Benzene and psychoactivity

[Greenport]

SwiM had compiled together a fairly comprehensive list of our psychoactive substances, especially those that are hallucinogenic in nature, and has noticed that almost every single one of them contains a Benzene ring at some point.

All of the phenethylamines obviously do, as they have a phenol basis. These include Amphetamine, Meth, Khat, many other breakoffs of that, the methylene-dioxy series (mda, mdma, mdea, bunches of others), 2-C*'s, DOM/STP, DOB, Mescaline, and many others.

Our six-carbon molecule is present in THC and all of its related compounds (Dronabinol, Nabilone, Parahexyl).

Benzene is present in many ergot alkaloids including LSD-25. It is found in the tryptamines including DMT, DET, Psilocin, Psilocybin, 5-MEO-*, and several others.

It does not appear to swiM to be in Salivorin-A, however.

Continuing on, almost all of our spices have Benzene rings in them. Many common chems don't really all smell that good, but the benzene-based ones smell like flowers. Is that some sort of a psychoactive effect as well?

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So with this in mind, what the hell is it about Benzene when it gets these various molecules tacked on that causes it to have such an effect on our bodies? It can affect everything from smell, taste, and even sight (in dyes), to our entire reality and emotions/feelings.

SwiM thinks that if we as a whole ever figure out how the Benzene molecule can cause such an interesting set of effects to our sensory system, and its route in doing so (and eventually the ability to calculate molecules to do certain things), it can be used to change almost any aspect of our psyche we desire.

It just requires some sort of link between some property of benzene-containing molecules, and action on the senses...

Maybe start by looking for a common characteristic between all of those that cause hallucinations. Or one that is there between all speed-like ones, or empathy related, or ones that smell good. Then, find out what is different in that relation between those various substances (why is MDA stronger than MDMA in the body?)

If there is ever a mathematical answer to this, swiM is sure at that time anything imaginable could be made (imagine a computer program that could calculate out molecules that would carry out certain functions 100% efficiently.) However, just to tap into it and be able to understand even on the most basic levels why this 6-sided molecule causes so much of an effect, would benefit the entire world.

Feel free to add anything swiY wishes to this.

[stoneinfocus]

Nothing mathematicla in swims opinion, as it boils down to the experiment and the ever-existing not-eliminateable unpredictablity of the human mind or conscious to an alteration of receptor-sides, that vary interindividually and from setting to setting. Mayne some single mechanics of sensuality and sensory modes could be tagged by exploring those "simpler" brainfunctionalities.


MDMA is intersting, as, as swiy mentioned, it can´t really be described in its action as an amphetamine:

-there´s no crosstolerance to MDA
-don´t know but prob. no cross-tolerance to amphetamines, too.
-it´s S- is more active than is its R- stereoisomere

and so it´s proposed to act on/at different loci in the brain and synapses.

Benzene doens´t seem to have hallucinogenic properties, but must CNS; active substances as well as some hormone, like catecholamines, where two OH-groups are found at the 3,4-positionliek in Dopamine, (Nor-) Epinephrine or the phenethylamines with substituted multiple aromatics, connectes in some way, like in triiodothyronine(sp?), with a phenethylamien and a fluorodisubstituded addet benzene, do all possess some of the features, that actualle make them nuerotransmitters, or hormone-like or something inbetween.

Let´s not mention receptorsides or why swim fells so damn well on testosterone and even better on methandrostenolone, which are much bigger and don´t seem like dopamine at all, but effect this substance and some opiod-receptors as well, as the these sides are simply close to the androgene-receptor.... *gg*

Aaaand don´t even begin to mention peptide-drugs D

[Greenport]

swiY's post made swiM wonder about the actual role of benzene molecules in human/animal life. Dopamine is used for motivation, Serotonin for mood regulation, Phenethylamine for love, Norepinephrine for wakefulness...these substances must give off some sort of powerful energy in the way they are used.

Amphetamine looks an awful lot like Norepinephrine...Meth looks an awful lot like Epinephrine...MDA looks most to swiM like Dopamine but knows it matches to Serotonin more in terms of effect. However there should be some sort of relation other than position of their molecules. There should be a way to calculate the reason that Amphetamine (and even Cathinone) acts on -and- looks like Norepinephrine perhaps. Same being true with the methylated for Epinephrine, and methylenedioxy-ated for Serotonin.

What is it about that relation there that is actually related in physical/chemical properties? Do they have other similar characteristics?

It's obvious that Benzene-based molecules are used to support human life. Otherwise we'd be motionless, emotionless, hating animals with no 'will' to do anything. The brain picks up on these naturally to function, but yet can be tricked by something involved in these certain chemicals we have found and that is what is on swiM's mind. There has got to be some sort of relation other than just the diagram of the chemical. Is electricity involved maybe?

THC seems to work on Anandamide which does not contain a Benzene ring. But THC does.

[Paracelsus]

I don't think that the benzene element has any "special" relevance. The fact that it is lipophilic enhances the ability of "benzene-molecules" to cross the blood-brain-barrier. But there are lots of drugs, neurotransmitters, and other necessary substances that don't have a benzene ring: alcohol, xanthines, nicotine, GHB and its analogs, nitrous oxide (it isn't even an organic compound); GABA, aspartate, glycine, adenosine; essential amino acids, vitamins (A, some of the B's, C, etc.), all minerals & micronutrients, etc.

[trptamene]

Originally Posted by Greenport

All of the phenethylamines obviously do, as they have a phenol basis. These include Amphetamine, Meth, Khat, many other breakoffs of that, the methylene-dioxy series (mda, mdma, mdea, bunches of others), 2-C*'s, DOM/STP, DOB, Mescaline, and many others.

Our six-carbon molecule is present in THC and all of its related compounds (Dronabinol, Nabilone, Parahexyl).

Benzene is present in many ergot alkaloids including LSD-25. It is found in the tryptamines including DMT, DET, Psilocin, Psilocybin, 5-MEO-*, and several others.

It does not appear to swiM to be in Salivorin-A, however.

Continuing on, almost all of our spices have Benzene rings in them. Many common chems don't really all smell that good, but the benzene-based ones smell like flowers. Is that some sort of a psychoactive effect as well?

Benzene is an aromatic compound (those with 4n + 2 pi electrons in a cyclic conjugated fashion). As you indicate many spices have aromatic systems and this is indeed where the name for aromaticity in organic chemistry comes from. Not all aromatic compounds smell pleasent though and in particular aromatic solvents benzene/toluene/etc are not the most smart thing to go smelling.

Aromatic systems have a unique magnetic character where the outer part is positive relative to the inner pi system such that there is a radial dipole. This may play some part in the biological activity of these molecules (a manifestation of their binding to receptors), but the binding affinity is affected by both the magnetic character and the 3D structure of said molecule.

Don't know if this adds anything, but some thoughts.

[stoneinfocus]

Electricity: in fact it´s not a molecule forming a covalent bond to a receptor it´s being constantly penetrated via electric charges and opposite attraction, opening ionophores and pentrating vesicles, forcing out the natural neurotransmitters... I think there´s no chance in calculating its effects other than proposing statements like:"this could be a hallucinogene", "this library of substances is probably harmless whithin its active dose".

it´s probably easier to calculate or predict human behaviour and reactions to influences and psychological impacts -humans are very alike in that one and one could estimate the influence of a charaktere of one person and calculate this influence in, as a variation in the same outcome, or another outcome, which is predictable, too, as options are not too many within life as are taking actions and reactions, so it seems.

the conscious mind is an endless exploration and has nearly no limits, especially when under the influence of an mind-altering, substance or how can tell how deep emotions are, when being around your loved ones? One could tell: "he is in his mind, he is himself!", "he´s having a deep experience", but numbers can´t tell or predict the quality of an experience, nor the intensity and the effects on one´s life it has, one can calculate there´s so much active substance in it, which binds with an appropiate affinity to recptor x,y,z and this should effect some physical and therefore psychological changes, but, and this is the uniqueness and the only way to test psycho-actives, our conciousness and mind can´t be calculated and neither can eb the experience.

One could say, benzene had just the right dimensional backbone and is in its planar structure optimally suited for putting three-dimensional, polar and non-polar groups to it, making them stand out in this and this and this angle and being this and this polar and, thus, they effect these receptors or concurate or inhibit or polarize these cells and functions and fix themselves and this group attached to it in this position, which might account for this special effect.

Swim is very intersted and feels like there should be much more research done on the amphetamine function and the non-amphetamine-like function of a so similaar molecule like methylenedioxyamphetamine.

it seem as if there should be "wings", something symmetrical, a facing of similar groups to the benzenering which makes up for a more friendly, and fearless entactogenic charakter.

Swim said, methandrostenolone, with the two opposing doublebonds in the A-ring makes it a very happy molecule for the user, making him feel warm and revealing a deeper emotional background.

I read once that when the methylenedioxybridge were on both sides of the benzene para to another (2,3,5,6-bis(methylenedioxy)) it would greatly potentiate MDMA effects, though swim doesn´t know what exactly this means and rat-test can´t tell.

[Greenport]

If only the majority of our psychoactive benzene molecules were not banned for research purposes...meh maybe one of the bees will figure it out completely for us

Paracelsus swiY's point is valid in that not all drugs require a benzene molecule, and it's definitely not the 'only' part of biological life. Maybe some of them though, are somehow related to those that do have benzene molecules in interesting ways we have yet to find. Or, maybe some work in ways that are completely unrelated to that.

Lol yeah Benzene is not good to be smelling - but swiM has (quite by accident) smelled it before, along with Toluene and stuff from spraypaints. SwiM has a pretty extensive selection of spices and understands that most of the tastes and scents from them are the result of benzene-derivatives. When swiM learned that there was maybe a relation to those scents and to psychoactivity, he was quite amazed.

Magnetic forces...wonder if there is any research already done on this maybe?

stoneinfocus: SwiM understands what swiY means when he says that one cannot 'calculate' the effects of a substance on the human body, because everybody is different. However, it can be generalized. We know that MDMA and MDA cause a feeling of empathy, just about regardless of whom takes it. Now, that still means each person reacts to it in their own way, and that is why an exact effect of anything could never be calculated like swiM mentioned before...

However, what swiM is more referring to is maybe a certain (set of) physical and chemical propert(y/ies) (electrical affinity, magnetism, solubility in various substances, melting/boiling point, anything that could be a basis.) that these share in common that maybe in a certain range are known to cause "empathic" or "speedy" or "hallucinogenic" qualities.

SwiM understands that everybody is wired just a bit differently Not everybody rolls the same as a result. But we can all still classify mdma as an empathogen.

[Paracelsus]

If only the majority of our psychoactive benzene molecules were not banned for research purposes...meh maybe one of the bees will figure it out completely for us

Actually, some research is being done. I recall reading a long paper on structure-activity relationships of some psychedelics (DO* compounds and the like), which contained a lot of information that went way over my head (mainly electron transfer in receptor binding - some things about the benzene ring were mentioned). I can't seem to locate it right now, unfortunately.

[stoneinfocus]

Hey greenport, ususally it´s the fourth atom at the benzene where the magic happens, like swom was trying out a 4-substiuted amphetaminem, and guess what? -He was telling of increased empathy, less fear in a positive sense, some blurred vision (hardly noticable), relaxed speaking and no aggresiveness whatsoever and some beautiful colours especially to swim the blue and the early morning sun´s bronze and gold -tones.

Anyway :P back to chemistry, if one´s is looking at the indole-amines (tryptamines) it´s not so much the benzenering, as there´s more to it, it´s a bulkier molecule and it shares the phenethylamine-property and -surpise, some 4 and 5 substituted species (the former being e.g. psilocybin and the latter serotonine) and in LSD, one rarely sees the indole ring-structure anymore as a layman as it looks like a house of molecules was build ontop of it, but then again, the amide or diethylamide is doing the trick once again, sticking far out from the 4th position, so it seems, that there just has to be an amine or a group of a certain lipohilicity and polarity at a certain bulky part, which has an inductive effect and is arranging these functional groups in line...

Fruity odours come most likely from attached aldehydes and carboxylic acids, sticking from the benzene or ketones, swim´s no expert at this subject, neither does he know about magnetic effects, one could look at the orbitals and the elctrons and decide wether dia- or paramagnetic effect might behold them..

If swiParcelsus might link us to his info, maybe it´s already here on DF? ;-)

[Politicalchalk]

Where I live, 40 % of the land is all Brownfields (toxic waste sight, lesser only to Superfund sites, the REALLY bad ones: Love Canal, etc.). Wether it's deposited into the soil, dumped into a river, pumped into the air, or any flavor of contamination you like, Benzene exposure seems to compel health to take a dive for the worse. Lupus, cancer, autism, just to name a few, are prevalent here.

In fact, my girlfriend and I have been getting samples from a local creek to test for benzene concentrations. (talk about a romantic time, eh?)

SWIM finds it amazing that, if understood correctly, many of the more beloved compounds don't alter the benzene ring per-se, but are simply connected to it. SWIM hasn't brushed up on his chemistry for a while, but wonders how much of a given substance is actually composed of benzene by volume? One thinks that, if it does "accumulate" as a composition of a larger compound, that the psychoactivity may be caused at least in part by benzene poisoning? It's been said that the only difference between a cure and a toxin (...or apparently spice) is the dose. Thoughts, anyone?

With many of the compounds being research chems, it seems plausible that they might be considered HAZMAT compounds.

NB: I never really considered the magnetics of receptor site binding. It kind of reminds me of Aldous Huxley's "Soma, delicious Soma!" in that he thought that, as mankind's knowledge of pharmacology increased, we would eventually be engineering states of ecstasy as everyday occurrence...can you imagine how a product like that would be marketed?!

[stoneinfocus]

this aldous huxley state swim already achieved for years with testosterone-derivatives, peptide drugs and pro-spoerts until his familiy decided he had not to be happy this way, as well as did the law, adn his sourroundin thinking a bi-sexual pro-athletes in their sourrounding is as good as a sodomist and paedophile next door and caused him a car crash, whelie he was on the rpoad for training.

Sort-cut, we already have the power which huxeley sought. we probalbly had it before, when no-one gave a damn what shrooms or plants one´s ingesting or extracting.