Activity assumptions on some exotic tryptamines...

[Bandil]

Hi!

After a little stroll in the park, a friend of a friend found the following, somewhat interesting looking, compounds beneath the foliage   :

Let 'R' denote:
https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000492931-file_0b7q.jpg" title="View this image">

Let 'R1' denote:
https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000492931-file_lobs.jpg" title="View this image">

and

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000492931-file_o9bq.jpg" title="View this image">

These are the two compounds available in excess. Any idea if they are active or perhaps toxic etc.? How about dosage etc., if some evil person where to subject their birds to the compounds?

Hope you have some input - i sure think they look interesting  

Regards
Bandil

[Lilienthal]

Great for making antipsychotics or antihistaminics, but for nothing else if you ask me...

[Rhodium]

The 4-piperidone ethylene ketal might be used for novel fentanyl analogs. Dunno about possible activity though.

[_mu_]

[Nicodem]

Bandil, you can alkylate the piperazine-tryptamine with benzylchloride or p-methoxy-benzylchloride and you will get a sigma agonist, probably quite selectiver for sigma 2 receptor. A similar compound having two indol-3-yl-ethyl moieties attached on both sides of the piperazine was found psychoactive in animals already some 40 years ago. It is consistent with the SAR requirements for sigma 2 agonism as well as the above proposed benzylic version.
Anyway you can still acetylate it to block the basicity of the second piperazine nitrogen and check if the N'-acetyl compound has any serotoninergic activity. It would be very interesting nevertheless.

[obia]

off topic granted.. but I would suspect that tryptyl fentanyl would be at least as active as fentanyl give the benzyl nucleus can be extensively modified or can be replaced with a wide variety of heterocyclic structures with retention of activity. the benzene moety can even be replaced with a methyl ester without loss of activity. (remifentanyl)

[ning]

if you hydrolyzed the ketal and used "some method" to remove the carbonyl, giving you an piperidyltryptamine.
See

http://www.erowid.org/library/books_online/tihkal/tihkal52.shtml

Where the good doctor says:

 The piperidine material, pip-T, is made via the glyoxylamide (mp 182-183 ¡ÆC) which is reduced with LAH to the target amine (mp 149-150 ¡ÆC, HCl salt 220-221 ¡ÆC). The morpholine analogue also came to be via the glyoxylamide (mp 187-188 ¡ÆC) and the reduction to the amine which can be an oil, but which has been reported to have a mp 145-147 ¡ÆC. The only trials I know of with either of these is with mor-T which, as the fumarate salt, had no effects at all upon the i.m. injection of a 30 milligram bolus.

Perhaps, as a favor to the good doctor if nothing else, your friend should consider producing and bioassaying the aforementioned material, and reporting his/her findings