predoc14
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LSD-25 to 2-Bromolysergic acid
Hello everyone,
I'm working on a paper for the synthesis of 2-bromo-LSD from LSD-25 and was wondering if someone could help me propose a synthesis for attaching
bromine. 2-Bromo-LSD is the non-hallucinogenic form of LSD that has some medicinal use in treating cluster headaches.
The synthesis of 2-bromolysergic acid diethylamide has been described by Troxler and Hofmann (HeIv. Chim. Acta 40:2160 (1957)) but it appears to be in
German. Does anyone have an idea where I can find synthesis information for 2-bromo-LSD?
LSD-25
2-Bromo-LSD
Thanks so much!
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Nicodem
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Quote: Originally posted by predoc14  | | The synthesis of 2-bromolysergic acid diethylamide has been described by Troxler and Hofmann (HeIv. Chim. Acta 40:2160 (1957)) but it appears to be in
German. |
Just what makes you think that articles written in German are not good enough?
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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DraconicAcid
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He's new, and probably doesn't know how to get a translation.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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Chemosynthesis
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I skimmed, but it looks like maybe J. Med. Chem., Vol. 16, No. 5 (1973) has relevance. Check table V for structure, and the next section has
experimentals.
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predoc14
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Where can I get a free translation?
I ordered this article in German and should have it by the end of the week. Substitutionen am Ringsystem der Lysergsäure. III. Halogenierung. 45.
Mitteilung über Mutterkornalkaloide (pages 2160–2170)
F. Troxler and A. Hofmann
Article first published online: 24 OCT 2004 | DOI: 10.1002/hlca.19570400716
What is the best way to get this translated for free? There has to be an English translated synthesis out there.
Thanks!
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ziqquratu
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Google translate is a good place to start. It'll give you the broad strokes, and it's not bad with chemical stuff, either - although copy-pasting from
old pdf's will require some fixing up!
This dictionary is also helpful:
http://www-sul.stanford.edu/depts/swain/beilstein/bedict1.ht...
Doing this over and over is how I've gained my rudimentary understanding of German chemical writing - I doubt I could intelligibly speak a word of it,
but I can usually manage to read a procedure now.
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Chemosynthesis
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Sometimes members offer to translate on this forum. I've actually had pretty good luck using various free internet translation services, a German
dictionary, and analogous reactions.
Speaking of analogous reactions, was my citation of any use? It appears to have the preparation of the isopropyl and n-butyl secondary amide
derivatives via bromination with NBS, and is in English.
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predoc14
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| Quote: Originally posted by Chemosynthesis | Sometimes members offer to translate on this forum. I've actually had pretty good luck using various free internet translation services, a German
dictionary, and analogous reactions.
Speaking of analogous reactions, was my citation of any use? It appears to have the preparation of the isopropyl and n-butyl secondary amide
derivatives via bromination with NBS, and is in English. |
I searched through volume 16 issue 5 and was unable to find the article you referenced. Do you remember the title?
Any ideas anyone on the synthesis of 2-bromo-LSD from LSD?
Thanks
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Chemosynthesis
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| Quote: Originally posted by predoc14 |
I searched through volume 16 issue 5 and was unable to find the article you referenced. Do you remember the title?
Any ideas anyone on the synthesis of 2-bromo-LSD from LSD?
Thanks |
Emetic activity of reduced lysergamides
Fatima N. Johnson, Istvan E. Ary, David G. Teiger, Ronald J. Kassel
pp 532–537
Publication Date: May 1, 1973 (Article)
DOI: 10.1021/jm00263a028
Pretty sure this is exactly the kind of thing you want.
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Dr.Bob
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Here is the important part of that paper. It looks pretty simple, just dissolve in dioxanes, add a slight excess of NBS and heat for a short time.
That sound pretty straightforward. Just don't lick your spatula weighing the SM.
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DraconicAcid
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And don't get caught with the starting material.
Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
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*FWOOSH*
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Shoot, but I always lick my spatula!
This is interesting, I'd never really looked into the medicinal potential of LSD derivatives. It makes sense though, look at whats been done with
tryptamines! (I realize LSD is technically a tryptamine, no smart asses please...)
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Steam
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Where exactly he got the starting material from is the question! XD
DISCLAIMER: The information in this post is provided for general informational purposes only and may not reflect the current law in your jurisdiction.
No information contained in this post should be construed as legal advice from the individual author, nor is it intended to be a substitute for legal
counsel on any subject matter. No reader of this post should act or refrain from acting on the basis of any information included in, or accessible
through, this post without seeking the appropriate legal or other professional advice on the particular facts and circumstances at issue from a lawyer
licensed in the recipient’s state, country or other appropriate licensing jurisdiction.
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gregxy
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How about starting from bromocriptine?
It already has the Br and is not difficult to get.
wikipedia.org/wiki/Bromocriptine
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Chemosynthesis
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| Quote: Originally posted by gregxy | How about starting from bromocriptine?
It already has the Br and is not difficult to get.
wikipedia.org/wiki/Bromocriptine
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Looked like Garbrecht's 1958 paper (J. Org. Chem. 24, 368-372 (1958)) applied to bromocriptine would be a good proposal for the paper. Not sure
exactly what you'd do about the halogen during the animations, but not going to spend much effort considering it. Definitely a reason bromocriptine
uses the same reaction I mentioned above to brominate last. Much less paperwork going a bromocriptine/ergocriptine route if ever applied practically
in a legitimate med chem setting, I would imagine. Speaking of, I wonder what the OP's paper is for, exactly.
[Edited on 3-4-2014 by Chemosynthesis]
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