POD 70: Unraveling Ariadne's thread with Dr. Mike Cunningham

Is this episode available to non subscribers? I would like to share it with someone who may find it interesting.

Ray Suelzer

I love when you have Mike on. I just relistened to the last one again and he’s really great.

gossamer

It's hard out here for a clandestine cook, man😂 Wondering what you've achieved with other catalysts.. ethanolamine acetate seems pretty brilliant as catalyst and solvent (70's+ thus far) wondering what other routes typically yeild

Oli

Not really, some places in US may consider it positional isomer of DOET but I didn’t encounter issues working with it at Columbia and we have DEA licenses wherever needed

Michael Cunningham

Just use alane when in doubt

Michael Cunningham

That would be a good conversation!

Plz do report back. I'm no authority on the limitations of various reducing agents, can only speak from limited experience (4-methylthio in this case). Red-Al (SMEAH) is available to the home chemist as well, non-pyrophoric and comparable to LAH.. haven't played with it yet tho

Oli

I pretty much always use LAH

Hamilton Morris

c:

Oli

Thank you! :)

Psychestim

Video taken down

Oli

Use 2:1 volume IPA/h2o, quick addition nabh4 (slight excess), v/ slow addition nitroalkane (no soyouz rockets), drop-wise addition cucl2 in h2o, reflux@80c 30 min, 50% rm volume addition naoh25% and allow to stand a while till h2 evolution ceases, phases separate immediately. allow to cool, extract with same volume IPA to pull remainder, evap IPA add acetone and then acid of choice. Doesn't work with 4-halogenated besides Cl and F. B safe, pass the knowledge, merry crimmas m8🎅

Oli

Do you have the link perhaps? I‘d aporeciate it because apparently there are a bunch of videos on reductions that came out recently.

Psychestim

There's actually a channel on youtube which recently put up a pretty foolproof nabh4 procedure using IPA, it's now my go-to. Have a look

Oli

That‘s good to hear, is one hour of refluxing enough? My friend suspects most of it wasn’t converted to the amine and stayed as the nitroalkane. Oh and did you use DCM or ether for the extraction? It could also be that he lost some in the work-up, so I’m interested to hear what solvents you used.

Psychestim

I've had reasonably high yeild with nabh4/cl2+ on the alkykthioPEAs. Zn/HCl's a bit tricky, but accessible. I wish ur friend SWIM luck

Oli

Can we get an episode on finasteride? Or dutasteride? Or just some more steroid talk? Get Derek from mpmd on here...

E Lee

How do you usually reduce 4-alkylthio-2,5-dimethoxy-nitrostyrenes to the corresponding phenethylamines? When my friend tried to reduce the 4-isopropylthio-2,5-DMNS with NaBH4/CuCl2 he only got 13% yield, whereas with 2,5-DMNS it‘s usually around 60%. We don‘t have access to LAH unfortunately, but perhaps Zn/HCl might work a bit better?

Psychestim

Ketamine doesn’t yield a psychedelic experience though

🌺ily🥀

Thank you. Lots of aldehyde n bases to play with, this one's worth optimizing

Oli

I can check my old notebooks but these days I usually use .04 Eq cyclohexylamine and .2 Eq ammonium acetate

Hamilton Morris

I'm just curious which route you followed for the Henry reaction with nitropropane. I.e. which catalytic amine you used. Or if there's any literature on an optimized synthesis beyond the one in PiHKAL (I admittedly haven't searched much beyond the usual clandestine reference sites).

Oli

Doing any speaking events for SXSW that don’t require a badge? Would be neat to attend a live talk!

This balance beam mouse ariadne thing is cool. The highest I ever dosed on LSD I had a serious increase in balance and I am not normally coordinated or good at walking across beams.

runningfromthemysterymachine

I thought ketamine was originally fast tracked specifically for treatment resistant depression

Cheminterested

If that is the case, then I would guess the same for the US

Cheminterested

Depends on where you live, in many EU countries it is due to analog laws

Alex Deleeck

Is the compound scheduled?

Cheminterested

Hamilton, did you low key announce that you're making a new documentary film?

Zach

Love 💕 Doctor Cunningham. Are there any psychedelics that don’t interact with antipsychotics ? Is it a priority to get compounds into treatment resistant populations or do they skew the results unfavourably in the sprint to market?

🌺ily🥀

Wonderful episode! I really enjoyed this conversation.

gossamer

Read the Ariadne paper several weeks ago and found it very interesting. How cool to hear Cunningham talk more candidly about this work!!

This was a really cool interview. I've always had a certain fascination with Ariadne, and it doesn't seem to get talked about often, so I liked this a lot. Mike also sounds a little bit like Sodapoppin, so that's funny.

Jacub White