• Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

  • N&PD Moderators: Skorpio | someguyontheinternet

Halogen element never been used in phenethylamines? At (Astatine)

To my knowledge Astatine is radioactive, no?

Is that the same substance that Shulgin mentions would literally fry receptors due to alpha-radiation? I am a bit in a hurry but I'll check when I have time...
 
From PiHKAL #33 (2C-I)

Where else can one go, from 2C-I? The iodine is the fourth, and the last of the so-called halogens, at the bottom of the classical periodic table. But, thanks to the miracles that have accompanied us into the nuclear age, there is a fifth halide now known, Astatine. All of its isotopes are radioactive, however, and it seems unlikely that there will ever be an entry (other than this one) for 2,5-dimethoxy-4-astatophenethylamine. What might be speculated as to its activity? Probably similar in potency to 2C-I, requiring maybe 10 or 20 milligrams. The duration would be dicey to measure, since the isotope with the longest known half-life is half decayed in about 8 hours, and the longest lived natural isotope (for those who insist on natural rather than man-made things) is half decayed in less than a minute. Two predictions would be pretty solid. You might have quite a job accumulating your 10 milligrams of Astatine, as the most that has so far been made at one time is only about 0.05 micrograms, approximately a millionth of the amount needed. And the second prediction? You would not survive the screaming radiation that would bombard you if you could get the needed 5 or 10 milligrams of radio-astatine onto that magic 4-position, and the resulting 2C-A into your tummy!
Click to expand...

Short answer - NO.
 
There are other 'pseudohalogens' that haven't been looked at, that are quite feasable and would give compounds that Shulgin never looked at. He did look at the 2-fluoroethyl group (DOEF - 2,5-dimethoxy-4-(2-fluoroethyl)amphetamine) but there are a few others possible with them substituted into the 4-position eg

2,5-dimethoxy-4-cyanoamphetamine

2,5-dimethoxy-4-thiocyanoamphetamine

As DOEF had qualities quite similar to DOB, you'd imagine that the two above would have similar profiles.

The azide ion is also classed as a pseudohalogen, but organic azides are unstable creatures (explosive qualities), so that one should be filed along with the astatine derivative
 
Last edited:
Fascinating stuff, thanks :)
Since i found Astatine on the table of elements I can't help but have a morbid curiousity about what it would be like to sample a radioactive phenethylamine so I'm glad Shulgin has done some interesting predicting for us!
 
From what I've heard, not only is astatine an extremely rare element (there is not enough astatine on Earth to fit within the size of a lollipop), but we've only been able to produce very minute amounts of it in a lab.
 
fastandbulbous said:
As DOEF had qualities quite similar to DOB, you'd imagine that the two above would have similar profiles.
Click to expand...

In "Comparisons Of Hallucinogenic Phenylisopropylamine Binding Affinities At Cloned Human 5-HT2A, 5-HT2B And 5-HT2C Receptors", DOCN is listed as being active. I'd be real interested in seeing what kind of activity 2C-CN would have. Plus, it's amusing to think of a psychedelic made from cyanide. True bromine is just as toxic, but it doesn't have the same association with death that cyanide has. :)
 
MGS,
psychedelic made from cyanide
Click to expand...
I thought there'd been several PEAs (including in the 2C-x fambo) that had been made from cyanide? I couldve sworn i read something along the lines of "cuprous cyanide" just recently in a 2C-x page from PIHKAL, although I could be mistaken
 
Cyanide and cyano compounds are frequently used as synthesis tools. They lend themselves nicely to many addition reactions and in many instances the products are easily reduced to amines.

As the CN moiety in some ways resembles the C=O group in so far as it's charge distribution is concerned, cyanides can add to grignard reagents to produce ketimines which can then be hydrolysed into ketones.

Starting with an aldehyde, if the chemist wanted to extend the carbon chain by 1, he could approach the problem in several ways. He might look at starting by doing a condensation with nitromethane. But often the nitro routes can result in poor or low yields, or conditions may not suit the type of aldehyde (e.g. aromatic ring or ring substitutes etc may react under same conditions)

Cyano routes can offer a different set of reaction conditions. With some reactions, there's the added bonus that hydrolysis of an alkyl-cyanide can often be acid or base catalyzed before reducing to the amine with LiAlH4.

Any concerns regarding the use of cyanides in drug chemistry should be in context. i.e. any chemist who can successfully work with these compounds will have no trouble ensuring the final product is completely free of cyanides.

Oh and just to add. The cyano group is sometimes employed in bio molecules. Depending upon the structure, this can change the toxicity completely.

For example, sodium cyanide is very toxic, sodium ferricyanide is much less toxic and sodium nitroferricyanide is somewhere in the middle. But the toxicity of the latter hasn't prevented it's use as an emergency BP lowering drug, for which it is very effective.
 
Last edited:
MGS

Thanks for the title of the paper, just wondering which journal (I'd never seen anything about DOCN before - you've made my day!); don't supposed it mentioned DOSCN or 2C-SCN(SCN is the thiocyanide ion - the 2C version should be similar to 2C-T-21 if the aryl-sulphur-pseudohalogen comparison holds true)
 
Regarding radioactive drugs, you might have better luck with Shulgin's hypothetical "Hardinamine":

from PiHKAL (2C-SE):
However, the atom below tellurium (and at the bottom of that particular column of the Periodic Table) is the element polonium. Here one must deal in terms of theory, as far as human activity goes, since there are no non-radioactive isotopes of polonium. The only readily available isotope is that with mass 210, which is also called Radium F, and is an alpha-particle emitter. If this were ever to be put into a living organism, and if it were to seek out and hang around some particular site of action, that area would be thoroughly and completely cooked by alpha-particle emission. It would be a fun academic exercise to make 2C-PO (2,5-dimethoxy-4-methylpoloneophenethylamine), but in no way could it ever go into anyone. I knew an eminent physiologist named Dr. Hardin Jones (now dead) who always argued that the continuing use of drugs would burn out the pleasure center of the brain. It is a certainty that 2C-PO would, quite literally, do this. If I ever made it, I would call it HARDINAMINE in his honor.

http://www.erowid.org/library/books_online/pihkal/pihkal038.shtml
 
fastandbulbous the paper was published in the Archives of Pharmacology. Abstract is available via pub med (1) and the full text is supposedly available via Springerlink, although I could not get to the pdf yesterday despite logging in :\
 
It's a good reality check ...
2C-PO (2,5-dimethoxy-4-methylpoloneophenethylamine)
Click to expand...
The name on its own just looks as "harmless" as any other PEA so this serves as a good example that every individual substance must be treated on its own merits, and not assumed to be safe simply because the name looks similar to a known safe compound
 
Certain inorganic elements are indeed used in radiotherapy. This does not really fall inside the hub of what is commonly acknowledged though. I think this is possibly because the side-effects of this sort of treatment mean chemists are more reluctant to blow their trumpets than with other discoveries such as penicillan.

Normally the all important radioactive atom is attached to a carrier that shows preferential uptake into the tumour. The problem is that I was given the impression that uptake of the carrier into the tumour is actually fairly poor. More of an area of science that has potential than something that one can feel truly contented with.

Intentional destruction of neuroreceptors seems more along the lines of an elaborate chemical weapon disguised as a drug molecule than something that is taken just for the hell of it.

What I mean is this is something I would expect to see used to purposefully harm somebody and not something that would be taken for recreation or along those lines.

[Ofcourse radioisotopes are also employed in analysis of drugs invivo eg DOI being used in SPECT and PET scans].
 
Last edited:
To really fuck people up in that way, you'd really need something that was an alpha emitter, but as that involves loosing two protons and two neutrons, it would change the element and hence all the chemical properties. Even beta emitters change element (neutron changes to a proton and an electron, which is them emitted), as anything changing the number of protons in a nucleus will change the element, so the only real option would be a gamma emitter, and that really narrows the number of radioactive elements you'd have to play around with.

So for anybody deranged enough to make something to poison people in that sort of way, it'd make more sense just to add a toxic impurity (like MPTP or a dioxin/polychlorinated biphenyl). If it was just to destroy a certain receptor, there's a large choice of compounds that are irreversible ligands, effectively taking the receptors out of action
 
Some examples please. Also I thought tetrachloro-dioxin as more of a cancer promoting irritant with long retention time than it being neuroactive. Certainly if a compound is possibly contaminated with traces of dioxin one would want to make absolutely sure that it is removed from the final product. A parallel argument applies to removing traces of mercury from MDMA.
 
Not a great idea.. its not going to be that much different of a drug. 2c-i and 2c-b feel identical to me except for duration. only 1 atom difference, and the atom has similar properties

(i realize there are exceptions, like the inactive 2c-f, or the weaker 2c-c. it seems to get more potent as you go down the line, 2c-i being the most potent)
 
You must log in or register to reply here.
Top