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What exactly is a tweetio?

Trogdor

Trogdor

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I'd like to learn a bit more about neuropharmacological organic chemisty (as time permits), and reading a few things I noticed that the word tweetio popped up routinely, yet I'm clueless as to what it is. Is it a specific type of isomer? Google and wikipedia are of very little help.

If you have any recommended reading I should get it would be appreciated. I've been meaning to fully read the online versions pihkal/tihkal and/or purchase the actual publications, but as of yet I haven't found the time.

Thanks
-Trog
 
Bear in mind that I by no means have an expansive knowledge on the subject, but according to Erowid(http://www.erowid.org/psychoactives/journals/psychoactives_journal8.shtml):

"Two additional centrally active structural variations of the prototype 2C-D have been observed and explored to a small degree. The -oxygenated analogs are known as the -methoxy--arylethylamine (BOX) series, and the materials with ethoxy groups in place of either of the methoxy groups are called the tweetios. Neither family is entered in table 3, but both are logical extensions of it.

The BOX compounds are -oxy analogs of phenethylamines, masked as the methyl ether. The X then is the initial or identifier of the 2C analog that has been oxygenated. This manipulation introduces an oxygen heteroatom at a position identical to that found in the neurotransmitters norepinephrine (NE) and epinephrine. But it also introduces a new chiral center, and in the corresponding amphetamine derivatives a threo-erythro system of diastereoisomers that resembles that of ephedrine and pseudoephedrine would be produced. The -methoxy analogs of 2C-,,2,5- trimethoxy-4-bromophenethylamine (BOB), and 2C-D (,2,5-trimethoxy-4- methylphenethylamine [BOD]) are a little more potent than their oxygen-free counterparts but not as interesting subjectively. There has been no research done on the pure enantiomers.

The two tweetio analogs (2-ethoxy and 5-ethoxy) of both 2C-D and 2C-B have been explored and have dramatically reduced activity. The 5-tweetio (5-ethoxy) compounds are of twofold lessened potency, and the 2-tweetio (2-ethoxy) materials are down by another factor of five. The bis-etios (2,5-diethoxy homologs of 2C-D and 2C-B) are not known to be active at all."
 
The 2C-X materials all have a methoxy at the 2 and the 5. A tweeto is a 2C-X with an extra carbon at the 2 position. Thus, instead of an 2-MeO we have a 2-EtO. If you try to sound out 2-EtO you get tweetio.

You can also put an EtO at the 5 position (a 5-EtO), or EtOs at both the 2 and 5 (2,5-diEtO).

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When you say positions, are you referring to the specific atoms on the indole ring? As I may have implied, I don't know much about the chemistry involved, but I would love to learn.

Looking at molecular structures for 2cx chemicals I can see the methoxy groups... I'm not exactly sure how to word this so, what is the molecular name for the ethoxy group (for example methoxy is CH3O)?

I have much to learn...
 
Well positions can refer to anyplace on the molecule. I am specifially refering to substitutions made on the phenyl ring (there is no indole ring in the 2Cs.

As seen in the picture, and ethoxy is CH3CH2O.

Again, check out the pic I posted.
 
Good thread... I'm just gonna move it to ADD since it's an "advanced" topic.
 
By golly, I did mess that up. I always prefer to draw the PEAs with the 2 on the top (opposite how Shulgin does in PIHKAL) but made this up so what he saw would relate to what was in Shulgin's book. But looks like habit took over half way through. :)

I'll have to fix em later.
 
I still understood it.

Et instead of Me. Sounds like a dumb and useless name for something we already have the capability of naming through conventional nomenclature.
 
Now here is an interesting spin on the tweetos. I’m VERY curious as to how adding fluorine atoms to the 2,5-methoxyl groups will change the behavior of the 2Cs. I just think of how fluorine changes 2C-D (2C-TFM), 2C-T-2 (2C-T-21), 2C-E (2C-EF)…and I feel this opens up some very interesting possibilities.

/me engages in chemical masturbation
 

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Bear in mind that, as far as I know, "tweetio" is just a funny word that Shulgin made up to mean something in particular, and it's not an official chemistry term that you would see in a textbook.
 
It's not really made up, it's just a bastardization of the term "2-eto." A slurring of speech, if you will.
 
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