2C-T-2

This is a recipe from PiHKAL. If you're interested in how the hardlinks were chosen, read noding PiHKAL for Everything2.

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#40 2C-T-2

2,5-DIMETHOXY-4-ETHYLTHIOPHENETHYLAMINE


SYNTHESIS: To a solution of 165 g 1,4-dimethoxybenzene in 1 L of CH2Cl2, in a well ventilated place and well stirred, there was cautiously added 300 mL chlorosulfonic acid. With about half the acid chloride added, there was a vigorous evolution of HCl gas and the generation of a lot of solids. As the addition was continued, these redissolved to form a clear, dark green solution. Towards the end of the addition, some solids were again formed. When everything was stable, there was added 2 L H2O, a few mL at a time, commensurate with the vigor of the reaction. The two phases were separated, and the aqueous phase extracted with 2x75 mL CH2Cl2. The original organic phase and the extracts were combined and the solvent removed under vacuum. The residue weighed 162 g and was quite pure 2,5-dimethoxybenzenesulfonyl chloride, a yellow crystalline solid with a mp of 115-117 °C. It need not be further purified for the next step, and it appears to be stable on storage. The sulfonamide, from this acid chloride and ammonium hydroxide, gave white crystals from EtOH, with a mp of 147.5-148.5 °C.

The following reaction is also a very vigorous one and must be performed in a well ventilated place. To a solution of 400 mL 25% H2SO4 (V/V) in a beaker at least 2 L in size, there was added 54 g of 2,5-dimethoxybenzenesulfonyl chloride, and the mixture was heated on a steam bath. The yellow crystals of the acid chloride floated on the surface of the aqueous layer. There should be 80 g of zinc dust at hand. A small amount of Zn dust was placed at one spot on the surface of this chapeau. With occasional stirring with a glass rod, the temperature was allowed to rise. At about 60 or 70 °C an exothermic reaction took place at the spot where the zinc was placed. Additional dollups of zinc were added, and each small exothermic reaction site was spread about with the glass stirring rod. Finally, the reaction spread to the entire solid surface layer, with a melting of the acid chloride and an apparent boiling at the H2O surface. The remainder of the 80 g of zinc dust was added as fast as the size of the reaction container would allow. After things subsided again, the heating was continued for 1 h on the steam bath. After the reaction mixture had cooled to room temperature, it was filtered through paper in a Buchner funnel, and the residual metal washed with 100 mL CH2Cl2. The two-phase filtrate was separated, and the lower, aqueous phase was extracted with 2x75 mL CH2Cl2. The addition of 2 L H2O to the aqueous phase now made it the upper phase in extraction, and this was again extracted with 2x75 mL CH2Cl2. The organic extracts were pooled (H2O washing is more trouble than it is worth) and the solvent removed under vacuum. The light amber residue (30.0 g) was distilled at 70-80 °C at 0.3 mm/Hg to yield 25.3 g 2,5-dimethoxythiophenol as a white oil. This chemical is certainly not centrally active, but it is a most valuable precursor to all members of the 2C-T family.

To a solution of 3.4 g of KOH pellets in 75 mL boiling EtOH, there was added a solution of 10.0 g 2,5-dimethoxythiophenol in 60 mL EtOH followed by 10.9 g ethyl bromide. The reaction was exothermic with the immediate deposition of white solids. This was heated on the steam bath for 1.5 h, added to 1 L H2O, acidified with HCl, and extracted with 3x100 mL CH2Cl2. The pooled extracts were washed with 100 mL of 5% NaOH, and the solvent removed under vacuum. The residue was 2,5-dimethoxyphenyl ethyl sulfide which was a pale amber oil, weighed about 10 g and which was sufficiently pure for use in the next reaction without a distillation step.

A mixture of 19.2 POCl3 and 18.0 g N-methylformanilide was heated briefly on the steam bath. To this claret-colored solution there was added the above 2,5-dimethoxyphenyl ethyl sulfide, and the mixture heated an additional 20 min on the steam bath. This was then added to 500 mL of well-stirred warm H2O (pre-heated to 55 °C) and the stirring continued for 1.5 h by which time the oily phase had completely solidified to a brown sugar-like consistency. The solids were removed by filtration, and washed with additional H2O. After being sucked as dry as possible, these solids were dissolved in 50 mL boiling MeOH which, after cooling in an ice-bath, deposited almost-white crystals of 2,5-dimethoxy-4-(ethylthio)-benzaldehyde. After filtration, modest washing with cold MeOH, and air drying to constant weight, there was obtained 11.0 g of product with a mp of 86-88 °C. Recrystallization of a small sample again from MeOH provided an analytical sample with mp 87-88 °C. Anal. (C11H14O3S) C,H.

To a solution of 11.0 g 2,5-dimethoxy-4-(ethylthio)benzaldehyde in 100 g of nitromethane there was added 0.5 g of anhydrous ammonium acetate, and the mixture was heated on the steam bath for 80 min (this reaction progress must be monitored by TLC, to determine the point at which the starting aldehyde has been consumed). The excess nitromethane was removed under vacuum leaving a residue that spontaneously set to orange-red crystals. These were scraped out to provide 12.9 g crude 2,5-dimethoxy-4-ethylthio-beta-nitrostyrene with a mp of 152-154 °C. A sample recrystallized from toluene was pumpkin colored and had a mp of 148-149 °C. Another sample from acetone melted at 149 °C sharp, and was light orange. From IPA came spectacular fluorescent orange crystals, with a mp 151-152 °C. Anal. (C12H15NO4S) C,H.

A suspension of 12.4 g LAH in 500 mL anhydrous THF was stirred under He. To this there was added 12.4 g 2,5-dimethoxy-4-ethylthio-beta-nitrostyrene in a little THF, and the mixture was held at reflux for 24 h. After the reaction mixture had returned to room temperature, the excess hydride was destroyed by the cautious addition of 60 mL IPA, followed by 20 mL of 5% NaOH followed, in turn, by sufficient H2O to give a white granular character to the oxides. The reaction mixture was filtered, and the filter cake washed first with THF and then with MeOH. Removing the solvents from the combined filtrate and washings under vacuum provided 9.5 g of a yellow oil. This was added to 1 L dilute HCl and washed with 2x100 mL CH2Cl2 which removed all color. After making the aqueous phase basic with 25% NaOH, it was extracted with 3x100 mL CH2Cl2, the extracts pooled, and the solvent removed under vacuum to provide 7.3 g of a pale amber oil. Distillation at 120-130 °C at 0.3 mm/Hg gave 6.17 g of a clear white oil. This was dissolved in 80 mL IPA and neutralized with concentrated HCl, forming immediate crystals of 2,5-dimethoxy-4-ethylthiophenethylamine hydrochloride (2C-T-2). An equal volume of anhydrous Et2O was added and, after complete grinding and mixing, the salt was removed by filtration, washed with Et2O, and air dried to constant weight. The resulting white crystals weighed 6.2 g.

DOSAGE: 12 - 25 mg.

DURATION: 6 - 8 h.

QUALITATIVE COMMENTS: (with 12 mg) I don't feel this for fully an hour, but when I do it is quite a weight. It feels good to work it through. It is OK to be with pain. You can't eliminate it. And it is OK to contact your deep pools of anger. And all of it stems from the lack of acknowledgment. All the macho carrying on, the fights, the wars, are ways of demanding attention, and getting even for not having had it in one's life. I am experiencing more deeply than ever before the importance of acknowledging and deeply honoring each human being. And I was able to go through and resolve some judgments with particular persons.

(with 20 mg) I chose 2C-T-2 at this dose level because the lateness of getting started, and I wanted a shorter experience with my daughter and her family around. I feel, however, that I have somewhat less of a body load with 2C-T-7. Today I was badly in need of the help that might possibly come from this material, and today it was my ally. I sorely needed the type of help that it afforded. The result was to work off the heavy feeling of tiredness and lack of motivation that had been hounding me. The next day I felt that I had dropped my burden.

(with 20 mg) There is a neutralness to this. I am at the maximum, and I am asking myself, 'Am I enjoying this?' And the answer is, 'No, I am experiencing it.' Enjoyment seems beside the point. It is a rather intensely matter-of-fact +3. Is it interesting? Yes, but mostly in expectation of further developments. Is it inspiring? No. Is it negative? No. Am I glad I took it? Yes. Not glad. Satisfied and contented. This is a controlled +3. No threat. The body is all right. Not superbly healthy--but OK. Of no interest, either way. If I were to define the body's state, I would have to define it in image. The image is of a not comfortable state of being clenched. Clenched? Well, carefully bound in control.

(with 22 mg) A slow onset. It took an hour for a plus one, and almost another two hours to get to a +++. Very vivid fantasy images, eyes closed, but no blurring of lines between "reality" and fantasy. Some yellow-grey patterns a la psilocybin. Acute diarrhea at about the fourth hour but no other obvious physical problems. Erotic lovely. Good material for unknown number of possible uses. Can explore for a long time. Better try 20 milligrams next time.

(with 25 mg) I was at a +++ in an hour! It is most difficult to do even ordinary things. I took notes but now I can't find them. This is much too high for anything creative, such as looking at pictures or trying to read. Talking is OK. And to my surprise I was able to get to sleep, and a good sleep, at the seven hour point.

EXTENSIONS AND COMMENTARY: There is a considerable parallel between 2C-T-2 and 2C-T-7, and both have proven to be excellent tools for introspection. The differences are largely physical. With 2C-T-2, there is more of a tendency to have physical disturbances such as nausea and diarrhea. And the experience is distinctly shorter. With 2C-T-7, physical disturbances are less common, but you are into the effects for almost twice as long. Both have been frequently used in therapy as follow-ups to MDMA.

A point of potential misidentification should be mentioned here. 2C-T-2 has occasionally been called, simply, T-2. This abbreviated nickname has also been used for T-2 Toxin, a mycotoxin of the Tricothecene group, formed mainly by the Fusarium spp. This is the infamous "warfare agent" in Southeast Asia, which was finally identified as bee feces rather than a Soviet military adventure. T-2 and 2C-T-2 are radically different compounds.

All three Tweetios of 2C-T-2 have been made and looked at through human eyes. The 2-EtO-homologue of 2C-T-2 is 2-ethoxy-4-ethylthio-5-methoxyphenethylamine, or 2CT2-2ETO. The benzaldehyde (2-ethoxy-4-ethylthio-5-methoxybenzaldehyde) had a melting point of 73-75 °C, the nitrostyrene intermediate a melting point of 122-123 °C, and the final hydrochloride a melting point of 202-204 °C. Fifty milligrams was a completely effective level. The effects were felt very quickly. Vision was blurred, and there were intense eyes-closed visuals and the generation of a pleasant, contemplative mood. Baseline was re-established in five or six hours, but sleep was restless, with weird dreams. Nasal administration showed considerable variation between individuals, but a typical dose was 10 milligrams.

The 5-EtO-homologue of 2C-T-2 is 5-ethoxy-4-ethylthio-2-methoxyphenethylamine, or 2CT2-5ETO. The benzaldehyde (5-ethoxy-4-ethylthio-2-methoxybenzaldehyde) had a melting point of 49 °C, but it was impure. The nitrostyrene intermediate melted at 107-108 °C, and the final hydrochloride had a melting point of 180 °C. At levels of 20 milligrams, there was a slow, gentle climb to a full effect at the third or fourth hour. The flooding of thoughts and easy conversation lasted for many hours, and on some occasion a sedative was needed at the 16 hour point. There was a feeling of being drained for the following day or two. Some intoxication was still noted in the second day. Again it is true here, as had been stated as a generality, that the 5-Tweetio analogues have potencies similar to that of the parent compound, but show a much longer duration. The nickname of "forever yours" had been applied. There may indeed be insight, but 24 hours' worth is an awful lot of insight.

The 2,5-DiEtO-homologue of 2C-T-2 is 2,5-diethoxy-4-ethylthiophen-ethylamine, or 2CT2-2,5DIETO. The benzaldehyde, 2,5-diethoxy-4-(ethylthio)benzaldehyde, had a melting point of 84-85 °C, the nitrostyrene intermediate a melting point of 123-124 °C, and the final hydrochloride a melting point of 220-221 °C. Levels that were evaluated from 10 to 50 milligrams were not particularly different in intensity, but were progressively longer in duration. At 50 milligrams there was a nervousness and edginess during the early part of the experience, but for the next several hours there was evident both energy and high attentiveness. There were few if any sensory alterations. There were no negatives on the following day. The duration was perhaps nine hours.

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INFO/BACKGROUND:

2C-T-2 (AKA 2,5-Dimethoxy-4-ethylthiophenethylamine, C12H19N02S) is a hallucinogenic drug in the phenethylamine class, first synthesized by Alexander Shulgin.

2C-T-2 is very closely related to 2C-T-7, which gained popularity and notoriety as a "smart drug" in Europe, and which until recently was in rotation at raves and parties in North America, where it was marketed as a kind of hallucinogenic "upper".

While 2C-T-7 is as of August 2002 on route to become a Schedule 1 Controlled Substance in the U.S.A. due to a very high profile article in Rolling Stone and a disturbing track record of very bad reactions from users, 2C-T-2 is still unscheduled and uncontrolled. However, the Federal Analog Act, which prohibits sale of drugs analogous to existing illegal drugs, does apply (though it's worth noting that very few cases have ever been persued under this act). 2C-T-2 is currently scheduled in Germany, Sweden, and the Netherlands.

The difference between 2C-T-7 and 2C-T-2 is that 2C-T-2 seems to be "safer" than 2C-T-7 both in its shorter duration and seemingly less severe effects, as 2C-T-7 has recently has been linked to at least two deaths due to recklessly large doses ingested via insufflation (snorting). The chemical company producing 2C-T-7 stopped its production following these deaths, and 2C-T-2 has stepped into the limelight due to its similar effects.

EFFECTS:

2C-T-2's effects last approximately 6-8 hours, total. The drug is usually taken orally, but some people choose to snort it so that the effects will take hold quickly. Note: THIS IS NOT RECOMMENDED Complications with "research chemicals" such as 2C-T-2 arise when people are irresponsible and when they don't know enough about what they're taking. Extensive experience from users of 2C-T-2 has shown that the drug seems to be safe when dosed and used properly and in moderation.

Light effects: 0-15 mg
Common effects: 15-30 mg
Strong effects: 30-50 mg

As with other hallucinogens, 2C-T-2 creates a change in mindset as well as visual hallucinations. There seems to be some debate as to whether or not 2C-T-2 produces "open eye visuals" like 2C-T-7 has been reported to. While there are those who claim 2C-T-2 is not a "visual" drug like 2C-T-7, many claim that it is just as visual, and, moreover, that the visuals are more manageable, unlike the "psychedelic soup" overload that many 2C-T-7 users report.

2C-T-2 has also been reported to produce extremely lucid and fantastic closed eye visuals, to the point of actually feeling physically in the vision.
The most common negative effect is similar to 2C-T-7 - stomach discomfort and likely nausea. This effect tends to vary in severity from user to user.

DISCLAIMER:

Just because 2C-T-2 is unscheduled and uncontrolled does not mean that it can be taken willy-nilly. Extensive education should be a requirement before even considering experimenting with 2C-T-2, or any research chemical for that matter. This is not because the user is in any danger if the drug is taken properly, but because the pharmacology of 2C-T-2 and similar drugs is incredibly complex, and contraindications with other drugs have yet to be completely deciphered. www.lycaeum.org and www.erowid.org should be required web sites to visit if someone is interested in these particular compounds.

This is a trip report describing my second experience with 2C-T-2, at a dose of approximately 20 milligrams, during which I experienced ego death. We had previously ordered 500mg of the compound, and had dissolved half of this into 250ml of distilled water. Of course there was no way to know for sure that we had 250mg of material dissolved in this solution but we were certain that the amount lay within 25% or so of this. Interestingly, most people who have taken 2C-T-2 find it to be interesting in that it leaves the thought patterns of the user largely intact, compared to say, LSD or psilocybin. However, I discovered that in combination with a fair amount of cannabis, the mental aspects can become very strange indeed.

Today was Wednesday, and the previous Monday (nine days ago) had been my first experience with 2C-T-2. I had had a reasonable experience, but with no insights or real sparkle, so I wanted to make this one a bit better. Last time I took 14ml of our solution (of about 1mg/ml, though we think it's actually 10-20% stronger than this). This time, I took 16.

I had only had four hours of sleep the previous night, and I was a tiny bit reluctant to take the compound, but I was sure it wouldn't cause any problems.

We took the 2C-T-2 and went out to the park to smoke a spliff before the comeup. Last time hadn't given me too much discomfort, but chris had experienced some at 18ml so I thought it prudent to ease my stomach this time. The nausea was definitely abated by using the cannabis.

Last time I took the 2C-T-2 I had come up in about five waves of increasing effect, similar to MDMA rushes. But this time I was playing a flight sim at the time I should have been coming up. I finished the game, and as soon as my mind was free of the concentration, I was hit with a huge wave, and had to lie down. At this point I was slightly worried because I was expecting five or so more waves, each one harder than the last, but I soon realised that my playing the game had caused all the comeup to be concentrated into one wave.

Soon we went out to walk round the park. It was a pleasant day, and the sunlight was giving me lovely rainbow visuals. The stones on the path were beautifully detailed, and I felt like I could have stared at them for hours without getting bored. A cut rock face (this park used to be a quarry) appeared to be the ultimate Mount Rushmore, with hundreds of faces appearing and disappearing in the jutting blocks of stone. Lichens on the stone were miniature mazes, intricate details zooming into the surface, and glowing with cycling colours. Bare trees were explosions of light beaming from underground.

Time was altered in an interesting way; it wasn't that it was passing more slowly or quickly than normal, but I found it difficult to tell how far in the past events lay. Our first spliff before we came up felt like last week, and I had no idea whether we had walked along this path hours or minutes ago.

The visuals were certainly intense and beautiful, and I found myself very interested in the spatial relationships between the levels of the ground (in fact, the ground was so discretely positioned in terms of height that I viewed the park as a giant platform game) but as with my last time on 2C-T-2, the mental was remarkably clear. But after about three hours, this was to change.

Still walking around the park, we took out our second (and larger) spliff, which we smoked, and then walked up to the bandstand with a view over the whole of the bay, and sat down.

One minute I was sitting there feeling progressively stranger, and then bang!

"Nothing."

It was as if my brain had been restarted. I understood nothing, there was nothing. After a time, my brain began to load its software up again.

"World"

This was the first concept that returned to me. I was aware of the world, and that was all I experienced. Now concepts began returning more quickly, new ways of deciding what the world meant returned at an exponential rate. Soon I was aware of:

"World", "Big"

I was aware of the world, or perhaps the whole universe, and I was aware that it was big.

"World", "Big", "Person"...

"Person-Object"

Now I was aware of an entity called a person, and that all persons had an object associated with them; a body.

"Person/World"

The interaction between the person (and its associated person-object) now made some sense to me. I was aware that a person-object is separate from the world, and there is a complex interaction between the two.

"I"

Now I was aware of "I". Up until now the concepts had all made fundemental sense. Each new concept could be described using the previously loaded concepts, but this one was strange. "I" made no sense because it was not part of the world, and was not an object. If I had been able to be confused, I would have been confused now.

I knew that there needed to be more information, more concepts, before this "I" entity would make any sense. I finally spoke, saying "Who the hell am I?" Chris carried on looking straight ahead, and asked "What do you mean?"

By this point, the basic concepts (which I will call the level one concepts) had been mostly loaded, allowing the more complex ones (the level two concepts) to load more quickly.

Now I could access my memory, in a rudimentary form. I was aware that the memories existed, and I could "read" them, but they could not run on the hardware of the brain yet.

So I was aware of all my personal details again, but I still didn't know what those details meant. So I replied to Chris; "Ah... It's coming back to me" (interestingly my ability to speak and regulate my body in every other way remained unaffected. Only my actual consciousness had been shut down and restarted.)
I was now aware of the concept of fear, but like many of the other level two concepts, it was not yet running. So I knew I was undergoing a frightning experience, but I felt no fear.

As the level two concepts returned to me, the data stream that my senses were feeding to my brain was interpreted using these concepts as they were added, and my conscious became more and more complex. Soon I was able to examine the experience that had just happened to me, over the course of a few seconds.

It required a fair amount of effort to keep my consciousness running at its normal level. I feel that if I had let go I could have returned to a very strange state of awareness, and I would not have been averse to this, had it not been for the fact that my body could have done anything. At the time I was sitting on a bandstand in a public park, so I didn't want to completely nod out for obvious reasons. I decided that we'd better walk around, which definitely occupied my mind and kept me from slipping back to strangeness.

We walked around the park for perhaps twenty minutes, and decided to go back to Chris's house before his family started returning so we could sit in his room and avoid having to talk to people. Before I had smoked the cannabis I think I could have appeared fairly normal, but this state of consciousness was so profoundly altered that I would not be able to guarantee I wouldn't talk utter crap. A sort of duality had now appeared; there was a part of me that could walk around, and could hold a normal conversation, and there was the part of me that was incredibly tripped out. The first part was almost like an autopilot; it could control my body in a way that would appear to be normal to anyone else, but the fact that the other part of me was totally zonked meant that there could be no real-time error checking. If the autopilot screwed up and I began talking about the lord of all cabbages, it would be a few seconds before I noticed that I was talking nonsense. The risk of this was too great to be talking to normals.

We watched a cartoon, and by the time this had finished I found myself thinking much more clearly, and soon after this, I took the train home and got a fitful night's rest.

I gained a fascinating insight into the way my brain works through this experience. I believe that the brain is a computer which fits its sensory inputs into certain concepts (software) which it can understand.

The basic level one concepts are intrinsic to the brain, and are like the "firmware" of a computer system; the BIOS, the information built into the hard disks which tells the CPU how to access the data, that sort of thing.

Then there are the level two concepts. These are stored in the brain, like the operating system is stored on the hard drive of a computer. These concepts allow us to make sense of the world, and to compare and contrast data, and to store and retrieve the memories and other data that make us who we are.