Sciencemadness Discussion Board

Someone is wrong (about organic chemistry) on the Internet!

Melgar - 6-4-2018 at 06:33

Okay, so I got roped into a debate that started on Reddit regarding this internet post:

https://drugs-forum.com/threads/methyl-ethyl-and-isopropylbe...

Can anyone pick out all the mistakes in the first post?

It's a bit worrying, because people are citing that post as an authority all over the internet, when it's clear that there are more than a few things wrong with the chemistry.

I'd been looking for information on Reddit following this thread I started a while ago:

http://www.sciencemadness.org/talk/viewthread.php?tid=75072

And that one post kept coming up. I tried to start an account there, but they make it really annoying for new users. You can't even post links, apparently.

So far, the mistakes I've found were as follows:

  1. "Methylphenylamines" is not a valid category of organic compounds.
  2. The image for n-methylbenzylamine is actually alpha-methylbenzylamine.
  3. Likewise, the image for n-ethylbenzylamine is actually alpha-ethylbenzylamine.
  4. None of these substances share a carbon skeleton with phenethylamines.

Can anyone find any other chemistry mistakes? I'm sure there are more, there have to be.

[Edited on 4/6/18 by Melgar]

[Edited on 4/6/18 by Melgar]

RawWork - 6-4-2018 at 06:56

I am not smart enough to answer that, but to complain about few more possible wrong definitions and lies...
Whole idea of "hunger" and "appetite" is a big lie. According to Herbert M Shelton they're not the same.
We can have appetite for sex, drugs, tobbaco, everything. But hunger for food only. Difference is:
During appetite you feel suffering, while during hunger you feel enjoyment.
According to him, nobody today can experience hunger, because everybody is sick. First thing sick people experience is appetite. Exactly same appetite for food or anything else. It's not needed for life, but acts against life.
During appetite there's feeling of anger, boredom, pain...while during hunger there's strength, joy, will...
I am not entitled to publish anything officialy, but it makes sense at least.
During appetite you feel bad taste in mouth and have bad breath. Toothbrushing won't remove any cause...
For more info read "fasting and sun bathing" by herbert shelton...this is still my investigation...not proven yet.
But noticed this makes sense in few examples.
Will need to change wikipedia and all other sources who define "hunger" or "appetite". Wikipedia treats them as same.

Melgar - 6-4-2018 at 07:03

Uh, if this was in whimsy, I'd be fine continuing this discussion there, but this is the "organic chemistry" forum, and so I was kind of hoping to discuss organic chemistry. Perhaps I should have made a more descriptive title, or even posted it somewhere else, but I was hoping to discuss the organic chemistry part.

edit: changed the title. Hope it helps.

[Edited on 4/6/18 by Melgar]

RawWork - 6-4-2018 at 07:14

Sorry for polluting your topic. I was focused on all in that subject except organic chemistry. I did not want to post my thread because I still have not enough data to post. Will do that one day later I hope after testing some theories.
If I am allowed to expand my previous post here, regarding organic chemistry, as you say.

This is more about ideology of Herbert Shelton which I think is correct, and mainstream ideology which I think is wrong.
According to him: "cooking is bad". He explains why it's bad using organic chemistry. I just want others to approve or disapprove these few citates (as reason why cooked food is dangerous):

(1) Cooking coagulates (hardens) the proteins of milk, eggs, meat, etc., making them tough and, with the exception of egg protein, less digestible, while impairing their food values.

(2) Cooking alters the fats in food rendering them less digestible and converting some of them into poisons.

(3) Cooking causes a great loss of the soluble minerals in the food.

(4) Cooking destroys the elementary plant form, tearing down its structure, changing its composition and bringing about certain destructive changes in the element-groupings in all foods, returning part of these elements, especially the organic salts, to their inorganic and, therefore, useless state, so that a large part of their mineral content is lost.

(5) Cooking renders starches less digestible and more prone to fermentation.

(6) Cooking destroys the vitamins in foods and impairs or completely destroys their anti-neuritic, anti-scorbutic, etc., factors.

(7) Cooking drives of part of the food into the air as gases.

(8) Cooking changes the flavor and odor of foods and renders them less palatable.

(9) Cooking food wastes much of its food elements and renders it less nutritious.

https://soilandhealth.org/wp-content/uploads/02/0201hyglibca...

Sigmatropic - 6-4-2018 at 10:40

The author of the 1st reddit thread is clearly hinting at pharmacophores although he must have been asleep while that subject was discussed.

'skeletal structure' or the pharmacophore of a receptor can be an aromatic ring spaced so and so much angstroms from a basic nitrogen (receptor based pharmacophore). Comparing benzyl amines (1C linker) with phenethylamines (2C linker) and beyond (3 atoms, 4 atoms) such as propranolol one clearly sees that this spacing is different and one gets vastly different effects. from no activity, to agonist, to antagonist. What I mean to say is 1 atom more or less spacing is a hell of a difference. (edit: I will attach a textbook example of this, if I can find it)

Next I would like to point out that regardless of the pharmacokinetics (all this receptor binding I just yapped about) is only secondary to pharmacodynamics. I would reason that N-substituted benzylamines are very likely to be devoid of in vivo activity is due to wonderful enzymes called monoamineoxidases. Seeing that they are in fact primary amines, or at least on one side, they are very likely to be substrates for said enzymes. Hence they will never reach your brain in meaningful quantities.

And now some confusion ;I disagree with the suggestion that TAAR1 is THE receptor for amphetamines. This class of drugs is rightly so called a dirty drug because it affects numerous other neurotransmitter systems (adrenergic, serotogenic, dopaminergic atleast) by affecting the biosynthesis, release, binding, reuptake and in activation of such neurotransmitters.

An attempt to explain compounds interacting with this system (that is your brain, behavior, cognition and mood) with a single pharmacophore is nonsensical. The abuse of the well established phenethylamine pharmacophore in that reddit post is a shame. But I wouldn't explain something I myself don't fully understand which is why I will end here.

I tend to ignore discussions of this kind as they are not likely to go anywhere except another round of echoes in an already big echochamber.


[Edited on 6-4-2018 by Sigmatropic]

JJay - 6-4-2018 at 12:21

Quote: Originally posted by Melgar  
Okay, so I got roped into a debate that started on Reddit regarding this internet post:

https://drugs-forum.com/threads/methyl-ethyl-and-isopropylbe...

Can anyone pick out all the mistakes in the first post?

It's a bit worrying, because people are citing that post as an authority all over the internet, when it's clear that there are more than a few things wrong with the chemistry.


Oh, teh horrorz.
Quote:


I'd been looking for information on Reddit following this thread I started a while ago:

http://www.sciencemadness.org/talk/viewthread.php?tid=75072



I saw something a couple of weeks ago stating that phenethylamine HCl is a common cutting agent for methamphetamine since it has similar chemical properties. I know almost nothing about this topic.
Quote:

And that one post kept coming up. I tried to start an account there, but they make it really annoying for new users. You can't even post links, apparently.

So far, the mistakes I've found were as follows:

  1. "Methylphenylamines" is not a valid category of organic compounds.
  2. The image for n-methylbenzylamine is actually alpha-methylbenzylamine.
  3. Likewise, the image for n-ethylbenzylamine is actually alpha-ethylbenzylamine.
  4. None of these substances share a carbon skeleton with phenethylamines.

Can anyone find any other chemistry mistakes? I'm sure there are more, there have to be.



I don't see why {o,m,p}-methylaniline couldn't be methylphenylamines.

[Edited on 7-4-2018 by JJay]

clearly_not_atara - 6-4-2018 at 16:17

I did some searching and found no mention of any benzylamines binding TAAR1, although one paper mentioned that phenethylamine binds at TAAR4 (an olfactory receptor) but benzylamine does not. In general, benzylamines do not have similar binding profiles to the corresponding phenethylamine.

TAAR1 has two isoforms, one which preferentially binds ligands that look like octopamine (3'-desoxy-norephedrine) and one which prefers beta,beta-diphenylethylamines. Neither of those sounds any closer to benzylamine. I'm feeling more confident his claim about N-monoalkylated benzylamines binding TAAR1 is false, but I haven't found the resources to prove it.

Reboot - 6-4-2018 at 16:39

And the obligatory:

https://xkcd.com/386/

unionised - 6-4-2018 at 16:54

I must be missing something.
It's asserted that isopropylbenzylamine is a stimulant- in some way comparable with methamphetamine.

If that's true, why does anyone bother to make meth?

Melgar - 6-4-2018 at 22:02

Quote: Originally posted by unionised  
I must be missing something.
It's asserted that isopropylbenzylamine is a stimulant- in some way comparable with methamphetamine.

If that's true, why does anyone bother to make meth?

That point seems to have come up later in the thread. It's an entertaining read starting halfway through the second page, when an actual chemist weighs in, starts cursing at everyone for being dumb, and then gets a warning from the staff. The chemist guy (onepot) was trying to get people from /r/chemistry to back him up, but without much luck.

@sigmatropic Yes, this is exactly the type of information that I didn't have enough background in to know one way or the other. It seemed like it had to be wrong somehow, but I wouldn't know where to start, as far as pointing out why.
Quote: Originally posted by JJay  
I saw something a couple of weeks ago stating that phenethylamine HCl is a common cutting agent for methamphetamine since it has similar chemical properties. I know almost nothing about this topic.

There are tests like ninhydrin and nitroprusside (?) for detecting whether an amine is primary or secondary. Maybe n-methyl PEA? Though that's something I know nothing about either.
Quote: Originally posted by JJay  
I don't see why {o,m,p}-methylaniline couldn't be methylphenylamines

They're typically called toluidine, no? Apparently "methylphenylamine" can actually mean "n-methylaniline", but I have no idea how that could work as a category of compounds. In any case, none of the compounds that he claims are part of that group actually are.

I kind of felt like I had to inform people about what they're putting in their bodies, but now I feel like it's best to just avoid that rabbit hole altogether.

Loptr - 7-4-2018 at 18:47

Why are we referencing that forum here?

What is it that you hope to gain?

j_sum1 - 7-4-2018 at 19:06

Ok this is a bit meta.

A discussion on a chemistry board about a discussion on a chemistry board.

I might be wrong but I cannot see this conversation going anywhere particularly useful.
If there is an actual question to be discussed that is suited to SM, then message a mod to have this reopened.