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They call it...

Fertile

Fertile

Bluelighter
Joined
Mar 31, 2022
Messages
1,627
If you find saying 'lysergic acid diethylamide' too long, LSD to formal, please refer to it as 'amide'. It's been bugging chemists for 70 years.

OR was that the point?
 
Yea I suppose beyond lysergamides, what other well known psychoactive amides are there? If any..

-GC
 
G_Chem said:
Yea I suppose beyond lysergamides, what other well known psychoactive amides are there? If any..

-GC
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Anandamide (with its relatives) and many synthetic cannabinoids (say, indazole-3-carboxamides), some FAAH inhibitors, some mu-opioid agonists (fentanyls, moramide, phenampromide), many nootropics, all peptides (e.g. endorphins) and a great number of GABAA receptor positive allosteric modulators (benzodiazepines, Z-drugs, barbiturates, glutethimide etc.).
 
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There are many 5HT2a ligands that are amines, DMT being the most famous. DMT is simply a fragment of the LSD scaffold. I presume the rest of the scaffold is there to keep the inolethylamine in the receptor..... oh, and to improve pharmakinetics and LogP.

F&B would know more - he's studied it for decades from what I know.
 
Does anyone actually know when exactly the term "acid" was first used for LSD?
 
HOOH said:
Does anyone actually know when exactly the term "acid" was first used for LSD?
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I think it's because Ken Kesey drove around the US holding huge 'acid tests' where they offered punch spiked with LSD. I cannot find c clear etymology definition and I did look in many places.

I suppose also the large fragment IS lysergic acid, the diethylamine being a much smaller fragment... and also MANY amides work.

Did you know the oxygen of the amide (and the oxygen's lone pairs) overlays the oxygen in the NBOMe series? I know some do not have an oxygen, but clearly the O or it's lone-pairs DO fi into a receptor cleft so without it' less affinity. It's amazing how people are mapping the 5HT2a receptor.
 
Amides are generally weakly acidic... but tertiary amides are almost neutral. It's not important, because clearly LSD HAS an amine but once again it's tertiary. But the indole has a secondary amine (they are usually the most basic. I think the pKa for LSD is 7.8 so ALMOST neutral.

'Hey man, y'got any neutral.'

No, it doesn't work does it? :)
 
Fertile said:
Amides are generally weakly acidic... but tertiary amides are almost neutral. It's not important, because clearly LSD HAS an amine but once again it's tertiary. But the indole has a secondary amine (they are usually the most basic. I think the pKa for LSD is 7.8 so ALMOST neutral.

'Hey man, y'got any neutral.'
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the indole amine isn't basic, the its the tertiary amine. tertiary amines are more nucleophilic than secondary or primary amines.
 
Fertile said:
There are many 5HT2a ligands that are amines, DMT being the most famous. DMT is simply a fragment of the LSD scaffold. I presume the rest of the scaffold is there to keep the inolethylamine in the receptor..... oh, and to improve pharmakinetics and LogP.

F&B would know more - he's studied it for decades from what I know.
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The conjugated spine, right up to the carboxamide group, from the indole nucleus, keep the molecule planar, which is the gold standard for 5HT2a receptor agonists (why bromodragonfly is so silly potent). The amide group has some effects, hence why LSZ is so similar - all to do with the amide adopting the lowest energy, gull wing shape.
 
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