drone 342
Member posted 12-03-98 11:13 PM
--------------------------------------------------------------------------------
Oh yes, yes, yes! I've been talking about it for a while, and I've been hoping someone would want to discuss this. There have been 2-napthalene isopropylamines, benzofurans, thianapthalenes, pyridines, and everything you can think of. The benzofuran and thianapthalene ones look the most fascinating to me. Which ones would you like info on?
-drone #342
Beagle
Member posted 12-04-98 01:49 AM
--------------------------------------------------------------------------------
Thianaphthene and benzofuran definately sound interesting. The nice part about these cpds is that rotating the point of attachment of the alkyl chain around the ring gives some interesting points to compare. When the chain is at the 3 position you have a tryptamine analog, when you move it over to the 5 or 6 position you have more of a MDA analog.
But all of the compounds you mentioned interest me. Do you know any particulars?
Beagle
Member posted 12-05-98 09:36 AM
--------------------------------------------------------------------------------
When I was checking to see what kinds of precursors for these cpds are commercially avial., I came across this item at Aldrich #357839: 1,5,6,7-Tetrahydro-4H-indol-4-one 98% 5g/31$. Cool, huh. Thats got to be the cheapest, easiest precursor to psilocin and other 4-OH indoles I've ever seen. Aromatization would be simple. I've always wondered about 4-OH-MIPT...
Beagle
Member posted 12-05-98 09:38 AM
--------------------------------------------------------------------------------
When I was checking to see what kinds of precursors for these cpds are commercially avial., I came across this item at Aldrich #357839: 1,5,6,7-Tetrahydro-4H-indol-4-one 98% 5g/31$. Cool, huh. Thats got to be the cheapest, easiest precursor to psilocin and other 4-OH indoles I've ever seen. Aromatization would be simple. I've always wondered about 4-OH-MIPT...
Lilienthal
Member posted 12-05-98 12:54 PM
--------------------------------------------------------------------------------
Welcome to the tryptamine fan club, beagle. If you are interested in discussing the OH-indole synthesis, please start a new topic (for short: your substance is cheap at Aldrich, but it's much cheaper and very easy to synthetize on your own. I heard of someone doing it. See Het. 22, 2313 1984).
Back to non-tryptaminic heterocyclic analogues: I had these dreams some years ago. Let's look into my old files:
(1) Here two scientists write about their heroic self experiments: "...and there can be no doubt that the 2-thienyl- and 2-furyl isopropylamines are relatively ineffective central nervous system stimulant...". What a pity!
(2) gives the synth of 5-substituted 2-thienyl isopropylamines from aldehydes: H, Br, I.
(3) gives the synth of 2-thienyl isopropylamine from aldehyde.
(4) Gives cool data and synth. of 3/4/5-Cl-substituted 2-thienyl isopropylamines (MAO inhibition, 5-HT decrease time course, 5-HT uptake inhibition time course. They look very neurotoxic.
(5) shows a method for 5-iodination of 2-thienyl derivatives
I heard of someone synthetizing 3-MeO-2-isopropylamino naphtalene as an DOx-analogue. It was tested up to 15 mg without noticeable effects. But a nice synthesis, starting with a perfumery compound.
Glennon wrote in (6) about 2-isopropylamino naphtalene, which has medium affinity to 5-HT2 receptors. But he gave no concrete data or refs. He somethere else wrote about it, but I can't find it at the moment. Beagle, maybe you could give us some infos.
(1) J. Pharm. Exp. Ther. 72, 265 1941
(2) J. Med. Chem. 35, 280 1992
(3) J. Pharm. Exp. Ther. ?, 807 1950
(4) J. Med. Chem. 21, 979 1978
(5) Tet. Lett. 36, 4883 1995
(6) J. Med. Chem. 30, 1 1987
Beagle
Member posted 12-07-98 01:04 PM
--------------------------------------------------------------------------------
Lilienthal: I have no idea how I managed to miss your reply for 2 days, but it certainly was a pleasant surprise to open this thread and find it. Thanks, I'm glad you are here!
Too bad about thienyl and furan analogs. Do you know how high a dosage was assayed. The fact that they are not valid stimulants certainly doesn't mean that methoxy analogs aren't worth looking at. I really get a thrill reading old articles like this where a chemist could synthesize a compound then describe what it tasted like after eating some him(her)self. And then go on to do self experimentation w/o being looked on as a leper.
I figured that the thienyl analog would have some toxicity. Seems pretty standard for any cpd. w/ thienyl ring.
I don't know anything about naphthyl analog that you mention, but am looking forward to checking out the refs you mention. Interesting about 3-MeO-2-naphthyl cpd.
I like the idea of the tryptamine fan club. New thread to come...
Lilienthal
Member posted 01-05-99 04:18 PM
--------------------------------------------------------------------------------
I posted the nearly complete list of references on the 4-OH-indole synthesis via 4-oxo-4,5,6,7-tetrahydrobenzofurane (4-OTHB) and 4-oxo-4,5,6,7-tetrahydroindole (4-OTHI) on the DMT-BB (DMT Related Chemistry / "my personal favorites: 4-hydroxy tryptamines" / Lilienthal 01-05-99).
All times are CT (US)
next newest topic | next oldest topic
Administrative Options: Close Topic | Archive/Move | Delete Topic
Hop to: Select a Forum or ArchiveList of Forums:General DiscussionAcquisition DiscourseChemistry DiscourseMethods DiscourseNovel DiscourseCrystal MethSerious Chemistry ForumThe Hive CouchSerious Tryptamine DiscourseAdmin Chill-out TentList of Archives:Couch ArchivesClassics!Law and OrderThe litter box.misc. PEAs
Contact Us | the Hive
Powered by: Ultimate Bulletin Board, Version 5.39a
© Infopop Corporation (formerly Madrona Park, Inc.), 1998 - 1999.
Journal of Pharmaceutical Sciences, 68(5), 591-595 (1979) (https://www.thevespiary.org/rhodium/Rhodium/pdf/heterocyclic.amphetamines.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/heterocyclic.amphetamines.pdf)(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/djvu.gif)
Pharmacology Biochemistry & Behavior 38(3), 581-586 (1991) (https://www.thevespiary.org/rhodium/Rhodium/pdf/nichols/nichols.amphetamine-sar.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/nichols/nichols.amphetamine-sar.pdf)J. Med. Chem. 25, 535-538 (1982) (https://www.thevespiary.org/rhodium/Rhodium/pdf/nichols/nichols-2-amino-1.2-dihydronaphtalene.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/nichols/nichols-2-amino-1.2-dihydronaphtalene.pdf)