Natural 2,4,5 phenethylamines

[eloil]

Hi, I'm new here.

Does anyone know examples of naturally occurring 2,5 or 2,4,5-substituted phenethylamines? I came across an article that mentions an interesting-sounding one in a bryozoan from around Tasmania, Amathia wilsoni. The formula is pretty similar to that of 2C-B: 2,4-dibromo-5-MeO-phenethylamine.

I wonder how many of the 2C series are out there in living things waiting to be discovered. Personally I think at least 2C-B, 2C-M and 2C-H are going to turn up sooner or later for sure.

A β-Phenylethylamine-Derived Possible Biosynthetic Precursor to the Amathamides, Alkaloids from the Bryozoan Amathia wilsoni
Journal of Natural Products, 52(2), pp. 436-438

 

[egor]

^^ what is 2c-m?
I have never heard of that one. Did you mean 2c-d?

 

[organicmusic]

What is your reasoning that those specific chemicals will be found?
Their effects, or their chemical make up?
i'm curious.
interesting thoughts

 

[Morninggloryseed]

2C-N, no way. After seeing this, I guess 2C-B is possible. Doubtful 2C-D.

 

[eloil]

^^ what is 2c-m?
I have never heard of that one. Did you mean 2c-d?

That is the one I meant, yes. I'm a bit fuzzy on the stuff in PIHKAL as someone borrowed my copy years ago and lost it.

My thinking on finding 2C-D and 2C-H in nature is just that there is a lot still to be discovered and different arrangements of methyls and methoxies on rings seem to come cheap. 2C-I is possible too as iodine turns up in marine alkaloids sometimes. I think the 2,4,5 isomer of mescaline is a possible find also. I found one report of an alkaloid with the 2,4,5-trimethoxy pattern on a phenyl group, 'buesgeniine':

A new benzophenanthridine alkaloid from Zanthoxylum buesgenii
Fitoterapia 76 (2005) 656–660

Here's a review of bromo and iodo marine alkaloids with lots of structures:
Bromo- and Iodo-Containing Alkaloids from Marine Microorganisms and Sponges
Russian Journal of Bioorganic Chemistry, Vol. 28, No. 3, 2002, pp. 170–182

 

[eloil]

Here's another alkaloid that's closer to the 2,4,5 isomescaline:

Reported in Australian plants of the Rutaceae family: Acronyohia baueri and Melicope fareana.

Alkaloids of the Australian Rutaceae. The Structure and Reactions of Acronycidine
Australian Journal of Scientific Research 3(1) 155 - 171

 

[eloil]

Here's a weird substituted DMT from another marine Amathia, A. convoluta:

Convolutindole A and Convolutamine H, New Nematocidal Brominated Alkaloids from the Marine Bryozoan Amathia convoluta
J. Nat. Prod. 2002, 65, 938-941

 

[Acyl]

http://www.erowid.org/archive/rhodium/chemistry/yadontsay/index.html

 

[kakti]

Thanks for the link Acyl, don't know how I've never seen that before

 

[Acyl]

Yeah I just ran into it yesterday actually, I wasted quite a bit of time looking around heh.

 

[Tribe]

TMA-2 is 2,4,5-trimethoxyamphetamine, from the pihkal reports it seems to be mild at low doses, but possible +3 at 40mg

quote from pikhal

with 40 mg) Beautiful plus 3. Some visuals, but not intrusive. Moderate, good-mannered kaleidoscopic imagery against dark. Music superb. Clear thinking. Calmly cosmic. This is a seminal, or archetypal psychoactive material. A very good experience and good for repeats. About 10-12 hrs. Sleep difficult but OK.

could possibly be fun! lol