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Topic: Why does diethylamide make lysergic acid more lipid soluble?  (Read 2518 times)

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Offline hellomynameis

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When Synthesizing LSD from Lysergic acid... the OH from the carboxylic acid group is replaced with diethlyamine  creating Lysergic acid diethylamide.

Why would the addition of this amine make it more lipid soluble and are there any other significances about the amide group in LSD?

Offline RaInBowDaSh1488

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Re: Why does diethylamide make lysergic acid more lipid soluble?
« Reply #1 on: June 09, 2013, 09:05:23 PM »
When Synthesizing LSD from Lysergic acid... the OH from the carboxylic acid group is replaced with diethlyamine  creating Lysergic acid diethylamide.

Why would the addition of this amine make it more lipid soluble and are there any other significances about the amide group in LSD?

Are you seriously asking why an alkyl amide would be more lipophilic then a carboxylic acid?

Were you on LSD when you posted this?

Offline camptzak

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Re: Why does diethylamide make lysergic acid more lipid soluble?
« Reply #2 on: June 10, 2013, 10:52:28 PM »
When Synthesizing LSD from Lysergic acid... the OH from the carboxylic acid group is replaced with diethlyamine  creating Lysergic acid diethylamide.

Why would the addition of this amine make it more lipid soluble and are there any other significances about the amide group in LSD?

Are you seriously asking why an alkyl amide would be more lipophilic then a carboxylic acid?

Were you on LSD when you posted this?

it has to do with polarity, if you take some chemistry classes or read some books it will become clear. however the real intent of your question is obvious, and this is one of the only sites where we can't talk about drug synthesis. to be honest i'm surprised this thread isn't locked already
there are plenty of other sites where they discuss this stuff openly, and you will probably have better luck there.
"Chance favors the prepared mind"
-Louis Pasteur

Offline Borek

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Re: Why does diethylamide make lysergic acid more lipid soluble?
« Reply #3 on: June 11, 2013, 03:01:54 AM »
So far this thread is not about LSD synthesis, but about simple properties of a large molecule.
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Offline 408

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Re: Why does diethylamide make lysergic acid more lipid soluble?
« Reply #4 on: June 11, 2013, 04:32:46 AM »
Because alkyl - substituted amides are far less polar than a carboxylic acid.

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