THIQs and Related Analogues

[Doctor Abalaba]

Isoquinolines can have the capacity of psychoactivity. I am a graduate student attempting to study Neuropharm (general toxicity). I've gone through the databases and found a few CNS compounds. I want to know if anyone knows of compounds, specifically psychoactive tetrahydroisoquinolines.
Any ideas?

 

[LuxEtVeritas]

i believe a search may help ya

 

[Ham-milton]

There's that one that replaces cocaine; TDIQ, I think?

What about methopholine and the 4'-nitro version.

 

[Doctor Abalaba]

I am not a proficient chemist so when I search for info on these esoteric compounds I'm limited to the few synonyms I may know.
Thus far my research has led me to berberines, hydrocotarnines, and 5,6,7-trimethoxyIQs.
Some IQs are MAOa/b inhibitors, some act on 5ht7 receptors. I'm mainly interested in potential serotonergic agents.

 

[Ham-milton]

In that case, I'm not aware of any.

I don't think the hydrocotarnines have any appreciable serotonergic nature; most were sigma agonists, no?

 

[Doctor Abalaba]

Yeah, I hadn't found anything useful about hydrocotarnine, but it looks to have potential as parent compound. A methylenedioxy group coupled to a benzene ring. There must be some analogues with interesting additions.

Also, finding no activity can be as valuable as finding activity.

Thanks for the help though.

 

[Ham-milton]

It definitely has activity, but I'm nearly certain it's a sigma agonist, it's abused occasionally.

 

[(zonk)]

1-aryl-1,2,3,4-THIQs are supposed to be NMDA antagonists/dissociatives. Listed in PCP related papers as benzo(f)quinones

 

[fastandbulbous]

Nomifensine, but it comes with a load of nasty side effects (like death if you're really unlucky). I'd be tempted to blame the aromatic amine function rather than the tetrahydroisoquinoline structure though

 

[Doctor Abalaba]

Thank you very much. Ill be looking in to these.
Anybody know anything about N-Methylushinsunine?

 

[Ham-milton]

These might be useful. Oliveroline is another name for the N-desmethyl version.


Inhibition of the G2 DNA damage checkpoint by oliveroline isolated from Duguetia odorata.
HC Brastianos, CM Sturgeon, M Roberge, RJ Andersen
Plant extracts obtained from the U.S. National Cancer Institute's Open Repository collection have been screened for their ability to inhibit the G2 DNA damage checkpoint. An extract of Duguetia odorata showed promising activity in the assay. Bioassay-guide…
Journal of natural products. 2007 Feb
Norstephalagine and atherospermidine: two smooth muscle relaxant aporphines from Artabotrys maingayi
D Cortes, MY Torrero, M Pilar D'Ocon, M Luz Candenas, A Cavé, AH Hadi
Nine isoquinoline alkaloids have been isolated from the bark of Artabotrys maingayi: four noraporphines (norstephalagine, 3-hydroxynornuciferine, anonaine, and nornuciferine), one 7-hydroxyaporphine (ushinsunine), three oxoaporphines (atherospermidine, lir…
Journal of natural products. 1990 Mar-Apr
MICHELINE A FROM MICHELIA CHAMPACA LINN.
SK BANERJEE, RN CHAKRAVARTI
Bulletin of the Calcutta School of Tropical Medicine. 1964 Jul
Activity of the principal alkaloids of Polyalthia oliveri Engler (Annonaceac) on the central nervous system and the cardiovascular system
A Quevauviller, M Hamonniere
Polyalthia oliveri leaf alkaloid, oliveroline, shows in Mice antiparkinsonian properties which decrease or disappear with the alkaloïds extracted from the bark of the trunk, oliveridine and oliverine. The latter alkaloid has an antihypertensive effect whic…
Comptes rendus hebdomadaires des séances de l'Académie des sciences. Série D: Sciences naturelles. 1977 Jan 3
Screening of isoquinoline alkaloids and their derivatives for antibacterial and antifungal activities.
IL Tsai, YF Liou, ST Lu
A screening test of antimicrobial activities for some of the isoquinoline alkaloids and their first and second Hofmann elimination products was conducted in this study. Results showed that (+)-actinodaphnine (1), (+)-N-Me-actinodaphnine (2), (+)-anonaine (…
Gaoxiong yi xue ke xue za zhi = The Kaohsiung journal of medical sciences. 1989 Mar

 

[(zonk)]

wow, soundz like some sort of japanesish wordplay on 'sunshine'
Methylmichelalbine... Michel Albine. These are some wierd ass names maybe I'm trippin'.

Anyway I just remembered that shulgin discovered or atleast knows about cactus containing a 5HT psychedelic isoquinoline but I dont know the name, I dont recall if he ever even mentioned it's name but I hope that helps point u in the right direction... as4 MethylUshiSunshine...?

 

[Doctor Abalaba]

Big help! Thanks guys.

 

[FrostyMcFailure]

Isnt THIQ supposedly a perma-binding agent that is made in the body of any opiate addicts drinking alcohol or something similar?

 

[haribo1]

Some THIQs are supposed to be formed in the body when alcohol is metabolized wrongly. I think research into alcoholism has layed out this stuff as a possible culprit.

 

[Hammilton]

For the addiction/ I'm pretty sure that's been discounted (it's also seen in frequent users of opiates, not sure if it only applies to traditional opiates though)