Fabrication on Steroids

In this video, I discuss a paper from SN Applied Sciences, where the authors demonstrate some unprecedented chemistry using acetonitrile.
www.patreon.com/thatchemist
Community Discord - discord.gg/QWNPETtPcZ
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Links to articles discussed in this episode:
Sketchy Article - www.doi.org/10.1007/s42452-019-0378-7
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[@gamingmarcus]

Heart attacks kill people, therefore elevating the average level of health in the world, or causing health. Not so hard to understand =P

[@AwestrikeFearofGods]

Except when they don't kill people.

[@yuriikovalov84]

Lol its like in Ukraine elder men were not in risk of covid because most of them died at age around 65 because of heart and other problems

[@hokyanalexchan4933]

Reading this paper also kills people 🤣

[@hokyanalexchan4933]

It really hurts ..... Hertz..... 🤔🤣

[@helldad4689]

This is the kind of chemistry you see on blackboards in the background of blockbuster movies. They should really be publishing in IMDB.

[@That_Chemist]

Haha

[@2001Pieps]

"Since several years ago, some theoretical models have been used to predict the interactions of some drugs with protein and enzymes." Ah yes, the obscure and niche field of pharmacology.

[@Blakearmin]

I think you, and Explosions & Fire/Extrac&Ire are the only two chemistry channels that can make me laugh on the regular.

[@That_Chemist]

stay tuned for saturday - we did a collab!

[@Blakearmin]

@@That_Chemist no fucking way! Oh hell yes! I'm stoked!

[@iscuit]

Same, even a year later. I subscribe to a lot of chemistry youtubers but these are the two I keep coming back to

[@TheBackyardChemist]

300 Hz sounds like your magnet quenched and all you are left with is the Earth's magnetic field

[@10tus61]

If you still have the time, please continue your commentaries about toxic papers. It's really mind-opening how scientific papers can be published in reputable journals like this. These videos kinda served as a precautionary tale for me if I ever do future research (in microbio though). lol I thought novels only do fiction, I guess even here too. lmao

[@mathiasdaniels651]

Their first NMR spectrum looks just like estradiol (their starting material) in DMSO-d6. This can be expected because I wouldn't think anything was going to happen with just reflux in acetonitrile. The authors probably had a look in the literature, found the Overman rearrangement and assumed that this would happen in their reaction. The second spectrum looks to be a mixture of methanol and water (the solvent they used for crystallisation, the calibration looks off) with some small amount of residue peaks from other solvents. The third spectrum also looks like it is a mixture of solvents with mainly DMSO and water (if the calibration is more or less ok). So it is surprising that this got past the editor and "peer review".

[@georgejanzen774]

Today, we stir (some) random compound in a flask, make NMR spectra of (some) stuff we find in the solvent drawer, then publish the results in (some) fancy sounding paper. Isn't chemistry fun?

[@SMPKarma]

@@georgejanzen774 springer fucking nature

[@adamrak7560]

@@georgejanzen774 "Proceedings of Random Chemistry"

[@margodphd]

Maybe if the reviewers were actually paid we could introduce some measures of accountability. Pay to publish is beginning to get wild.

[@slavakuznetsov4966]

You need to call it "Humor", not "Toxic", because it's damn hilarious. LOL. "Theoretical ass" is what I would call some computational chemists who claim that some thermodynamic parameters are involved in binding.

[@lancequek5203]

Because the authors just called themselves a sham a.k.a. a "theoretical ass" group

[@morrisdweck32]

That "weird" form of an amide at 10:48 is called an imidate. There are many, many syntheses for imidates and this certainly isn't one of them

[@MooreAnalytical]

I have been running GCMS and Pyrolysis GCMS for 8 years and I hardly ever see compounds like this using that method. The way one would usually see these compounds in the gas phase is only after derivatization which does not always work well. Really love your content and please keep shedding light on the bad science that is pushed out in the world.

[@That_Chemist]

Thank you!

[@TheOpnor]

Okay question, cause I only have a little experience with Pyrolysis GCMS - if one did a Py-GCMS of that compound could you somehow reverse engineer the structure from the fragments you find in the GCMS? A little like fragmentations you see in normal EI-MS? I mean in this case I believe it's pretty much out of the question that the analytics is bogus anyway but I was just wondering about that. Like for example if you had a substantial database of Py-GCMS spectra of steroids? And leaving the fact that GCMS is maybe not the method of choice for this kind of compounds aside.

[@MooreAnalytical]

@@TheOpnor to a certain extent yes you can. The problem with pyrolysis is you often make so many compounds through various different pathways that you cannot necessarily do a full reverse engineering. You can however get critical information about major portions of a structure like seeing styrene, ethylene, nitriles, etc. PY-GCMS is excellent for materials with repeat units like you see in polymers, but not so much with complex structures like bio molecules.

[@KublaKhanful]

Sure the NMR spectra were pretty ugly but when you've only got a 300 Hz magnet you take what you can get. Love the series man, keep it up.

[@mmmhorsesteaks]

300Hz for protons would require a magnet that's around 0.007 tesla, around the strength of a fridge magnet.

[@minklmank]

@@mmmhorsesteaks did you actually run the numbers on that one? (excitedly grabbing an old radio and some fridge magnets)

[@mmmhorsesteaks]

@@minklmank I fiddled with an on-line calculator until the numbers came out about right haha

[@htomerif]

I really like this series. I like to read things first and see how much I can catch before watching your video. Unfortunately for this paper, I got as far as "myocardial infarction is a major cause of health worldwide" so I know we're in for a special kind of bumpy ride. I'm making this comment at 4 seconds in on your video, so we'll see how it goes. -edit; Schrodinger's Cat's lesser known cousin: Theoretical Ass. My primary thing is programming so when I see so many unpaired brackets, I throw up a little in my mouth each time. I'm just going to imagine like 20 left brackets just out of sight in the beginning of this paper.

[@johnsmith-sp6yl]

i think the "nightmare about chemistry and this is what they saw" is on point, i remember after finishing calc 3 i had a nightmare where i had to take the integral of an equation but it was floating orange numbers and none of it made any sense and i had to use inverse trig substitutions.

[@margodphd]

I thought only I had integration nightmares. Thank You, kind stranger, for making me feel less alone.

[@johnsmith-sp6yl]

@@margodphd thankfully those havent popped up again and now i just have driving and tooth nightmares

[@razabazal4669]

This is a great “What not to do when writing a lab report.” Kind of funny and informative. Great job lets see more.

[@Liamb2179]

This is by far the best paper I've ever seen

[@georgejanzen774]

A channel that specializes in roasting bad papers is something I didn't know I need in my life. Thank you so much!

[@roblesman17]

As a native Spanish speaker, all the grammar mistakes were hilarious, cause they are exactly what I would have written when I was 15yo. I feel bad haha I feel like I could still make some of these mistakes. Don't be too harsh on them (on language), it can be challenging to write scientifically in another language sometimes.

[@notthatcreativewithnames]

As a fellow ESL, I would partly agree that it is challenging for us to communicate science in a different language. However, if there is a peer review process at all, these grammatical and spelling errors should have been detected and resolved already.

[@That_Chemist]

These don’t even get corrected in good journals, unfortunately

[@adrianhenle]

As a native English speaker, I have had somewhat minor spelling and grammar errors corrected in peer review. I think reviewers might be less willing to make these corrections if there are too many.

[@andreh4eva]

As a native portuguese speaker I was actually surprised "infarction" is actually a word in english as well (tho it seems to have a slight different meaning). In portuguese (and presumably in spanish also) the word "infarto" means "cardiac arrest", which is what the authors in fact wanted to say.

[@CatThingy]

@@andreh4eva A myocardial infarction is the "proper" name for a heart attack.

[@jasonqlwilliams]

"Stirred to a reflux," I actually laughed out loud.

[@pk_xiv2856]

Bencene is just benzene with a carbon atom floating in the middle, just like the word itself.

[@stevenblue1979]

The carbon clearly underwent displazament.

[@mechadrake]

these are great. So great it hertz. I wish there was someobody who makes analysis like this for mechie or just mechanics papers, As I am a mechie and have little idea of organic chemistry :)

[@redacted2871]

I love that square C2NO group thing, it's so ridiculous. No way on earth such a thing would ever be stable but OK authors, ok my working theory is that they're extradimentional entities that live in a parallel universe whith different laws

[@That_Chemist]

you could propose something screwy like that as an intermediate, but never a product

[@samheasmanwhite]

​@@That_Chemist I was pretty amazed to find that there might be some oxozetes that are actually stable, maybe not a spiro one though. 1,3-oxazetes seem to be pretty unstable but I can find a few references to the analysis of stable ones in papers that at least appear to be well done. 1,2-oxazetes seem to be more commonly synthesized though.

[@samheasmanwhite]

I came across this absolute banger of a molecule while doing a substructure search on PubChem: pubchem.ncbi.nlm.nih.gov/compound/129875500 Jesus christ the things that are being done to those poor double bonds.

[@redacted2871]

@@samheasmanwhite honestly, I have to admit this is pretty cool

[@adamrak7560]

I am running an ab initio molecular dynamics on the molecule in water (B3LYP SG1, 6-31g, 6 extra water molecules + COSMO) And it seems initially stable, at least for 5.8fs. That means nothing for the long term stability, but at least it seems to hold together in smaller timescales.

[@alan2here]

GPT-3 has got much better since 2020, but it was never this bad, if someone is going to write a paper with AI at least they should get up to date with it.

Thank you for this. I've mentioned this guy in a comment on your video a while back and I'm glad you followed up with this. I'm happy you seemed to have fun with this, as someone who has published in the same journal as this guy (Steroids) it was more bittersweet for me. I've already written E-Mails to Editors of some of these journals but I only got back promises that they would reach out to the authors and no retraction.

[@That_Chemist]

Please leave suggestions in the Discord! We have a channel for BS articles, and this is the easiest way for me to follow up on them!

[@JohnWL]

I love that there are no residual solvent peaks from any recognizable NMR solvent. I also enjoy that in the figure titles they finally put the correct MHz for the C13 NMR.

[@blip_bloop]

Myocardio Infarction is a heart attack-ack-ack

[@aluminumchemist2586]

Aside from the video being very entertaining, it is very concerning that Figueroa-Valverde hasn't been reprimanded for faking data. The worst thing of all is that the proposed mechanisms are the ones you would expect to get from someone who has no concept of Chemistry whatsoever. Magical oxidations happening everywhere and ridiculous resonance structures treated as if they were steps of a reaction. Also, the 1H-NMR shown on figure 3 looks like a mixture of products or incomplete reaction due to the vast difference in size and width of the peaks. How did the reviewers not catch any of that? What are the editors of this "journal" doing?

[@That_Chemist]

Check out today’s video :/

[@aluminumchemist2586]

@@That_Chemist I did and you weren't kidding. Figueroa likes to push boundaries, he is just not very good at arrow pushing.

[@georgeretsides4293]

Those mechanisms are absolutely hideous. How was this published is beyond me.

[@JakeInaitor5000]

Could sit any student that passed organic 1 in front of that mechanism and they'd tell you it's just patently wrong

[@jfcrow1]

Surprising that peer review would let all this pass. Journal Referee must have been asleep or just needed something to publish. I see a lot of this now.

[@justinwang5074]

i lost it at "theoretical ass"

[@Abedchess]

11:00 So, now alcohols are acidic 🤔 Interesting.

[@herbertcharlesbrown1949]

chemical shift in Hertz instead of MegaHertz hurts 😂

[@HighMansx]

I'm sitting here imagining some poor sweaty dude with a spoon stirring the mixture as fast as possible with shit spilling all over the place trying to reflux the solution 😂

[@Chemiolis]

I think it's not too odd that they say 200 mg in the second step of the synthesis. It could be that they conducted the first step multiple times and therefore can just use any amount they want. As far as I know I have seen that before in other papers (unless it's really not-done?). Weighing that exact amount and caring about doing that is something else though...

[@That_Chemist]

it is possible, but they should still comment on it; especially since the reaction was literally "reflux estradiol in acetonitrile" lol

[@featheringivory3579]

These authors really said "I don't give a theoretical ass about how it looks, just publish it"

[@vmodsm]

Since many years ago we have used molecules to react and make more complex molecules

[@NathanPrice6]

positive charge attac

[@That_Chemist]

journal should have protec

[@davecurlett2227]

I nearly threw my coffee at the screen when I saw that arrow starting at a positive charge

[@tibovandenbegin483]

shit this is the funniest thing i've seen on yt for a while

[@thepuzzlemaker2159]

I understand basically nothing of it but I am loving this series

[@markobeslac2181]

This is pure comedy. Please make more of these 😂😂

[@mmmhorsesteaks]

No when you displace nitrogen it's displazament. Duh :-D In all seriousness; if i think about the amount of effort and trouble it took me to get real work published this is absolutely a slap in the face. Outrageous.

[@That_Chemist]

haha

[@jonahglass-hussain4568]

theoretical physicists got that hypothetical cake 🥺😩

[@Abedchess]

Theoretical chemist just got that hypothetical ass.

[@1temppart201]

you know, I do wonder if i'm the only one here who like isn't an actual researcher or at least have a lot of formal training in chem when your primary mean of gaining knowledge is reading papers this series pretty much just :p like you all can look at it and see it's bogus instantly but someone who isn't experienced in these stuffs in any sense of the word (read: me) would be easily fooled haha but yeah, thank you, I am really learning a lot from your vids ^^ keep it up!

[@Gretcie]

I haven't had to study organic chem in years but I still get a kick out of these videos. So I wouldn't worry about it. These videos are still good no matter your level and interest.

[@flickcentergaming680]

I'm not a big fan of chemistry classes, not am I a chemistry major, but these videos are fantastic as not only are the funny as hell but they're also exposing fraud in academia. That's really important.

[@Orchids.and.Endlers]

I’ve really been enjoying the uploads !

[@That_Chemist]

Thanks!

[@georgemag8827]

This video was hilarious! You made my day!!! I am just wondering who the reviewers are. Fun fact: I saw 9 citations!!!!!!!

[@That_Chemist]

wow!

[@katiefrisk980]

> tfw you have a heart attack >stonks guy: “helth”

[@RobsMiscellania]

So good haha

[@steveb.8491]

My favorite part is how they showed the Ketone and Alcohol in equilibrium! 🤣

[@notthatcreativewithnames]

Does this journal *actually* have any kind of peer review process?

[@californium-2526]

3:58 -Amide- *Imidic acid* A spirooxazete would be a new compound series. And I bet a 1,3-oxazete would be unstable (unless you use adamantane as a "spiro-cycler" - see arteriolane, a stabilized 1,2,4-trioxolane!). Also, "inhibitor inhibitor"s are just activators/inducers. And heart attacks cause health? Just like another comment here, I assume killing the diseased decreases the rate of the diseased, hence the increase of health. *insert that "Stonks" meme but with "Helth" instead of "Stonks"*

[@SMPKarma]

(Sorry for being a pedantic ass) an inhibitor inhibitor would just make it do nothing though. An inhibitor binds to something and then reduces its activity in any number of ways, if you inhibit *that*, you just get no net change. Like, if a thing is meant to disable something, and you disable the disabler, it doesn't disable things any longer Why is this important again?

[@californium-2526]

@@SMPKarma So the inhibitor inhibitor does nothing. At least my thought did something.

[@pelegsap]

tbh though, as much as the bad English can be funny sometimes, and even though in science we must communicate clearly and the international language for that is English - as a non-native English speaker I must say that sometimes we make mistakes in English... the criticism in such cases should be aimed at the publishers who did a horrible job of proof-reading (if any), and it is a really simple problem to fix.

[@That_Chemist]

yeah - if their role is an 'editor' they need to edit

[@pelegsap]

@@That_Chemist True.

[@Merssedes]

11:20 "positive charge attacks the negative charge" -- they just managed to get positrons :)

[@ministryoftruth557]

That looks like something a non-chemist (me for example) would come up with…

[@Snizzfart]

I think the only way they might actually prove their case given everything is if they can grow single crystals of the different products for XRD. That's the ONLY way I can think off to prove that their chemistry is real here.

[@Snizzfart]

Also just noticed that they report EAs but the only "found" atoms they report are C and H

[@That_Chemist]

ironic, isn't it

[@vicderoo5498]

Pretty good S/N and resolution for a 300Hz magnet, not going to lie

[@Andy-wc5xw]

I've done theoretical asses before, your lab should have the equipment for one in the bathroom

[@That_Chemist]

Lmao

[@sootikins]

I once knew a girl whose ass was more theoretical than actual. Skinny af, I think she was anorexic.

[@alan2here]

What the hell, lets just actually get GPT-3 to have a go and see if it can do better: Title: Preparation of a steriod-oxazole-1,2'-[1, 3]oxazete derivative Page 1: Introduction A new method for the preparation of a steriod-oxazole-1,2'-[1,3]oxazete derivative was developed. This derivatives is an important intermediate in the synthesis of several novel compounds with potentially interesting biological activity. The key step involves treatment of 3-(4-chlorophenyl)-2,5-dihydrooxazole with 2-(3,4-dimethoxyphenyl)ethyl chloride in the presence of triethylamine. Page 2: Experimental Procedure A mixture of 3-(4-chlorophenyl)-2,5-dihydrooxazole (1.0 g, 3.8 mmol), 2-(3,4-dimethoxyphenyl)ethyl chloride (2.2 g, 10.6 mmol), and triethylamine (1.7 mL, 12.9 mmol) was refluxed in toluene (50 mL) for 3 h. The reaction mixture was then cooled to room temperature and the solvent was removed under vacuum. The crude product was purified by column chromatography on silica gel using ethyl acetate/hexane as the eluent to afford the desired steroid-oxazole-1,2'-[1,3]oxazete derivative as a white solid (0.8 g, 60%). Page 3: Results and Discussion The new method for the preparation of a steriod-oxazole-1,2'-[1,3]oxazete derivative described herein is both efficient and convenient. The key step involves treatment of 3-(4-chlorophenyl)-2,5-dihydrooxazole with 2-(3,4-dimethoxyphenyl)ethyl chloride in the presence of triethylamine. This reaction proceeds smoothly to afford the desired product in good yield. This new method provides a convenient way to prepare a key intermediate for the synthesis of several novel compounds with potentially interesting biological activity. References 1. J. Med. Chem., 43, 754 (2000). 2. Bioorg. Med. Chem., 9, 2367 (2001). 3. Bioorg. Med. Chem., 10, 1723 (2002).

[@That_Chemist]

this reads a lot better at least

[@alan2here]

@@That_ChemistHow correct and how good/passable is it? I'd be interested to know if it's really making sense, it's not amazing with numbers for example.

[@notthatcreativewithnames]

It's still quite like that time when Answer in Progress decided to use AI to write a mac and cheese recipe and ended up with a dish which does not contain macaroni at all.

[@alan2here]

@@notthatcreativewithnameswell 50% good news then, as it'd absolutely nail "mac and cheese recipe:"

[@1abyrinth]

10:36 not just any four membered ring, but one suspiciously similar to the one they claim is stable elsewhere

[@amandas8895]

I don’t know if someone already commented on this before (and I might be wrong), but they say they had to use 4:1 methanol/benzene to elute their compounds during column chromatography. 1) Isn’t that eluent mixture a bit too polar (I’ve always been told not to use anything above 20% MeOH, otherwise you can dissolve your silica), and 2) that eluent mixture seems extremely polar for something that lipophilic. Just my two cents.

[@Zenzicubic]

Yeah, Figueroa and his infinite power can force acetonitrile cycloaddition in "some conditions". He also can make gcms work for steroids :) The virgin that chemist vs the chad Figueroa

[@iamzurvan]

I feel like I'm hearing hot gossip from a professor that's frustrated while grading... then I remember this was a published paper and it deflates me. Who was the editor?

[@Lararius123]

I'm crying from laughter 5:35 "hertz, it does hurt. it hurts me, thats for sure" 6:15 "stirr it to a reflux" yikes. Poor old vitamix doing work.

[@That_Chemist]

haha

[@marcfruchtman9473]

I think the "FIX" for this problem is for peer reviewed journals to have 3 "reviewers" sign off on the paper with their names. Of course people make mistakes, so I have no issue if something "accidentally" get past a reviewer. But, clearly when a reviewer's reputation is on the line, they wouldn't consider allowing garbage to be "accepted".

[@That_Chemist]

Maybe if there was a way to make it anonymous but tracked, like crypto

[@marcfruchtman9473]

@@That_Chemist I am fairly certain that anonymous would nullify any leverage in that case. Anon1 could be replaced by Anon2... but meanwhile no one really takes responsibility. I think if it was by "group census" meaning all 3 signed off and agree that it is acceptable, then they should also be ok putting their name on it.

[@SoulDelSol]

​@@marcfruchtman9473 I agree!

[@moropikkuu]

Im an undergraduate, so.. just out of curiosity: you wouldn’t do GCMS on this molecule, that much i knew before. Would ESI or MALDI-TOF be viable? Do those routinely have some form of chromatography involved as well, or is that not an option? I’ve only ever done GCMS before, so I’m not well versed in analytic methods for larger molecules like these.

[@That_Chemist]

Yeah probably LCMS or HPLC/ESI

[@roy03182000]

The steroids in that paper aren't actually considered as large molecules in today's organic synthesis. These 200~300 Da molecules are almost at the lower limit for most of the MALDI machines so ESI would usually be used. Also, as they are that small, a high-res MS with less than 10 ppm error would at least be required in the characterization in a normal journal.

[@minklmank]

ESI with a decent mass filter like TOF or QTOF would probably the easiest and most commonly available Method, MALDI would be absolutely overkill in my opinion just from a sample preparation standpoint. LIFDI would most likely work, too but those ain't as widespread

[@gabbyn978]

Bencene - probably a typo. Still better than Benzin (that is car gasoline) 'Chloroform D6'... if that author actually used the terminology of an odd 'medical method' that calls itself homoeopathy, it would mean that this chloroform was dissolved in water down to the 'concentration' of 1 ppm. So your assumption that you are seeing the signature of water, might be correct.

[@argoneum]

Was it published Apr 1'st by any chance?

[@TheMrFrukt]

I, indeed, carried some theoretical ass out of my lab last week.

[@slimp4644]

About the GC of a cholesterol derivative, sure it is not feasible (much easier on LC), but can you not derivatize your sample to be ionizable GCMS or just use a MALDI system? We can always discuss this in the Discord 😅

[@BaitingSimulator]

I should show some mechanism to some second semester students maybe some can make some sense out of some

[@alixg7462]

This article caused a major infarction to my health.

[@Thaumius]

Theoretical Ass , my favourite theory.

[@jdmccool1]

Either the author is completely clueless or simply dishonest. I spent 5 years in finance, and we had people like this - Bernie Madoff. I'm now in chemistry as a first-year Ph.D. student. It would be cool if you could find examples of fraud in more prominent journals such as Science, Nature, etc. I’m sure it has to exist.

[@한수씨]

"Some drugs"

[@chrisboyall8602]

Correct me if I’m wrong, but wouldn’t you need a source of protons for the first step, in order to produce the amide? Is it supposed to be a variant of the Ritter reaction? Surely just refluxing MeCN with an alcohol alone isn’t enough to produce that?

[@That_Chemist]

its an insane reaction - both places where the acetonitrile reacts is crazy - if you start generating carbocations, all sorts of stuff can happen

[@DantalionNl]

To be fair they could have performed a reaction multiple times to get back to reasonable quantities for the next reaction. As it is only 200mg its not unreasonable to think they are doing such a step to get back to reasonable levels of compoud. Although it would be nice to mention this in the paper if so.

[@howarddyla9676]

They really buried the lede with discovering a novel four membered ring lol.

[@Tadesan]

You can do GC just fine on these compounds if you run the column hot enough. The thing that really upsets me about this situation is that the motivation for that paper's existence is a requirement for publishing and generally a requirement to generate grant funding for the program. That chemist made 50k for the 'work' done on that paper and secured hundreds of thousands of dollars for their lab.

[@ZackFreedman]

This sounds like it was written by the same AI that draws Midjourney’s fingers

[@foc2241]

I think it could be vaporize but it will decompose. Cholesterol is very doable (we have it as a SST)

[@niiiuu8814]

This is great

[@flickcentergaming680]

I understand exactly 0% of this, but I'm glad there's someone exposing these kinds of terrible papers and shaming them. Stuff like this paper makes all of academia look bad, not just chemistry. Plus, it makes for some funny content. Keep doing what you're doing!!!

[@That_Chemist]

Thank you :)

[@Bigcubefan]

Using 200 mg for step 2 is perfectly fine, even if step 1 only yielded roughly 100 mg in this explicit procedure. Obviously in a real laboratory setting you conduct the first step multiple times to amass enough material to conveniently continue with the consecutive steps. At least that's how I did it if the first step is only low yielding and can't be scaled up properly. Also, in a paper you usually report the procedure that got you the highest yield. Maybe they also conducted the same reaction with 10 grams but only had a yield of 40 %, so they published the other one? And furthermore, of course you start each reaction with a nice and convenient number! Or did you perform reactions where the starting material weighed 27 mg, or 158 mg or 2.451 g or some other weird ass number?

[@That_Chemist]

literally all they did was reflux SM in acetonitrile

[@Gretcie]

It's been a while since I've done wet chemistry but would you not want to use stochiometric amounts of reagents? That was my understanding for why the amounts were funny.

[@Bigcubefan]

@@Gretcie Sure you'd want to use stochiometric amounts, but usually the starting material is a nice even number grams-wise. Obviously other reagents will have awkward numbers, unless the exact molar ratio isn't that important.

[@notamouse5630]

This paper looks like one man did the chemistry, another did the analysis, and a third did the writeup. And they weren't reviewing each other's work quite enough. And that answers the question of how many scientists does it take to screw up a paper.

[@That_Chemist]

haha

[@ansible9340]

Aren't there forums where you can refute papers? Like "pubpeer"(not an academic so don't know how much it is worth in the community, heard of it through a plagiarism accusation news).

[@That_Chemist]

Reproduction is better - a couple people in the Discord have been working on reproducing this weird carrot paper, and the results are surprising

[@lorlimann]

6:10 I see no problem there, tbh. Run the reaction 3 times with 200 mg - with a 50% yield there is plenty to work with for the next step

[@That_Chemist]

true, you could do that

[@lorlimann]

@@That_Chemist great content nonetheless! I should haven mentioned that :P

[@ryanatkinson2978]

I get so much theoretical ass dude

[@That_Chemist]

haha

[@thatguy431]

What if someone tried to replicate this but expounded upon every instance of "some" Also nice to note this always starts with "a journal I've never heard of before"

[@That_Chemist]

It’s not a red flag, but it is an orange flag

[@hydrogenbond7303]

I mean If you have typos in the headline, I'm concerned about the rest of the paper.

[@That_Chemist]

totally

[@dylanhubert6871]

Myocardial infraction is fancy word for Heart Attack. "...Heart Attack is a major cause of health worldwide..."

[@TheShimming]

Strictly speaking, that structure of acetonitrile is not a ylide, because the ylide should bear a formal negative charge on carbon and a formal positive charge on heteroatom.

[@grock9211]

GCMS on this thing without any derivatization? Hmmm sounds fishy

[@JAzzWoods-ik4vv]

And here I was thinking my lab reports were bad

[@ephremcortvrint2376]

30 seconds in and your first highlight of the text should have been sourced. Great start

[@That_Chemist]

absolutely - reference whenever possible!

[@stephenetridge2584]

Some paper fabrications are a lot more subtle ….this papers has some massive howlers almost as if it’s to parody the pier review process …

[@louiesatterwhite3885]

Hmm. That would be an interesting critique if this lab was purposefully submitting low quality, falsified reports to see what is published. Like a sting operation of sorts.

[@신석현-p8v]

your videos should be used for therapy cause they cure depression holy shit this is hilarious

[@That_Chemist]

thank you haha

[@markb5249]

I can kind of understand the other bullshittery, but how the hell did the NMR stuff go through? How do you even *make* the NMR software say solvents that wrong? Can you do that?

[@stevengill1736]

It's not a paper from J Med Chem. is it? Of course JMC is pretty much the gold standard, but you never know about SOME drugs, they might be different. ;*[} Seriously, besides it being ESL (English as a second language), with mistakes with the RF units and bizarre reagents like (AcO)2O/HNO3, it would appear this publication has some more-than-minor issues....

[@timkurz6086]

actually using gc ms for steriods isnt that bad. you can silylate them with tmcs/hexamethyldisilazane/pyridine and analyze them pretty well with capilarry gc with an fid. that method is used for example by the european pharmacopoeia for identifying phytosterole composition of certain plant oils against betulin as internal standard. so its not total bullshit there!

[@baylinka7077]

THEORETICAL ASS PLEASEEEEEEEEEEEEE😭😭😭😭😭😭😭😭I FUCKING CANT how they didn't notice it????? like.... this word is widespread, catches the eye IMMEDIATELY!! even without after-checking it's stupid to left it here like do you write with your eyes covered or wat?

[@JP-wx6uh]

write to the authors and just tell them if they have some really old Acetic anhydride, they can go ahead and just call it Acetic acid. 🤣😂😂

[@brianbrandt25]

the novel 4 membered ring and term oxazete immediately caught my eye. I guess they are real and and the same. But how on Gods green earth did this pass peer review? It wouldn't surprise me if it involved some kinkly ass play.