(2-Benzo[d]isoxazol-3-yl-ethyl)-dimethyl-amine

[Zaprenz]

Although not strictly a tryptamine SWIM thought the tryptamine forum may be best to discuss this compound as it is a very similar analogue.

So far SWIM has no information on the Benzo[d]isoxazole type compounds and believes most likely very few have been made.

It appears there is very little information on 2-Benzo[d]isoxazol-3-yl-ethylamine. Could be some very interesting chemical finds in the future.

SWIM only knows one highly substituted compound - risperidone. Risperidone is an atypical anti-psychotic (I know very unfun) which antagonises 5ht-2a receptors(the same important sub group that LSD and the like stimulate). Chemistry can quickly turn an antagonist into an agonist and making comparisons with anti-psychotic indoles like sertindole the Benzo[d]isoxazole compounds may share many properties. Therefore the more simple Benzo[d]isoxazole compounds e.g. the DMT equivalent may be of special interest

SWIM would just like to state though these compounds truely are unknown as of yet so really are Unknown RC chemicals - not to be messed with lightly.

Reputation Comments on this post:

Insightful; witty, smart poster :)

[Nagognog2]

Are you suggesting this may be a possible molecular structure for a typical "Pro-Psychotic" drug? That would be interesting!

[Zaprenz]

Well depends on the definition of pro-psychotic.

If the structure of sertindole (anti-psychotic) is compared to risperidone (anti-psychotic) one can see the similarities. So my point is Benzo[d]isoxazole may well be a very good substitute for INDOLE.

IF this is true (I'm making a few assumptions I'll admit but still) all the tryptamines in TIHKAL may have an equivalent Benzo[d]isoxazole. Could be interesting stuff.

Although having searched for compounds which contain this structure it seems very rare so probably involves some rather complex chemistry.

The DMT or AMT analogue to SWIM seems a very interesting idea. SWIM does realise though its one thing visualising the 2-d molecule and its another thing actually making it. SWIM is not in any position to be able to make some but would be very interested to hear any research that may involve these chemicals.

[Nagognog2]

Yes - considering the typical reduction used for synthetic DMT would tear the molecule of it's O's. This would require a different ring-closure is my guess. And be grounds to shoot up a few rats. Don't tell PETA.

Reputation Comments on this post:

interesting chem info

[Zaprenz]

Definately yeah. Wouldn't want to try these in any hurry. Still might be some new frontiers to the PEA / Tryp family, who knows.

http://www.freepatentsonline.com/5707988.html

http://en.wikipedia.org/wiki/Zonisamide

One other drug I found with the structure contained in it. (almost the tryptamine eq but with a sulphur stuck in the middle)

[Nagognog2]

DMT with a sulfur-chain in the 5-position commonly exists. It goes by the name Sumatriptan. Used for migraines. Maybe if one could flip the sulfur to the 4-position, one could make a hallucinogen that causes migraines!

[Isochrist]

Originally Posted by Nagognog2

Maybe if one could flip the sulfur to the 4-position, one could make a hallucinogen that causes migraines!

Ha, the world doesn't need another 5-MeO-AMT! :P

[radiometer]

Originally Posted by Nagognog2

DMT with a sulfur-chain in the 5-position commonly exists. It goes by the name Sumatriptan. Used for migraines. Maybe if one could flip the sulfur to the 4-position, one could make a hallucinogen that causes migraines!

My wife takes sumatriptan (on prescription), and reports excellent results. Not the best relief imaginable, but tolerable. It's the best she's found yet for her migraines, which seem to be tied to her menses. I couldn't help but notice its resemablance to - say, bufotenine - when she brought the prescription home and I looked it up!

[Nagognog2]

I've always found that interesting about Sumatriptan being derived from DMT. Just like another, older, standard remedy used for migraine - ergotamine. Ergotamine being related to LSD. Both work by acting as powerful vasoconstrictors.

Bongo inherited migraine headaches and can vouch for the horrible pain they cause (they have since stopped, but that's another story). Ergotamine was tried. Placed under the tongue in the form of a tiny, green pill. They didn't work. This was before Sumatriptan made it's appearance on the market.

[fastandbulbous]

Originally Posted by Nagognog2

DMT with a sulfur-chain in the 5-position commonly exists. It goes by the name Sumatriptan. Used for migraines. Maybe if one could flip the sulfur to the 4-position, one could make a hallucinogen that causes migraines!

Actually replacing the nitrogen of the indole nucleus with an oxygen atom produces tryptamine analogues of between a half and a fifth the potency of their tryptamine equivalent. This makes sense as it's the oxygen lone pair electrons that allow the 2,5-dimethoxyPEA series to occupy serotonins actions at the receptor. Even the ones with one fifth the potency do not seem a bad proposition when considering things like the benzofuran equivalent of psilocin. It only really becomes unfeasable when talking about compounds like DMT that would require a quarter of a gram (just far too much for anyone to consume!).

The benzothiophenes, with a sulphur replacing the indolic nitrogen, also have activity at the 5HT2a receptor, but I have no data on the degree of activity

Reputation Comments on this post:

this guy knows his shit. i admire your knowledge

[Nagognog2]

Thanks! Very interesting. Oxygen, that is. I wouldn't let my lab ape, Bongo, be the one to test-pilot a sulfur derivative. Sulfur scares me.

[snapper]

What would be the metabolic intermediate of this kind of skeleton (benzofuran?) ?
SWIM thinks that besides MAOI cleaving the arm of short chain N-substitutions, the next natural point of attack would be the nitrogen of the indole. If an oxygen were in it's place, could it end up as a free radical or maybe an aldehyde ? Not that this is necessarily a problem in low doses, but it could be more toxic than an amine (once furan is cleaved).