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Hamilton Morris
Hamilton Morris

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Synthesizing Ariadne in Alexander Shulgin's Lab

Last fall, The Shulgin Foundation invited me to film the synthesis of some compounds in Alexander Shulgin's lab in an effort to teach the public about about Shulgin's chemistry. Over two days I filmed the synthesis of ariadne and DiPT (still unfinished) and made this short doc about the experience. The final proton NMR is posted after the end credits, yield of the recrystallized HCl salt was about 80%. I plan to reupload with some adjustments to the sound mix (and possibly update the diagrams) in the coming days, but wanted to share this with everyone as it seems some people are getting impatient for a release. I will release a shortened version of this piece on YouTube in the coming months as well, but this production was partially paid for with funds from the Patreon so I wanted to give you all the first look!

The Shulgin Foundation

Comments

Concluding it with being outside at night with you walking off screen and the view of Lafayette in the background was perfect.

Edjusted

Lovely to watch!

Dave Wright

Omg so lucky but also so deserving the fact you were in such awesome inspiration and awareness of the god father himself absolutely beautiful vid ❤️ thank you hamilton jah bless brother!! I traveled around the country hitchhiking and trainhopping id be honored to share some of my affirming experiences regarding "god" or something omnipotent that blessed me through my travels i know you dont consider yourself spiritual but id love to share some of my experiences and see if you could make sense of them other than divine intervention lol much love

joshua faver

The little LAH fire was cool! That stuff is intimidating

Geof Sawaya

Yes, you're right. When I said aggressive style I was referring to his use of more LAH equivalents and longer reflux times, particularly with glyoxylamides, not his method of substrate addition which (as you said) would have either been an addition funnel or a soxhlet. I have done hundreds of these additions and adding the substrate with an addition funnel is *definitely the norm* and recommended, particularly on a larger scale. I often don't reflux LAH reductions of PEAs and get high yields with gentle warming to around 30ºC, but it depends on the scale and the specific substrate. This one wasn't refluxed, only warmed slightly for about 24 hours, that's why no reflux condenser.

Hamilton Morris

Very nice short film, it looks amazing. In regards to Shulgin's "aggressive style", I'm a little confused. The procedure in PiHKAL in regards to Ariadne calls for bringing the THF to reflux, and then dropwise addition of the nitrostyrene diluted in plenty THF. In the video, you show what seems more akin to a rock'n'roll, dump&run-style synthesis. Not even a reflux condenser. Honestly, if I didn't know any better, I'd guess this was the first time you'd run a LAH reduction. Do you know something we don't know? I haven't checked every PiHKAL procedure, but I can't remember it ever suggesting adding all the nitrostyrene at once. Some procedures even call for the quite clever Soxhlet-style slow addition. But maybe Shulgin in reality used quite different conditions than he published (and of course not all procedures in PiHKAL&TiHKAL are by Shulgin). With some of his procedure it seems to me like he was a maniac trying to make as many compounds as possible before anyone would stop him, not being concerned with great yields or elegant chemistry, but that it worked and "bist du nicht willig, so brauch' ich Gewalt". This remark is not to question your competence, by the way, I'm genuinely curious. I know if I was standing in that particular lab I'd fumble weighing out a solid and break a Schlenk line in the process, and that's without camera. Very grateful for you bringing this chemistry to us, and with such an amazing compound no less. By the way, a friend of you had once made a nice little movie called "a delightful DMT synthesis" - do you know why they took it off YouTube eventually? It seemed like a very nice little project.

Hippo

♥️

Stefan Scheffer

Amazing work and a beautiful film! I would think a proper synthesis in that lab would require some self experimentation, but with the level of joy you appear to be experiencing, it would have been hard to discern an antidepressant effect!

Hank

This was really lovely and has greatly cheered me.

Meek

This venture must have been a magnificent trip down nostalgia lane for you. It was only appropriate you followed Sasha's LAH reduction protocol for the synthesis, rather than wimping out with milder conditions. I wouldn't expect anything less from someone who is a cliff side rock climber! You could have even added a muh aaah aaaaah evil laugh at the end and it wouldn't have been cheesy in the least. We'll apply for a pardon if you're prosecuted for committing manslaughter against one of Sasha's pet spiders!

ab irato

This is beautiful Hamilton! I noticed Keeper Trout in the special thanks! Oh my god I'd love to hear a full cactus nerd-out Pod with Keeper Trout!

Aidan

}{ Time to wash some stuff… Carry on }{

Pvt. Idaho

Beautiful❤️ I wish you'd gotten the re-x of the nitrobutene a little more clearly, but it's been a privilege watching you present chemistry again dude

Oli

Fantastic truly bravo! The excitement at the end was palpable 👏👏👏👏

Grichy

We really enjoyed this piece. Thank you. The music accompanying the film was excellent as well.

Mike

This was so beautiful and heartwarming, a touching synthesis 🥂

Drew LaBarre

Daddy long legs?!

Michael Egger

Ariadne was a fantastic choice. Imagine what a kick Sasha would get from seeing others continue the work in his special space. He would probably be so stoked on this.

Dylan

This was genuinely amazing. Makes me so excited to study chemistry

Aidan Lam

Personally I like Patreon a little better as far as apps go 😏 Seriously though, all of them--just flick your thumb and watch it scroll fast like a casino game and randomly click and there's a good one 👆🏼

5hydroxytryptameme

Cheers Sir Hamilton. Newly subscribed to the patron. Very much looking forward to both what's coming and also getting to go through the archived shows! Would anyone recommend a couple MUST LISTEN FIRST Episodes? Appreciate it. Truly

Kris Martinez

Beautiful man, thank you for including us on this journey.

Chase Ammons

Brilliant! 🥹 well done Hamilton, and thanks for another peek into this mesmerizing lab 🥼 🧪 🧫

Marta

So fun to watch! Thanks!

Bryan Burris

Oh my god, please never stop. You might be the only person that makes genuine intellectually stimulating, enjoyable, worthwhile content. Everything else is a waste of time. ❤️

Isaac Anastas

I love this so much!

Cole

I forgot how much I needed Hamilton whisper explaining things i don't fully understand in my life

avery maynard

I am very interested in the deracemization using biocatalysis (stereoselective imine reductase or amine oxidase). I believe computationally-designed enzymes are the next frontier in asymmetric synthesis. Thanks for sharing!

John Billingsley

Ok. 1. Paul looks awesome in that lab coat 2. Congratulations on this milestone. This is amazing and thank you for sharing this 3. Please get back to me when you can, I sent you a message awhile ago. I’d love to talk to you about my experiences at the lab thus far. I recently did a small personal project with Dr Daley and I’d love to tell you about it. This was so satisfying to watch on so many levels. As always, your work makes me really happy and thank you for sharing it with us all.

Etienne Atlan

I would have paid attention in chemistry class in high school if I had access to this content . Nice work- very cool to see it all in action.

rottogrotto

I'm so excited for more of the upcoming video content. The podcast is already brilliant and this is so well shot. Cheers Hamilton! Appreciative for your work.

Shaun

Pretty sure it was EtOAc with ~10% EtOH and ~1% TEA

Hamilton Morris

He shoots and he scores!

Sean Qualischefski

I've been to the lab years ago at one of Sasha's 4th of July celebrations. This brings tears to my eyes. The lighting and cinematography are just wonderful!

Skogel

Thanks for the video release Hamilton, I loved it. What a funny coincidence that I made some Ariadne this month out of curiosity. Can you tell us what solvent system you used for your TLCs in this video?

SoStupendous

The shot of your parents is great. Love the music choice. Hope you allowed yourself to revel in some of the preciousness! I can only imagine how wild/cool/emotional that might've felt! ❤️❤️❤️

mia

Thank you Hamilton this was a great video, I was wondering about the ratios of 1-nitropropane to the (2,5) compound, in Pihkal it looks like Sasha used significantly less nitropropane, I’m curious to know why you used more? Also if I did my math correct I thought it would be about 49.5mL of nitropropane to 10g of (2,5) for 10 eq, it looks like you used a little over 40mL. Thank you, I’m looking for constructive feedback 👍

Felix Ramirez

Those subaseals are looking a little sad lol

Thor Correia

All this equipment is highly standard. Most expensive thing is the rotovap which usually run 2-5k ish.

M

Daddy long legs are good luck

M

This is amazing content. Thank you Hamilton!! Can't wait to shake your hand. 🤝

M

Woah! This is so epic!!!!!!!

M

There are none

Hamilton Morris

Bushy Haired Stranger

What a great film! I really appreciate and enjoyed in its entirety. So if this compound is non regulated would that also mean it's readily available? If any of you know a RELIABLE vendor to secure a supply for scientific and research purposes? Please share 🙏🏽

Tampasami

The quality of this doc is so good. Cutting edge content.

Anthony Sheredy

It’s the original audio recording from The Nature of Drugs lecture that is the basis of the books. Ann Shulgin’s daughter Wendy Tucker (who runs The Shulgin Foundation) was kind enough to send me the ariadne clips, AFAIK this is the first time the original audio has been made public.

Hamilton Morris

Thanks, Hamilton!

oliversees

Yes, we did. See Bristol patent and attached paper

Michael Cunningham

I build houses for a living. People are impatient and often want to move in before it’s done. Never works out. Thanks for sharing the bts all the same. Mazel!

Demo Stathis

bravo!

Chad Barthalamew

I'm not a chemist, I'm an engineer and a psychonaut so I need someone to dumb this down for me How typical is this type of lab setup? Is this highly advanced for an individual? Is it $100k worth of glassware and agitators (or whatever mechanical wizardry you chemists use) Is a lab of this size and style something to be proud of? Can any chemist walk in off the street and how to use the lab? Do chemists have strong preferences for where different things are located? Are there standards? I'm comparing this lab to the video released recently showing the LSD synthesis and what looked like a university chemistry lab Sasha shulgun's lab looks more like what I would expect to see on a Saturday morning cartoon about chemistry My only other frame of reference is breaking bad, I just assume that Pfizer has a lab that looks like that but with more pill presses

Bob

Where does the Sasha Shulgin audio come from?

Peretz Golding

This synthesis yielded racemic Ariadne. Have any studies been done with either of the pure enantiomers to see if they have different effects, or different potencies?

Brian

Partially using the automated capture on Adobe Fresco (for the Henry mechanism) Partially using screen recording, every way I tried had problems. Still haven't figured out the best way to do this.

Hamilton Morris

How did you end up doing the animations?

Christopher Fye

The prospect of you filming more of this dedicated chemistry work and continuing the podcast is very exciting.

lab zee

ariadne… wonderful name. love all the tiny mythologies tucked into Ann and Sasha’s lives. They provided a model of compassionate & animistic precision medicine for the common folk.

Beatrix

I wouldn't have expected shulgin to have been storing his chemicals in coffee containers. So cool to see the precursor to my favorite 2c made by the man himself

RF

What love– so inspiring to see you taking your work in this direction. Thank you

Vincent

Hamilton, I just wanted to say that I recently watched your father's documentary about the Chicago School of Economics, "Tune out the Noise", and I have to say I found it to be really great. It was beautifully shot, interesting, informative, and it has greatly influenced my current approach to investing for the future.

Cheminterested

Brilliant! So good to see you doing this kind of work in front of the camera again.

Cheminterested

So cool!

George Trevor

That was very cool to see! Thank you for filming it!

Noel

Incredible video! Seeing the reaction drawn out, with the explanation and music filled me with a wild nostalgia I did not anticipate. I'm a Bio guy, but every time I hear you (or Sasha) talk about chemistry I think that I might actually be a chemistry person. Of course I always end up remembering that chemistry is just math in disguise 🤢. But the point is you are incredibly inspiring in your passion, just as Sasha was. Always stoked to be getting more content from you 🖤

Forrest Norcott

love the documentary style content hamilton!

rayah

Not playing.

RoseMarie

The public certainly needs more of these kinds of chemistry videos. Well done 👍

Nathan

check the edit, one of the VO tracks was switched so ham-dog is reuploading a corrected version

mycomagi

Sorry. Maybe I'm just being dumb, but is there a video here? I only see the three PDFs

Cheminterested

Beautiful work on hallowed ground ❤️

Jason Fedor

Idk anything about chemistry - what does the daddy long legs have to do with it? Lol

Ruby Mars

Absolutely lovely, masterful work as always

Ben

Obviously some people enjoy DOM at some doses under some circumstances. If I said "everyone has always hated DOM" that would be an untrue blanket statement, but saying "most people didn't like DOM very much" in reference to use in the 1960s is a generalization reflective of the historical record. I think DOM is OK at low doses, but I found 5mg to be anxiogenic and non-visual. 2C-D is vastly superior as a psychedelic in my experience.

Hamilton Morris

That reminiscent in many ways 💎 Thank you Hamilton 💘

Simon Musimix

this is so epic. thanks for sharing hamilton

rizzler

“People don’t like DOM”….untrue blanket statement. DOM in low dose 2mg up to 5mg is well tolerated, even enjoyable. Ted & Sasha both produced high quality DOM. That first street release of DOM in 1967, was unfortunately poorly manufactured in dosage. 30mg of DOM, for the uninformed, uninitiated, those with zero tolerance is a staggering overdose. I do appreciate this presentation.

Bushy Haired Stranger

Super cool share. Thank you.

Alisha Mazur

Keeping the spirit of shulgin alive, amazing! Very beautiful film, Shulgin would be happy seeing this.

Greg Shitbox

Awesome, can’t wait to visit that lab some day

Keenan Troll

Man I want some so bad, I'm gonna have to get to work myself

hashhermit

Sasha was the real Gandalf. A true wizard! This was great! Soooo, did you ever try it?

Team TJ

Really glad to see a nicely assigned 1H.

Thor Correia

You should go on Gobcast <3 https://www.twitch.tv/videos/2543461370?t=00h13m03s

Kaleb

Thank you Hamilton!

lab zee

Wowwww yesss!

FiveBinkie

Whaaaatt??

WarioGiant


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