Making denatonium benzoate - the world's most bitter chemical

Hey guys, today we're going to be making denatonium benzoate from lidocaine, benzoic acid and benzyl chloride that I made in previous videos.
Benzyl chloride video: • Making Benzyl Chloride
The intro video was made by user Linus Tuttle (www.youtube.co.... Thank you!
The music for it is from Incompetech (Severe Tire Damage Kevin MacLeod (incompetech.com)
Licensed under Creative Commons: By Attribution 3.0 License
creativecommons...)
Procedure adapted from: www.google.com/...
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Nile talks about lab safety: • Chemistry is dangerous.

[@mattk6315]

Nile Red always uses the most scientific measurements like, "a bunch"

[@LilGugz]

+Kid Kirby Perfect SI unit ;)

[@namibjDerEchte]

At least not something horrible like fluid ounce.(No, as I'm from central Europe I do not even know how much that is exactly, I think somewhere in the region of 1 liquor shot)

[@mattk6315]

namibjDerEchte The US uses freedom units, You use heathen units. Freedom units > heathen units.

[@Robocop-qe7le]

Yup, nilered is quite sloppy. But we don't mind.

[@SeungCanFade]

Did you see that his stirbar is actually a paper clip?!

[@theCodyReeder]

I used this to keep the horse from chewing on our trees.

[@ScienceWithJames]

Cody'sLab Hi Cody!

[@mrslinkydragon9910]

Vix vapour rub works too

[@vanarppayhsak1330]

Cody'sLab that's awesome

[@hgmercury7279]

i think i will use Denatonium Benzoate to stop some crazy peoples form eating/drinking me

[@henryjiang9664]

mercury How would you drink it yourself? Maybe a dummy straw? But I’d probably forget about it and getting the taste stuck in my mouth for weeks.

[@DerFlugzeugTV]

You don't need an intro, you're classy already

[@NileRed]

+DerFlugzeugTV I probably wont include it in the future videos, but it was made for me and I wanted to credit the person for making it. They took their time to do it and it was the least i could do

[@montyparadox219]

+Nile Red keeeeep it is awesome

[@chesterthemolester9155]

+Nile Red I'd suggest using it in about half of the videos, as some people like it and some don't.

[@avtaras]

Chester TheMolester Yh I agree. Well tbh I think no intro necessary but if you want one then at least include your logo and stuff

[@Gisaboiad]

@@NileRed You should've kept the intro it looks so cool man.

[@MrGurkentomate]

Your story about bitterness was still less insane than my organic chemistry prof's story. He made a small amount of sweetener(I don't remember which one, but he said it was about 10.000 times sweeter than normal sugar) for an experiment, and decided to try a little bit of it. It tasted sweet but not insane, just like regular sweetness. He then tried to wash it off, surprisingly it didn't wash off. A day later, still, everything tasted sweet. A week later still the same picture. He couldn't get the sweetness out of is mouth for 3 weeks. Literally everything he ate was sweet for 3 weeks.

[@NileRed]

+MrGurkentomate that is crazy. At least it was enjoyable though?

[@superturkeylegs]

He could have drunk straight up black coffee for that whole period of time to assert how much of an alpha male he was.

[@petevenuti7355]

What is it?

[@GoodestGOAT]

​@@petevenuti7355 Probably neotame, it's roughly 10,000x sweeter than sugar. I believe it's the 3rd most sweet substance out there

[@ferretyluv]

Did he accidentally make miraculin, the stuff on miracle berries?

[@Sciencedoneright]

Your search is over. This is the only NileRed video with an intro. Congratulations

[@addyshorhnr3544]

Really?

[@Sciencedoneright]

@@addyshorhnr3544 yes

[@fishHater]

This is a monumental discovery

[@paininnitwr]

Oh cool

[@mrtophat12]

Hahahaha. Thank you. I literally was going to search.

[@supersmashsam]

I think the reason the multiple acetone-evaporation cycles worked is that you were removing some water each time. Wet denatorium benzoate was probably soluble in acetone, but the dry one, much less.

[@NileRed]

+supersmashsam That might be possible!

[@sha-384thegreatest]

I watched a whole bunch of videos from 2010-2019 but I haven't seen an intro.

[@revengefrommars]

Based on another comment it looks like he only used it once as a favor to the person who created it.

[@bradleyholland4984]

Brandon, I figured it out, I finally did it ! “Nodnarb “ IS JUST BRANDON IM SO STUPID OMG

[@Tommo.]

@@bradleyholland4984 WHO'S brandon!?

[@fractal5764]

@@Tommo. Nodnarb is Brandon.

[@jakekimds]

The stir bar looks vaguely paperclip like.

[@henryjiang9664]

Jake Kim It is

[@noahshomeforstrangeandeduc4431]

Indeed

[@tyt0uoff146]

It is the stir bar for the oil Bath

[@CameronK665]

The stir bar is in the round bottom flask --- the shadow on the hot plate makes it look big and paperclip-like.

[@MannOfTheHill345]

It's really Clippy from Microsoft word. In all seriousness though, the paperclip is used to stir oil bath to evenly distribute the heat. There's another stir bar in the round bottom flask.

[@Daniel_lebieR]

nice video. interesting substance. like the intro. "... it's honestly probably better to use a seperatory funnel. But I decided not to for some reason..." comments often remind me a bit of myself when I'm in the lab ;)

[@RoroTheDeer]

That was the cheesiest intro I have ever seen. I love it.

[@NileBlue]

+NeedSkillNow haha thanks

[@bensullivan420]

+Nile Blue wha-

[@DasEtwas]

+Ben Sullivan XD

[@absinthe7266]

@@NileBlue what

[@jcwingsofficial]

Linus Tech Tips worthy?

[@sourlem0ns981]

I work at an ice cream factory and we use bixtrex in our pasteurization process. It’s a fail save so we know if anything goes wrong. I tried some straight up because I’m dumb, and yeah extremely painful bitter and then that taste lingered for days. Don’t mess with it 😂

[@spaceyboi6651]

Glad your channel is growing and nice intro

[@NileRed]

+Janusz Januszowski Thanks!

[@jinhyunpark8448]

Best chem channel everrrrr

[@terrymcanear1638]

I thought nurd rage was the best, but when I found Nile Red about a year ago, I changed my mind totally. He releases a lot of videos, all of the videos are high quality and he does a brilliant job of explaining the steps and what reactions are taking place.. Only problem I have with this channel is that he doesn't have enough subscribers. This channel deserves a lot more.

[@NileRed]

+Terry McAnear Thanks :)

[@Agustx0]

4k, awesome intro and quality active content. What's next?! Amazing Nile Red. Keep it up!

[@Agustx0]

Oh, I forgot, new mic?

[@billied2003]

+ZeroGames intro is gay

[@Agustx0]

billied_2003 Thx for the feedback! :D

[@aeriumsoft]

+ZeroGames wtheeck

[@DeathIlustrated]

+billied_2003 me too

[@alex3mirillas]

We should fix a goal for Nile, the day he puts al reagents in the beginning of this video, he would get some sort of bonus.

[@maryudomah4387]

Like a free hot plate paid for by patreon?

[@zanpekosak2383]

I think he does it on purpose.

[@strawbkittycake]

At 9:33, you labeled denatonium chloride as "denatonium hydroxide." Great video, by the way!

[@DarkWolf22K]

I came back here because I was shocked to learn... HE ACTUALLY HAD AN INTRO

[@thehearth8773]

You claim in the title that denatonium benzoate is the most bitter compound known, but wikipedia claims that denatonium saccharide is five times more bitter, being detectable at 0.01 ppm as opposed to the benzoate's 0.05 ppm threshold. Both of these are still absurdly bitter, of course.

[@AngeloArrifano]

Sounds like you just found ourselves a new challenge for playing cards 🤣

[@GRBtutorials]

Ironically, saccharides are usually sweet.

[@aemiko8726]

@@GRBtutorials reminds me, saccharin actually has a nasty bitter aftertaste

[@5naxalotl]

basically people lump the denatoniums together. the practical difference is trivial

[@CNSninja]

Time for some super-scientific self experimentation.

[@emanuelriveratorres2951]

Hey Nile, I've been watching your videos for sometime and I really like them, and are one of the things that made me REALLY interested in organic Chemistry. They also helped me with making a project that I have to do in my Organic Lab course :D THANKS!! I would like to see the Calcium Acetate from Vinegar and Egg shells! and for future videos Nonivamide and Vanillylamine have my votes. I also second +TheRedKnight 's motion for organometallics reactions if you can.

[@NileRed]

+Emanuel Rivera Torres I am glad you enjoy! The video you want will be out eventually :)

[@daBuzzY90]

+Nile Red Hey Nile! I'm really enjoying your videos... A question, how much money have you spent on equipment so far?

[@NileRed]

InbredDucks I would go with "a lot". I dont have a dollar amount though. At least a couple thousand dollars on glassware and chemicals

[@Prototype5151]

Wow, really interesting compound, I could only imagine how bitter it is. Also, kudos for your new mic and intro. Keep up the good work, I can't wait for more videos!!!

[@luluciferia1948]

I really enjoyed science in school but I didn't do well because tbh didn't really have friends and there was a lot of group work. But your channel reignited my love for science and I really appreciate it.

[@jennifersaar1611]

You and me both. Nothing like hearing the teacher say, “Divide yourself into groups,” or “Find a partner,” to cause soul-crushing depression.

[@Tuftsss]

"From his fingers, to the cards, to his friend's cards, to his friend's fingers, to his friend's mouth". This should be used as an experiment to demonstrate how COVID can spread.

[@andrewbloom7694]

I'm not surprised lidocaine is involved. The lidocaine suspension I got after GI surgery was horrific. The only thing that's maybe worse is the barium chalk drink before a CT

[@SmokeyAndTheBud]

The gift that keeps on giving...

[@jingerjesus4621]

“This chemical ruined my life for a few days nonstop” “Anyway we’re making it with these few ingredients”

[@saosaqii5807]

Now teach us how to get this thing out of my hand sanitizer

[@JustinKoenigSilica]

Try distillation

[@hiiammatthew8735]

Oh god this aged like milk

[@Tactix_se]

@@hiiammatthew8735 LMAAAO

[@kirayoshikage4057]

Not using hand sanitizer in the first place works just fine. If you accidentally took a shit straight into your palm, try soap or something, should be more than enough. If you work in medical field... Just use pure alcohol?

[@TheRedKnight101]

Could you do some organometallic reactions?

[@jamie91995]

YES PLEASE!!!!!!!!!!!

[@SwordOfApollo]

+The Chemistry Kid n-Butyllithium flamethrower, baby! ... Oh, and useful stuff like Grubbs catalysts too....

[@jamie91995]

+Sword of Apollo I would LOVE to see dimethyl Mercury, but it is incredibly toxic, which is like saying the sun is a bit warm.

[@elephystry]

DO DIETHYL ZINC IT IS PYROPHORIC

[@hawks1ish]

madz bush do you mean the positive nitrogen ion on the right with the negative chlorine ion? That's funny 😉

[@batubulgur]

Nile you are awesome. I wish some glassware or chemical compound company sponsors you or something. Your channel and style is so good. I love it. Keep going man.

[@NileRed]

+Batuhan Bulguroğlu Thanks :). I have actually had someone offer in the past to donate glassware to me, but right now I dont really need it. The biggest thing i need now is a good vacuum pump. Maybe ill shop a little for it today.

[@zuthalsoraniz6764]

Could you use this stuff to dissuade/find out an office food thief, by lacing your food with it?

[@namibjDerEchte]

Yes.

[@Cyberw4y]

Would you jump through so many hoops just for that? There are cheaper things you can buy at the pharmacy.

[@HaloDJumper]

Cyanide works better. Nobody will ever steal your food again. Unless you're caught.

[@ethangoldsmith9332]

Staple their fingers,

[@f1redemon966]

@@ethangoldsmith9332 it hurts when that happens

[@caseydarrah]

It's also used to coat some smaller video game cartridges to keep kids from putting them in their mouths.

[@Jeffrey_Wong]

Nice intro!

[@friedchickenUSA]

i just noticed that the stir rod in the oil bath is a paperclip. so good.

[@fashiharz8584]

Hi Nigel, would you make a bitter blocker substance? That would complement this video nicely.

[@kevinbyrne4538]

The quality of your videos just keeps improving.

[@thomaswburkhart]

I love the fact he’s using a paper clip as a stir bar lmao I’m going back and rewatching a lot of your videos

[@kacperolszowski1331]

Fun fact: it's also used for covering of nintendo switch game cards, so kids wouldn't eat them

[@Gisaboiad]

Damn, that's an epic intro. If only you kept it.

[@johnladuke6475]

"When I was playing cards one day..." It's cool, man. We know you're not playing poker, blackjack or baccarat. You can tell us. Was it MTG, Pokemon, or Yu Gi Oh?

[@Noob___Noob]

I like that washing technique. One less separatory funnel to wash.

[@nicholasfriar8612]

Sounds like a great torture device. Give someone a full course meal, and have them eat, but its heavily laden with the bitter chemical, and they have to eat all of it

[@stenmarcusmalva5153]

Hi Nile. Can you do some different thermite reactions to capture different metals like manganese, silicon etc. Keep up with good work!

[@JohnFKennedy420]

I feel like I’m the only person watching NileRed that isn’t studying to be a chemist 😂 I just love seeing the process and end result, I have zero comprehension of the science behind it, when when he explains it in meticulous detail.. damn it Nile your videos make me feel stupid in the best way possible😂

[@mattheww9656]

Guess you just don’t have the brains for it. ¯\_(ツ)_/¯

[@pushbutton8548]

Your description makes me want to eat this stuff

[@edenmartinez783]

I love that a numbing agent is used to make bitter

[@masochisticcooking7078]

This was the first video I watched on this channel and I hooked me now 3 years later i still love this channel

[@cvspvr]

masochistic cooking sounds like it'd be the greatest cooking show ever

[@ehfoiwehfowjedioheoih4829]

Please no intro. It does not fit with your videos

[@joannabaker7402]

"Making the most bitter chemical in the world" but every time Nile says acetone it gets faster

[@Anonymous-df8it]

Lol!

[@destinyb7114]

Nice sound branding! (I don't know what its called😅) I watch your videos everyday (don't judge me😅🤣), but hadnt seen the little intro audio branding dealie yet, I like it!👍👍

[@erinmayo5170]

I found nail polish remover that said 100% acetone and I was going to use it as a solvent but the I looked at the ingredients and it said acetone and denatonium benzoate. 100% acetone my ass.

[@weeaboo_weirdo]

It might’ve said that because the amount of acetone in the nail polish remover is so close to 100% that they just rounded up

[@Monstrosity285]

its also used as the bitter coating on nintendo switch games

[@omarallabban8242]

Nile explaining how the reaction works: Me: hahaha, say the funny words science man 🤪

[@blueberry1c2]

If some jerk synthesized 50 tons of this stuff and dumped it in the ocean... rip everyones tastebuds for the next 200 years lol

[@yee6870]

😮

[@BAgodmode]

We weaken it, aerosolize it, and use it to test it respirator fit. We put on the respirator, then a hood over it and pump it with the aerosol. The idea is the tester can tell if the mask fits because you’ll make a face for sure if it’s getting through. Super ice cold water makes it disappear, that’s how I got bitrex off my hands and tongue.

[@goc19777]

NileRed uploaded: *Impossible.*

[@thatkidavid]

My favorite NileRed phrase "I decided to/not to for some reason"

[@bigrockets]

how about some methanol synthesis?

[@fvckyoutubescensorshipandt2718]

La Beast thinks eating it straight is more nauseating than bitter.

[@phiodite7850]

2:56 - 3:32 Me not knowing at all what he’s talking about: “I like your funny words magic man.”

[@christiananderberg3646]

9:36 says denatonium hydroxide both places

[@navidahmed1]

This is very interesting and how you explain everything in detail is commendable. I have some remarks though: 1. You maybe should have used a separatory funnel to separate the toluene and water layer. Maybe this contributed to your poor yield? 2. I guess what happened is little bit of acetone got dissolved in your denatonium benzoate which is why it formed a jelly, like in your calcium acetate/alcohol jelly experiment. Does this sound probable? 3. You didn't wash your final product with water to get rid of acetone, is it safe then? :) Best regards to you and thanks for patiently considering my points.

[@ballisticbonzai]

10:07 maybe u should try sending it to its room

[@meatyboi2503]

my mom once put that anti nail biting stuff I couldn't eat

[@loganmante3321]

Do you know why the cost of potassium (1,095/kg) is so much more than sodium (220/kg). Is it because it is more hard to make potassium via electrolysis than sodium or is it because of regulations on the sale and production of potassium. If anybody knows please help. Just wondering, thinking about making a small electrolysis cell to make some lithium and sodium based off of some patents I have been reading and was wondering if I could do it for potassium because it was not specifically talked about in the patents or anywhere else.

[@loganmante3321]

Prices are based off of gallium source so they are probably quite high

[@Cornz38]

DTB (Bittrex) is used in rodenticide to prevent ingestion. I can attest it tastes foul but I have seen dogs wolf down trays of rodenticide and they say dogs can taste it.

[@mudkip9531]

What if I wash my face with acetone?

[@Gameboy2218]

Mud Kip If you do that you can frame your face and put it on he wall

[@absinthe7266]

it'll be the last time you'll ever wash your face

[@retrohipster994]

Your face will probably just get a little bit irritated and dry, but the denatonium benzoate but still be there and you'd still be bitter as s***. Lol 😂

[@dpasek1]

To remove the bitter residue from your skin, try washing with distilled white vinegar (5%) straight from the bottle. This seems to be more effective than plain water or soapy water.

[@WheresMyBlanket2000]

Finally! I have been waiting for this video forever! Time to have the family over for dinner.

[@Keshaire]

+Linus Tuttle I'm going to let all of my family's silverware soak in a solution of this for days. Lmao!

[@Keshaire]

+Linus Tuttle Actually, nevermind I have a good idea on how to infect everybody at my school. xD

[@nugboy420]

I wonder if this is on the switch cartridges to prevent choking Edit I checked! It is and it’s freaking disgusting lol. It’s gotta be a minuscule amount tho because it doesn’t transfer to your hands upon using them I love tricking people into trying it to see their reaction my son was the best lol

[@nugboy420]

Lick your Switch carts everyone

[@AmberLF]

This would be a great way to experiment how far something can travel between people.

[@paracovo]

Spray it on a pile of coins. Pay the bus fare with said coins. Pure evil.

[@Aztesticals]

Since this tuff is in most compressed air. You can turn the air can upside down and extract it out of the liquid as well by evaporating it in a deep rimmed glass tray

[@the_inquisitive_inquisitor]

I misread the title as "Detonatium" and got really excited.

[@MostFolkCallMeOrangeJoe]

Regarding future videos, I'd quite like to see a synthesis of something with a methylenedioxy group, but I appreciate you won't as it'll likely be a precursor to MDMA, so nonivamine gets my vote.

[@NileRed]

+Adam Harrington The nonovamide is on hold right now because im having a hard time making vanillylamine

[@MostFolkCallMeOrangeJoe]

+Nile Red What trouble are you having with it?

[@NileRed]

Adam Harrington None of the syntheses that claim to make vanillylamine work.

[@marioborras9964]

Not really enjoying new intro, but great video :D

[@NileRed]

+Mario Borras Why dont you like it?

[@marco56702]

+Nile Red In my opinion the intro is fine, it adds value to the content (which is great :) )

[@josefumi]

+Nile Red I agree with Mario, it feels slow and out of place in my opinion. Amazing video as always though :D

[@martynasmalikenas1736]

+Nile Red Well it seems like a good edited intro, but I think it's a little too long and the music doesn't quite fit.

[@NileRed]

Martynas Malikėnas yeah true. I felt like that could be the case. Thanks for the input. I put it in because it was made for me and I wanted to show my thanks. I probably won't include an intro in the future

[@huyphung7507]

I think the odd here (denatonium benzoate hard to crystallize) is due to the contamination of toluene left.

[@0xScourge]

Here comes everyone that put the new zelda game in their mouth

[@David-qj1mr]

Scourge i forgot that was thing. Just grabbed my copy of zelda and licked it to test it out. Fucking gross how bitter it was.

[@ovaltineforlife4778]

@@David-qj1mr oof

[@Manamonke]

I did use something with this chemical in to stop biting my nails but it honestly just added flavour

[@Charadoesthatgaming]

Is it the same thing Nintendo uses to make their cartridges sour?

[@kevinprasetyo7862]

Ah the one they use in Nintendo cartridge thingy?

[@armanrgun47]

did you see that nazi nitrogen atom?

[@evan2587]

oy brotha!

[@maggiep9007]

Savage nitrogen

[@Emooo99]

I guess N does not stand for Nitrogen there😂

[@rj6110]

no, i did nazi it

[@grimmington2569]

Nitro Nazi... sounds like some sort of metal band

[@stonent]

The N at the end of the Denatonium Chloride looks like a dude playing basketball with a benzene ring while throwing a chlorine in the trash.

[@robmckennie4203]

diabolical prank idea: dump a concentrated solution of denatonium benzoate into a swimming pool. primary effect, no one is going to want to swim for the rest of the day. secondary effect, i expect it would be pretty difficult to clean out, unless there's a way to do it chemically that's safe for use in a swimming pool

[@frognik79]

Codeine from headache/flu tablets :P

[@sweatin]

The man has evolved to get 1.8 Million views in a day!

[@johnpfeifer6049]

Why do I feel like you used this for a prank?

[@pinksapphire2898]

dudee same i was like this would be so awesome to pour into someones sweet drink like your expecting a sweet milk pr sugar nope

[@luisalvaradoflores1121]

John Pfeifer this would be a ver bad joke

[@notpulverman9660]

They will physically attack you once they finish vomiting.

[@0x8badf00d]

*If* they ever finish vomiting...

[@MisterCOM]

use the anti nail biting stuff and put a dab of it on a stick of lip balm or something

[@rotam8680]

im pretty sure im more bitter than this. my bitterness lasts years

[@nihilism242]

Is this the stuff they add into Nintendo Switch's cartridges to make them taste terrible? Awesome vid!!

[@brillopad1392]

There is a way to make it more bitter stiil; by adding a certain amount of (you won't believe this) saccharin! But that combination makes it, some claim, the bitterest substance on earth.

[@flame3723]

He sounds pretty bitter about all the bitter in his mouth

[@WhittyWhitts]

Bro that intro was LIT

[@minitos1]

cringe-tro

[@zafinger8779]

Anyone else got this reccomended 5 years later.

[@godfreypoon5148]

Is this compound responsible for causing feminism?

[@Gameboy2218]

Godfrey Poon Nothing is that bitter

[@helpme5785]

Godfrey Poon no but it's clearly responsible for this comment.........

[@goofyangelina3224]

Modern 21st century feminism is too ridiculous to be compared with a glorious chemical chemists used brains to synthesise

[@Anonymous-df8it]

@@helpme5785 Yep!

[@krystianmazgajewski1663]

Acrolein, the metabolite of cyclophosphamide cured with mesna. Also, bromobenzene+grignard rxn ---> ---> trityl carbocation --> ---> crystal violet or malachite green ---> organge II or methyl organge :)

[@bynlb]

My mum used to put this on my figers to prevent me from biting them when I was a kid. Despite the bitterness of it, I did it anyways lmao.

[@shapphirethewolf8814]

Wait what?

[@sleepful1917]

wish we could get that nitrous oxide video, its such an interesting chemical

[@jamie91995]

Can you please do a lab tour?

[@baranorak4080]

For anyone wondering, this is the same substance they use on Nintendo Switch cartridges to deter ingesting them...

[@donniemiles8982]

mouthwash seems to be the best way for you to wash stubborn smells from skin, perhaps it could work with this.

[@qazsertyer]

Nice intro! But maybe you can add something related to chemistry. One idea could be putting a molecule inside the red circle and depending on the video you could change it.

[@Nerad137]

Also in some arsing brands of hand sanitizer. Told the operator in the cafeteria at work that if he wanted me to sanitize my hands before I put them on my food, stop buying that bitter infused crap. I did that once and spent the rest of the day trying not to throw up.