LSD analogues

[Incunabula]

Was just wondering what opinion you guys have on this part of "Recreational Drugs" by Professor Buzz?

"Substituents

LSD analogs (lysergic acid amides) can be prepared by substituting amines in place of diethylamine. The potency usually drops anywhere from 33% to 75% depending on the substituent. Diethylamine is highly suspicious, and the substituent will produce a lysergamide that is most likely legal, as legislation has only singled out lysergic acid diethylamide. Little work has been done on the potency of substituted Iysergamides, so a little experimentation by you may be in order. Personally, I would like to try substituting a potent phenethylamine or phenylisopropylamine such as DOM (STP) or 4-bromo-2,5-dimethoxyamphetamine. If I could get a government grant, or maybe a grant from a major pharmaceutical corporation, like Upjohn or Lilly, then I could play around with such experiments.

The following substituents give lysergamides with potencies as indicated in doses per gram (remember that LSD gives about 6,000 to 9,000 doses):
Ethylpropylamine 2,000 to 5,000
Morpholide 600 to 2,000
Methylpropylamine 600 to 1,000
Dipropylamine 600 to 1,000
Methylethylamine 400 to 600
Dimethylamine 300 to 400
Pyrrolidide 300 to 400

As a point of reference, DOM (STP) is one of the most powerful amphetamines, at 200 doses per gram. At $5 a line, its value is about 5 times 200 = $1,000 a gram. For more info see JMC, 16, 532 (1973)."

I know that morpholide is active, but the rest, is it just bullshit or what?

 

[sekio]

No, he speaks truth, the other lysergamides are active, but most of them are around 1/4 to 1/10 the potency of LSD.

Other known analopgs are the 2-pentyl and 2-butyl amides, & methyl isopropyl amide.

I'm pretty sure none of these are sold at "street level" though - if you're able to get ergotamine & a lab but cant make diethylamine... that says something

 

[trip.more]

2-butyl amide is even more potent than LSD

 

[Vader]

DOM (STP) is one of the most powerful amphetamines, at 200 doses per gram. At $5 a line

A line? Snort 5mg of DOM? You first mate.

 

[Transform]

Fluorinated analogues hold promise. Some have even been studied and show to have higher potency than LSD in vitro.

I'm surprised it hasn't been used to skirt schedules more to be honest.

 

[Cortexiphan]

2-butyl amide is even more potent than LSD

Do you have a link to a study showing this?

 

[sekio]

The (R)-2-aminobutyl analog is slighly more potent than LSD. Racemic lysergic acid 2-butyl amide is still less potent.

 

[ebola?]

Racemic lysergic acid 2-butyl amide is still less potent.

Aren't most commercial syntheses selective for a single stereoisomer (out of the potential four)?
...
Hmm...the high potency of lysergic acid 2,4-dimethylazetidide suggests that there's a lot of wiggle room for the amide substitution (http://en.wikipedia.org/wiki/Lysergic_acid_2,4-dimethylazetidide).

ebola

 

[Cortexiphan]

I guess the stereochemistry mentioned is the 2-carbon of the 2-butylamide. I found this on the Heffter Institute homepage, and yes, the (R)-2-butylamide is ever so slightly more potent than LSD, but then the error bars in DD are quite big too.

The SS-azetidide is twice as potent but as soon as you 'wiggle' those methyl groups in other directions the ED50 drops by 4-6 fold.

 

[Incunabula]

No, he speaks truth, the other lysergamides are active, but most of them are around 1/4 to 1/10 the potency of LSD.

Other known analopgs are the 2-pentyl and 2-butyl amides, & methyl isopropyl amide.

I'm pretty sure none of these are sold at "street level" though - if you're able to get ergotamine & a lab but cant make diethylamine... that says something

Thanks for the answers. very interesting. I guess ergotamine is the precursor for all of these?

 

[sekio]

Yeah, all the ergoloids and derivatives (LSD, LSA, PRO-LAD, etc) need precursors like ergotamine.

 

[Incunabula]

Fluorinated analogues hold promise. Some have even been studied and show to have higher potency than LSD in vitro.

I'm surprised it hasn't been used to skirt schedules more to be honest.

You mean why we haven't seen them as RC's? Sekio just gave the reason, You'd need ergotamine to make any of them, which it self is a scheduled and controlled compound.

If you can make LSD, why make something less potent just because it's legal?

Then again, I do actually believe that we have seen some of these LSD analogues on "the streets" in blotters. But we have a whole thread in PD for that discussion

 

[sekio]

The beauty of the 2C-x, DOx, and tryptamine RC's is that the synthetic core is so easy to make and very industrially useful.

You can approach the skeleton of most phenethylamines or amphetamines, starting from common lab reagents, with no more than 3 or 4 reactions, and have "useful" drugs after a few more procedures. To make things even easier practically none of the phens/trypts are chiral, or both enantiomers are active and no seperation is needed (amphetamines/MDxx). At no stage in the setup do you have to do work with chromatography or work in the dark. The products are relatively stable to acid/base/heat and fairly easy to purify.

LSD and the ergolines don't have that convenience... the ergoline ring is a comparatively humongous, relatively fragile organic molecule. Your choices of precursors are expensive illegal sources, or growing and culturing fields of a toxic fungus that grows on rye. Lysergic acid and derivatives are chiral - only dextro-LSD is active, so you need to seperate the isomers or you get 50% inactive junk. The ergoline ring likes to degrade in extreme conditions and will sometimes rip open when exposed to light. LSD will isomerize to inactive l-LSD, or degrade entirely if conditions are imperfect. At times you need to work in a dark room. Column chromatography skills are also needed to seperate certain intermediate products.

Thus most people who are making LSD don't want to introduce more complexity into their setup by making essentially unknown analogs of LSD. There is much less reliable documentation on making LSD analogs than e.g. phenethylamine synthesis.

 

[Epsilon Alpha]

Yeah, all the ergoloids and derivatives (LSD, LSA, PRO-LAD, etc) need precursors like ergotamine.

Isn't that stuff sold online as a "nootropic"? I mean counterfeit drugs aside, one must wonder if its watched as a precursor.

 

[sekio]

The ergot alkaloids are all controlled/watched in US/UK/Canada as far as I know

 

[Sturnam]

Isn't that stuff sold online as a "nootropic"? I mean counterfeit drugs aside, one must wonder if its watched as a precursor.

I believe you are talking about what is commonly called hydergine. I noticed it is missing the 9,10 double bond, and has a huge, bulky substitution on the nitrogen where the diethyl is on LSD. I'm not good with chemistry, but I assume that these changes make it sufficiently hard enough to not be practical.

 

[sekio]

The 9,10-double bond is required for psychedelic activity. Dihydro LSD is inactive IIRC

 

[Epsilon Alpha]

I believe you are talking about what is commonly called hydergine. I noticed it is missing the 9,10 double bond, and has a huge, bulky substitution on the nitrogen where the diethyl is on LSD. I'm not good with chemistry, but I assume that these changes make it sufficiently hard enough to not be practical.

Yeah, my bad on that one. Still, given the doses involved, the availability over the internet, and how difficult most precursors are excluding MG extracts (questionable) if someone would find a way. But, I'm going to end my tangent there lol.
I'm actually not a supporter of the whole "designer drug" movement, I'm incredibly worried that someone will crank out some supposedly uber potent untested compound that will literally cause your blood to clot in your veins.

Its just very disturbing to see how potent people want their compounds, nanomolar or hell even picomolar activity drugs start to look more like chemical weapons than anything else.

 

[Incunabula]

Isn't that stuff sold online as a "nootropic"? I mean counterfeit drugs aside, one must wonder if its watched as a precursor.

Ergotamine is acctually jused as migraine medicine, togther with caffeine. They are called Cafergot and contain 1 mg of ergotamine per tablet (and 100 mg caffeine).
The interesting part is that some pharmaceutical factory (in asia?) is mass producing ergotamine legally.

 

[Help?!?!]

Ergotamine is acctually jused as migraine medicine, togther with caffeine. They are called Cafergot and contain 1 mg of ergotamine per tablet (and 100 mg caffeine).
The interesting part is that some pharmaceutical factory (in asia?) is mass producing ergotamine legally.

IDK about the Asian factory but its true they do prescribe Ergotamine though its pretty rare considering how serve side effects in comparison to the Triptans can be. They also prescribe Dihydroergotamine for migraines though i'm not sure if that has any use for LSD/ana's. I've heard though use of the tablets is rare since so many would be needed but who can really be sure(i've just heard rumors myself).