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Another plant with kavain and dehydrokavain

chandra

Kava Enthusiast
I was always under the impression that the six kavalcones we hear about aren't because the others would have no effects in larger amounts, but because there isn't enough of them in the Kava plant to have much effect. Someone should be the guinea pig and try it out. :giggle:
 

verticity

I'm interested in things
This is good post from a member of the original kava Forums. I finally found it after searching off and on for about a week. I could only remember that he discovered another plant that had Kava compounds. It's called alpinia zerumbet, more widely known as Shell Ginger, and it contains the kavain and dehydrokavain.
http://kavalounge.yuku.com/reply/2522/a-type-of-ginger-root-that-has-kavain-in-it-#.V3xlvPkrLIU
That is interesting.
But the kavalactones it contains are DDK and DK, not kavain and DHK which are what give kava it's euphoric effect. "DK" has a double bond at the 5,6 position, whereas kavain does not. Similarly DDK differs from DHK by having a double bond at the 5,6 position:
This is the figure from the article:

ddk.jpg


Now compare the structures of the "big 6" kavalactones. It appears that "DK" is in fact actually DMY, whereas "DDK" is not one of the 6 common kavalactones, but is kind of like a cross between DMY and DHK, structurally speaking (i.e. it is like DHK with a 5,6 double bond)

kls.gif


Also, according to the GC-MS analysis in the article, "DDK" and "DK" (aka DMY) are the only kavalactones in the plant (with about 4X as much DDK as DMY). So if you ingest this stuff... who knows, it might be sort of like a combination of DMY and DHK. In fact,
@sɥɐʞɐs, it would be relatively easy to separate out the DMY to get pure DMY extract from this, for the "pure DMY experience," whatever that is...
 

Piper Methysticum

Let Kava Take The Wheel
That is interesting.
But the kavalactones it contains are DDK and DK, not kavain and DHK which are what give kava it's euphoric effect. "DK" has a double bond at the 5,6 position, whereas kavain does not. Similarly DDK differs from DHK by having a double bond at the 5,6 position:
This is the figure from the article:

View attachment 6579

Now compare the structures of the "big 6" kavalactones. It appears that "DK" is in fact actually DMY, whereas "DDK" is not one of the 6 common kavalactones, but is kind of like a cross between DMY and DHK, structurally speaking (i.e. it is like DHK with a 5,6 double bond)

Great info. Shows how far we have come in such a small amount of time. There is a distinction between them that was not easily understood by most not too long ago. I was just doing some googling on this and there's enough info to keep you busy until the next ice age.
 

verticity

I'm interested in things
So, here is another one: "Barnyard Grass (Echinochloa crusgalli)" apparently contains kavalactones as well. In this case, 7,8-dihydro-5,6-dehydrokavain (also known as DDK) and also 7,8-dihydrokavain (also known as dihydrokavain, or DHK: one of the 'Big 6'). This stuff is considered to be a major weed around the world. It can actually suppress other plants it grows among, such as rice. The attached paper looked into the question of what chemicals (phytotoxins) barnyard grass might be exuding that prevented other plants like rice and lettuce from growing. They found a bunch of chemicals, but the most potent phytotoxins they found were, yes, DDK and DHK.

So seemingly kavalactones evolved independently in at least three different plants. This also suggests that the evolutionary 'purpose' of kavalactones in wild kava (P. wichmannii) might actually have to do with their ability to suppress competing plants and fungi..
 

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verticity

I'm interested in things
And one more:

P sabulosa.jpg


This plant contains several kavalactones that do not occur in kava, that sort of resemble methysticin, in that they have an -OCH3O- ring attached to the benzene ring, but at a different position. It might be more accurate to call them kavalactone analogs (because they don't occur in kava that I know of) but seem to have similar biological activity (local anesthetic, puts mice to sleep)
 

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chandra

Kava Enthusiast
The shell ginger seems like it would grow well where I live in Tennessee. Does anyone have enough understanding of these kavalcones to speculate on what sort of effect they would give in the amounts found in this plant? I'm starting to feel like I'm failing chemistry class here.
 

verticity

I'm interested in things
The shell ginger seems like it would grow well where I live in Tennessee. Does anyone have enough understanding of these kavalcones to speculate on what sort of effect they would give in the amounts found in this plant? I'm starting to feel like I'm failing chemistry class here.
The effects of DDK and DMY on humans are not well understood. In the case of DDK, not understood at all. They are probably sedating, because they are kavalactones. But are they kavain-like, or tudei-like? I have no idea. The thing is this plant is not cultivated as a psychoactive. That is, it does not have the 3000 history of selection by Pacific Islanders that turned wild kava into domesticated kava, selecting the kava with the best effects. It also has lots of other chemicals in it besides kavalactones, that would have who knows what effect on a person. In other words, it might well make you barf. I nominate @sɥɐʞɐs to be our guinea pig. :D
 

sɥɐʞɐs

Avg. Dosage: 8 Tbsp. (58g)
Review Maestro
The effects of DDK and DMY on humans are not well understood. In the case of DDK, not understood at all. They are probably sedating, because they are kavalactones. But are they kavain-like, or tudei-like? I have no idea. The thing is this plant is not cultivated as a psychoactive. That is, it does not have the 3000 history of selection by Pacific Islanders that turned wild kava into domesticated kava, selecting the kava with the best effects. It also has lots of other chemicals in it besides kavalactones, that would have who knows what effect on a person. In other words, it might well make you barf. I nominate @sɥɐʞɐs to be our guinea pig. :D
I'm definitely interested in it and I'm assuming DDK would feel a lot like DHK...but I suppose there's no way to tell if that small difference is negative, positive or indecipherable until it gets consumed. :hungry: Like you mentioned, this plant would have many other chemicals in it, that aren't in kava and I don't know enough about them to be sure it's safe to consume.

Since it already appears to have caught the attention of pharmacological chemists, it obviously looks like it could be a safe and promising substance...at least when it comes to purified DDK crystals. I just wish there was an example of historical cultural recreational use attched this plant to observe.
 

kavadude

❦ॐ tanuki tamer
That's so potent it's actually hard to believe. Literally half of the plant consists of DDK?
this is oddly worded, but I think it's talking about some kind of extraction, which makes more sense

DDK contents in fresh leaves, stems and rhizomes range from 80 to 410 mg/g, requiring solvent extraction procedures to ensure high DDK yield. This is best achieved by hexane extraction from fresh rhizomes that were previously boiled in water, allowing DDK yields of up to 424 mg/g.
 

verticity

I'm interested in things
this is oddly worded, but I think it's talking about some kind of extraction, which makes more sense

DDK contents in fresh leaves, stems and rhizomes range from 80 to 410 mg/g, requiring solvent extraction procedures to ensure high DDK yield. This is best achieved by hexane extraction from fresh rhizomes that were previously boiled in water, allowing DDK yields of up to 424 mg/g.
Yeah, that would make a lot more sense if they are saying 40% of the extract is DDK, not 40% of the whole plant. Especially since the extraction method is optimized to maximize DDK..
 

Piper Methysticum

Let Kava Take The Wheel
I wish the original poster could chime in on this and respond to us. I'd like to know if he still works with shell ginger and what results he can confirm but it looks like he might have left the forum before the new kava forum got started. I located a site In Japan that sells it the form of essential oil after translating it this was one of the selling points

"The sedative effect, relieve stress and anxiety, also, smell Innovation Sue, let up the concentration and memory." This effect resembles Kava.
 
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