Friman1987
Bluelighter
- Joined
- Oct 4, 2013
- Messages
- 56
I saw that I had made some typographical mistakes that are not so visible, but I have now corrected the image and added some extra things.
http://s7.postimg.org/alpeyk3ix/1_P_LSD_METABOLISM_date2.jpg
The image shows nearly the most possible metabolic pathways 1P LSD can go through. The major part of this image shows the LSD metabolites that are already known. The rest of them are speculation. The picture is also not so complete, for example, certain metabolites as LEO or 2-oxo (LS (X)) are missing.
Here are some images from the literature that I have used as sources.
Image 1:
MAPS: http://www.maps.org/research-archive/w3pb/2008/2008_Passie_23067_1.pdf
Image 2:
Oxfordjournals: http://jat.oxfordjournals.org/content/24/7/550.full.pdf
But I guess the most important step that many are wondering over is the conversion from 1P-LSD to LSD. What I have illustrated is only based on speculation. An important metabolic mechanism of LSD is the oxidation of the indole ring. 1p-LSD has two amide. Checke the new image. The second amide (Amide 2) is much weaker Because the nitrogen is part of the aromatic ring which attracts the electron-densities. And this will Allows ketone So it open an pathway for the next step altso oxidation. The first amide (Amide 1) is perhaps to hard to handle with.
Amidase is an known enzyme involved in the metabolism/transformation of tryptophane and also involve in the oxidation of LSD.
1. http://bitnest.ca/external.php?id=%7DbxUgX%5DCY%04%05p%7Bv%19%05VZL%02UJv%60d
2. http://www.athero.org/commentaries/comm1146.asp
What amidase does is to break down the amide group:
LSD: Form-amidase can metabolize FOMBK to AOMBK. [1]
Tryptophane: Something similar happens even in biotransformation of tryptophane (form-amidase converts L-formylkynurenine ==> L-kynurenine). [2]
I speculate that the amidase may be the enzyme that also breaks down 1P. The process can also made from other pathways. There is also reason to believe that there are other enzymes/mechanism that are involved.
1P LSD is closely related to 1A-LSD or 1Acetyl-LSD.
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Here's what Albert Hofmann said about 1-Acetyl-LSD:
High Times: Are you familiar with an LSD-like substance called ALD-52 that figured prominently in an acid trial two years ago?
Albert Hofmann: Yes. ALD-52 is 1-Acetyl- LSD, a modification of LSD that proved to be as active, because acetyl is removed in the body and you have the effects of LSD. It has only been used experimentally. We sent it to the Drug Rehabilitation Center in Lexington, Kentucky, for testing some years ago.
high times NO. 11, 1976: https://www.erowid.org/culture/characters/hofmann_albert/hofmann_albert_interview1.pdf
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Here's what Alexander Shulgin said about 1-Acetyl-LSD:
ALD-52: 1-Acetyl-N,N-diethyllysergamide. This material has been explored in the 50-175 microgram range and there are a number of human trials reported, with varying conclusions. One found that there was less visual distortion than with LSD and it seems to produce less anxiety and was somewhat less potent than LSD. Another report claimed it was more effective in increasing blood pressure. Yet another could not tell them apart. ALD-52 just may have been the drug that was sold as "Orange Sunshine" during the "Summer of Love" in the late '60's. Or "Orange Sunshine" may have been, really, LSD. This was the focus of a fascinating trial where two defendants were accused of distributing LSD, whereas they claimed that it was ALD-52 which was not an illegal drug. The prosecution claimed that as it hydrolyses readily to LSD, for all intents and purposes it was LSD, and anyway, you had to go through the illegal LSD to get to ALD-52 by any of the known chemical syntheses. The defendants were found guilty. And yet, I do not know who has actually measured the speed or ease of that reaction. If ALD-52 hydrolyses so easily to LSD, and the body is indeed a hydrolytic instrument, then these two drugs should be absolutely equivalent in every particular, This is the ergot equivalent of the psilocybin to psilocin argument, except this is an acetamide rather than a phosphate ester.
Tihkal (1997) https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml
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And here is some speculation from David E. Nichols (1-Propionyl-LSD):
"I am sure that the 1-propionyl would also hydrolyze off of an indole, but I don't know whether in vivo conditions would work. In a chemistry lab, you can get off an N-benzoyl, so an N-propionyl will probably come off too. But in the body? I don't know the answer to that. The compound would not be active as the N-propionyl however. Way that LSD docks into the 5-HT2A receptor, the indole NH hydrogen bonds to serine 5.46. With the propionyl, it won't fit into the receptor."
(Unreliable source - 2015?): https://en.wikipedia.org/w/index.php?title=Draft:1P-LSD&oldid=647406505
-------------------------------------------------------------------------
Only enjoyable to read what the great scientists have to say about these molecules.
RIP Alexander Shulgin
The image shows nearly the most possible metabolic pathways 1P LSD can go through. The major part of this image shows the LSD metabolites that are already known. The rest of them are speculation. The picture is also not so complete, for example, certain metabolites as LEO or 2-oxo (LS (X)) are missing.
Here are some images from the literature that I have used as sources.
Image 1:
MAPS: http://www.maps.org/research-archive/w3pb/2008/2008_Passie_23067_1.pdf
Image 2:
Oxfordjournals: http://jat.oxfordjournals.org/content/24/7/550.full.pdf
But I guess the most important step that many are wondering over is the conversion from 1P-LSD to LSD. What I have illustrated is only based on speculation. An important metabolic mechanism of LSD is the oxidation of the indole ring. 1p-LSD has two amide. Checke the new image. The second amide (Amide 2) is much weaker Because the nitrogen is part of the aromatic ring which attracts the electron-densities. And this will Allows ketone So it open an pathway for the next step altso oxidation. The first amide (Amide 1) is perhaps to hard to handle with.
Amidase is an known enzyme involved in the metabolism/transformation of tryptophane and also involve in the oxidation of LSD.
2. http://www.athero.org/commentaries/comm1146.asp
What amidase does is to break down the amide group:
LSD: Form-amidase can metabolize FOMBK to AOMBK. [1]
Tryptophane: Something similar happens even in biotransformation of tryptophane (form-amidase converts L-formylkynurenine ==> L-kynurenine). [2]
I speculate that the amidase may be the enzyme that also breaks down 1P. The process can also made from other pathways. There is also reason to believe that there are other enzymes/mechanism that are involved.
1P LSD is closely related to 1A-LSD or 1Acetyl-LSD.
-------------------------------------------------------------------------
Here's what Albert Hofmann said about 1-Acetyl-LSD:
High Times: Are you familiar with an LSD-like substance called ALD-52 that figured prominently in an acid trial two years ago?
Albert Hofmann: Yes. ALD-52 is 1-Acetyl- LSD, a modification of LSD that proved to be as active, because acetyl is removed in the body and you have the effects of LSD. It has only been used experimentally. We sent it to the Drug Rehabilitation Center in Lexington, Kentucky, for testing some years ago.
high times NO. 11, 1976: https://www.erowid.org/culture/characters/hofmann_albert/hofmann_albert_interview1.pdf
-------------------------------------------------------------------------
Here's what Alexander Shulgin said about 1-Acetyl-LSD:
ALD-52: 1-Acetyl-N,N-diethyllysergamide. This material has been explored in the 50-175 microgram range and there are a number of human trials reported, with varying conclusions. One found that there was less visual distortion than with LSD and it seems to produce less anxiety and was somewhat less potent than LSD. Another report claimed it was more effective in increasing blood pressure. Yet another could not tell them apart. ALD-52 just may have been the drug that was sold as "Orange Sunshine" during the "Summer of Love" in the late '60's. Or "Orange Sunshine" may have been, really, LSD. This was the focus of a fascinating trial where two defendants were accused of distributing LSD, whereas they claimed that it was ALD-52 which was not an illegal drug. The prosecution claimed that as it hydrolyses readily to LSD, for all intents and purposes it was LSD, and anyway, you had to go through the illegal LSD to get to ALD-52 by any of the known chemical syntheses. The defendants were found guilty. And yet, I do not know who has actually measured the speed or ease of that reaction. If ALD-52 hydrolyses so easily to LSD, and the body is indeed a hydrolytic instrument, then these two drugs should be absolutely equivalent in every particular, This is the ergot equivalent of the psilocybin to psilocin argument, except this is an acetamide rather than a phosphate ester.
Tihkal (1997) https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml
-------------------------------------------------------------------------
And here is some speculation from David E. Nichols (1-Propionyl-LSD):
"I am sure that the 1-propionyl would also hydrolyze off of an indole, but I don't know whether in vivo conditions would work. In a chemistry lab, you can get off an N-benzoyl, so an N-propionyl will probably come off too. But in the body? I don't know the answer to that. The compound would not be active as the N-propionyl however. Way that LSD docks into the 5-HT2A receptor, the indole NH hydrogen bonds to serine 5.46. With the propionyl, it won't fit into the receptor."
(Unreliable source - 2015?): https://en.wikipedia.org/w/index.php?title=Draft:1P-LSD&oldid=647406505
-------------------------------------------------------------------------
Only enjoyable to read what the great scientists have to say about these molecules.
RIP Alexander Shulgin
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ive asked others who have said no like but i trust you more than theirs