5-IT

[paracelsius]

This compound was made in Russia (well..Soviet Union) long time ago in the 70s. Quite clever synthesis how they made it from plain amphetamine! very clever indeed.

It is the benzimidazole homolog of 5-IT (https://en.wikipedia.org/wiki/5-IT)

Notice 5-IT is a stimulant not a tryptamine in terms of effects! even tho it is an aminoethyl indole! It is more like 4-MAR oxazolines types releasers (ratios of DA-NE-SERT release wise). Was actually described by Shulgin in TIHKAL : "at 20 milligrams orally, [it] is a long-lived stimulant producing increased heart-rate, anorexia, diuresis, and slight hyperthermia for about twelve hours..." I guess it is slightly empathogenic.

I wonder if the corresponding N-methyl compounds have ever been made. Especially that of the benzimidazole above. It looks relatively more balanced toward DA-NE than SERT. 5-IT is more like 4-MAR (ratio release dat-net-sert ~ 1:1:8 and 1:1:10 for the latter ). I suspect the benzimidazole would have less serotonergic and more like meth (~1:1:30) than 4-MAR or somewhere in between 4-MAR and METH. Why? because increasing polarity of the five member ring decrease SERT release (cf Naphthalene v MD v di-Me ..etc). Decreasing SERT would make it safer but I worry about 5-HT2b issues like with MDMA and APBs.
edit: Being more polar it would probably have less of the ultra long duration of 5-IT described by Shulgin.

 

[izo]

This compound was made in Russia (well..Soviet Union) long time ago in the 70s. Quite clever synthesis how they made it from plain amphetamine! very clever indeed.

i remember reading that paper years ago, not much infos despite the usual synthesis, never heard of a bioassay.

Notice 5-IT is a stimulant not a tryptamine in terms of effects! even tho it is an aminoethyl indole! It is more like 4-MAR oxazolines types releasers (ratios of DA-NE-SERT release wise). Was actually described by Shulgin in TIHKAL : "at 20 milligrams orally, [it] is a long-lived stimulant producing increased heart-rate, anorexia, diuresis, and slight hyperthermia for about twelve hours..." I guess it is slightly empathogenic.

shulgins info is not correct. i was briefly sold from the uk around 2014 when the mxe hype slowly found its end, but just got pulled of the market some weeks after its introduction. it was patented by albert hofmann in a french patent and it was the only compound being patented therein iirc. i got lucky and was able to get one whole dose of it which is around 100mg. it was by far the best amphetamine entheogen i ever had. better than methylone (which i really liked) and also better than 6-apb (which is close second).

to describe it i have to say that im not a big fan of mdma, i just get somewhat melancholic on it. and i find 5apb, 5mapb and 5eapb to be almost indistinguishable from mdma. i find these compounds so boring in the meantime that i decided to go to sleep half an hour after the last of my experiments with 5eapb started. so i layed down and 5minutes later i fell asleep. woke up fit and totally refreshed after 8 hours or so. totally not my drug. methylone (as ethylone also) otoh i found to be very enjoyable and useful. light and fluffy high that is a complete joyride around 150mg and a rather nice antidepressant in lower doses (around 70mg). 6apb i would describe as a somewhat interlectual version of 5apb or mdma, it provides a much clearer headspace and feels way less mindblowing (which i mean in a bad way, with all the face goulash going on with mdma and the rather harsh comedown). it is totally not my drug, got no real use for mdma nowadays. but 5-it absolutely takes the cake. it is so light and fine in its high, totally in contrary to mdma and the like. fascinating what a one proton smaller atom can archieve when you compare it to 5-apb. just seen 6-it on a pdf from a analytical standards chem company but there are no papers out there dealing with this compound and i never heard that it reached the maket. must be a great drug, too. as are the cathinone derivates of these two for sure.

ps: they pulled 5-it so quickly from the market because of an allegedly high number of deaths related to it (14 only in sweden), which is a bit hard to believe as this compound isnt really that potent and has a wider safety margin than say mdma. its not btmg anlage 1 over here so no way that this compound will come back on the open market over here. sadly, because this substance has more use as a psycholytic tool contrary to the more neurotoxic mdma which seems to be oh so relevant when it comes to the frontier of entactogenic therapeutic tools. but what can you say, they really just tried using n2o as an ad in the united states. so maybe its better to stick to smoking banana peels and wait until mondern psychiatry will get its head out of its ass.

 

[HOOH]

i remember reading that paper years ago, not much infos despite the usual synthesis, never heard of a bioassay.

Do you have the paper? I can't seem to find it

 

[izo]

this is the paper concerning 5-it:

1962 - Nouveaux derives de l'indole et leur preparation FR1344579A

and this must be the benzimidazole paper:

1976 - DRUGS FROM A SERIES OF 6-PHENYLISOPROPYLAMINE DERIVATIVES VI. BENZIMIDAZOLE ANALOGS OF B-PHENYLISOPROPYLAMIN.

 

[paracelsius]

i remember reading that paper years ago, not much infos despite the usual synthesis, never heard of a bioassay.

Yeah that is the paper I am talking about (doi.org/10.1007/BF00758684). The Russians probably did biossay but I think it got eclipsed by alfa-AMT marketed by Russian as antidepressant around that time. Synthesis they described is neat but nowadays they are better ways like similar to PN2P from dirt cheap 5formyl-benzimidazole.

shulgins info is not correct. i was briefly sold from the uk around 2014 when the mxe hype slowly found its end, but just got pulled of the market some weeks after its introduction

....but 5-it absolutely takes the cake. it is so light and fine in its high, totally in contrary to mdma and the like. fascinating what a one proton smaller atom can archieve when you compare it to 5-apb....
....it was by far the best amphetamine entheogen i ever had. better than methylone (which i really liked) and also better than 6-apb (which is close second).

Now you got me more interested. "better than methylone and 6-APB"?? at what dose range ROA you tried it? if you don't mind me asking. Thats what I thought about Shulgin describing it as stimulant (then again he's talking at 20mg tho!). For sure it would have some entactogen (way less that MDMA or APBs for sure). The benzimidazole probably even less. That one probably somewhere between plain aminorex and meth. I am amazed why aminorex oxazolines are not more available. I mean plain aminorex (at 25mg)is quite possibly the most euphoric clean stim with no crash and actually an antidepressant effect the day or 2 after.
Too bad some overweight old ladies trying loose weight took the drug daily for six months straight and ended up with pulmonary hypertension issues and the drug pulled out of the market. But that is really a nice stim better imo than 4-MAR ( but 4-MAR got all the holy grail glory and aura of stimulants, ppl forget to pay attention. I heard actually 3-MAR is even better.

ps: they pulled 5-it so quickly from the market because of an allegedly high number of deaths related to it (14 only in sweden), which is a bit hard to believe as this compound isnt really that potent and has a wider safety margin than say mdma. its not btmg anlage 1 over here so no way that this compound will come back on the open market over here.

yeah kind of hard to attribute the deaths only to the drug. most have MDMA, 5(6)APB and "other drugs" in their system. and no dosing info. That's is the problem with RCs in general. Even if one can identify a substance you have no idea how much is there and what other drug is there let alone if one is taking a med like say SSRI. I mean you guaranteed possible serotonin syndrome!!!.

 

[izo]

Now you got me more interested. "better than methylone and 6-APB"??

yes, for shure. the best entheogen i ever had, tried it at 100mg as i said. it was just pure bliss. and this comes from someone that doesnt like mdma at all.

 

[fastandbulbous]

I'm sure I read something about 5-IT being a very potent competetive inhibitor of MAO. Combine that with monoamine neurotransmitter release and it could be rather nasty (DA & NA - hypertensive crisis, 5-HT - hyperthermia). Add in other drugs and you are well and truely fucked.

 

[izo]

I'm sure I read something about 5-IT being a very potent competetive inhibitor of MAO. Combine that with monoamine neurotransmitter release and it could be rather nasty

5-it is already a monoamine releaser ala mdma, but somewhat weaker. its not more a MAOI than being a protein substrate nothing inhinbiting it. thats for sure.

 

[paracelsius]

True 5-IT and lots of ring fused isopropanolamines are reversibe MAOIs but it is relative. The IC50 for MAO inhibition of 5-IT is ~ 500-1000x less than its IC50 for DA-NE-SERT release so unless ovedose, MAOI is probably not relevant to its toxicity. I would worry more about too much SERT release and serotonin syndrome!

 

[izo]

I would worry more about too much SERT release and serotonin syndrome!

there are guys munching over 600mg mdma in 8 hours or so, they still survive without bigger problems. i wouldnt go over 150mg, never. and 5-it is much more shallow than mdma, thats why i liked it so much.

 

[fastandbulbous]

there are guys munching over 600mg mdma in 8 hours or so, they still survive without bigger problems. i wouldnt go over 150mg, never. and 5-it is much more shallow than mdma, thats why i liked it so much.

Really, seeing how potent a 2HT2b agonist MDMA is? I would hold judgement until they reached my stage of aged decrepitude...

 

[izo]

Really, seeing how potent a 2HT2b agonist MDMA is? I would hold judgement until they reached my stage of aged decrepitude...

clearly not the healthiest way of living going on a rave every weekend and dropping xtc like smarties. i read an article about the man who took the most xtc tablets, it was a brit. forgot the number though, it was in the thousands through some years. if you google maybe you find it, maybe david pearce's bltc site...

 

[Fertile]

Considering the multiple reports, 2 things suggest themselves. 1 persons experience isn't data. You cannot assign a confidence interval to a cohort of 1. Also, who says WHAT it was? It's not like vendors don't have a terrible history of substituting product.

AMT was indeed used as an antidepressant in Russia. I guess they didn't go for 7,alpha dimethyl tryptamine with it's x10 greater SERT activity. That said, it was rather a pig to make. One has to produce the 7-methylindole-3-carboxamide.

Anyone who has looked into the synthesis of ring-substituted indoles will appreciate that it is neither easy nor cheap. US-3296072-A covers it.

 

[izo]

there are soo much indole synthesises, i looked through the wiki name reaction page and there were dozens. is it right that fischer is still mainly used?

amt was sold in 5mg tabs as indopan. and upjohn tried aet in the usa sold as monase.

 

[Fertile]

Try placing something at the 7 position. No indole synthesis covers all possible ring substitutions and 7 is a pain. Refer to patent.