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Iodine, 2C-I, and the Thyroid Gland

I am by no means an expert in chemistry but my background in organic chemistry regards Iodine as a very good leaving group (reactive to nucleophiles). The low bond strength also make Iodine like to participate in free radical reaction pathways. This would be of concern to your health as would any free radical in the body.

Since you are talking about an Iodine on a benzene I dont think these two things will happen as readily. Nucleophilic aromatic substitution is a pretty tough reaction to get to go (if I remember correctly) even with a good leaving group. You have to go through a benzyne intermediate (lots of steric strain, unstable) to get the substitution product.

Electrophilic aromatic substitution is a bit easier but I dont know if that would be related to the thyroid issues you are talking about.

EDIT:Now that I read the entire thread it looks like the thyroid issue is about thyroxine mimicking rather than actual iodine chemistry. Just disregard my post, I wont delete it as it might have a sliver of relevance :)
 
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I most likely think that at the levels being consumed it would likely only be a problem if looking at chronic levels of toxicity. I mean there are small amounts of iodine in sea salt anyway. But an alkyl iodide would act as an alkylating agent. I recall reading that dob accumulates in the lung for some mystery reason [see pihkal]. by this rubric, does doi accumulate in the thyroid?
 
Smyth said:
I most likely think that at the levels being consumed it would likely only be a problem if looking at chronic levels of toxicity. I mean there are small amounts of iodine in sea salt anyway. But an alkyl iodide would act as an alkylating agent. I recall reading that dob accumulates in the lung for some mystery reason [see pihkal]. by this rubric, does doi accumulate in the thyroid?
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Alkylating a benzene Iodine is more difficult than a primary secondary and probobly even a tertiary carbon.

Does anyone know of any medicinal compounds that use iodine in places other than on the benzene?
 
From what I understand, halobenzene derivities are fine but haloalkyl groups are a no-no as they can act as alkylating agents. This is why DOMCL (4-chloromethyl-2,5-DMA) is a no-no even though animal testing shows it to be a powerful psychedelic, much stronger than DOM itself.
 
^ Yep, halogens attached to a benzylic carbon (one attached to a benzene ring) are very active alkylating agents because of the effect of the delocalized pi electrons of the benzene ring on charge separation in the molecule. Halogens attached directly to the aromatic ring are much, much harder to coax into reacting (they dont alkylate amines, thiols etc in alcoholic soln) unlike the simple alkyl halides such as bromoethane
 
fastandbulbous said:
^ Yep, halogens attached to a benzylic carbon (one attached to a benzene ring) are very active alkylating agents because of the effect of the delocalized pi electrons of the benzene ring on charge separation in the molecule. Halogens attached directly to the aromatic ring are much, much harder to coax into reacting (they dont alkylate amines, thiols etc in alcoholic soln) unlike the simple alkyl halides such as bromoethane
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Hmm... does that apply to fluorine as well? 2C-T-21 has a fluoroethyl group attached to the thiol. Or maybe I am misunderstanding?
 
Fluorine tends to be a pretty shitty leaving group, and alkyl fluoro compounds tend to be pretty stable, i.e. teflon. And even if that wasn't the case, fluorine isn't on a benzylic carbon in 2C-T-21, and so precludes stabilization of the carbocation by extension of that aromatic system.
 
Fluorinated groups behave more like alkyl groups than halo groups. Fluoroalkyl chains (as in 2C-TFM, 2C-EF, and 2C-T-21) will not behave like a 'regular' halo-alkyl group.
 
While we are on this tangent, does anybody know what 4-TMF-amphetamine is like?
 
"Halogens attached directly to the aromatic ring are much, much harder to coax into reacting (they dont alkylate amines, thiols etc in alcoholic soln) "

Yes,harder,but they still do.Theres an entire class of reactions "Palladium catalysed alkylation of amines,anilines,amides,alkines,phenols,boronates etc. like Suzuki,Buchwald-Hartwig".Even aromatic fluorides can react (Nitrofluorbenzenes,somewhere I've seen someone alkylating an indole with Fluorpyridin). Obviously,its about metal catalysis making the reaction possible altough there are examples not needing a precious metal help.
I wouldn't expect it in the body but I know practically zilch about metals and enzymatic reactions in our bodies.

"This is why DOMCL (4-chloromethyl-2,5-DMA) is a no-no even though animal testing shows it to be a powerful psychedelic, much stronger than DOM itself."--Hmm,is that one known?I guess its an irreversible ligand.Forever tripping.I know at least two who tried the 4-Fluoromethyl derivative,but without success.


Smyth:do you mean 4-TFMamphetamin?Thought about that one too.
 
^ Yes, but nitror substituted halobenzenes are a special case because of the effect of the nitro group(s) on the aromatic ring. Methoxy groups (a la psychedelics) just aren't going to give the halogen enough pzzazz to alkylate...

Hmm,is that one known?I guess its an irreversible ligand.Forever tripping.
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Never thought about it like that! I was thinking much more about the possibility of alkylating a DNA base and causing all sorts of horrible things to go wrong; then again, permanent tripping doesn't sound like a barrel of laughs!
 
My thyroid gland is perfect and I was stupid enough to abuse 2C-I at low to high doses for nearly a month every day straight and getting around 1-2 hours of sleep every two nights.
 
morninggloryseed said:
What is known is that users have reported sore thyroids after use of normal doses of 2CI
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Just wondering, do you have any sources? And if so, how long did these symptoms last?
 
The question that needs to be answered is how much of the iodine in 2CI becomes available as atomic iodine. A 15mg dose of 2CI contains 6.2mg of iodine and a 20mg dose contains 8.3mg (math at bottom). According to this iodine toxicity overview the daily iodine requirement for adults is 0.15mg per day and the tolerable upper intake level is 1.1mg per day. So a typical 2CI dose potentially contains much more Iodine than one should be consuming.



mw 2CI: 307g/mol mw I: 127g/mol
127/307 * 15 = 6.2
 
I am very allergic to iodine. I worked my way up with 2c-i from 500ug to make sure I was not going to self produce anaphalaxis from the drug. I dont find 2c-i to be at all pleasant, but I have not had an allergic reaction to it. I also tried DOI at a few levels and found it far more pleasurable. I had an epi-pen present for all trials and a sober driver in case of immediate need for medical intervention. Low thyroid levels are also common in my family. My mother is on levothyroxin daily and my brothers recent bloodwork shows he has low levels also. I have never had my thyroxin levels tested as I do not have any issues with energy.
 
OutOnTheVeranda said:
The question that needs to be answered is how much of the iodine in 2CI becomes available as atomic iodine. A 15mg dose of 2CI contains 6.2mg of iodine and a 20mg dose contains 8.3mg (math at bottom). According to this iodine toxicity overview the daily iodine requirement for adults is 0.15mg per day and the tolerable upper intake level is 1.1mg per day. So a typical 2CI dose potentially contains much more Iodine than one should be consuming.



mw 2CI: 307g/mol mw I: 127g/mol
127/307 * 15 = 6.2
Click to expand...

No it pertains to ionic iodine ie as potassium iodide etc. Iodine attached to an aromatic ring isn't going anywhere unless it's surrounded by nitro groups (which it isn't in 2C-I). If iodine in any form was dangerous, they wouldn't be using any of the radiopaque dyes for x-ray contrast agents as that involves putting a fair bit of the dye into the body (they contain iodine as it somehow prevents x-rays from passing through so easily).

All the shit about worrying about iodine-131 from things like the Chenobyl accident refers to iodine contained in soil ets as potassium/sodium/other metal ion iodides
 
I do not think that the iodine, esp a one time exposure, is of any significance unless one is allergic to it. However, 2CI consistenly causes bronchoconstriction for me (several different batches over the years). I have to keep an inhaler around, or it gets unpleasant, though never to the point where there is truely any danger of suffocating. I do not think this is a thyroid problem because my entire bronchial tree is affected.
 
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