indole alkaloids and flavonoids in peanut skins

[entheogenic-gnosis]

When I was young I read in "the anarchist cookbook" that if you collected the skins off of peanuts and smoked them some sort of intoxication would result.

...and just like "bananadine" (smoking banana peels) I assumed that there was nothing to it, maybe a crude joke or simply an underground myth of sorts, which it is, don't get me wrong, but I found it interesting that these peanut skins actually contain two indole alkaloids ( 2-methoxy-3-(3-indolyl)-propionic acid and 2-hydroxy-3-[3-(1-N-methyl)-indolyl]-propionic acid) as well as 8 flavonoids.

Now, I'm not saying there's anything psychoactive here, but was simply amused that there actually were alkaloids in peanut skins.

Abstract
Separation of the water-soluble fraction of peanut skins led to the isolation of 8 flavonoids and two novel indole alkaloids. Two new flavonoid glycosides have been identified as isorhamnetin 3-O-[2-O-beta-glucopyranosyl-6-O-alpha-rhamnopyranosyl]- beta-glucopyranoside and 3',5,7-trihydroxyisoflavone-4'-methoxy-3'-O-beta-glucopyranoside. Two alkaloids are 2-methoxyl-3-(3-indolyl)-propionic acid and 2-hydroxyl-3-[3-(1-N-methyl)-indolyl]-propionic acid. These isolated flavonoids were evaluated for their free radical scavenging activity and protein glycation inhibitory effects.

Alkaloids and flavonoids from peanut skins - PubMed

Separation of the water-soluble fraction of peanut skins led to the isolation of 8 flavonoids and two novel indole alkaloids. Two new flavonoid glycosides have been identified as isorhamnetin 3-O-[2-O-beta-glucopyranosyl-6-O-alpha-rhamnopyranosyl]- beta-glucopyranoside and...

www.ncbi.nlm.nih.gov

I'm no fan of these urban drug myths, and I'm not trying to generate confusion or spread misinformation, but I enjoy researching how some of these myths begin, and though there's nothing psychoactive here, I was fascinated that there was something chemical here...

-eg

 

[Auxin]

Odd that they call them alkaloids, classically they would not be considered alkaloids.
That indole nitrogen is so weak that in order to get them to form hydrochlorides the compounds would have to be dissolved in anhydrous ether and gassed with anhydrous hydrogen chloride under nitrogen or argon, and then exposure to just moist air would decompose them :lol:

Its quite likely, however, that they are specialized auxins made from tryptophan by an unusual biosynthetic route.
Mmmm, sexy auxins.

Smoking [unsalted] peanut skins isnt quite an urban myth. As a early teen I smoked them straight and made extracts to smoke, it is active its just among the weakest of the 'legal highs' to the point that if ones brain is pickled in THC it may not be perceptible.
As a 14 year old, after finding them weakly but distinctly active, I was curious if it was just smoking anything could give those minor effects so I tried smoking dried dandelion leaves. Those were not active (its too bad, ay)

 

[kerelsk]

Bananas do contain serotonin, dopamine, and norepinephrine, so they are not devoid of alks.

I wish I could find this forum post where someone detailed the interesting chemistry of banana peels and how it related to the smoking banana peal myth...

 

[entheogenic-gnosis]

Odd that they call them alkaloids, classically they would not be considered alkaloids.
That indole nitrogen is so weak that in order to get them to form hydrochlorides the compounds would have to be dissolved in anhydrous ether and gassed with anhydrous hydrogen chloride under nitrogen or argon, and then exposure to just moist air would decompose them :lol:

Its quite likely, however, that they are specialized auxins made from tryptophan by an unusual biosynthetic route.
Mmmm, sexy auxins.

Smoking [unsalted] peanut skins isnt quite an urban myth. As a early teen I smoked them straight and made extracts to smoke, it is active its just among the weakest of the 'legal highs' to the point that if ones brain is pickled in THC it may not be perceptible.
As a 14 year old, after finding them weakly but distinctly active, I was curious if it was just smoking anything could give those minor effects so I tried smoking dried dandelion leaves. Those were not active (its too bad, ay)

"Alkaloid" is actually a bit more broad of a term than most realize, and there is often dispute involving this classification and the prerequisites for placement in it.

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From Wikipedia:

Compared with most other classes of natural compounds, alkaloids are characterized by a great structural diversity and there is no uniform classification of alkaloids.[32] First classification methods have historically combined alkaloids by the common natural source, e.g., a certain type of plants. This classification was justified by the lack of knowledge about the chemical structure of alkaloids and is now considered obsolete.[5][33]

More recent classifications are based on similarity of the carbon skeleton (e.g., indole-, isoquinoline-, and pyridine-like) or biochemical precursor (ornithine, lysine, tyrosine, tryptophan, etc.).[5] However, they require compromises in borderline cases;[32] for example, nicotine contains a pyridine fragment from nicotinamide and pyrrolidine part from ornithine[34] and therefore can be assigned to both classes.[35]

Alkaloids are often divided into the following major groups:[36]

"True alkaloids", which contain nitrogen in the heterocycle and originate from amino acids.[37] Their characteristic examples are atropine, nicotine, and morphine. This group also includes some alkaloids that besides nitrogen heterocycle contain terpene (e.g., evonine[38]) or peptide fragments (e.g. ergotamine[39]). This group also includes piperidine alkaloids coniine and coniceine[40] although they do not originate from amino acids.[41]
"Protoalkaloids", which contain nitrogen and also originate from amino acids.[37] Examples include mescaline, adrenaline and ephedrine.

Polyamine alkaloids – derivatives of putrescine, spermidine, and spermine.
Peptide and cyclopeptide alkaloids.[42]

Pseudalkaloids – alkaloid-like compounds that do not originate from amino acids.[43] This group includes terpene-like and steroid-like alkaloids,[44] as well as purine-like alkaloids such as caffeine, theobromine, theacrine and theophylline.[45] Some authors classify as pseudoalkaloids such compounds such as ephedrine and cathinone. Those originate from the amino acid phenylalanine, but acquire their nitrogen atom not from the amino acid but through transamination.[45][46]

Some alkaloids do not have the carbon skeleton characteristic of their group. So, galantamine and homoaporphines do not contain isoquinoline fragment, but are, in general, attributed to isoquinoline alkaloids.
-Wikipedia

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As for smoking peanut skins, it's not my place to say you did not experience something, but chemically it seems doubtful that anything contained in peanut skins could produce any mind altering effects. I always try to be very polite when these things come up, because I don't know from first hand experience, but I think it's very doubtful there's anything to the "peanut skin intoxication" myth.

The general consensus in the psychedelic community is that the "smoking peanut skins" myth is complete nonsense, a fabrication, possibly a bit of honest misinformation, but nonsense none the less, similar to "bananadine" (which involved some work, skinning bananas, obtaining a special part of the peel, and baking it in an oven to obtain a black powder, which is smoked, again, this is completely bogus) www.erowid.org says it nonsense, but since that question was worded using the word "peanut shell" not "skin", I'm not posting the response from that site here, though the anarchist cookbook was cited for starting the rumour in that response, and in this link Purported legal highs it claims that any felt alterations in consciousness are purely psychosomatic, a placebo effect.

I have never tried this, and honestly do not see any reason to further investigate any purported psychoactivity.

...Though the indole compounds in the peanut skins are interesting from a chemical perspective, fairly novel.

Though I'll admit I'm not familiar with these compounds, and have only begun to briefly research them, honestly it's fairly low priority study, it's interesting though.

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Auxins interest me as well, specifically indole-3-acetic-acid, which is a plant root growth hormone, Indole-3-acetic acid (IAA) has been identified as the major in vivo metabolite of DMT as well, which caught my attention, also IAA can be used as a starting point to synthesize N,N-dimethyltryptamine.

2-phenylacetic acid was another auxin that caught my attention, but only because of my interest in phenethylamine compounds and their chemistry.

...fascinating stuff.

-eg

 

[Auxin]

Well its not quite fair to compare it to bananadine and say it must therefore be a myth.
Lets look at your statement here...

As for smoking peanut skins, it's not my place to say you did not experience something, but chemically it seems doubtful that anything contained in peanut skins could produce any mind altering effects. I always try to be very polite when these things come up, because I don't know from first hand experience, but I think it's very doubtful there's anything to the "peanut skin intoxication" myth.

And paraphrase it to match the statements of dozens of people just a few years ago here...
'As for Salvia divinorum, it's not my place to say you did not experience something, but chemically it seems doubtful that anything contained in Salvia divinorum could produce any mind altering effects. I always try to be very polite when these things come up, because I don't know from first hand experience, but I think it's very doubtful there's anything to the "Salvia divinorum intoxication" myth.'

 

[entheogenic-gnosis]

Comparing peanut skins to salvia divinorum is an unfair comparison.

Salvia divinorum was a known enthonobotanical with a long history of human use in Mexico by the mazatec and other people's of the region. Salvia divinorum was a known entheogen and was known to be shamanically important. there was never any dispute that there was something going on with salvia divinorum, it was just very difficult to pin-point exactly what it was that was going on. The traditional methods of consumption were not well known, and some work needed to be done in that area as well. When it came to chemical analysis there were no alkaloids found, which was another set back to researchers, but not a real problem.
(Marijuana' s active compound THC, which is not an alkaloid or an amine, and like salvinorin-a it contains no nitrogen, both compounds (salvinorin-a and THC) are diteroeniod hydrocarbons, however salvinorin-a is a kappa opioid receptor agonist while THC is a cb1 + cb2 receptor agonist...I only mention THC because it's a great example of how plants that do not contain alkaloids can still be very active, plus it shares a mild relation in chemical structure to THC)

Now, the first record of human use of "peanut skins" as a mind altering substance comes from the 1971 publication of "the anarchist cookbook" by William Powell, who admits that the "peanut skins" entry was based on second hand anecdotal reports supplied to him by a friend, he also admits to never having personally tried smoking peanut skins. Furthermore very detailed chemical analysis has been preformed on peanut skins, and to date not a single mind altering compound has been identified.

It's very possible that Mr. Powell, as an anarchist published these things to mess with the establishment, and to possibly provoke fear based knee-jerk legislation banning peanuts and bananas as drugs, hence exposing the hypocrisy and soft-handedness related to making plants illegal...Or it may have been honest disinformation passed to him from a friend, who knows.

I compare bananadine and peanut skins because they share the same source (they are even on the same page), "the anarchist cookbook" and because they are both nonsense. The anarchist cookbook 1971 publication was full of misinformation and mistakes, so I feel my initial comparison was fair.

Again, it's not my place to say what you have experianced, and I did not mean to come off as rude in any way or offend you, it's just my personal opinion that the "smoking peanut skins" is a piece of early 70s urban drug mythology and should be taken with a grain of salt, I seriously doubt that there is anything to it at all, it's total nonsense.
(This is also the general consensus in the psychedelic community)

-eg

 

[Morris Crowley]

there was never any dispute that there was something going on with salvia divinorum, it was just very difficult to pin-point exactly what it was that was going on.

Not to run off on a tangent, but there was indeed significant dispute that there was anything going on with Salvia divinorum until the late '80s to early '90s, when Blosser discovered a reliable quid method and Siebert confirmed psychoactivity of salvinorin A.

Sure, there was a burst of interest in the late '60s, and it became part of the psychedelic canon that the plant was a shamanic inebriant, simply because Gordon Wasson said so. But in terms of actual psychoactivity, the only support came from some very tepid firsthand accounts from Wasson and some friends and family. If you actually read the accounts, they read like placebo. And in subsequent years, most people who tried the plant (including Sasha Shulgin) had no success achieving any effects.

By the mid-'80s, Wasson had convinced himself that the effects he reported were probably his imagination, and that there was nothing interesting to be found in the plant. This is recorded in a letter (later published in the Entheogen Review) from Wasson to Leander Valdés, who sought Wasson's advice when he began considering S. divinorum as a thesis subject.