Sciencemadness Discussion Board

Increasing Alkaloid Content of Papaver Somniferum By Supplementing Biochemical Intermediates

ithurtswhenipee - 7-12-2009 at 17:25

Biosynthesis of morphine

According to this source, morphine derivatives are synthesized by shikimate biosynthesis of L-tyrosine, then the following; L-tyrosine---> dopamine + 4-hydroxy-phenylacetaldehyde---> (s)-norcoclaurine--->(s)reticuline--->thebaine---morphine + codeine. Theoretically, not considering the possibility of an enzyme or precursor deficiency, one could add supplementary amounts of one of these intermediates to increase yields of opium alkaloids from the plant. I believe the most practical of these would be L-tyrosine, being the cheapest and most commonly available. Does anybody have any opinions or information about this?

roamingnome - 7-12-2009 at 19:08

First let me predict the future

This is your first post which is about narcotics which will at minimum be shunned, or flamed, locked, and or moved. Then since i appeared from the ether to post it will further be locked shuned or ignored.

especially since i dont have a journal reference to offer. organisms with their enzymes will do something with that tyrosine. i was seeing that toluene is converted to benzyl alcohol by enzymes, or course pyruvate decarboxylase got it fair share of attention.

the reason i reply here is that, does a good yielding poppy really need enhancement from like what 14% alkaloids? well maybe it does. injecting with a syringe into the maturing pod seems a technique similar to the cactus growers with san pedro. In a large field many experiments could be done. Different concentration of dopamine or amino acid, buffers etc. Afghanistan needs more scientists right?

my back burner question is what to enrich soil of growing Phalaris grass. This really does need address.

well i hope your urine gets back to normal

ithurtswhenipee - 7-12-2009 at 23:21

But isn't your question similar to mine? Why is mine without merit? I know it's unpractical, but haven't you ever wanted to optimize something to the fullest extent? Where as I have heard of supplementing indole producing organisms with the corresponding amino acid (which I am also interested in), this is something I have never heard of before, doing this to papavers. If it's a stupid idea, that's okay, not every idea is going to be worth trying, this is why I ask peoples opinion. If moderators want to lock this thread, that is okay too, it is at their discretion. I just thought it was worth asking, that's all.

I think the answer to your back burner question is tryptophan, which you probably know anyway. Thank you for replying.

stygian - 8-12-2009 at 00:31

There's one book I've come across that you may want to see: Opium Poppy: Botany, Chemistry, and Horticulture. It has some of this type of information.

roamingnome - 8-12-2009 at 18:43

geewiz batman ...im always misunderstood

your inquiry is more valid then climategate...rock on!

thankyou..i will water the grass with turkey giblets and leftovers

[Edited on 9-12-2009 by roamingnome]

ithurtswhenipee - 12-12-2009 at 20:44

"They also indicated that exogenously supplied ascorbic acid and tyrosine were able to stimulate the production of alkaloids."
Found here.

unome - 12-2-2010 at 19:46

Reticuline would be the precursor of choice (it is the one they determined the biosynthetic path from, using radiolabeled reticuline). Reticuline would be a great precursor, except for the obvious problem of it being the product of a multi-step synthesis, via a modification of which you'd get levorphanol without the hassle of bioconversion and the losses inherent therein (via classical Grewe cyclization 85% H3PO4 or 48% HBr from memory)

majortom - 6-6-2010 at 16:20

Quote: Originally posted by roamingnome  
First let me predict the future

This is your first post which is about narcotics which will at minimum be shunned, or flamed, locked, and or moved. Then since i appeared from the ether to post it will further be locked shuned or ignored.

especially since i dont have a journal reference to offer. organisms with their enzymes will do something with that tyrosine. i was seeing that toluene is converted to benzyl alcohol by enzymes, or course pyruvate decarboxylase got it fair share of attention.

the reason i reply here is that, does a good yielding poppy really need enhancement from like what 14% alkaloids? well maybe it does. injecting with a syringe into the maturing pod seems a technique similar to the cactus growers with san pedro. In a large field many experiments could be done. Different concentration of dopamine or amino acid, buffers etc. Afghanistan needs more scientists right?

my back burner question is what to enrich soil of growing Phalaris grass. This really does need address.

well i hope your urine gets back to normal


Phalaris grass? Is dat some DMT I'm smelling?

kclo4 - 6-6-2010 at 16:34

I believe adding salicylic acid solutions increase alkaloid content as well. Might be worth looking into.

Sedit - 6-6-2010 at 17:43

I thought that the salicylic acid solution was to used in plants because it acts as a rooting hormon in a sence or atlest something along them lines. The papers over at Thevespiary somewhere detailing the effects of salicylic acid on plant growth. I ust can't remember exactly what the mod of action it had but I don't believe it was involved in alkaloid enhancement.

kclo4 - 6-6-2010 at 20:34

it does a lot of things, one of the papers mention alkaloids in poppies. It increases alkaloids, growth rate, chlorophyl content, and a bunch of other things - and it sounds like it is effective at least on the studies for tomatos.. etc
read over it again maybe?

zed - 12-6-2010 at 05:20

Tyrosine supplementation might boost alkaloid content. It seems to help many Parkinson's patients. Boosts their endogenous Dopamine levels. Ascorbic acid seems to be helpful too. Unfortunately, there is too much morphine in the world already.

The trend in Poppy Manipulation, is to alter the type of alkaloid produced. Down under, they have developed commercial strains of mutant Papaver Somniferum, that produce Thebaine as the major alkaloid. Of course, it always was the major alkaloid constituent of several common poppies that can be legally grown, but that is another matter.

Thebaine itself is pretty toxic. Moreover, it is somewhat more difficult to chemically manipulate than morphine, making diversion less of a problem. What makes the product even more valuable, is the fact that many commonly used modern opiates are easily synthesized from thebaine, while the synthetic pathways from morphine
are difficult.

So, a better question might be....."Can the alkaloid content of Thebaine type poppies be raised by supplementing biochemical intermediates?"

jon - 6-10-2010 at 13:57

thebaine can easily be manipulated into a narcotic 118 times the potency of morphine in two steps
peracid oxidation to 14-hydroxycodieneone then esterification with cinnamoyl anhydride to give rise to the 14 cinnamoxy ester 118 times the potency of morphine.

zed - 11-10-2010 at 15:05

Thebaine is also, the starting material used in the synthesis of Etorphine (Immobilon). A material the US Military, once held the patent on. I suppose they considered a potential chemical weapon. Might be more toxic than Sarin. WMD type stuff.

Usually only used for knocking down Rhinos and such. Even the smallest doses render humans comatose, often killing them.

Because of its great potency, folks have tried to greatly dilute it, and add it to other opiates as a booster. Generally, this only serves to boost local overdose deaths.

Mostly, Thebaine is used to produce things like the ever popular Oxycontin (Percodan), and it's rarely available cousin Numorphan.

[Edited on 11-10-2010 by zed]

dr. nick - 21-11-2010 at 05:06

According to "Opium Poppy" by Kapoor even the Latex (and most poppy plant cells) itself is able to convert Tyrosine and other precursors into Morphine ... strange and veeery interesting :)
If it is possible to keep the latex or the cells "alive", active and fresh?

What i wonder is what would be an adequate concentration of, say, tyrosine when experimenting with feeds for live plants or root cultures ...

Paddywhacker - 27-3-2011 at 23:27

An old topic, but some things never die.

Look up "hairy root culture". Basically, a plant is infected with a species of Agrobacterium that does a natural genetic modification, turning some of the plant cells into permanent roots. You take some of those plant cells and grow them on agar until they recreate root tissue, then propagate the hairy roots in liquid medium.

Salicylic acid is a stress hormone. Applying it should cause the plant's stress response, typically causing it to grow short and stocky and produc more anti-grazing toxins such as tannins and alkaloids.

dr. nick - 28-3-2011 at 09:16
Quote:

Salicylic acid is a stress hormone. Applying it should cause the plant's stress response, typically causing it to grow short and stocky and produc more anti-grazing toxins such as tannins and alkaloids.


great hint, thanks!

some things are more worthy an eternal life then others, aren't they? ;)

Bot0nist - 28-3-2011 at 13:58

According to the poppies.org crew, simply giving the plant nitrogen toxicity near just when it's bolting leads to increased alkaloid production. Also, if its thebiane your after they say that topping the bolting plants many times will decrease morphine and codeine amounts, but improve thebiane yields. Some large research facilities have been 'mowing' the tops off of entire fields several times. This creates many smaller pods, but more thebiane per kilogram of plant matter is produced then when no topping is done.

EDIT: Sorry, here's the <a href="http://forum.poppies.org/index.php?showtopic=9202&hl=">link.</a>





[Edited on 29-3-2011 by Bot0nist]

dr. nick - 29-3-2011 at 12:06

no, that leads too far, just a way for keeping plants sturdy, as short as possible with as large heads as possible and highest possible "standard" alkaloid content would be the ideal. thinking about some kind of aeroponics or high air flow at the roots and pulsed lights in combo with tyrosine feed, for example. complete overkill probably, i know - it's just a project i'vebeen dreaming of for years.

under controlled conditions, maybe just 3 or 4 plants, first to get the plants to grow in the desired form, then concentrating on alkaloids and so on. lighting seems to be another key

But thanks for the link, some pretty interesting threads there at poppies

GreenD - 7-4-2011 at 19:28

I second the phalaris comment.

This really needs a year long team study. The phalaris grass will eventually be a huge deal to society (at least in my hyper-spaced vision)

chemrox - 7-4-2011 at 22:12

Jesus! all these assertions and not one decent citation in the whole bunch. A little academic rigor might add a modicum of respectability to this discussion.

jon - 9-4-2011 at 14:34

the tazies already beat you all to the punch their poppies are genetically enginerred to produce 20% morphine from the opium.
just grow the tazzy poppies or better yet ask this guy

http://gal.darkervision.com/wp-content/uploads/2009/06/walla...

yet i have no papers at hand i think doing root cultures and extracting the goods would be a fun approach to morphine (did i say that?) production

just to give this discusion an appearance of academic debate i referenced this since, likely you won't be scraping capsules if you know what's good for you in the united socialist republic of amerika.

Extraction of morphine from poppy capsules and its recovery by ion exchange
C. L. Mehltretter, F. B. Weakley
DIGITAL OBJECT IDENTIFIER (DOI)
10.1002/jps.3030460315
Journal of the American Pharmaceutical Association
Volume 46 Issue 3, Pages 193 - 196
Published Online: 23 Sep 2006
Abstract
An efficient method for obtaining morphine from domestically grown poppies has been developed. Morphine was completely extracted from dried poppy capsules with water-saturated isobutanol containing 0.23% ammonia. By passage of the extract through a cation exchange resin bed, practically all of the alkaloid was adsorbed. Quantitative elution of morphine from the bed was achieved with dilute aqueous alkali. Crude morphine obtained by precipitation from the neutralized and concentrated eluate could be converted to pharmaceutical grade hydrochloride without difficulty. The overall recovery of morphine was 90%.



[Edited on 9-4-2011 by jon]

[Edited on 9-4-2011 by jon]

[Edited on 9-4-2011 by jon]