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View Diary: Pique the Geek 20090621.  Drugs of Abuse III:  the Psychedelic Indoles (143 comments)

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  •  last lecture in organic chemistry (7+ / 0-)

    Many years ago, when I was an undergrad, the professor finished off the second semester of organic chemistry by writing down the steps that would be required to synthesize lysergic acid diethylamide, starting from indole.

    He did point out that the yield would be very low.

    grok the "edku" -- edscan's "revelation", 21 January 2009

    by N in Seattle on Sun Jun 28, 2009 at 06:37:31 PM PDT

    •  That is some extremely demanding (7+ / 0-)

      chemistry, so demanding that no synthesis of LSD starts from indole, but from lysergic acid itself, usually derived from ergot, a fungus parasitic on rye mostly.  Since lysergic acid (and its isomers) has two asymmetric centers, there are four possible ones.  Only one produces an active product, so complex stereospecific synthetic methods and elaborate separation techniques are required.

      Warmest regards,

      Doc

      Time for real health care reform, not just to patch the patches.

      by Translator on Sun Jun 28, 2009 at 06:40:50 PM PDT

      [ Parent ]

      •  understood (3+ / 0-)
        Recommended by:
        G2geek, Translator, Otteray Scribe

        He certainly wasn't recommending that we undertake the synthesis, though he did point out that indole (unlike lysergic acid) is readily available in large quantities.

        I think the idea was to review the variety of synthesis steps and techniques that we'd learned during the semester, put into a "familiar" context.  It was 1970, after all.

        grok the "edku" -- edscan's "revelation", 21 January 2009

        by N in Seattle on Sun Jun 28, 2009 at 07:47:46 PM PDT

        [ Parent ]

        •  As an intellectual exercise, (4+ / 0-)

          it is excellent.  And it can be done.  With enough expertise, facilities, and money, one can make anything from carbon, air, water, and just a few other materials.  As Lex Luthor once said, after the authorities gave him extremely limited access to some medical laboratory facilities, "Those fools!  They don't know that I can make an atomic pile out of a sand pile!"

          Now, starting with indole it is possible to make many of the materials described here, but I do not ever to be accused of writing a drugs "cookbook" blog.  That is not my intention, and do not need the heat from the authorities that this would entail.  I have very purposely failed to mention any synthetic methods or to link to any, with the exception of Shulgan's book, which has significant historical significance in addition.

          Warmest regards,

          Doc

          Time for real health care reform, not just to patch the patches.

          by Translator on Sun Jun 28, 2009 at 07:55:46 PM PDT

          [ Parent ]

          •  Shulgin lost his Sched I license over that book. (4+ / 0-)

            I know him, and he's an absolute genius and an oldschool renaissance man, somewhere between Hofmann and Huxley.  For him and for another person I know who is not a public figure, the interest in these things is all about pure science: structure-activity relationships, neurophysiology, and empirical results in terms of perception & cognition.  

            FDA's position was, in essence, that his books (one on phenethylamines, one on tryptamines) unleashed a mess of possible proliferation of illicit manufacture, for which the penalty was loss of the license.  Strictly speaking, retaliation for an act of protected speech, but he didn't feel like fighting it at the time.  FDA could argue it's a privilege rather than a right, thus revocable arbitrarily including in retaliation for protected speech.  The counter-arguement would be that revocation of a privilege in response to an act of protected speech, is still penalizing the speech, thus impermissible.  

            Anyway, the current crop of scientists doing human-subject research with psilocybin are exceptionally cautious.  I wrote to one of them to discuss his findings in light of a possible medical application, and in my email said that this was a private inquiry and not for publication; and he wrote back affirming that he wanted to keep that discussion private.   These folks would rather that their peer-reviewed articles speak for them, and they know they are setting precedents that could lead to further expansion of human subject studies but only if each of these projects is handled very very carefully.  

            What I find terribly tragic, is that it's OK to use these compounds in pursuit of religious insight, but not in pursuit of scientific insight (such as studying the mechanisms of synaesthesia).  At the time the Founders drafted the 1st Amendment, religion was the lens through which humans looked into the deepest mysteries of existence, and science was seen as having a more mundane role.  Today science is for most of us the lens through which we look at the deepest mysteries of existence; and so, freedom of science is every bit as important (potentially more so).

            It's a good thing that certain churches have gained access, but the whole framework of Schedule I has got to be scrapped and rebuilt as nothing more than a temporary holding pen for substances that are involved in clear & present public health crises (e.g. LSD in the 60s).  There should be automatic sunset back to Sched II upon an empirical finding that a public health crisis has passed.  

            And there need to be special provisions for folks such as Shulgin who are no threat to anyone and just need a bit of protected space in which to legally pursue their research activities.  Frankly, as a culture, we are terribly backward when it comes to supporting the geniuses in our midst, and that situation will continue to cost us mightily until it is changed.  

            •  Just a very minor, technical correction. (2+ / 0-)
              Recommended by:
              G2geek, Just as a Beverage

              It is DEA (Drug Enforcement Administration), not FDA (Food and Drug Administration) that is in charge of Schedule I licenses.  Otherwise, your comments are very accurate.  I just do not like a trivial, but incorrect, point to be perpetuated here.

              Thank you for your very detailed and insightful comments all evening and the next day.  I very much appreciate readers like you who are not afraid to share there expertise.  Please keep on commenting!

              Warmest regards,

              Doc

              Time for real health care reform, not just to patch the patches.

              by Translator on Mon Jun 29, 2009 at 08:58:09 PM PDT

              [ Parent ]

              •  interesting about DEA... (1+ / 0-)
                Recommended by:
                Translator

                Shulgin had helped out DEA on a number of occasions, prosecuting illegal drug operations.  The way I heard the story about their visit to retrieve the license, was that the guys who came out there knew him and were more or less reluctantly following orders.

                What I find odd is that the CSA is partitioned like that.  But now it makes sense that FDA is authorizing more human subject research and DEA isn't saying much about it.  One hand taketh away and the other hand giveth:-)

                •  FDA falls under Heatlth and Human Services, and (1+ / 0-)
                  Recommended by:
                  G2geek

                  DEA falls under Justice (I think, maybe Homeland Security now), but the point is that they have different chains of command, and their own turfs that they tend to protect, regardless of how it "helps" normal citizens.

                  Warmest regards,

                  Doc

                  Time for real health care reform, not just to patch the patches.

                  by Translator on Tue Jun 30, 2009 at 08:09:35 PM PDT

                  [ Parent ]

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