Benzene ring in pharmacology

[Working_Class]

I'm doing a side project on studying why the aromatic Benzene ring is so prevalent in Pharmacology when it is such a prominent known carcinogen. I'm just interested in why this seems to be a huge component of most pharmacological entities. So it deserves further attention, and I seek better understanding, seeing as one of my biggest hobbies is the understanding of biologically magnificent cascades, that are drug and chemical reactions in the body.

I'm also curious to know if the addition of the Benzene ring to other side chains changes it's pharmalogical and reactive properties and possible risk profile within the body. I am just overall curious to understand it.

Also, it is definitely worth noting that endogenous amines, such as dopamine, norepinephrine and serotonin also include a Benzene ring. So it is very curious to know that this widely known carcinogenic structure is also endogenous and always present within all of our natural biological neurochemistry.

So this whole being a topic of Interest, definitely raises the question as to what kind of risk we are exposing ourselves to when consuming things like psychedelic phenethlamines or hetrocyclic amines of synthetic origin. And possibly in what concentrations these compounds naturally exist in the peripheral and CNS. It is of my understanding that the endogenous amines are held in vesicles in the presynaptic membrane in the periphery NS and the CNS, and when they are released they're typically either reabsorbed or digested by monoamine oxidase.

I'm an avid psychonaut, in school to become an RMT, but I am always studying chemistry and trying to connect some concepts as I go. Once RMT school is over, I will absolutely be extending my academic base into organic chemistry, pharmacology and biochemistry. But, for now, I'd like to spark this discussion for the midnight bluelighters who may already know some of the answers, the basement chemests, the academic heavyweights, and the avid psyconauts, who always reach for a more complete understanding of nature, chemistry and the world inside and around them.

So, what say you Bluelight? Who has some light to shed on the topic of the day?

 

[checktest]

Benzene / phenyl group has lots of stability (resonance, π orbitals by orbital theory, 'bond angles', etc...) and is often thermodynamically, energetically favorable to form. Simple carbon structure.

Properties of an individual component may not always apply to compounds and larger structures. The general, if stretched, metaphor is salt. I wouldn't eat chlorine or sodium individually [would be the last meal of my life haha] but together they are ok. Ignoring blood pressure effects etc...

Hopefully a proper chemist could guide you further.

 

[Working_Class]

This is really good information, seeing as I couldn't find it anywhere on Google. And you are 100% percent correct, while sodium and chloride ions are definitely part of a healthy functioning body, I sure as hell wouldn't take them in in Elemental form.

Which raises more queries about multivitamins, and their proposed safety and even health benefits. I'm not going to talk shit about multivitamins just yet. I've taken them for years, but now the more and more I learn about chemistry and health, the more I come to question things that I thought I knew all about. Is it even safe to take in some of these multivitamin supplements that may provide exceeding amounts of vitamins that may not be needed by the body. Are the forms they are present in, safe to consume?

Is it the over consumption of carbohydrates that more largely contributes to the retardation of properly functioning LDL particles, not necessarily saturated fat itself that contributes to atherosclerosis?

Question everything. From my perspective, the pondering and asking is welcome stimulus. After all, this is how some of the greatest discoveries were inevitably discovered. By inquisitive minds who never stopped asking, reading, experimenting reaching or learning. This is the age of the information explosion. What a time to be alive.

 

[polymath]

The benzene ring is carcinogenic only when there's no easier way for the body to oxidize it to water-soluble form than epoxidizing the ring. The substance has to become water soluble for it to be excreted by kidneys (in the case of benzene, which has a quite low boiling point, a large part is also excreted from the lungs to exhaled air). Something like toluene is already much less toxic because it can enzymatically convert to water soluble benzoic acid and then hippuric acid without the aromatic ring getting oxidized.

 

[sekio]

Is it even safe to take in some of these multivitamin supplements that may provide exceeding amounts of vitamins that may not be needed by the body. Are the forms they are present in, safe to consume?

The water soluble vitamins at least (B1-12, C) are not a problem because the excess your body doesn't need is readily removed by the kidneys. Vitamins A and D can cause hypervitaminosis but that has a fairly large window before it becomes toxic.

The most toxic component in multivitamins sued to be iron, of all things... have a breakfast of 2 XL bottles of Flinstones gummy vitamins and. hey, wait why does my liver hurt?

 

[psy997]

Is it the over consumption of carbohydrates that more largely contributes to the retardation of properly functioning LDL particles, not necessarily saturated fat itself that contributes to atherosclerosis?

Question everything. From my perspective, the pondering and asking is welcome stimulus. After all, this is how some of the greatest discoveries were inevitably discovered. By inquisitive minds who never stopped asking, reading, experimenting reaching or learning. This is the age of the information explosion. What a time to be alive.

Atherosclerosis: An alternate hypothesis

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3492120/ Neovascularization of coronary tunica intima Dr. Kruse, I've read you and listened to you enough...

forum.jackkruse.com

Atherosclerosis and the Tensegrity 7 blog.

https://www.jackkruse.com/tensegrity-7-black-hole-sun-come/ Then realize that hemoglobin and the arterial tree are designed to have the same spectral...

forum.jackkruse.com

 

[vecktor]

some fantastic quackery at the bottom of this thread.

benzene rings, which are called phenyl groups when they are attached to other stuff are nothing special and usually not carcinogens. Benzene itself is a pretty weak carcinogen but it was noticed because it produces quite distinctive cancers.
every protein has benzene rings, phenylalanine tyrosine and tryptophan are all natural amino acids that have the benzene ring buried in their structure.

Atherosclerosis probably has very little to do with diet, instead it is an inflammatory process which then leads to plaque formation. As fo it having to do with light and spectral vibration.... extraordinary claims require extraordinary evidence and there is none zero nada zilch, I read Jack Kruse and I see a smorgasbord of scientific terms jammed together in nonsensical ways. He is to summarize, full of shit.

Multivitamins are a scam, eat a reasonable balanced diet and every vitamin and mineral is there in sufficient quantities. The real issue is that mutivitamins contain levels of some minerals and vitamins that are close to being harmful, with vitamins and trace minerals none is bad, some is good and more is certainly not better. On the other hand they do limited harm and if they make people think about their own health in a proactive way then that is a good thing.

 

[polymath]

Things like 2-naphthylamine, which caused bladder cancer practically to every worker exposed to it in the chemical industry in early 1900s, are apparently toxic because the ring oxidation is easier with an amino substituent present and the oxidation produces some kind of reactive intermediate compounds. In the "random molecule" thread I described ring amino-subtituted versions of methylphenidate and amphetamine - those probably have a short duration of action and short shelf life because of their easy oxidation, and can in the worst case be really toxic compounds.

 

[psy997]

I read Jack Kruse and I see a smorgasbord of scientific terms jammed together in nonsensical ways. He is to summarize, full of shit.

He can't present for shit, but his theories keep being proven, over and over again

 

[Working_Class]

This is all really interesting stuff, thanks fellas, for your responses!

I took a little read-through doctor jacks stuff, and while it's definitely not my cup of tea, I suppose everybody's entitled to follow whatever they might feel like following in regards to Pseudo science. I'm into some pretty "out there" stuff myself.

Vibrations and all that stuff aside, it does make sense that basic Benzene ring structure, where already strongly bound to other atoms, would have stability in those bonds. I suppose another factor would be what sorts of products metabolism would produce, and the amount and frequency of administration as for the propensity for something to be causing enough DNA disruption for cancer to occur. But, that's enough of my babbling.

I was curious to hear from somebody who knows better than I, because it seems like such a prevalent base structure for so many different things. And that really did answer my baisic bitch question. The only other way to really "find out" would be to just go full basement chemestry, and test out things on tissue samples and creatures in your own clandestine laboratory. But that would time and resources, and there's too many other things to focus on, to be donating a
such a significant amount of time, effort and resources on such an archaic form of scientific masturbation.

I also understand that you can probably induce cancer with just about too much of anything in a rodent model. I would imagine in many cases, all it would take, is for the system to become overloaded with something reactive enough that it becomes a complete toxic hindrance to the immune system, and have it be reactive enough to destroy / alter DNA.

There seems to be studies done on people who supplement with multivitamins that show an increased tendency to develop various types of cancer after about 1.5 decades of following VS control. But again, it'll always be a question of; who is doing the study, under what parameters was said study done, and many other factors blah blah.

Roll them dice baby and never think twice!

 

[izo]

i remember hearing something about pi stacking has to do with the recognition and interaction of aromatic systems on a molecular level. but i have no idea, can shed someone some light onto this?

 

[jose ribas da silva]

when a benzene ring is added to a molecule which is solubilized in a polar solvent, it markedly decreases the solvent's entropy and consequently the global entropy of the system

 

[Working_Class]

Benzene Structure and Properties Chemistry Tutorial

Benzene structure and properties tutorial with worked examples for chemistry students

www.ausetute.com.au

Just actually had to learn the basics of the benzene ring for Chem 11. This is very cool stuff, the basics are actually a delight to get a grip on. It connects concepts in biology very clearly and is an exciting topic to develop conceptually. This link is decent.

 

[sekio]

i remember hearing something about pi stacking has to do with the recognition and interaction of aromatic systems on a molecular level. but i have no idea, can shed someone some light onto this?

Simplest explanation: the two "faces" of the benzene ring have their pi bonding electrons all smeared out in a donut-shape on each side. This makes the two sides of the ring capable of being attracted to other atoms (or other rings) electrostatically.

You can even get metals that coordinate to the benzene center too. This explains the strange structure of e.g. bis(benzene)chromium and ferrocene. (cyclopentadiene instead of benzene)

Pi stacking is actually one of the possible explanations for the evolution of DNA/RNA too. It's one explanation for how you could produce a "stack" of nucleotides, and from there you just need to link em together and you've got DNA/RNA.

 

[jose ribas da silva]

Pi stacking is actually one of the possible explanations for the evolution of DNA/RNA too. It's one explanation for how you could produce a "stack" of nucleotides, and from there you just need to link em together and you've got DNA/RNA.

it is well-known that the stack of sugar rings is the main stabilizing force that keeps nucleic acid strands thermodynamically stable

 

[DoriansDelorean]

This might be off topic, but is diazapine by itself active?