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Re:Making chloroform so I can sleep better at night by kortex on Tuesday January 24, 2023 @03:14PM (#34509572)
> Join us for our continued lecture series, covering topics such as

Please share/blog these! I too have several degenerate chemistry undergrad stories.

> The poor efficacy of DMSO in assisting drug translocation through skin

Yep. During one particularly sleep-deprived finals week, and after recently learning about DMSO's transdermal transportation abilities, my friend and I tried making caffeine skin patches. It worked...vaguely increasing alertness. However, it itched and burned worse than just about anything I've ever experienced.

Also I can concur that chloroform isn't some instant knock-out juice. But one time, a lab mate and I were running massive columns and had accumulated several hundred liters of DCM (dichloromethane) fractions in flasks (yes, it was a loong day). Despite the walk-in hoods running at full bore, by the end of the day, coworker and I were loopy, giggly idiots. Was it above OSHA PEL? Possibly, but probably not. I think the disinhibition was a combination of energy drinks, fatigue+boredom of running hundreds of fractions, and suggestibility, as much as it was the fumes. But my lab manager did walk in at one point and immediately recoiled from the fumes (which we were nose-deaf to at that point).

Re:Making chloroform so I can sleep better at night by zoklet-enjoyer on Tuesday January 24, 2023 @04:24PM (#34510655)
You have to really dilute DMSO if you're going to put it on your skin.
Re:Making chloroform so I can sleep better at night by kortex on Tuesday January 24, 2023 @05:43PM (#34511655)
I mean, pure DMSO on the skin feels fine, albeit not the safest.
Re:Making chloroform so I can sleep better at night by throwawaymaths on Tuesday January 24, 2023 @08:20PM (#34513087)
Can you not taste the garlic in your mouth for hours after?
Re:Making chloroform so I can sleep better at night by ta988 on Wednesday January 25, 2023 @05:08PM (#34524835)
Not everybody does.
Re:Making chloroform so I can sleep better at night by joosters on Tuesday January 24, 2023 @04:48PM (#34510978)
But my lab manager did walk in at one point and immediately recoiled from the fumes (which we were nose-deaf to at that point).

I don't know whether it's true or not, but I remember a chemistry lecturer telling me that you don't need to worry about terrible smells in the lab, our noses are sensitive to extremely miniscule levels of chemicals. It's when the levels are so high that they have overpowered our senses and knocked out our sense of smell, that's when you need to worry! A wonderfully paradoxical piece of advice...

Re:Making chloroform so I can sleep better at night by kortex on Tuesday January 24, 2023 @05:41PM (#34511635)
More or less, but with caveats. It's true that many smells (eg H2S, HCN) are detectable before toxic levels, and then become un-smellable at higher levels (saturates and depletes olfactory receptors). But you should still worry about certain terrible smells, because that's often the first sign that something is going wrong. Containment failure, reaction runaway, maybe someone dumped the wrong thing in the wrong waste barrel and now it's reacting, etc.

There's also things which are toxic at the same levels as olfaction, and of course there toxins which are dangerous by the time you have smelled them, or you lack the gene to smell. Most really smelly things aren't acutely toxic like that though. Take DMS (dimethyl sulfide, byproduct of Swern oxidation. Smells like boiling cabbage at low concentration, and liquid ass at high concentration. If you are running a Swern in a fume hood, you are likely quite well-contained even if you've made the whole lab smell like a cesspit.

When we ran cyanation at the kilo scale, you better believe we had HCN detectors all over the place, wore full-face respirators, etc.

Re:Making chloroform so I can sleep better at night by jamesash on Tuesday January 24, 2023 @10:25PM (#34514016)
I pass along this amusing advice, no doubt familiar to you, but probably not to the general HN readership.

"Gattermann (Ann. 357, 318 (1907)) recommends that the operator smoke during the preparation [of HCN], for he found that a trace of hydrogen cyanide is sufficient to give the tobacco smoke a highly characteristic flavor. This preliminary warning is useful in case of leaky apparatus or a faulty hood" - from Org Syn http://www.orgsyn.org/demo.aspx?prep=CV1P0314

Re:Making chloroform so I can sleep better at night by somebodynew on Tuesday January 24, 2023 @05:35PM (#34511561)
Hydrogen sulfide is a severe example: it initially smells strongly of rotten eggs but quickly damages the nose until it is undetectable and further exposure can be lethal. For most other chemicals, smells only fade to the background during prolonged lab work through mundane desensitization.
Re:Making chloroform so I can sleep better at night by toss1 on Tuesday January 24, 2023 @06:03PM (#34511896)
Yup, similar to frostbite. Normal skin temp is around 86°F. as it is cooled, it goes from cool to cold sensation, to very painful at around 55°F. Below that, you don't feel anything as it continues to cool to the point where it freezes solid (which wouldn't be a problem if the freeze-thaw cycle didn't create so many little spiny ice structures that break the cell walls; a type of frog has 'anti-freeze' in it's makeup so it can freeze and re-thaw). So, when your skin stops being painful, that's when you really need to warm it up NOW.
Re:Making chloroform so I can sleep better at night by jefftk on Tuesday January 24, 2023 @07:12PM (#34512520)
> a type of frog has 'anti-freeze' in it's makeup so it can freeze and re-thaw

Nit: it can't actually recover from freezing solid. It just has lowered the freezing point of the remaining liquid to below the temperatures it's going to encounter.

Re:Making chloroform so I can sleep better at night by toss1 on Tuesday January 24, 2023 @08:44PM (#34513296)
Thanks, you provoked me to look it up in more detail, and we're both oversimplifying, and it's even wilder than I thought. From [0]:

>> On an organismal level, they are completely frozen to death — their heart stops beating and breathing ceases. Image via Facebook

>> The frog’s death-defying trick actually comes down to one simple factor: nucleating proteins. When the frog’s skin begins to freeze, these proteins cause the water within the frog’s blood to freeze first, which in turn serves as a vacuum for most of the water out of the cells. Simultaneously, their bodies pump out large amounts of glucose to serve as stuffing material, which prevents the cells from collapsing.

>> Essentially, frogs fill their bodies full of sugar to keep themselves alive through winter. When warm temperatures melt the snow around their hibernacula, frogs slowly thaw back to life. Water melts and returns to the bloodstream, begins circulating, and restarts their heart and breathing. Within an hour or so the frog returns to normal life, completely unscathed.

Just wild!

[0] https://roaring.earth/frogs-literally-freeze-during-winter-a...

Re:Making chloroform so I can sleep better at night by jefftk on Tuesday January 24, 2023 @09:24PM (#34513598)
It's definitely wild!

But "completely frozen" isn't quite right: if you slowly lowered the temperature of a "frozen" frog enough the tiny bit of water still within the cells would freeze, and the frog would die.

Re:Making chloroform so I can sleep better at night by pantalaimon on Wednesday January 25, 2023 @04:38AM (#34516356)
They also froze hamsters and revived them with a microwave

https://youtu.be/2tdiKTSdE9Y

Re:Making chloroform so I can sleep better at night by brutusborn on Wednesday January 25, 2023 @05:33AM (#34516710)
I noticed a similar effect getting 3rd degree burns. It was very painful for a moment, then much less painful as the nerves burnt away.
Re:Making chloroform so I can sleep better at night by FPGAhacker on Tuesday January 24, 2023 @08:18PM (#34513061)
"Why Microwave Assisted Reactions in DMSO are a Dangerous Idea" -- by chatGPT

Microwave assisted reactions in DMSO (dimethyl sulfoxide) have become increasingly popular in recent years as a way to speed up chemical reactions. However, there are several reasons why this method should be used with caution, especially when it comes to safety and health concerns.

One of the main dangers associated with using DMSO, and other polar aprotic solvents such as DMF and DMAc, is their ability to dissolve and transport small molecules through the skin and into the bloodstream. These solvents can permeate through traditional protective barriers like nitrile, vinyl, and latex gloves, making them ineffective in protecting the user from potential harm.

When working with these solvents, it is crucial to match the glove to the solvent. Aliphatic polymers such as LDPE or laminates like mylar (aluminized polyester) are recommended for strong solvents like DMSO to provide adequate protection.

Furthermore, DMSO is highly flammable, which can be a significant safety hazard when heated in a microwave. The high temperatures generated by the microwave can cause the DMSO to break down and release toxic fumes, which can be harmful to both the experimenter and the environment.

Re:Making chloroform so I can sleep better at night by mschuster91 on Wednesday January 25, 2023 @04:04AM (#34516094)
> But my lab manager did walk in at one point and immediately recoiled from the fumes (which we were nose-deaf to at that point).

Reminds me of NileRed's attempts to create enormously stinky substances [1][2]. In one of the videos he said he's basically smell-blind.

[1] https://www.youtube.com/watch?v=C_eYLWLsWPg

[2] https://www.youtube.com/watch?v=LmAG8-V_WQY