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Understanding chemotypes

nickbroken

Kava Enthusiast
I have difficulty understanding chemotypes well and how they work, I get that a certain number in a certain place will produce certain effects, but say Nene has a chemotype of 463xxx I think. Wouldn't that indicate that it was more of a heady kava as I understand that 2 and 5 are the more sedating chemotypes?
 

Gourmet Hawaiian Kava

Kava Expert
Kava Vendor
This is what Dr. Schmidt says about tudei kava and the kavalactones and there relation to each other (chemotype), just a small paragraph---"
The best cultivars show a relatively high
content of kavain, and, in relation, low contents of dihydromethysticin,
yangonin, and desmethoxyyangonin, i.e., of the more
lipophilic kavalactones. The hypothesis is that these highly lipophilic kavalactones undergo enterohepatic cycling, thus causing
a hangover [49].
1650
Kuchta K et al. German Kava Ban… Planta Med 2015; 81: 1647–1653
I hope this helps a bit. Aloha.

Chris
 

Krunʞy

Wear a mask.
Admin
Check out this post, it may give you some insight on chemotypes.
Just for reference:
1 = demethoxy-yangonin
2 = dihydrokavain
3 = yangonin
4 = kavain
5 = dihydromethysticin
6 = methysticin

Interesting to see how high the Yangonin and demethoxy-yangonin is present in the wild varieties considering they're usually the lactones in lowest concentration in the kava on the market. I personally am curious about the pharmacology of these lactones due to their (albeit low) affinity for CB1, but alas, there is too little research.

Where did you get the chemotypes listed in this paragraph?
"A typical wild kava (piper Wichmannii) has a chemotype of 215634, notice that the #4, the kavalactone we like so much is at the last position, this is a kava you do not want to drink. The kava called Koniak has a chemotype of 256134, a kava called Borogu has a chemotype of 246531, a kava called Borogoru has a chemotype of 245613."​

BTW Deleted User01, I don't think Chris was trying to assault Koniak, but it is of interest to see the chemotype listed although we don't know what source Judd's comes from and what source he had.
It's my understanding though, and please correct me if I'm wrong Chris, that PNG is not known for being a country that drinks kava or exports it, let alone has much of a kava culture. Is it also true that most of the kava grown there is tudei? I only make this assumption based on the fact that all the kava I've come across (or heard about) that was from PNG was tudei, without a doubt. Granted, they might be starting to cultivate and start to selectively breed more "noble-esque" kava, though I don't know. I'm interested in what you know about this.

Also Chris, when you say an optimal kava has the DHM in the 4th position, that would seem contrary to what a lot of people seem to enjoy about the sedative, muscle-relaxant nature of kavas containing more DHM.
For instance, if the "optimal kava" has a chemotype of 462351 and Borogu has a chemotype of 246531 and Boroguru has a 245613 chemotype then why do they consume these in the amount they do, let alone export them (since they have to be noble for export)?
 

verticity

I'm interested in things
It is generally thought that 4 (kavain) is the "heady" kavalactone, and that 2 (DHK) and 5 (DHM) have "heavier" effects. This is I think based on people's experiences with noble vs. tudei kava, the former being dominated by kavain, and the latter being dominated by DHK and DHM. However, it should be noted that DHK (2) is often high in noble kava as well, so I'm not quite as convinced that DHK is truly "heavy" as I am about DHM--which definitely is. It's possible DHK could be sort of intermediate between kavain and DHM in effects.

Also, the effects of 6 (methysticin), 1 (DMY), and 3 (yangonin) are even more poorly understood by us. And by "us" I mean not scientists, but experienced kava drinkers. I have drunk a lot of kava, and looked at a lot of chemotypes, and yet I still don't really have a good feeling for what 1, 3, and 6 actually feel like, because the gross effects seem to be dominated by 2, 4, and 5. Methysticin, DMY, and yangonin probably contribute to the subjective effects in a more subtle way, but I couldn't really tell you how.

So, to answer your question about that chemotype, and whether it is consistent with how we generally think of Nene as a mildly sedating cultivar: The dominant KL, kavain, is not very sedating, but in the second and third position there are 2 kavalactones that are rather mysterious, so just looking at that I couldn't tell you anything other than that it is definitely a noble kava that is not likely to be super duper heavy like a tudei or even a heavy noble like borogoru, but it could well be mildly heavy.

Another thing to keep in mind is that there are other kavalactones not in the "big 6" in kava that can also contribute to the effects in mysterious ways, as well as possibly other non-KL psychoactives that might contribute a subtle effect.
 

verticity

I'm interested in things
This is what Dr. Schmidt says about tudei kava and the kavalactones and there relation to each other (chemotype), just a small paragraph---"
The best cultivars show a relatively high
content of kavain, and, in relation, low contents of dihydromethysticin,
yangonin, and desmethoxyyangonin, i.e., of the more
lipophilic kavalactones. The hypothesis is that these highly lipophilic kavalactones undergo enterohepatic cycling, thus causing
a hangover [49].
1650
Kuchta K et al. German Kava Ban… Planta Med 2015; 81: 1647–1653
I hope this helps a bit. Aloha.

Chris
At the risk of getting a little "in depth" here...

That hypothesis about why certain KLs are heavier is interesting (basically that they are recycled from the liver to the intestines and then back to the liver so that they take longer to be eliminated). In that paper [attached here], that fact is attributed to unpublished conference proceedings by Lebot, so I can't find the details about what the basis for it is. So without more details, I'm not sure if I believe that. First, the fact that a substance takes longer to be eliminated does not imply that it will have a heavier effect, simply that whatever effect it does have will last longer. In other words, if a substance stays in your system longer, yes it could be more likely to cause something that feels like a hangover the next day, but that does not imply that the acute effects would feel sedating. Second, I'm not sure if the statement that DHM, Y and DMY are more lipophilic than the other KLs is a true statement. In a paper titled "Isolation an Purification of Kava Lactones by High Performance Centrifugal Partition Chromatography" by JR Mikell and colleagues (J. Liquid Chromatography, v. 26, no. 18, p. 3069) they developed a solvent system for separating KLs based on their relative affinities for non-polar (lipophilic--having an affinity for fats or oils) vs polar (more affinity for water) solvents. Other research has shown that they are all lipophilic (and not water soluble), but differ slightly in how much they are (the KL numbers here follow the usual convention):
kl_partition.png

Now if I understand correctly, in this table, the KLs are ordered from most lipophilic (top) to least (bottom), since I think the partition coefficient refers to the ratio of the concentration in the upper phase (hexane/acetone, a more lipophilic mixture) to that in the lower phase (methanol/water, a less lipophilic mixture), this shows that the most lipophilic KLs are: DMY (1), DHK (2), and yangonin (3). So it is true that DMY and Y are among the most lipophilic. But DHM (5) is actually less lipophilic than kavain (4). So, possibly Lebot confused DHK and DHM in his talk or something (or maybe Schmidt misinterpreted Lebot's oral presentation as in a game of telephone), but since DHM is generally established as the heaviest, and K as the headiest, this theory (that the more lipophilic KLs are also the heaviest or most likely to cause hangovers) does not seem to hold water.

This grouping of the KLs from most to least lipophilic is also roughly consistent with their relative retention times in HPLC chromatograms, and exactly consistent with the ordering of retention times on HPTLC slides, which might in fact be the origin of Lebot's numbering system.
 

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Krunkie McKrunkface

Kava Connoisseur
Another thing to keep in mind is that there are other kavalactones not in the "big 6" in kava that can also contribute to the effects in mysterious ways, as well as possibly other non-KL psychoactives that might contribute a subtle effect.
yup. 18 known KL's...... so far.

But I suspect that as with nutrition continually finding new vitamins over the decades, there may be more. And as we find with micro-nutrients and phytochemicals, even some things in tiny amounts may be crucial to our experiences (and health effects) and might explain why two people react differently to the same kava.

Then of course, the KLs are only half the picture. On the receiving end we all have receptors, crucial, and they vary and also change over time as they get trained and untrained. And finally, but not least, situational dependencies.

Lots of variables.
 
D

Deleted User01

Guest
Chemotypes are only a guuide because your own physical chemotype also comes into play. The only thing I can say for sure is that any kava that begins with 2 is going to be very heavy and subject to tudei effects. Those beginning with 4 are considered safer for everyday use. But it's fun to look at the chemotypes and project the effects. I have seen posts where someone says, "I bought that heady kava and it put me right to sleep". You never know.
 

Krunkie McKrunkface

Kava Connoisseur
Chemotypes are only a guuide because your own physical chemotype also comes into play. The only thing I can say for sure is that any kava that begins with 2 is going to be very heavy and subject to tudei effects. Those beginning with 4 are considered safer for everyday use. But it's fun to look at the chemotypes and project the effects. I have seen posts where someone says, "I bought that heady kava and it put me right to sleep". You never know.
All I know is after chugging a couple of litres of Squanch it makes me feel..... bloated. Plus it makes me feel like I gotta pee.
 
D

Deleted User01

Guest
Frequent urination is another topic. There are some Kavas that send me to the loo more than others. I also need Lip Balm with those. I wonder what chemotype is responsible for that? Those that encourage urination can also be used for certain medical conditions in lieu (loo) of diuretics so it ain't all bad.
 

Krunʞy

Wear a mask.
Admin
Frequent urination is another topic. There are some Kavas that send me to the loo more than others. I also need Lip Balm with those. I wonder what chemotype is responsible for that? Those that encourage urination can also be used for certain medical conditions in lieu (loo) of diuretics so it ain't all bad.
I wonder if that too can be noted as difference in how we individually react to kava or if it is an overall consensus on drinking too much liquid.
 

Krunkie McKrunkface

Kava Connoisseur
Frequent urination is another topic. There are some Kavas that send me to the loo more than others. I also need Lip Balm with those. I wonder what chemotype is responsible for that? Those that encourage urination can also be used for certain medical conditions in lieu (loo) of diuretics so it ain't all bad.
kava cured everything related to my entire plumbing system. No complaints here. I thought that stuff was just "old age" but kava fixed it. So it wasn't "old age."

Weird how we just accept getting fat and sick and weak and in pain and goofy plumbing, cuz it's just the curse of old age, normal, our fate. But it's not normal at all. Just more bs for kava to strip away. I love the way kava strips away bs. of course, then we have to deal with what little is left, which might have been comfortably hidden, or hiding, but it's probably better this way.
 
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Krunʞy

Wear a mask.
Admin
Also, the effects of 6 (methysticin), 1 (DMY), and 3 (yangonin) are even more poorly understood by us. And by "us" I mean not scientists, but experienced kava drinkers. I have drunk a lot of kava, and looked at a lot of chemotypes, and yet I still don't really have a good feeling for what 1, 3, and 6 actually feel like, because the gross effects seem to be dominated by 2, 4, and 5. Methysticin, DMY, and yangonin probably contribute to the subjective effects in a more subtle way, but I couldn't really tell you how.
This may be a stupid question, but are there any kavas that start with the chemotype 6XX? I don't think I've ever seen one.
 

nickbroken

Kava Enthusiast
Is there any possible way to isolate and collect a certain chemotype for better testing of the effects or am I a moron for asking?
 

verticity

I'm interested in things
Is there any possible way to isolate and collect a certain chemotype for better testing of the effects or am I a moron for asking?
A chemotype can be isolated just by drinking kava from a single batch of a specific cultivar. In other words, each serving from a single bag is normally the same chemotype. But if what you mean is: can you isolate a single kavalactone? Yes, that can be done, but it is very expensive. You can buy pure kavalactones, such as kavain, for a couple hundred dollars per gram. That is way too expensive for most people who are not extremely wealthy to test ingesting. Also the pure KLs are not sold for purposes of human consumption, but as testing standards. I have seen reports of people consuming pure kavain, and it is reported to have a stimulating effect, but I don't know of anyone who has tried to use pure samples of the other KLs on themselves. A problem with trying to test the effect of pure KLs--however--is that it has been shown in mice that the KLs have a synergistic effect when combined together: the effect of kavain or DHM when consumed with broad spectrum kava extract is stronger (and possibly different) than the effect of pure kavain or DHM by themselves. So because of that, it could be really hard to tease out the effect of the individual KLs.
 

chandra

Kava Enthusiast
This is so interesting, but it's also part of the fun of drinking kava. When you drink beer, you know how it will affect you. If tequila makes you mean, all tequila will make you mean. When it comes to kava, the effects of each kava are always a bit of a surprise, no matter how much research you do beforehand. The mystery and the experimentation are part of the fun.
 

Krunkie McKrunkface

Kava Connoisseur
This is so interesting, but it's also part of the fun of drinking kava. When you drink beer, you know how it will affect you. If tequila makes you mean, all tequila will make you mean. When it comes to kava, the effects of each kava are always a bit of a surprise, no matter how much research you do beforehand. The mystery and the experimentation are part of the fun.
Yup. I still don't know what nambawan does to me. I just know that I like it. But I *will* figure it out, ragnabbit. Maybe not today, but not for want of trying.

And just to be totally on topic here, I believe that it is some bizarre chemtype, maybe not in the first 6 KLs but somewhere in the other 12.
 
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