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Psychoactive Lichen!!!...Novel Entheogen needs Research!

Migrated topic.
..thanks for the drawing Hyperspace Fool, can you post another cool one..?:)
and thanks also for the photo & botany Tordyveln..

Hvalfangeren wrote:
I will also pick alot of different color variations from the Xanthaparmelia conspersa to test the various acids and theyre potancy;
2. (1) Marg K+ yellow–beige (fumarprotocetraracid) . . . . . 3. X. protomatrae
2. Marg K+ red (salazinacid) . . . . . 4. X. stenophylla
Marg K+ yellow–orange or red(stictinacid, ± norstictinacid) . . . .
Click to expand...

..great to see some reagent action! thanks..:) perhaps the Norwegian/Russian Sticta/Lobaria spp. can be chemically transformed by brewing process..? good to know they're not toxic...
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..hey, i just noticed that Xanthoparmelia (or Parmelia) furfuracea was found to contain:
0.63% methyl-ß-orcinolcarboxylate & atranorin and 1.13% 5-chloroatranorin [Caccamese et al. 1985 Journal of Neuro Pharmacology 48(1)]

P. conspersia (or X. conspersia) contained , as well as usnic acid, salazinic, stictic and norstictic acids, but doesn't appear to have been tested for alkaloids..

Parmelia sulcata has been reportedly used to treat 'cerebral maladies' in India [Kumar & Upreti 2001] and during the Middle Ages in Spain to treat 'disorders of the brain' ..4-5 other Indian parmelias are used as soporifics and sedatives, and to treat headache..[Voogelbreinder 2009 p.262]

at this stage, i think smoking would be the safest bio-assay method of parmelia spp..
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ps heres a little on methyl-ß-orcinolcarboxylate & related alkaloids:
Structure of 2-methoxy methyl -orcinol carboxylate (methyl 4-hydroxy-2-methoxy-3,6-dimethylbenzoate)
and
1,3,7-TRIMETHYLGUANINE FROM THE LICHEN STEREOCAULON
RAMULOSUM Vila et al_
the latter paper shows various structures of lichen compounds from Stereocaulon ramulosum, ..some anti-oxidant activity found..
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Very interesting info nen888! The substances you list are not alkaloids, as they don't contain any nitrogen. Interesting nonetheless, I wonder what the most active ones are, and if an extraction could be worthwhile. Maybe one that removes the usnic acid. I will look into this soon myself, when I'm done with the first stage of my project on Phalaris grass.
 
Okay, I made a collection of all (?) the information we have gathered on psychoactive lichens and liverworts thus far. Most of this is copy and paste, with some additional research as well.

Parmelia family syn. Xanthoparmelia
  • Whole family active as sedatives?
  • They all contain usnic acid, an antimicrobial that has been used as a weight-control medication. Usnic acid is toxic to elk, and in humans it is reported to induce liver toxicity after prolonged oral use and/or very large doses.
  • Best bet would be to find what the active substances are (can we remove the usnic acid?), and make an extract - "lichen hash". Here's several articles on usnic acid.

    Parmelia conspersa
  • Traditionally used by the Pima and Papago of South Arizona and North-West Mexico.
  • Ginkgo reports that the effects are similar to cannabis, although not quite. Effects lasts maybe two hours, and not very potent.
  • ۩ reports that it is highly active and on par with good cannabis, see the post below. Personal differences or difference in content of active constituents?
  • Contains usnic acid, salazinic acid, stictic acid and norstictic acid.

    Parmelia molliuscula
  • Used by natives in Canadian Rocky Mountains as a narcotic.

    Parmelia cirrhata
  • Used in India to produce the drug 'chharila', an Ayurvedic aphrodisiac, analgesic & calmative.

    Parmelia furfuracea
  • 0.63% methyl-ß-orcinolcarboxylate & atranorin and 1.13% 5-chloroatranorin.

Parmotrema menyamyaense
  • Known as rock blooms and sold in many ethnobotanical shops.
  • Said to be psychoactive and to increase the potency of psychedelics.

Collema family
  • The family with the fabled Icelandic hallucinogenic lichen?
  • In Collema flaccidum and Collema fuscovirens, insignificant small amounts of bufotenine and 5-Hydroxy-N-methyltryptamine have been found, at top respectively 14.2 μg (0.0000142%) and 18.3 μg per 100 g (0.0000183%). Collema cristatum and Collema callopismum were devoid of these alkaloids, but had some tryptophan, tryptamine and serotonin.
  • The fact that the enzymes for bufotenine and other tryptamines synthesis are present may mean that other species in this family, or special growing conditions, produce high enough quantities for it to be active.

Dictyonema family
  • An unidentified species of this family, possibly Dictyonema sericeum, is used in an infusion by the Huaorani of the Amazon jungle of Ecuador. Reported to cause intense hallucinations, supposedly used for malevolent shamanism, and to cause sterility (!). Could be typical western fear for indigenous people and their culture.

Nephroma articum
  • An infusion of this lichen is used in Alaska and West Canada to give strength to someone in a weakened state.

Lobaria pulmonaria syn. Sticta pulmonaria
  • Used to increase appetite, combat asthma, and as anti-inflammatory.
  • Reports of highly intoxicating beer brewed with this lichen from Siberia and Russia.
  • Contains stictic acid, desmethyl stictic acid, gyrophoric acid, tenuiorin, constictic acid, norstictic acid, peristictic acid, and methylnorstictic acid.

Gymnocolea inflata - liverwort
  • Traditionally used as a vomit-inducing drug. One secondary source says it is active as a hallucinogen.
  • Contains the bitter diterpenoid gymnocolin A, which causes vomiting. May be hallucinogenic, like salvinorin A (see post below).

Radula family - liverwort
  • 172 species covering next to all areas with moderate humidity and moderate to subarctic temperatures.
  • At least three species contains the cannabinoid (!) perrottetinene and related substances.

    Radula marginata
  • Found to contain 0.56% of the cannabinoid perrottetinene and 0.087% of perrottetinenic acid, with unknown potency at cannabinoid receptors.
  • Said to be active, but not very potent.
  • Endemic to New Zealand.

    Radula perrottetii
  • Also contains perrottetinene.
  • Endemic to Japan.

    Radula laxiramea
  • Also contains perrottetinene.
  • Endemic to Middle America.

Lycopodium clavatum - clubmoss
  • Contains 0.1-0.2% alkaloids, lycopodin and many relatives.
  • Active, likely acetylcholinesterase inhibititor and NDMA antagonist, but may be poisonous, especially in large doses.
  • Used medicinally for a broad range of purposes, but not commonly used.

Additional species

Peace! Let me know if I've missed something... (Of course I have)

:)
 
Ginko! Thank you so much!

My only concern is this: "Effects lasts maybe two hours, and not very potent."

I smoke high quality medicinal cannabis. Usually GDP when I can afford it. It's very strong stuff! With that said, I was absolutely FLOORED by a bong bowl of P. Conspersa. I didn't even want to move I was melted/giddy, even more couchlocked than I would be from smoking GDP. So personally I would suggest changing this to something more along the lines of "On par with good cannabis" which is rather remarkable but from my perspective is true.


During the experience I made an effort to try and differentiate the fx between what I was feeling then, and cannabis (which I have used almost daily for 11 years) and I really couldn't put my finger on it. This was highly amusing at the time! I would love to hear about others' experiences with it.
 
Wonderful to hear, thanks! Will have to try the lichen again later.

On the subject of Gymnocolea inflata, I found an article stating that the bitter substance that causes vomiting is a diterpenoid called gymnocolin A. I thought I recognized the structure from somewhere, and indeed, the diterpenoid salvinorin A is kinda similar. Maybe it has a similar activity, as the liverwort is reported to cause hallucinations?

gymnocolinsalvinorin.png
 
thanks again Ginkgo, the chemical plot thickens..

۩ wrote:
During the experience I made an effort to try and differentiate the fx between what I was feeling then, and cannabis (which I have used almost daily for 11 years) and I really couldn't put my finger on it. This was highly amusing at the time! I would love to hear about others' experiences with it.
Click to expand...
wow! not many plants/substances that this can be said of..remarkable...
 
..still haven't been able to find a substance category to put these things in..

Methyl-ß-orcinolcarboxylate is also known as METHYL 2,4-DIHYDROXY-3,6-DIMETHYLBENZOATE or Atraric acid, it's also sold commercially as a 'flavour/fragrance', it was first isolated in 'oak moss' Evernia prunastrii

Atranorin, is a really interesting looking 'thing', it's also found in the S.E. Asian tree Hopea sangal (Dipterocarpaceae)
here is it's structure:
 

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  • Atranorin.jpg
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Thanks! And special thanks to PsilocybeChild, a cannabionoid (!) from liverworts is very interesting. First occurrence of cannabinoids except in Cannabis spp. and in humans. I've updated the list with additional information. Radula spp. is common throughout most of the world.

perrottetinenethc.jpg
 
Well liverworts are a huge class of many different genuses and close to 10 000 different species. The Radula genus is big itself, with at least 172 members. You could take a look at this webpage, with maps of some observations. Generally the genus is spread throughout most of the world, with several species covering Europe, Asia and parts of USA. The genus seems to in large parts avoid tropical and very hot areas, enjoying moderate temperatures and moderate humidity, and many also enjoys sub-arctic conditions.

Take note that the three mentioned species - Radula marginata (New Zealand), Radula perrottetii (Japan) and Radula laxiramea (Middle America) - are the only ones known to contain perrottetinene. Other species may also be active, although I doubt they all are, but I find it hard to believe that only 3 out of 172 species are active. Only one way to find out! :)
 
Awesome picture! That's a cup lichen or Cladonia spp., looks to me like Cladonia stellaris, possibly Cladonia arbuscula. It is important as food for reindeers, but is not psychoactive. Have some antibiotic compounds though.
 
..hey, just to try and help your commendable organisation thanks Gingko:)
other lichens with parmelia type compounds:
Stereocaulon ramulosum (Bolivia) - 1,3,7-trimethylguanine, perlatolic acid , methyl β-orcinolcarboxylate , atranorin and galactitol.
Everniastrum cirrhatum - methyl β-orcinolcarboxylate (anti-oxidant, anti-viral & bacterial, anti-cancer)

the Japanese lichen Solorina crocea contains Norsolorinic acid, found to be a Monoamine oxidase inhibitor [Okuyama et al 1991]

and Atranorin (in var. parmelias) has been found to be a Trypsin inhibitor (Trypsin hydrolyses peptides into amino acids in the intestine)

nice pic thanks Hyperspace Fool...

& thanks PsilocybeChild! the cannabinoid liverwort thing is begining to sink in..:surprised
 
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