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Bananahuasca

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werver

Rising Star
A thought I came up with in my teenage years was the idea of bananahuasca. I believe everybody heard at some point that smoking banana peels would give you a high like mushrooms. But maybe that was just a local urban legend going on in my hometown. Since bananas contain serotonin in their peels however, I thought it would be a neat little idea to extract that and make a legal high from it, combinig it with a MAOI. My ego thought of itself as being very witty to trick the law by producing something both legal and definitely making high. Also I wanted to sell that stuff as a drink, but was already at that time worried about party people who would abuse it combined with alcohol.

Since I approached psychedelics again in my thirties the idea popped up again. I've learned about serotonin syndrome. So I'm pretty glad I didn't start this idea without the collective knowledge of the internet. And I learned that the tyramine content of the peels is said to give some people on ayahuasca headaches. So I did some more research and found that walnut contains a considerable amount of serotonin too, but without the tyramine alongside.

So I decided to cook up some rue and some walnuts to try it in a crude extract. I would have to look into my notes to see how much I really ingested, but I can already say that my first encounter had literally no effect. I believe it must have been around the equivalent of 300g of walnuts.

Still there is of course the danger of overdosing serotonin to a syndrome, but I wonder if anybody else had the idea of doing so. Everything I have heard about serotonin syndrom is connected to endogenous serotonin. But I believe following the gastrointestinal path is another thing than blocking the endoplasmatic reticulum and has a lesser risk of inducing serotonin syndrome. Since DMT is an endogenous tryptamine and there are people ingesting it, I do see it as something to be careful with, but not something to strictly stay away from. If in the end one or another alchemist chooses to include walnut extract in his brew or changa I would gladly give my younger self a little pat on the head for a nice little niche idea.

So is there somebody with experiences of bananas or walnuts related to ayahuasca or somebody with more info on serotonin syndrom (so far I've mostly heard about it in connection with SSRIs or MDMA and MAOIs, mostly the pharmaceutical irreversible ones)?

I'm interested in the discussion and don't have to push an agenda, since the law changed anyway and probably any drink containing harmines would be considered an illegal thing nowadays in my country.
 
The "bananadine" rumour was first published in the anarchist cookbook, it included a detailed technical procedure, but ultimately was complete non-sense, some hippie got a kick out of knowing he got a good deal of people to smoke banana peels by getting that piece of disinformation published, the other theory is that it was an attempt to scare the government inducing a knee-jerk reaction where the government would be making bananas out to be drugs.

Serotonin is a key neurotransmitter with many crucial functions.

Serotonin is not orally active because it has an open amine group which makes it amenable enzymatic deamination by mono amine oxidase enzymes. It also has a free hydroxy group at position 5, which acts as a polar hydrophyllic lump preventing passage beyond the blood brain barrier.

there is already serotonin present in your brain (and gut) right now, your brain can not function with out it.

Serotonin has no psychedelic or psychoactive potential. By consuming large amounts of serotonin, and then by preventing your bodies means of destroying it, you risk creating a toxic situation, serotonin syndrome.

Mono amine oxidase enzymes are enzymes which deaminate mono amines. By inhibiting these enzymes with an MAOI you are allowing mono amines to reach your system which would otherwise be neutralized enzamatically.

I think you are taking potential risks with absolutely no potential gain...

-eg
 
I already know about the problems of passing the blood barrier, this can be counteracted with MAOIs. Or maybe even safer by vaporizing it. Meddling with reuptake or breakdown does have additional dangers, that's very true.

The hydroxy group on the fith C-atom is basically the same like 5meoDMT as far as I understand. Or am I wrong?

There is already DMT present in your blood. And your system probably can't work without it. Still people decide to add more.

I know about the tyramine. That can be counteracted by either using walnuts or there might be a tek that serves as a workaround.

Serotonin syndrome has hallucinations as one of its symptoms. So to say serotonin isn't hallucinogenic seems not to be true.

After all, there are a lot of people inducing DMT syndrom on purpose here. And the symptoms resemble serotonin syndrom quite well. Try looking at a 5meoDMT experience like this through the eyes of a medic with no experience in entheogens and describe the symptoms!

Banana mead sounds nice, too. :) Is it as sweet as it sounds?
 
entheogenic-gnosis said:
The "bananadine" rumour was first published in the anarchist cookbook, it included a detailed technical procedure

Oh yes. We were 15 and followed it to the "T". :oops: 😁
 
DansMaTete said:
entheogenic-gnosis said:
The "bananadine" rumour was first published in the anarchist cookbook,
Wikipedia doesn't agree.

bananadine was featured in a New York Times Magazine article titled, "Cool Talk About Hot Drugs". -Wikipedia

Nonetheless, bananadine became more widely known when William Powell, believing the Berkeley Barb article to be true, reproduced the method in The Anarchist Cookbook in 1970, under the name "Musa sapientum Bananadine" (referring to the banana's old binomial nomenclature -Wikipedia

Looks like it was first featured in a new York Times article, but did not gain popularity until published in the anarchist cookbook.


Hmmm...looks like I got a piece of the motivation right:
Although the original hoax was designed to raise questions about the ethics of making psychoactive drugs illegal and prosecuting those who took them ("what if the common banana contained psychoactive properties, how would the government react?"),[3] Cecil Adams reports in The Straight Dope -Wikipedia

-eg
 
werver said:
I already know about the problems of passing the blood barrier, this can be counteracted with MAOIs. Or maybe even safer by vaporizing it. Meddling with reuptake or breakdown does have additional dangers, that's very true.

The hydroxy group on the fith C-atom is basically the same like 5meoDMT as far as I understand. Or am I wrong?

There is already DMT present in your blood. And your system probably can't work without it. Still people decide to add more.

I know about the tyramine. That can be counteracted by either using walnuts or there might be a tek that serves as a workaround.

Serotonin syndrome has hallucinations as one of its symptoms. So to say serotonin isn't hallucinogenic seems not to be true.

After all, there are a lot of people inducing DMT syndrom on purpose here. And the symptoms resemble serotonin syndrom quite well. Try looking at a 5meoDMT experience like this through the eyes of a medic with no experience in entheogens and describe the symptoms!

Banana mead sounds nice, too. :) Is it as sweet as it sounds?

Part of me doubts that this was a serious thread, and I am a little surprised that nobody else wants to chime in on this one, any way, I decided to respond regardless...

werver said:
I already know about the problems of passing the blood barrier, this can be counteracted with MAOIs. Or maybe even safer by vaporizing it. Meddling with reuptake or breakdown does have additional dangers, that's very true.

An MAOI would only counteract enzymatic deamination.

Parenteral administration still does not address the polarity of the free hydroxyl grouping at position 5.

werver said:
The hydroxy group on the fith C-atom is basically the same like 5meoDMT as far as I understand. Or am I wrong?

Yes. You are wrong.

5-methoxy-DMT has a methoxy grouping at position 5, not a hydroxy grouping as is the case with serotonin, and no, it's not the same at all.

A methoxy grouping would counter the polarity restrictions of the free hydroxyl grouping.

( let's take serotonin, and say we put a methyl grouping on the alpha carbon of the ethylamine side chain to protect the amine grouping from enzymatic deamination, then let's take a methyl group and place it on the free hydroxy group on position 5 so it could counter the the polarity restriction, allowing the compound to pass beyond the blood brain barrier. at this point you would have a psychedelic molecule (alpha-o-dimethyl-serotonin ; 5-meo-AMT ) )

werver said:
There is already DMT present in your blood. And your system probably can't work without it. Still people decide to add more.

the DMT present n your body is in miniscule amounts, where it likely serves as the endogenous ligand to the "orphan" sigmar-1 receptor.

People "decide to add more" because DMT possesses unique pharmocological properties which induce an altered state. Serotonin does NOT possess these pharmocological properties.

werver said:
Serotonin syndrome has hallucinations as one of its symptoms. So to say serotonin isn't hallucinogenic seems not to be true.

Serotonin is not a hallucinogen, if you have hallucinations as you are dying from toxicity of the compound, it's different than the pharmacology of the compounds inducing psychedelic hallucination.

Serotonin is not a psychoactive, at least not in a recreational sense, it is already in your brain where it serves as a neuromodulater and neurotransmitter, flooding your system with serotonin will not produce any psychoactive effects in a recreational sense.

werver said:
After all, there are a lot of people inducing DMT syndrom on purpose here. And the symptoms resemble serotonin syndrom quite well. Try looking at a 5meoDMT experience like this through the eyes of a medic with no experience in entheogens and describe the symptoms!

There is no such thing as "DMT syndrome"

I think you may be misinterpreting these reports of 5-meo-DMT as well as serotonin syndrome. In my opinion they are nothing alike, and any similarities are coincidental.

------

If serotonin could serve as a recreational psychoactive, then why do SSRI medications not induce this response?

This is my understanding of the mechanisms of SSRI medications:
The serotonin transporter or "SERT" is a monoamine transporter protein, a membrane protein that transports 5-hydroxy-tryptamine from the synaptic cleft into presynaptic neurons, SSRI compounds function by blocking the serotonin transporter (SERT), preventing the reuptake of serotonin. As the reuptake of 5-hydroxy-tryptamine is blocked it leaves an increased level of 5-hydroxy-tryptamine in the synaptic cleft which then becomes available to bind to the postsynaptic receptor.

-----

-eg
 
Well thank you for answering my questions regardless of what a part of you thinks is true. I am sorry if it appears as though I'd be trolling. The rest of you is right. Maybe it seems as if because I'm kind of letting my teenage mini me roam free with an idea it used to find fantastic. I hope that's okay because this place looks like an awesome playground.

I would love to hear more views on the whole topic, too. Also I enjoy the discussion, because as far as I know there's no legal issue with extracting serotonin.

The polarity keeping the serotonin out is very new to me. I have to expand my horizon on this matter. And I genuinely appreciate your effort and time to educate me on this.

There's some part, I've not told. I'm a sucker at throwing things away. And at some point I already got some walnuts that were pressed for their oil (for salads and so on). So they are physically reduced in their oily contents. And even though they were free I just hate to throw things away. A first extraction approach on them would have been a very elegant entry to the world of extraction imo. But if it's pointless because of the polarity and therefore uselessness of the end product I know I have a hard time motivating myself.

So maybe the proper question now would be: Is there anything remotely useful to do with some or a huge load of kgs of oil reduced walnuts? This stuff gets fed to pigs otherwise. So it can be achieved really, really cheap (do I act against the rule of talking about dried plant material? If so I will edit my post asap, please let me know!).

My first thought on benefitting somebodies experience with a (bodily) well known tryptamine to make it less alienating seems to have died, but maybe it can be used as a fertilizer for plants that are destined to produce tryptamines, maybe it's worth trying to turn the serotonin into something else, although I suppose enzymes are both expensive and hard to come by,...

PS: I love the term "cool talk about hot drugs!" :D
 
werver said:
Well thank you for answering my questions regardless of what a part of you thinks is true. I am sorry if it appears as though I'd be trolling. The rest of you is right. Maybe it seems as if because I'm kind of letting my teenage mini me roam free with an idea it used to find fantastic. I hope that's okay because this place looks like an awesome playground.

I would love to hear more views on the whole topic, too. Also I enjoy the discussion, because as far as I know there's no legal issue with extracting serotonin.

The polarity keeping the serotonin out is very new to me. I have to expand my horizon on this matter. And I genuinely appreciate your effort and time to educate me on this.

There's some part, I've not told. I'm a sucker at throwing things away. And at some point I already got some walnuts that were pressed for their oil (for salads and so on). So they are physically reduced in their oily contents. And even though they were free I just hate to throw things away. A first extraction approach on them would have been a very elegant entry to the world of extraction imo. But if it's pointless because of the polarity and therefore uselessness of the end product I know I have a hard time motivating myself.

So maybe the proper question now would be: Is there anything remotely useful to do with some or a huge load of kgs of oil reduced walnuts? This stuff gets fed to pigs otherwise. So it can be achieved really, really cheap (do I act against the rule of talking about dried plant material? If so I will edit my post asap, please let me know!).

My first thought on benefitting somebodies experience with a (bodily) well known tryptamine to make it less alienating seems to have died, but maybe it can be used as a fertilizer for plants that are destined to produce tryptamines, maybe it's worth trying to turn the serotonin into something else, although I suppose enzymes are both expensive and hard to come by,...

PS: I love the term "cool talk about hot drugs!" :D

I know I can be a grumpy and pretentious person at times...

Again, assuming this is a serious thread, and I hope it is, because I actually enjoy explaining these things, provided it's for an individual who seriously wants to have these things explained...

I do make mistakes from time to time, but as others catch them I can correct them and update my knowledge, this is my understanding of the situation:

when it comes to serotonin as a psychoactive, this path is a dead end, the pharmacology just isn't there...im willing to bet that serotonin is the most heavily researched tryptamine known, it's properties are fairly well documented...

Don't give up on tryptamines though, buy a copy of TIHKAL...

consider this, all your higher neurotransmitters are tryptamine or phenethylamine molecules ( tryptamine neurotransmitters: 5-hydroxy-tryptamine (serotonin), N-acetyl-5-methoxy-tryptamine (melatonin), 6-methoxy-tetrahydro,beta-carboline (pinoline) phenethylamine neurotransmitters 3,4-dihydroxy-phenethylamine (dopamine), beta-hydroxy-N-methyl-3,4-dihydroxy-phenethylamine (epinephrine), beta,3,4-trihydroxy-phenethylamine (nor-epinephrine)...these are the compounds that facilitate proper mental and emotional functioning, they facilitate cognition and are key to higher brain function...

Now, all true psychedelics are tryptamines or phenethylamines, they are alterations of our endogenous neurotransmitters, and most of them are actually freeing our brain of serotonin's rather repressive control mechanisms. They bend the alpha-helical proteins of the 5HT2a/c receptors into a novel shape, inducing a novel neurological repsonse, such as thalamic gating, decreased blood flow to the thalamus, the posterior cingulate and the medial prefrontal cortex, agonism at 5HT2a/c receptors, etc...

Alterations of neurotransmitters are what you are looking for, not something that is identical in structure, but very similar...
Maybe there is something to the concept that when you imitate a neurotransmitter too closely, you get a hybrid gemisch of activity. -shulgin;TIHKAL

werver said:
The polarity keeping the serotonin out is very new to me. I have to expand my horizon on this matter. And I genuinely appreciate your effort and time to educate me on this.

Very few compounds with a free hydroxyl group in this fashion will be able to cross the blood brain barrier (psilocin being a notable exception, with its free hydroxy grouping at position 4), the free hydroxy grouping acts as a polar, hydrophilic "lump" protruding from the side of the molecule preventing passage through the lipophilic Blood Brain Barrier...


Misc. Information

As far as walnuts go, I'm not sure, I'm sure there may be some use.

And as far as looking for beneficial tryptamines, don't give up there. Buy a copy of PIHKAL and TIHKAL.

As far as using common items to produce psychedelic molecules, look into Vanillin, Safrole, eugenol, Myristicin, etc...

Actually, shulgins "essential amphetamines" May interest you:

What are these relationships between the essential oils and the amphetamines? In a word, there are some ten essential oils that have a three carbon chain, and each lacks only a molecule of ammonia to become an amphetamine. So, maybe these essential oils, or "almost" amphetamines, can serve as an index for the corresponding real amphetamine counterparts. I had originally called this family the "natural" amphetamines, but my son suggested calling them the "essential" amphetamines, and I like that.

(1) The 4-methoxy pattern. The pivotal essential oil is 4-allylanisole, or methyl chavicol, or estragole (called esdragol in the old literature). This allyl compound is found in turpentine, anise, fennel, bay, tarragon, and basil. Its smell is light, and reminiscent of fennel. The propenyl analogue is called anethole, or anise camphor, and it is found in both anise and camphor. It is a waxy solid, and has a very intense smell of anise or fennel. At low concentrations, it is sweet, as in magnolia blossoms, where it is also found. The drinks that turn cloudy with water dilution (Pernod-like liqueurs, and ouzo and roki), are heavy with it, since it was the natural flavoring in the original absinthe. That drink was very popular in the last century, as an intoxicant which produced an altered state of consciousness beyond that which could be ascribed to alcohol alone. It contained wormwood, which proved to be neurologically damaging. The flavorings, such as anethole, are still big things in synthetic liqueurs such as vermouth. Old anethole, when exposed to air and light, gets thick and sticky and yellowish, and becomes quite disagreeable to taste. Maybe it is polymerizing, or maybe oxidizing to stuff that dimerizes. Whatever. These changes are why old spices in the cabinet are best discarded. And adding ammonia to any of these natural product oils produces, in principle, 4-methoxyamphetamine, 4-MA.

(2) The 3,4-dimethoxy pattern. The main actor here is methyleugenol, or 4-allyl-1,2-dimethoxybenzene. This is located in almost every item in the spice cabinet. It is in citronella, bay (which is laurel, which is myrtle), pimiento, allspice, pepper, tree-tea oil, and on and on. It has a faint smell of cloves, and when dilute is immediately mistaken for carnations. The propenyl analogue is, not unreasonably, methylisoeugenol, a bit more scarce, and seems to always be that little minor peak in any essential oil analysis. The compounds missing that methyl group on the 4-oxygen are famous. The allyl material is eugenol, 4-allylguaiacol, and it is in cinnamon, nutmeg, cloves, sassafras and myrrh. You taste it and it burns. You smell it and think immediately of cloves. And its property as an anesthetic, in the form of a clove, is well known in the folk-treatment of toothaches. Actually, flowers of clove (the gillyflower, like the carnation) are the small, pointy things that decorate baked hams and, when stuck into apples, make pomander balls. This anesthetic property has recently led to a drug abuse fad, called clove cigarettes. Very strong, very flavorful, and very corrosive things from Southeast Asia. The eugenol that is present numbs the throat, and allows many strong cigarettes to be smoked without pain. The propenyl analogue is isoeugenol, with a smell that is subtle but very long lasting, used more in soaps and perfumes than in foods. The amine addition to the methyleugenol world produces 3,4-dimethoxyamphetamine, or 3,4-DMA. The isomer with the other methyl group missing is chavibetol (3-hydroxy-4-methoxyallylbenzene) and is found in the pepper leaf that is used with betel nut. A couple of positional rearrangement isomers of methyleugenol are known in the plant world. The 2,4-isomer is called osmorrhizole, and the conjugated form is isoosmorrhizole or nothosmyrnol; both are found in carrot-like vegetables. They, with ammonia, would give 2,4-DMA. And the 3,5-dimethoxyallylbenzene isomer from artemisia (a pungent herb commonly called mugwort) and from sage, would give rise to 3,5-DMA. This is an unexplored isomer which would be both an antidote for opium as well as a stimulant, if the classical reputation of mugwort is transferred to the amphetamine.

(3) The 3,4-methylenedioxy pattern. One of the most famous essential oils is safrole, or 4-allyl-1,2-methylenedioxybenzene. This is the mainstay of sassafras oil, and it and its conjugated isomer isosafrole have a smell that is immediately familiar: root beer! These are among the most widely distributed essential oils, being present in most of the spices, including the heavies such as cinnamon and nutmeg. I am not aware of the 2,3-isomer ever having been found in nature. Adding ammonia to either would give MDA.

(4) The 3-methoxy-4,5-methylenedioxy pattern. The parent compound is myristicin, 5-allyl-1-methoxy-2,3-methylenedioxybenzene, and the source of this is nutmeg (or the botanically parallel material, mace). The nutmeg is the seed of the tree Myristica fragrans and mace is the fibrous covering of the seed. The two spices are virtually identical as to their chemical composition. Myristicin and the conjugated isomer isomyristicin are also found in parsley oil, and in dill. This was the oil that was actually shown to be converted to MMDA by the addition of ammonia by passage through an in vitro liver preparation. So here is the major justification for the equation between the essential oils and the Essential Amphetamines. Care must be taken to make an exact distinction between myristicin (this essential oil) and myristin (the fat) which is really trimyristin or glyceryl trimyristate from nutmeg and coconut. This is the fat from myristic acid, the C-14 fatty acid, and these two similar names are often interchanged even in the scientific literature.

(5) The 2-methoxy-3,4-methylenedioxy pattern. This is the second of the three natural methoxy methylenedioxy orientations. Croweacin is 2-methoxy-3,4-methylenedioxyallylbenzene, and it takes its name from the binomial for the plant Eriostemon crowei from the worlds of rue and the citrus plants. It corresponds to the essential amphetamine MMDA-3a. This oil is found in plants of the Family Rutaceae. My memories of this area of botany are of Ruta graveolens, the common rue, whose small leaves smelled to me, for all the world, like cat urine. This plant has always fascinated me because of a most remarkable recipe that I was given by a very, very conservative fellow-club member, one evening, after rehearsal. He told me of a formula that had provided him with the most complete relief from arthritic pain he had ever known. It was a native decoction he had learned of many years eariler, when he was traveling in Mexico. One took equal quantities of three plants, Ruta graveolens (or our common rue), Rosmarinus officinalis (better known as rosemary), and Cannabis sativa (which is recognized in many households simply as marijuana). Three plants all known in folklore, rue as a symbol for repentance, rosemary as a symbol of remembrance, and pot, well, I guess it is a symbol of a lot of things to a lot of people. Anyway, equal quantities of these three plants are allowed to soak in a large quantity of rubbing alcohol for a few weeks. Then the alcoholic extracts are clarified, and allowed to evaporate in the open air to a thick sludge. This then was rubbed on the skin, where the arthritis was troublesome, and always rubbed in the direction of the extremity. It was not into, but onto the body that it was applied. All this from a very conservative Republican friend!

The methoxy-methylenedioxy pattern is also found in nature with the 2,4,5-orientation pattern. The allyl-2,4,5-isomer is called asaricin. It, and its propenyl-isomer, carpacin, are from the Carpano tree which grows in the Solomon Islands. All these plants are used in folk medicine. These two systems, the 2,3,4- and the 2,4,5-orientations, potentially give rise, with ammonia, to MMDA-3a and MMDA-2.

(6) The 3,4,5-trimethoxy pattern. Elemicin is the well studied essential oil, 5-allyl-1,2,3-trimethoxybenzene, primarily from the oil of elemi. It is, like myristicin, a component of the Oil of Nutmeg, but it is also found in several of the Oils of Camphor, and in the resin of the Pili in the Philippines. This tree is the source of the Oil of Elemi. I had found a trace component in nutmeg many years ago that proved to be 5-methoxyeugenol, or elemicin without the 4-methyl group; it is also present in the magnolia plant. The aldehyde that corresponds to this is syringaldehyde, and its prefix has been spun into many natural products. Any natural product with a syring somewhere in it has a hydroxy between two methoxys. The amphetamine base from elemicin or isoelemicin would be TMA, the topic of this very recipe.

(7) The 2,4,5-trimethoxy pattern. There is an essential oil called asarone that is 2,4,5-trimethoxy-1-propenylbenzene. It is the trans- or alpha-isomer, and the cis-isomer is known as beta-asarone. It is the isomerization analogue of the much more rare 1-allyl-2,4,5-trimethoxybenzene, gamma-asarone, or euasarone, or sekishone. Asarone is the major component of Oil of Calamus obtained from the rhizomes of Acorus calamus, the common Sweet Flag that grows wild on the edges of swamps throughout North America, Europe, and Asia. It has been used as a flavoring of liqueurs and, as almost every other plant known to man, has been used as a medicine. In fact, in Manitoba this plant was called Rat-root by the Cree Indians in the Lake Winnipeg area known as New Iceland, and Indian-root by the Icelandic pioneers. It was used externally for the treatment of wounds, and internally for most illnesses. There apparently is no report of central effects. The corresponding propanone, acoramone (or 2,4,5-trimethoxyphenylacetone), is also present in Oil of Calamus. The styrene that corresponds to asarone is found in a number of plants, and is surprisingly toxic to brine shrimp. The older literature describes an allyl-trimethoxy benzene called calamol, but it has never been pinned down as to structure. The isolation of gamma-asarone or euasarone from Oil of Xixin (from wild ginger) has given rise to a potential problem of nomenclature. One of the Genus names associated with wild ginger is Asiasarum which looks very much like the name asarone, which comes from the Genus Acorus. And a second Genus of medical plants also called wild ginger is simply called Asarum. There is an Asarum forbesi from central China, and it is known to give a pleasant smell to the body. And there is Asarum seiboldi which is largely from Korea and Manchuria. It has many medical uses, including the treatment of deafness, epilepsy, and rheumatism. The amphetamine that would arise from this natural treasure chest is TMA-2.

(8) The 2,5-dimethoxy-3,4-methylenedioxy pattern. The parent allyl benzene is apiole (with a final "e") or parsley camphor, and it is the major component of parsley seed oil. Its conjugated isomer is called isoapiole, and they are valuable as the chemical precurors to the amination product, DMMDA. Whereas both of these essential oils are white solids, there is a green oily liquid that had been broadly used years ago in medicine, called green, or liquid apiol (without the final "e"). It comes from the seeds of parsley by ether extraction, and when the chlorophyll has been removed, it is known as yellow apiol. With the fats removed by saponification and distillation, the old term for the medicine was apiolin. I would assume that any of these would give rise to white, crystalline apiole on careful distillation, but I have never tried to do it. The commercial Oil of Parsley is so readily available.

(9) The 2,3-dimethoxy-4,5-methylenedioxy pattern. The second of the three tetraoxygenated essential oils is 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene, commonly called dillapiole and it comes, not surprisingly, from the oils of any of the several dill plants around the world. It is a thick, almost colorless liquid, but its isomerization product, isodillapiole, is a white crystalline product which melts sharply. This, by the theoretical addition of ammonia, gives DMMDA-2.

(10) The tetramethoxy pattern. The third and last of the tetra-oxygenated essential oils, is 1-allyl-2,3,4,5-tetramethoxybenzene. This is present as a minor component in the oil of parsley, but it is much more easily obtained by synthesis. It, and its iso-compound, and the amination product, are discussed under the last of theTen Essential Amphetamines, TA.

One must remember that the term "essential" has nothing to do with the meaning of needed, or required. The word's origin is essence, something with an odor or smell. Thus, the essential oils are those oils that have a fragrance, and the Essential Amphetamines are those compounds that can, in principle, be made from them by the addition of ammonia in the body.
-PIHKAL; SHULGIN

-eg
 
werver said:
Banana mead sounds nice, too. :) Is it as sweet as it sounds?
That would depend on the starting gravity of the brew and the degree to which it is allowed to ferment out. Adding a bit of malt to the must (making it a mash, one might mention) really completes the beverage. I could give you the recipe if you like. It's more like bananahuasca than you would think.

Regarding eg's post about the essential amphetamines, adding appropriate spices to the mash also works.

Bear in mind that the theory regarding in vivo amination of allylbenzenes to yield amphetamines has been pretty much entirely discredited.
 
Thank you for reminding me on buying TIHKAL, eg! That was the exact point at which I left reading about psychedelics in my teenage years. Couldn't afford it due to constantly being skint.
I can be grumpy and pretentious too at times, especially in online communication. So I got used to forgiving myself. Since we're all the same on some level there's no problem treating you with the same kind of courtesy. After all I'm here to learn, not for a spa weekend.

Phenethylamines never really caught my attention as much as tryptamines, but thank you anyway for the whole lot of information.

I would love to hear the recipe for banana mead since I wanted to brew mead anyway but never had the critical amount of motivation. This might be the spark. :)
 
Here is the recipe:

Banana Malt Melomel

5lb organic bananas, in their skins
2 peeled, sliced eating apples
4oz rosehips (optional - ?)
1 tsp citric acid
1 tsp pectic enzyme
1 tsp wine tannins
1 tsp yeast nutrient
1 tbsp glutamine
2 tsp yeast compound
bakers' yeast
1kg glucose
500 g medium malt powder
200g runny honey
Gervin wine yeast
juice of half a lime
more honey
more glucose
more glutamine
more citric acid

*Sterilise all brewing containers and equipment with Campden tablets (sodium metabisulphite) immediately before use.

About 2.3 kg (5lb) ripe organic bananas were washed, sliced, and frozen in their skins for a month or two. They were then removed from the freezer, placed in a large stock pot and allowed to thaw. About 4.5 L (1 gallon) of boiling water was added, along with 2 peeled, sliced eating apples, 1 tsp (3 g) citric acid and the pulp from 330 g (9oz) rosehips that had previously used to make syrup.

The pot was brought back to the boil, cover with a close-fitting lid and allowed to simmer for 2 hrs. After cooling to body temperature 1 heaped tsp pectic enzyme, 1 tsp wine tannins, 1 tsp yeast nutrient blend and 1 tsp glutamine were added. The mixture was allowed to stand for 48 hrs. (The addition of anything but pectic enzyme at this point was probably rather premature - the remaining ingredients are best added after straining.)

The mash was strained then pitched with 2 tsp wine yeast compound. This yeast was possibly too old or was killed by excess Campden tablets. The 6 L of mash with 1kg glucose, 500 g medium malt powder and 200g runny honey failed to start so one 5 g sachet of bakers' yeast was stirred in along with 1 tbsp glutamine and a reptile heat mat was placed under the 8 L fermentation vessel. Brisk fermentation ensued in a matter of hours, especially after stirring with a baster to mix in a syrupy layer of slow-to-dissolve malt extract. The brew was typically kept at 20°C.

After about 18h the S.G. was 1123 when corrected to 15°C. 3 days later the S.G. had decreased to 1035 and fermentation began to slow down. The flavour of the must was much drier by this point. Acidity was possibly the result of high CO2 levels (although it would appear that the use of glutamine as a nutrient noticeably increases the acidity of a brew).

680 g honey was dissolved in 1800 mL freshly boiled water and 1 tbsp glutamine and ½ tsp citric acid were added. SG at 53°C was 1125 correcting to 1138 at 15°C. The liquid was allowed to cool to 30°C. During this time, a wine yeast starter was prepared by mixing 100 mL of the honey solution with 100 mL of boiling water, cooling in a water bath to 45°C and then adding 1 sachet of Gervin wine yeast. After allowing 15 minutes for the yeast to get started, the starter was added to the remaining bulk of the honey solution and all of this was added to the main fermenting vessel containing the banana brew. 90 minutes after mixing the S.G. was 1150 when corrected to 15°C and allowing for suspended solids.

This was allowed to ferment for three days by which time the fermentation had slowed noticeably. More honey solution was made up using 570 g honey brought up to 2½ L with boiling water. 2 g glutamine was added along with the juice of half a lime and the solution was cooled to <40°C before adding to the main fermenting vessel. This mixture was now sufficient to fill two 1 gallon fermenting demijohns and was fermenting steadily.

After a month or so the fermentation had pretty much stopped so the brew was racked - carefully syphoned into clean demijohns - and left at a steady, cool temperature to clarify. When clear it was bottled and consumed surprisingly quickly.

You may want to simplify it a bit but the fermentation was carried out in stages in order to develop the alcohol tolerance of the yeast. Glutamine is not strictly necessary but the yeast seems to like it - a lot. Rosehip pulp is also very much optional.

The effects of this brew were noticeably different from that of other alcoholic beverages - clearer and more euphoric, None of the slurring and stumbling one might expect from drinking a whole bottle of 17% ABV brew.
 
downwardsfromzero said:
werver said:
Banana mead sounds nice, too. :) Is it as sweet as it sounds?
That would depend on the starting gravity of the brew and the degree to which it is allowed to ferment out. Adding a bit of malt to the must (making it a mash, one might mention) really completes the beverage. I could give you the recipe if you like. It's more like bananahuasca than you would think.

Regarding eg's post about the essential amphetamines, adding appropriate spices to the mash also works.

Bear in mind that the theory regarding in vivo amination of allylbenzenes to yield amphetamines has been pretty much entirely discredited.

While in vivo amination of these phenylpropene compounds derived from the essential oils of common spices has been vastly discredited, this has little to do with the value of the information regarding these essential oils and the "essential amphetamines", think of the use of apiole, dillapiole, Eugenol, elemicin, myristicin, etc..in organic synthesis.

To the OP, yeah, I felt the phenethylamines may not be completely on topic, however, when you mentioned bananas, and began to ask questions regarding the potential of innocuous items to be converted to psychoactives I immediately thought of the "essential amphetamines"

There's a book by Jared ledgard titled "a laboratory history of narcotics vol. 1: amphetamines and derivatives" I highly recommend this as a partner to PIHKAL. This book explains things like extraction of mescaline from cacti, synthesis of mescaline from store bought vanilla extract, MDMA from safrole, DMMDA from apiole, and so on, it also details common laboratory chemicals and equipment, giving all the essential information, including several illustrations and diagrams. This book includes all the most general basics of organic chemistry. An individual with little chemical knowledge could use this book to educate themselves without becoming confused or frustrated, yet at the same time it's not so patronizing that an educated chemist would not enjoy it.

Again, PIHKAL/TIHKAL are almost like a bible to me, these books have been at my side every day for at least the last 6 years, so I tend to recommend them gratuitously without much consideration for the individuals interest in chemistry or psychedelics, or consideration for the fact that these books are "old news" to some degree, and that most people here have explored them ad nauseam.

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Banana-O-RAMA
(Misc. Banana information.
All parts of the banana plant have medicinal applications (Amit and Shailandra, 2006 ): the flowers in bronchitis and dysentery and on ulcers; cooked flowers are given to diabetics; the astringent plant sap in cases of hysteria, epilepsy, leprosy, fevers, hemorrhages, acute dysentery and diarrhea, and it is applied on hemorrhoids, insect and other stings and bites; young leaves are placed as poultices on burns and other skin afflictions; the astringent ashes of the unripe peel and of the leaves are taken in dysentery and diarrhea and used for treating malignant ulcers (Girish and Satish, 2008 ); the roots are administered in digestive disorders, dysentery and other ailments; banana seed mucilage is given in cases of diarrhea in India (Bhat et al., 2010 a ).

Antifungal and antibiotic principles are found in the peel and pulp of fully ripe bananas (Brooks, 2008 ). The antibiotic acts against Mycobacteria (Omojasola and Jilani, 2009 ). A fungicide in the peel and pulp of green fruits is active against a fungus disease of tomato plants (Ponnuswamy et al., 201 1). Norepinephrine, dopamine, and serotonin are also present in the ripe peel and pulp (Ratule et al., 2007 ). The first two elevate blood pressure; serotonin inhibits gastric secretion and stimulates the smooth muscle of the intestines (Anhwang et al.,
2009).

Some of the specific diseases known to be cured by banana are Anaemia: High in iron, bananas are
believed to stimulate the production of haemoglobin in the blood and so helps in cases of anaemia (Amit and Shailandra, 2006 ). Blood Pressure: Banana is extremely high in potassium yet low in salt, making it the perfect food for helping to beat blood pressure (Debabandya et al., 2010). Depression: This is because bananas contain tryptophan, a type of protein that the body converts into serotonin known to make you relax, improve your mood and generally make you feel happier (Girish and Satish, 2008 ). Heartburn: Bananas have a
natural antacid

effect in the body so if you suffer from heartburn, try eating a banana for soothing relief (Mokbel et al., 2005 ). Morning Sickness: Snacking on bananas between meals helps to keep blood sugar levels up and avoid morning sickness (Amit and Shailandra, 2006 ). Mosquito bites: Before reaching for the insect bite cream, try rubbing the affected area with the inside of a banana skin. Many people find it amazingly successful at reducing swelling and irritation (Odebiyi and Sofowora, 1978 ). Nerves: Bananas are high in B vitamins that helpcalm the nervous system (Singh and Bhat, 2003 ). Smoking: Bananas can also help people trying to give up smoking, as the high levels of Vitamin C, Al, B6, B12 they contain, as well as the potassium and magnesium found in them, help the body recover from the effects of nicotine withdrawal (Mokbel et al., 2005). Stress: Potassium is a vital mineral, which helps normalize the heartbeat, sends oxygen to the brain and regulates the body's water-balance (Girish and Satish, 2008 ).

Strokes: eating bananas as part of a regular diet can cut the risk of death by strokes by as much as 40% (Amit and Shailandra, 2006 ). Temperature control: Many other cultures see bananas as a cooling fruit that can lower both the physical and emotional temperature of expectant mothers (Mokbel et al., 2005 ). Ulcers: The banana is used as the dietary food against intestinal disorders because of its soft texture and smoothness (Girish and Satish, 2008 ). And Warts: Those keen on natural alternatives swear that, if you want to kill off a wart, take a piece of banana skin and place it on the wart, with the yellow side out (Amit and Shailandra, 2006 ). Alleged hallucinogenic effects of the smoke of burning banana peel have been investigated scientifically and have not been confirmed (Anhwange et al., 2009 ).

It has been observed that antimicrobial activity of the plants is associated with the presence of some chemical components such as phenols, tannis, saponins, alkaloids, steroids, flavonoids and carbohydrates (Singh and
Bhat, 2003 ).

Phytochemical Analysis

The extracts of Musa sapientum peels were analysed for alkanoids, tannins, glycosides, steroids,
flavonoids, saponins, volatile oil and resins using standard procedures.

Test for Glycosides: To 1ml of the extract was added 2ml of acetic acid and then cooled in an ice bath at 4°C. To this mixture 1ml of concentrated tetraoxosulphate (vi) acid (H 2 S0 4 ) was added dropwise. The formation of an oil layer on top of solution indicated the presence of glycosides (Odebiyi and Sofowora, 1978 ). Test for Alkaloides: To 3ml of the extract was added 1ml of 1% HCL. This resulting mixture was then treated with few drops of Meyer's reagent. The appearance of a creamy white precipitate confirmed the presence of alkaloids (Ogukwe et al, 2004 ).

Test for Saponins: Five drops of olive oil was added to 2ml of the plant extract and the mixture shaken vigorously. The formation of a stable emulsion indicated the presence of saponins (Trease and Evans, 1996 ) Test for Tannins: Two drops of 5% FeCl 3 was added to 1ml of the plant extract. The appearance of a dirty- green precipitate indicated the presence of tannins (Trease and Evans, 1996 )

Test for Flavonoids: To 1ml of the extract was added 3 drops of ammonia solution (NH 3 + ) followed by 0.5ml of concentrated HCL The resultant pale brown colouration of the entire mixture indicated the presence of flavonoids (Odebiyi and Sofowora, 1978 ).

Test for Steroids: To 1ml of the plant extract was added 1ml of concentrated tetraoxosulphate (vi) acid (H 2 S0 4 ). A red colouration confirmed the presence of steroids (Trease and Evans, 1996).

Test for Resins: To 5ml of the extract was added 5ml of copper acetate solution. The mixture was shaken vigorously and allowed to separate. The appearance of a reddish-brown precipitate indicated the presence of
resins (Elmahmood and Doughari, 2008 ).


-eg
 
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