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Phenethylamines 2-CI-TMA (2-CTMA) & 2-I-TMA (2-ITMA); A Collection of Bioassavs

Gusteau

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2-chloro-3,4,5-trimethoxyamphetamine (2-CTMA) and 2-iodo-3,4,5-trimethoxyamphetamine (2-ITMA); A Collection of Bioassays
2-CTMA and 2-ITMA are novel analogs of TMA, the alpha methyl analog of mescaline. Their structure is similar to TMA differing only by a halogen (chlorine or iodine, respectively) bound to the second position of the aromatic ring.

Find the report for the 2-bromo equivalent, 2-BTMA here:

https://www.bluelight.org/community/threads/2-bromo-3-4-5-tma-a-novel-mescaline-tma-analogue.940367/

This post is copied/pasted from an online community focusing on chemical synthesis, I don’t know the rules around that topic on bluelight so have removed anything relating to such discussion.

INTRODUCTION: The bioassays for 2-CTMA and 2-ITMA that are covered in this post were done and written a number of months ago. Both compounds are covered in the same post because 2-ITMA produced little to no effects up to 40mg. I intended to continue to higher doses of at least 60mg for each but haven’t felt like I’ve had the time and I’d like to post these trip reports now instead of sitting on them without making further progress and then forgetting to post them at all. If myself or any friends take higher doses of either compound I will update this thread.

RELEVANT INFORMATION:

- Mass: 85 kg

- Relevant drugs I am familiar with: 2-BTMA, TMA, Mescaline. A bunch more.

- During all experiments no other psychoactive drugs (including caffeine, nicotine, etc) were ingested.

- The 2-CTMA and 2-ITMA used during these experiments were synthesized by myself and characterized by NMR.

- All dose amounts are reported as the mass of the HCl salt.

- Doses were titrated up from 500ug over the course of many weeks to avoid tolerance.

2-CTMA:

DOSAGE:
20-40+ mg

DURATION: 6-8 h

QUALITATIVE COMMENTS: (with 10mg) Nothing.

(with 20mg) Within 30 minutes there was a sense that something was going on. The textures in fabric were more eye catching than normal. I felt relaxed.

After the first hour had passed the visuals had not developed further and the intensity overall was low, but the mind had found a different way to entertain itself. Perfectly ordinary thoughts kept popping up: Should I go to the beach today? When am I going to do the laundry? I like this album. But for some reason, each thought felt like the punchline to a hilarious joke. Even realizing that I was finding normal thoughts funny was, itself, hilarious. Overall it was a light hearted enjoyable headspace to be in.

The intensity did not build much from that point on and I remained at a low, uneventful ++ for a few hours before returning to baseline. To my surprise, for the two weeks that followed this experience I was incredibly motivated to take care of myself and overall felt much happier in day to day life. It is rare for me to experience afterglow following psychedelic use so this was surprising especially considering the dose must not have been that far North of the threshold.

(With 40mg) In contrast to the 20mg trial, the onset was slow and the headspace was weird. After an hour had passed I was beginning to wonder if the previous experience was mostly placebo. But the signs began to show themselves, this time in the body. My coordination got a little worse and my muscles felt a little tight.

I was invited to a party and elected to go despite not really knowing anyone there. Preoccupied with meeting people and blending in, I hardly noticed as the effects began to manifest. There was a slight increase in social anxiety but once I got to chatting with people it faded. I was having a bit of trouble gauging how well I was fitting in and if the directions I was taking conversations were reasonable for the setting. There was a quality to the experience reminiscent of dissociatives or alcohol where I felt like I was having trouble keeping up with the words coming out of my mouth, only confidently knowing what they meant after hearing them aloud. A few times I caught myself getting more philosophical than was socially appropriate amongst drunk strangers.

I was delighted to spark up a conversation with a chemical engineer I had met briefly once before, but quickly discovered that the given environment and prospect of meeting attractive women combined with my diminished ability to coordinate my thoughts in a linear way only intensified their general lack of interest in discussing flow reactors and organic chemistry.

When I finally took a break from the crowd, three hours after dosing, I began to realize I was fully into the effects of 2-CTMA. The letters on my phone screen were dancing around and the white background was changing colour. Typing messages required more focus. 2D fractals resembling the Mandelbrot set revealed themselves on the floor of the washroom and followed me for the rest of the evening, shifting and rearranging in the grass, trees, and sky. This was perhaps equivalent to 15-20mg of 2C-B and had some characteristics reminiscent of MDMA and alcohol, but far less social. I was not sad to be attending the party but wish for the sake of the experiment I had spent some more of the day alone.

By the fifth hour the intensity began to drop off. After finding my way home I enjoyed my time laying in bed with my thoughts. By the eighth hour I was left with a slight headache that was gone by next morning.

EXTENSIONS AND COMMENTARY: 2-CTMA is more potent than 2-BTMA by a reasonable margin. My experience with 40mg of 2-CTMA was near or equivalent to the intensity of my experience with 60mg 2-BTMA. Without a doubt, the dose could be pushed comfortably into the 60mg range for a more intense experience.

2-ITMA:

DOSAGE:
greater than 40mg.

DURATION: unknown.

QUALITATIVE COMMENTS: (with 40mg) I might have felt something at the four hour mark in the form of some body load but it could just as easily be placebo. Maybe a threshold.

EXTENSIONS AND COMMENTARY: 2-ITMA has proven to be the least potent of the 2-halo TMAs—a fascinating contrast to the pattern allegedly seen with the 2-halo mescalines where 2-IM is most potent. Personally I am yet to try the 2-halo mescalines so have not personally verified this though.

It is possible in the case of 2-ITMA that the bulky 2-iodo group interacts with the alpha methyl group on TMA in a way that is unfavourable for 5-HT2A agonism. This pattern raises questions about the potential of the 2-fluoro analog, 2-FTMA.
 
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2-chloro-3,4,5-trimethoxyamphetamine (2-CTMA) and 2-iodo-3,4,5-trimethoxyamphetamine (2-ITMA); A Collection of Bioassays
2-CTMA and 2-ITMA are novel analogs of TMA, the alpha methyl analog of mescaline. Their structure is similar to TMA differing only by a halogen (chlorine or iodine, respectively) bound to the second position of the aromatic ring.

Find the report for the 2-bromo equivalent, 2-BTMA here:

https://www.bluelight.org/community/threads/2-bromo-3-4-5-tma-a-novel-mescaline-tma-analogue.940367/

This post is copied/pasted from an online community focusing on chemical synthesis, I don’t know the rules around that topic on bluelight so have removed anything relating to such discussion.

INTRODUCTION: The bioassays for 2-CTMA and 2-ITMA that are covered in this post were done and written a number of months ago. Both compounds are covered in the same post because 2-ITMA produced little to no effects up to 40mg. I intended to continue to higher doses of at least 60mg for each but haven’t felt like I’ve had the time and I’d like to post these trip reports now instead of sitting on them without making further progress and then forgetting to post them at all. If myself or any friends take higher doses of either compound I will update this thread.

RELEVANT INFORMATION:

- Mass: 85 kg

- Relevant drugs I am familiar with: 2-BTMA, TMA, Mescaline. A bunch more.

- During all experiments no other psychoactive drugs (including caffeine, nicotine, etc) were ingested.

- The 2-CTMA and 2-ITMA used during these experiments were synthesized by myself and characterized by NMR.

- All dose amounts are reported as the mass of the HCl salt.

- Doses were titrated up from 500ug over the course of many weeks to avoid tolerance.

2-CTMA:

DOSAGE:
20-40+ mg

DURATION: 6-8 h

QUALITATIVE COMMENTS: (with 10mg) Nothing.

(with 20mg) Within 30 minutes there was a sense that something was going on. The textures in fabric were more eye catching than normal. I felt relaxed.

After the first hour had passed the visuals had not developed further and the intensity overall was low, but the mind had found a different way to entertain itself. Perfectly ordinary thoughts kept popping up: Should I go to the beach today? When am I going to do the laundry? I like this album. But for some reason, each thought felt like the punchline to a hilarious joke. Even realizing that I was finding normal thoughts funny was, itself, hilarious. Overall it was a light hearted enjoyable headspace to be in.

The intensity did not build much from that point on and I remained at a low, uneventful ++ for a few hours before returning to baseline. To my surprise, for the two weeks that followed this experience I was incredibly motivated to take care of myself and overall felt much happier in day to day life. It is rare for me to experience afterglow following psychedelic use so this was surprising especially considering the dose must not have been that far North of the threshold.

(With 40mg) In contrast to the 20mg trial, the onset was slow and the headspace was weird. After an hour had passed I was beginning to wonder if the previous experience was mostly placebo. But the signs began to show themselves, this time in the body. My coordination got a little worse and my muscles felt a little tight.

I was invited to a party and elected to go despite not really knowing anyone there. Preoccupied with meeting people and blending in, I hardly noticed as the effects began to manifest. There was a slight increase in social anxiety but once I got to chatting with people it faded. I was having a bit of trouble gauging how well I was fitting in and if the directions I was taking conversations were reasonable for the setting. There was a quality to the experience reminiscent of dissociatives or alcohol where I felt like I was having trouble keeping up with the words coming out of my mouth, only confidently knowing what they meant after hearing them aloud. A few times I caught myself getting more philosophical than was socially appropriate amongst drunk strangers.

I was delighted to spark up a conversation with a chemical engineer I had met briefly once before, but quickly discovered that the given environment and prospect of meeting attractive women combined with my diminished ability to coordinate my thoughts in a linear way only intensified their general lack of interest in discussing flow reactors and organic chemistry.

When I finally took a break from the crowd, three hours after dosing, I began to realize I was fully into the effects of 2-CTMA. The letters on my phone screen were dancing around and the white background was changing colour. Typing messages required more focus. 2D fractals resembling the Mandelbrot set revealed themselves on the floor of the washroom and followed me for the rest of the evening, shifting and rearranging in the grass, trees, and sky. This was perhaps equivalent to 15-20mg of 2C-B and had some characteristics reminiscent of MDMA and alcohol, but far less social. I was not sad to be attending the party but wish for the sake of the experiment I had spent some more of the day alone.

By the fifth hour the intensity began to drop off. After finding my way home I enjoyed my time laying in bed with my thoughts. By the eighth hour I was left with a slight headache that was gone by next morning.

EXTENSIONS AND COMMENTARY: 2-CTMA is more potent than 2-BTMA by a reasonable margin. My experience with 40mg of 2-CTMA was near or equivalent to the intensity of my experience with 60mg 2-BTMA. Without a doubt, the dose could be pushed comfortably into the 60mg range for a more intense experience.

2-ITMA:

DOSAGE:
greater than 40mg.

DURATION: unknown.

QUALITATIVE COMMENTS: (with 40mg) I might have felt something at the four hour mark in the form of some body load but it could just as easily be placebo. Maybe a threshold.

EXTENSIONS AND COMMENTARY: 2-ITMA has proven to be the least potent of the 2-halo TMAs—a fascinating contrast to the pattern allegedly seen with the 2-halo mescalines where 2-IM is most potent. Personally I am yet to try the 2-halo mescalines so have not personally verified this though.

It is possible in the case of 2-ITMA that the bulky 2-iodo group interacts with the alpha methyl group on TMA in a way that is unfavourable for 5-HT2A agonism. This pattern raises questions about the potential of the 2-fluoro analog, 2-FTMA.
Very interesting. I wonder why with the extra carbon and not 2-Cl-3,4,5-trimethoxy-phenethylamine.

Also, given the magic on the 4 position, I don't think I have seen any 4-Cl,3,5-trimethoxy-amphetamine like compounds around. There is Escaline and Proscaline, their 3 carbon (amphetamine) variants being 3C-E and 3C-P.
 
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Very interesting. I wonder why with the extra carbon and not 2-Cl-3,4,5-trimethoxy-phenethylamine.

Also, given the magic on the 4 position, I don't think I have seen any 4-Cl,3,5-trimethoxy-amphetamine like compounds around. There is Escaline and Proscaline, their 3 carbon (amphetamine) variants being 3C-E and 3C-P.
Yes that’s a reasonable question. I would guess the average enthusiast might be more curious about 2-chloromescaline (2-CM) and 2-iodomescaline (2-IM) given how well known mescaline is relative to TMA, and how much more enjoyable it is for most.

The reason that 2-CTMA and 2-ITMA were synthesized and 2-CM/2-IM have not been yet was simply that between having used some mescaline to synthesize 2-bromomescaline (2-BM) and my friends and I eating the rest there was no more mescaline left to be used as a reagent to synthesize 2-CM and 2-IM!

The idea of substituting the 4-methoxy group in 3,4,5-trimethoxy structures with something that is not an alkoxy group (like what I believe you are suggesting with 4-Cl) is a good one. Surely a lot of these compounds would be active. The problem is that they are more challenging to synthesize. Selectively putting the Cl there is not as trivial as with 2C-C or 2-CTMA. But an example of one of these types of compounds that comes to mind from PiHKAL is DESOXY where the 4-methoxy group of mescaline is replaced with a methyl group. Formally known as 3,5-dimethoxy-4-methylphenethylamine
 
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Yes that’s a reasonable question. I would guess the average enthusiast might be more curious about 2-chloromescaline (2-CM) and 2-iodomescaline (2-IM) given how well known mescaline is relative to TMA, and how much more enjoyable it is for most.

The reason that 2-CTMA and 2-ITMA were synthesized and 2-CM/2-IM have not been yet was simply that between having used some mescaline to synthesize 2-bromomescaline (2-BM) and my friends and I eating the rest there was no more mescaline left to be used as a reagent to synthesize 2-CM and 2-IM!

The idea of substituting the 4-methoxy group in 3,4,5-trimethoxy structures with something that is not an alkoxy group (like what I believe you are suggesting with 4-Cl) is a good one. Surely a lot of these compounds would be active. The problem is that they are more challenging to synthesize. Selectively putting the Cl there is not as trivial as with 2C-C or 2-CTMA. But an example of one of these types of compounds that comes to mind from PiHKAL is DESOXY where the 4-methoxy group of mescaline is replaced with a methyl group. Formally known as 3,5-dimethoxy-4-methylphenethylamine
I realised there is one out there which fits the bill, 3,5-dimethoxy-4-bromoamphetamine. It doesn't have any real psychedelic effects at the dosages tested.

DESOXY does however sound more interesting... And the phenethylamine derivative of 3,5-dimethoxy-4-bromoamphetamine. Well for me personally.
 
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