APBT's - The next generation of psychedelic/entactogenic/empathogenic amphetamines is coming!!! Bring on the benzothiophenes!

[simstim]

(2-Aminopropyl)benzo[β]thiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice - Neuropsychopharmacology

Derivatives of (2-aminopropyl)indole (API) and (2-aminopropyl)benzofuran (APB) are new psychoactive substances which produce stimulant effects in vivo. (2-Aminopropyl)benzo[β]thiophene (APBT) is a novel sulfur-based analog of API and APB that has not been pharmacologically characterized. In the...

www.nature.com

According to this article benzothiophene based "amphetamines" are more potent releasers of serotonin than their benzofuranyl analogs. They also have a higher affinity for the 5-ht-2 receptors and cause rats to develop the stereotype head twitch which indicates psychedelic like activity.

Benzothiophenes are just like benzofurans except benzothiophenes have a sulfer where benzofurans have an oxygen (and indoles have a nitrogen).

The three chemicals that they picked out to highlight were 3-APBT, 5-APBT, and 6-APBT.

5 and 6-APBT are analogous to 5 and 6-APB, and are therefore relatives of MDA.

3-APBT is analogous to aMT! It is in fact aMT with a sulfer substituted for the nitrogen on the indole ring.

It should be possible to make benzothiophene analogs of many (or all) tryptamines (just like there are already analogs of tryptamines which are benzofuranyl rather than indolyl).

The three chemicals highlighted in the article are reported to be non selective monoamine releasing agents... read triple releasing agents.

Oddly though they seem to lack locomotor stimulant properties so it doesn't sound like any of them will become the next MDMA.

There you have it! You heard it here first. A new class of psychedelic, entactogenic, and empathogenic "amphetamines" will arise.

Bring on the benzothiophenes!!!

 

[Pfafffed]

Full text now available

 

[deficiT]

I'm here for it.

 

[Xorkoth]

Wow, how fascinating! Given AMT is one of my favorite substances, I would love to try 3-APBT. Of course, it is already a very potent serotonin releaser as well as an MAOI, so too much increase in either of those categories could be quite dangerous.

 

[izo]

Given that the sulfur Atom is Bigger than the o of the apbs the compounds are more related to naphtylaminopropanes. Serotonine releasers nontheless.

 

[f1mula0ne]

Heck yeah!!!

 

[0.o_LaCuNa_o.0]

Bring it on!

 

[Bare_head]

Interesting thread. Makes me want to move out of england asap

 

[heerutosen]

None of these are available out of China right? Do not want to roll the dice with them. 50% chance you get something else that has not been tested in humans before.

Would love to know reputable site if it is going to be legal in Europe

 

[Wiserthanearlier]

Wow, this could be very exciting

 

[simstim]

3-APBT

5-APBT

6-APBT

 

[Opi_Kid_Rock]

After someone tries it, please share experience. Empathogenic stuff I have an interest in.

 

[Fertile]

Early days. S will oxidise and they do not test the action of such probable metabolites. Might be just fine, might be a problem. I guess it was on someone's 'to do' list.

 

[realgar]

Early days. S will oxidise and they do not test the action of such probable metabolites. Might be just fine, might be a problem. I guess it was on someone's 'to do' list.

Another benzothiophene derivative, BTCP, has been proven to be toxic.

BTCP science and toxic effects

Supposedly this material has appeared on the market, there appears to be a lack of even basic research literature search by those promoting this substance. this thread is for discussion of the science anything off topic will be deleted. This on the face of it does not look good, especially for...

bluelight.org

An overview of metabolism and toxicity of thiophenes can be found here:

"Pharmacokinetics and Metabolism in Drug Design", edited by D. A. Smith, H. van de Waterbeemd, D. K. Walker, R. Mannhold, H. Kubinyi, H.Timmerman, 2001 Wiley-VCH Verlag GmbH, ISBNs: 3-527-30197-6 (Hardcover); 3-527-60021-3 (Electronic).

Library Genesis

Library Genesis is a scientific community targeting collection of books on natural science disciplines and engineering.

libgen.rs

(p. 112)

Dalvie D.K., Kalgutkar A.S., Khojasteh-Bakht S.C., Obach R.S. and O'Donnell J.P.
Biotransformation reactions of five-membered aromatic heterocyclic rings
Chemical Research in Toxicology, 2002, 15(3), 269-299.
DOI: 10.1021/tx015574b

Sci-Hub | Biotransformation Reactions of Five-Membered Aromatic Heterocyclic Rings. Chemical Research in Toxicology, 15(3), 269–299 | 10.1021/tx015574b

 

[Fertile]

Nothing on the specific aromatic but S tends to oxidize. I came across an ODD metofoline derivative that I deduced had a benzylic S=O but my guess is they added an S, noted activity and discovered it was the metabolite. Thus C=O or better C-OH would work. I mean beta hydroxy fentanyl & phenoperidine both use that moiety to increase activity a LOT.

 

[Skorpio]

Wow, how fascinating! Given AMT is one of my favorite substances, I would love to try 3-APBT. Of course, it is already a very potent serotonin releaser as well as an MAOI, so too much increase in either of those categories could be quite dangerous.

I would certainly be leery of these compounds, especially 5-abt, as it's sulfur is positioned just like 4-mta.

I don't know enough medchem to be able to guess if a benzothiapine would be stable enough to not jam up MAO, maybe @fastandbulbous or @Fertile could give a perspective.

 

[simstim]

I would certainly be leery of these compounds, especially 5-abt, as it's sulfur is positioned just like 4-mta.

By that logic 5-APB should be an MAOi for having an oxygen in the same position as pMA and pMMA but it does not appear to be too a significant extent.

On the other hand 5-API (5-IT, the indole of this) is an MAOi so it is possible for the substituent at the para position to still affect MAOi activity.

The article for sure mentions that 3-APBT inhibited MAO-A which is not surprising given it's relationship to aMT. It goes on to say that further testing is needed to determine if the other APBT isomers are indeed MAOis or not.

What is exciting is that 3-APBT, 5-APBT, and 6-APBT have all been shown to be "full agonists" of the 5ht2a receptor.

 

[Fertile]

By that logic 5-APB should be an MAOi for having an oxygen in the same position as pMA and pMMA but it isn't.

On the other hand 5-API (5-IT, the indole of this) is an MAOi so it is possible for the substituent at the para position to still affect MAOi activity.

The article for sure mentions that 3-APBT inhibited MAO-A which is not surprising given it's relationship to aMT. It goes on to say that further testing is needed to determine if the other APBT isomers are indeed MAOis or not.

What is exciting is that 3-APBT, 5-APBT, and 6-APBT have all been shown to be "full agonists" of the 5ht2a receptor.

Are we sure 5APB has no MAOI activity? Or just that it's dose range means it's not a hazard? For what it's worth, 6APB is the more potent and the safer.

As for 4MTA, is it the compound with potent MAOI activity or a metabolite? I don't know but note that 2-C-T-2 & 2-C-T-7 and related have all seen fatalities. I don't ask to infer I know. I don't. I just know their seems to be a hazard so I avoid said hazard. I believe it's termed 'defensive design'.