evening, and then I felt absolutely wonderful."

(with 15 mg, orally) "My 'early warning system' alerted me at fifteen minutes, then all was quiet for a while. I start building up again, and I am awfully glad that I am familiar with this transition. Visual distortions. Things distract me. I can't find the cap to my pen -- must I keep writing forever? At this point I couldn't drive, let alone write, and it is just a bit more than a half hour since I took it. The furniture in my office is moving up and down. I lie down, and close my eyes. THIS is where it is at. Visuals are wild. Even with eyes open, with no visual target, there are imaginative visual effects. I imagine a dark room with a fire place going in the middle of the night, with no other inputs, and with my eyes closed I have the body image of being seated in front of that fire and I am amazed by the hallucinations and distortions I am seeing there only there is no fireplace as I am still lying in my darkened bedroom. Sort of a 2x removed hallucination. This is a night-time drug -- the day-light washes everything out. I tried but could not repeat the fireplace thing, and must be dropping rapidly. At three hours I ask if I would try some other experiment. OK, but there are some reservations. At four hours, no reservations."

(with 15 mg, orally) "As soon as I felt the chill and the alert, I lay down and closed my eyes. Indian motif. Abundant fruits, vegetables, leaves, straw, wood, vines. Very responsive sexually. Beautiful, stern, rich encounter with livingness and Indian Gods and serenity. Color and peacefulness. A couple of hours, then elaborateness dropped slightly. At this point top of temple easy, but it was a South American temple, with earth floor, straw, vines full of fruit. Familiar feeling. We are naked and we are children-adults, daring to be there, regarded benignly (stern, amused) (rising through the floor). This is one of the true ones, this plant experience.

(with 12 mg phosphate ester, intramuscularly) "This is strong. There were a lot of wild images in about two hours, and I thought that the day would never end. At about six hours I knew it would, but in fact in the evening I took 100 milligrams of seconal which allowed me to drift into a fine sleep. The next day I was fine."

(with 3 mg phosphate ester, intravenously) "The effects are immediate (in 30 seconds) and I did not have the time to build up any worry -- it was simply too fast. In about an hour I was back where I started from."

(with 12 mg phosphate ester, intravenously) "I had had eight milligrams earlier, with a very good reaction. Here, today, I feel that everything has disintegrated, and I am extremely anxious. I am very confused."

Psilocybe cubensis: (with 1.5 g, orally) "At best, some speckled patterning with my eyes closed, and in general a light intoxication. Certainly not the sparkle of LSD. Dropped quickly and felt heavy and tired, good sleep."

(with 3.5 g, orally) "Took a gram to start with, and it started in ten minutes, but not strong enough, so did the other 2.5 grams. Everything was coming at me in waves, boxing me in, the visuals were in waves and in dark earth colors, orange and brown, not the wide spectrum of acid. I was sea-sick, and vomiting helps some, and a little dope quieted the tummy. Started dropping, and everything became very good, and by midnight I was out. No hangover at all."

very cool do you think this procedure would work with all of the 4-aco sub tryptamines? 

very cool do you think this procedure would work with all of the 4-aco sub tryptamines? 

cleavage of acetates to alcohols is well known can be achieved by either strong base or strong acid

This is the color you want to stop at, super dark blue, add a piece of crushed vitamin c tablet (ascorbic acid) to the vial, swirl it and either drink it right away or freeze it. Vitamin C turns it into the salt, halts any oxidation, and may even reduce any post psilocin degradation products (o-quinone?) back into psilocin (someone at advanced mycology section of shroomery conjectures on his experiments on vitamin C and psilocin).

in one of my experiments, i drank the solution when it was at the green stage, but it was still only "4-aco-dmt" this is stage when i believe the fumarate salt is coming off, it was definately 4-aco-dmt as it caused me terrible sedation, loss of muscular control, flu-like symptoms (i'm allergic to 4-aco-dmt).

I have sampled the super dark blue solution in 3 seperate trials, and it is indeed 4-ho-dmt, now i need to take a long break from this tolerance.

this was one of latest experiments prepared as follows, and resulted in a very powerful intense 4-ho-dmt trip at only 10mg:

1. heated 30ml vial with 4ml of distilled water in it for 7 seconds in the microwave, water will boil 1/2 the way up the vial.

2. added 15mg of naoh

3. measured temp of water = 140 degree F

4. 9:15 added 10mg of 4-aco-dmt

5. held vial under running hot tap water while swirling it and occasionally holding up the vial to a bright light to gauge the color, the temp of the running hot tap water was measured at 133 degree F.

6. vial = clear
7. vial = light green
8. vial = green
9. 9:17 vial = dark green
10. 9:25 vial = super dark blue (stop! add 1/4 of a crushed vitamin c tablet)
11. vial = will turn a tan to very light tan color right after the viamin c table is added.
12. drink or freeze it.

stages over 10 minute period (time will vary to get to super dark blue color depending on amount of naoh used, temp of water, how long you kept swirling it under running hot tap water, etc.)
-----------------------------------------------------
Pictures are shown from top to bottom in order:

stage 1 = clear
stage 2 = light green
stage 3 = green
stage 4 = dark green
stage 5 = super dark blue (stop) psilocin

Excellent question. Thanks for the link to that thread, I'm reading it now. Psilocin is very under-researched as far as it's characteristics, this is about all i really could find below from advanced mycology forum, and a person posted there that pure psilocin crystals turn blue and stay that way when left out exposed to air....and a quote from Stafford that "psilocybin and psilocin when added to water turns the water a bluish-brown color." The 10mg of super dark blue solution I drank took me on a very intense deep and visual psychedelic trip no different than what I experienced in the past when I ate several grams of potent Hawaiian Pan Cyans (which are believed to contain only psilocin, psilocybin and hints of serotonin believe it or not), but which do not contain baeocystin and friends which often are the cause of "confusion" when people eat psilocybe cubensis, which contains those additional alkaloids.  2 more experiments on different days confirmed to me at least that the blue solution once again took me on powerful psychedelic trips. When I had stopped at the green stage however, it was only still 4-aco-dmt and caused awful allergic reactions in me (i'm allergic to 4-aco-dmt) with sedation, loss of muscular control, and flu-like symptoms. Very odd I know, but i'm not the first to report uncomfortable symptoms with 4-aco-dmt.

In my very first experiment, i used a bit too much lye (20mg) and too much heat and the colors quickly progressed thru the stages, plus i let it sit way too long and it eventually progressed to a very dark black color (o-quinone?), i still drank it (all 10mg) and experienced no effects at all. So yes, it is possible for the hydrolysis to go on too long and eventually advance to a last stage of decomposition/degradation.

This is what I've gathered from research: Psilocin is unstable in hot alkaline environment exposed to oxygen but thankfully the percentage of oxygen is less than 1% in water, (i am also careful not to shake the solution but only swirl it continuously)  but you have to watch what is going on carefully.....without anti-oxidant protection from ascorbic acid and freezing, it probably doesn't stand much of a chance of surviving exposed in that environment for very much longer than 15 minutes past the stage where it turns super dark blue, at least that is what I could tell from my experiments. If I had access to expensive lab equipment, I would have the answers though for sure.

Interesting that poster below thinks it may even be possible for ascorbic acid to "possibly" reduce any oxidized psilocin back into psilocin. I also observed that my super dark blue psilocin solution turned an instant light tan color (nearly clear) immediately when a piece of crushed vitamin C table was added. So what is going on here exactly? ascorbic acid is a weak reducing agent, which is why it makes a good 'antioxidant' in biological systems and an oxygen scavenger in solution.

Psilocin Oxidation/ Vitamin C Experiment Proposal +
#3129834 - 09/13/04 01:48 PM (7 years, 5 months ago)
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Background:
In the late 90s, while working on preservatives and antioxidant preparations to enhance the storage of mushrooms, I found that when mushrooms are placed in an aqueous solution the water turns blue over a period of several hours. Then the interesting part happened, I discovered that by adding ascorbic acid (vitamin C) the solution would return to a crystal clear color.

Hypothesis:
Psilocybin is readily and rapidly dephosphorylated into psilocin. The psilocin then further undergoes oxidation to an, as yet undetermined, compound. This oxidation is associated, although may not totally account for, the formation of a blue product. This blue product is completely destroyed or altered into a non-blue product by the addition of ascorbic acid. The psilocin in the solution, which may or may not actually be the blue product, is either reduced back into psilocin or decomposes into other non-psychoactive reaction products.

Proposal:
Without access to complicated and expensive analytical equipment, the most reasonable way to determine weather the oxidized psilocin is converted back into psilocin would be to ingest a quantity of the substance and note any increase in psychoactive effects relative to the oxidized solution.

Methods:
Dried mushroom powder is placed into aqueous solution (adjusted to a pH of 4 using acetic acid) and allowed to stand for at least 1 hour. The solution is then heated in a boiling water bath for 8 to 10 minutes, or until the solution reaches about 70?C, to convert most of the psilocybin into psilocin. [1] The solution is then cooled (optionally using running water) and filtered to remove the mushroom sediment. Next the solution is basified to a pH of 7-8 and allowed to stand until the solution is blue and no further darkening is observed. This step may be hastened by bubbling air through it. Once the solution's color has stabilized it is divided into two equal amounts. Half of the solution is consumed immediately and any effects noted. If this solution produces noticeable effects the remaining solution is stored for around one week under refrigeration so that any tolerance will dissipate. Prior to consumption, ascorbic acid is added to the second part of the solution until a clear color is obtained. The solution is then consumed and any effects noted, paying particular attention to the relative strength of effect compared to the first solution.

Alternate method:
Fresh or dried mushrooms are placed in water and allowed to stand for at least 1 hour with occasional or constant stirring. The solution is then filtered to remove mushroom debris and allowed to stand until the water develops a blue color. When no further darkening is observed the solution is divided in half and the first half is consumed. Effects are noted for a period of at least several hours. After any tolerance dissipates, ascorbic acid is added to the second solution until any blue color disappears and the solution is consumed. Effects are noted and compared to the first solution.

Results:
Any increase in the potency of the solution after addition of ascorbic acid would indicate that at least some of the oxidized psilocin was converted back into psilocin.

Discussion:
I will be attempting this experiment at some time in the future. I'm looking for collaborators to also perform this experiment due to the subjective nature of psychoactive effects. I'm also interested in hearing any comments or discussion on this proposal.

References:
[1] J. F. Casale "An Aqueous-Organic Extraction Method for the Isolation and Identification of Psilocin from Hallucinogenic Mushrooms"
J. Forens. Sci. 30(1), 247-250 (1985)
Link

Merk Index:

8110. Psilocin. 3-[2-(Diumethylamino)ethyl]-1H-indol-4-ol; 4-hydroxy-N,N-dimethyltryptamine; psilocyn. C12H16N2O; mol wt 204.27. C 70.56%, H 7.89%, N 13.71% O 7.83%. The minor hallucinogenic component of Teonanacatl, the sacred mushroom of Mexico. Isolated in trace amounts from the fruiting bodies of Psilocybe mexicana Heim, Agaricaceae: Hofmann et al., Experientia 14, 107 (1948); Heim et al., Helv. Chim. Acta 42, 1557 (1959). Prepn: Heim et al., Ger. pat 1,087,321 (1960 to Sandoz). Synthetic precursor of psilocybin: Hofmann, Troxler, U.S. pat. 3,075,992 (1963 to Sandoz). Psilocin, the 4-hydroxy analog of psilocybin, is formed by metabolic dephosphoylation of psilocybin and is the active species in thh central nervous system: Hoita, Weber, Toxicol Appl. Pharmacol. 4, 730 (1962). Crystal structure: T.J. Petcher, H.P. Weber, 730 (1962). Crystal structure: T.J. Petcher, H.P. Weber, J. Chem Soc. Perkin Trans. II 1974, 946. Review Hofmann, Bull. Narcotics 23, 3 (1971)

Plates from methanol, mp 173-176°. Amphoteric substance. Unstable in soln, esp. akaline soln. Very slightly sol in water. uv max: 222, 260, 267, 283, 293nm (log E 4.6, 3.7, 3.8, 3.7, 3.6).

Just now found this in archives:

yoyoman
07-08-2006, 15:12
Ok, well I put ~30mg 4-aco-dmt fumarate in a small clear glass thing with distilled water (not that much water) + NaOH added (about 20mg NaOH). Swirled it around / made sure it was all dissolved.

I lit an alcohol lamp for a heat source.. well when I went to look to pick up the container with the 4-aco-dmt in it, it was already turning to a very light blue. Well I added a little heat anyway.. it seemed to just turn to a darker blue then went a little bit greenish (bluegreen i guess). So I just dumped the bluegreen liquid into a cup, added some acetic juice to it and drank it down

------

Kicked in within 15mins after i drank it. It does feel more like a 'pure' trip, at +0.40mins ... well lol what else can i say? i prefer this kind of trip over the 4-acetoxy-dmt just the differences are hard to put into words the visuals are more like mushrooms...head feels more like mushrooms

... more DMT like fluidity here.. colors more *brighter* in the way mushrooms do it wheres 4-ace-dmt they .. well its just "different" hehe..

I think some - not much though - was oxidised to a non-goodygoody product when it went darker blue / greenish blue w/heat..

well uh.. off the computy i go.

http://www.bluelight.ru/vb/archive/index.php/t-284046.html
"4-aco-dmt redundancies" (4 pages BL)
xorkoth:

And for the record, I also have experimented a fair amount with pure synthesized psilocin (4-HO-DMT) and found it to be different from mushrooms too, though very similar indeed. It was almost nothing like 4-AcO-DMT for me though. Pure psilocin had an intense ego-crushing aspect to it where I would quickly approach nonexistence/"godness", whereas 4-AcO-DMT never feels very spiritual to me except in one +4 trip with AMT where I felt that I was channeling the god energy directly and radiating intense love, and in that instance the spiritual state was quite a bit different in character and more ego-focused and as someone else mentioned, quite sober for a peak psychedelic experience. With psilocin (and mushrooms) it is a much more intense, unstable and awe-inspiring roller coaster ride of ego dissolution.

And I totally agree that the pure compounds are much "easier" experiences, although I've had a very intense ego-crushing and terrifying trip on pure 4-HO-DMT. Mushrooms are much more complex and I prefer them, but also am the most cautious of them.

It's weird... for me, 4-AcO-DMT is pretty sedating. I've actually passed out on very strong experiences and gotten very drowsy during low-dose experiences. DMT doesn't have this effect but it is still relaxing. However, psilocin and mushrooms make me pretty stimulated (except for a few mushrooms I've had) and very wanting to move around.

Well I think in general, yes, the acetoxy counterparts are much more gentle and forgiving. However, like I said before, I don't find 4-AcO-DMT and 4-HO-DMT to have basically the same feel at all. I find 4-AcO-DMT to feel like slow smoked DMT, and 4-HO-DMT feels much different, not DMT-like at all in feel. Much closer to mushrooms. I don't find many similarities between mushrooms and 4-AcO-DMT.

I've seen those nitrogen dispensers for wine, i've thought about using that to dispense nitrogen into the vial before capping it and beginning the swirling under the running hot water, i'll look into that, i just wish they weren't so darn expensive. in a few days, will transform some more into the 4-ho and report findings. would carbon dioxide environment work instead of a nitrogen environment? i think i've heard of carbon dioxide dispensers too.

As a mild to strong reducing agent, it's possible that the ascorbic acid converts any oxidized psilocin back into psilocin, this has been theorized by a few at the advanced mycology forum. This could be what is actually going on....especially due to the observable color change from deep blue to nearly clear/tan with the addition of the vitamin C.

I like the mushroom 4-ho-dmt for a seperate trip one month, as it is easy to fall asleep later, and you get good sleep.

I like the mescaline + 25i-nbome for a seperate trip on another trip one month, as it is a much longer lasting trip. you get to bed much later, and mescaline of course lasts a long time.

So they are each great in their own ways.

i'll give the converted 4-ho-dmt another go this weekend after tolerance is back down to normal, and report on the trip.

" would carbon dioxide environment work instead of a nitrogen environment? "
It might -- but the NaOH will react with it.. so it would form a vacuum or something?
Personally I would suggest using a propane atmosphere in this situation - fairly easy to use (easier then most) and is unreactive.

Also -- perhaps the blue oxidized stuff could be a neat psychedelic on its own, if the case is that the Vitamin C is reducing the blue stuff back into 4-ho-dmt as is suggested by the color change?

Perhaps what is forming is the 4-O=dmt stuff? Might be metabolized differently and give a different trip/different duration.
Try to use an acid that is non-reductive unlike Vitamin C - perhaps acetic, or citric acid? See if the color changes from that? It might just be acting like a pH indicator as well...

I.e the 4-ho-dmt might convert into 4-O=dmt depending on the pH for whatever reason one might be more stable -- like i said earlier, not totally sure they are *truly* different molecules.

The acid catalyzed hydrolysis of acetyl-psilocin to psilocin worked much better than the base (naoh) catalyzed hydrolysis, all of the psilocin seems to have been preserved (none of it oxidized)....psilocin is unstable in hot alkaline solutions, but is stable in acetic environments. Light was also turned off during 20 minute reflux, 10mg was sampled, and it was 100% different from 4-aco-dmt. 4-ho-dmt came on quickly within 20 minutes, was stimulating and felt like an amphetamine, very awake, very euphoric and definately psychedelic. Pupils fully dilated, extremely visual and psychedelic, not even a hint of sedation or loss of muscular control, able to move around freely in strong psychedelic state. it also felt as if I had taken 80mg of mdma (just as Shulgin states on his below 10mg dose of 4-ho-dmt)...very nice. There was a wave-like phenomena noticed the whole trip, it would pull me in and out like a sine wave, quite remarkable, the colors of the walls kept changing and i saw visual stuff shooting across room leaving sparkly trails. Very enjoyable.


I based this experiment on the University student experiment on the acid catalyzed hydrolysis of acetyl-salicilic acid (aspirin) to salicilic acid. now to take it again in 2 weeks when I have no tolerance to psychedelics.

1. heating mantle set to 3.75 setting
2. 50ml round bottom flask, it sat in water bath which was brought to a temp of 140 degree F, and held there for 20 minutes. 10ml of distilled water was added with stirbar.
3. 2 drops of muriatic acid was added to water in flask (ph=2), along with 50mg of 4-aco-dmt.
4 this was allowed to spin at 6.5 setting for 20 minutes, reflux tube put on flask opening, and ice cold water run thru condenser, this was to prevent any hcl acid from evaporating off.
5. after 20 minutes, flask transfered to freezer for 20 minutes to cool down. color = clear.
6. then 1 smidgen of baking soda added to flask, ph then measured, ph = 8, this neutralized the acid, to make it palatable, then 1/2 vitamin c crushed table added, the 10ml (50mg) of 4-ho-dmt was then storred in freezer to preserve it.
7. 10mg of the solution was sampled, definately active and it was NOT any longer 4-aco-dmt but felt 100% like 4-ho-dmt. (psilocin). 

vesp said:

Also.. might be a neat thing to try adding NaOH to the HCl produced 4-OH-DMT to see if it "instantly" turns blue.

Yes, those were my thoughts exactly, i'll do this for sure, a color test (like today will do).

Actually, using the acid based catalyst caused the 4-ho-dmt to feel more powerful, this being due to much less if any of it being broken down (as i'm sure there was some amount of degradation using the alkaline catalyzed hydrolysis). Or the powerful trip i had on it could be due simply to that as well as it actually being turned into 4-ho-dmt this time!

I stored away the other 40mg produced by the acid catalyzed batch in the freezer, and will be sampling it again over the coming weeks when my tolerance is near zero (and doing color tests on it by dropping it into naoh solution)

Vesp said:

This would do some trouble shooting as it seems to me like:
1. 4-OH-DMT is clear at neutral pH, or in acidic conditions but changes to blue in a basic solution.
2. 4-OH-DMT is oxidized in a basic solution to form 4-O=DMT.

4-O=DMT might have interesting uses - Perhaps it could be reduced to DMT via HCl/Zn or used to produce other unique 4-?-DMTs by some sort of reduction. 

yes, agreed with these statements. Thanks for all your help & information too Vesp! much appreciated. I think when psilocin is dropped into an alkaline liquid environment, it starts to degrade rapidly, and thus the color change to blue.

By the way, i was going back thru erowid 4-aco-dmt vaults as well as the bluelight 4-aco-dmt big and dandy threads and read of several accounts of people falling asleep while using 4-aco-dmt, one person's left arm became numb at erowid, another had a seizure at a concert, several people report feeling as though a towel of ether had been placed over their mouth, just wanting to pass out on the stuff, i totally agree, 4-aco-dmt to me is not even a drug but some sort of foreign invader that my body rejects, it is not safe imho, but  4-ho-dmt is totally safe that i could tell from all my trials, and now my favorite psychedelic right along with mescaline.  It is identical to mushrooms.

DwayneHoover (15-10-2010, 20:36):

"Feel like I could just go to sleep right now..." You well may...it can be very sedating for some...over 20mg and it just gives me a strong weird head buzz the puts me right out just like someone held a rag of ether over my face...no visuals, no psychedelic anything. Some have suggested I try it with a stimulant, and there are excellent sounding reports of doing it after coming up on some 2c-i which i love, which i will need to try. by itself though, for me it acts like a very fast knockout pill of some osrt...weird. oh well.

My thoughts exactly...it was not psychedelic at all to me at 20mg (or even the lower doses), it felt just like the same kind of "knock me out" experience as that poster, spot on. I was actually very frightened of the extreme sedation and very uncomfortable body load, it was one of the worst feeling times i've ever had, like i had the flu.  This was not a fluke, because she was feeling the exact same way with the same dosage. Sampling small doses of the stuff on odd days also caused the flu feeling and symptoms to come back along with loss of muscular control (especially in the arms). 

friend of mine asked:

I'm still wondering why you think the acid-catalyzed hydrolysis will not occur in your stomach though.

I think it helps to look at the hydrolysis of aspirin to answer the question.

acetyl-salicylic acid = aspirin

salicyclic acid = parent molecule
-----------------------------------
acetyl-psilocin = psilacetin

psilocin = parent molecule

Salicylic acid is a natural analgesic present in the leaves and bark of certain plants. It is generally unsuitable for internal use, since it is a strong gastric irritant and can cause internal bleeding. In fact, aspirin was invented for this very reason; the acetylated molecule isn't as rough on the digestive tract, although it does hydrolyze to some degree in the stomach (a small percentage of it).

I've read several hydolysis experiments on aspirin (acetyl-salicyclic) to salicylic acid, all of them recommend heating at around 140 to 150 degree F for about 30 minutes. Heat + acid = rapid hydrolysis. I'm sure there is some percentage of hydrolysis in the acid of the stomach, but it's not all that great. What's really weird is that I came up with the 20 minute figure and 138 degree F procedure for hydrolysis even before i read the aspirin experiments, those were my findings too, that it takes about 20 minutes for a good hydrolysis of 4-aco to occur, and that the running faucet hot temp at 138 degree was about the right minimum temp, for what it's worth, but what I found matches what the experiments recommend to the students.

He said:

The condensation of acetic acid + HO-DMT into 4-aco-dmt can be thought of as a Fisher Esterification reaction. Although this is typically catalyzed by an acid, it must be done under anhydrous conditions and is therefore unlikely to be a concern for this particular topic.

Very true, if there was any amount of water present in the acid, then it would lead more towards hydrolysis, and away from esterification for sure.

I wonder if evaporation of the dilute HCL solution of 4-ho-dmt (all 10ml of it) poured off in a pyrex dish after the heating at 140 degree F for 20 minutes would yield 4-ho-dmt that could be scraped up??? or would it tend to be re-esterified due to the pure hcl that remains on the molecule before the last of the water evaporates? usually glacial acetic acid is used for this type of thing though, but i wonder what would remain on the dish exactly after evaporation, is it pure 4-ho-dmt?

4-aco-dmt to me (after having tried it many times) puts me in an alienated space, no emotions, barely psychedelic, and so sedated i can't even get up and move around, my muscles become flacid and i find it hard to even raise my arms, i feel like shit.

4-ho-dmt on the other hand is energetic, fully psychedelic and awe-inspiring. Psilocin to me is like a shorter LSD trip, only more visual. With closed eyes on the acid catalyzed 4-ho-dmt at 10mg before going to bed, i kept seeing so many incredible forever changing neon-multi-colored visuals that I found it hard to believe that I was seeing what I was seeing. CEV's were incredible.

i'm begining to wonder if 4-aco-dmt is even a drug, it seems like something really foreign to my body that i reject every time, i read one story of Church having to go to emergency room after a 4-aco-dmt dose, he reacted badly to it, there are several horror stories on erowid, in one trip report, a kid after 20mg several hours in, his left arm went numb and he had to ride an amblulance to the hospital, xorkoth and weikeill report drowsy and sedated states every time they took the stuff, really weird freaky sucky RC imho. It is gloomy (just as someone else reported at erowid) and was only enjoyable the very 1st time i took it (probably because i mixed it into a glass of water for a while before i drank it)...but never again after that, all other experiences sucked after that.

Plain water can also hydrolyze the 4-aco-dmt to 4-ho-dmt (just as it can hydrolyze aspirin), but plain water hydrolysis is incredibly slow, and this is why no one uses it, even for any kind of real world hydrolysis experiments. however, acid catalyzed hydrolysis is rapid. In my very first trial with 4-aco-dmt (my only good trip)...i had dissolved the 4-aco-dmt into a cup of water, stirred it and let it sit a long while before I drank it, I also by chance read of a similar report of a person dissolving their 4-aco-dmt into gatorade (which is acidic around ph=4) waited a while then drank it slowly (as I did, drank slowly)...they said the trip was much different from 4-aco-dmt, and preferred the gatorade dissolved stuff. I still don't recommend plain water hydrolysis cause it is very very slow, and we don't have any idea how much is actually hydrolyzed over the course of 1 hour for example.

Figure 7. The choice of acid makes a remarkable difference. Dilute HCL produces salicylic acid and acetic acid; concentrated sulfuric acid yields mostly phenolsulfonic acid and CO2.

http://www.crscientific.com/article-aspirin.html
hxxp://www.crscientific.com/article-aspirin.html