The volitile components of tobacco, their possible effects on taste and the feelings of smoking

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Drael

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(AKA draels e-cig forum essay :p)

Didnt know where to post it, theres no tobacco consituents/biochemistry section :D Hope here is okay!

I will start with what I end with, just so its a _bit_ clearer what I am talking about, even if this is a little technical:

"What is the contribution of volitile chemicals like terpenes to the mental/physical effects of trade tobacco?

And possibly just as fun to talk about- if a more effective means were established for extracting these, as isolated components, storing them, is it possible to entirely replicate the smell and taste of tobacco? (not the yucky burning, just the plant itself)"


(Note the last post of mine below: Joyetech already has a terpene, linalool in their e-fluids)



Okay, so lets dig into what I am driving at here:

The volatile components of a plant are those that degrade quickly, enter into the air easily - they make the majority of the taste and smell of a given plant.

While many of these types of components are common to many species, they are also often bioactive in nature (they have an effect on the mind/body of a person or animal).

There are some easy examples.

1. Linalool, a terpene, which has a woody, floral, spicey note, is thought to be the primary active ingredient of lavender. Its quite well studied, and seems to be a potent CNS sedative, potent enough it relaxs muscles and slows the heart from low level inhalation of the smell alone, and via absorbtion via the skin!

Interestingly its also in tobacco.


2. Isovaleric acid has a strong pungent cheesy or sweaty smell, but its volatile esters have pleasing scents and are used widely in perfumery. It has been proposed that it is the anticonvulsant agent in valerian."


Its long been a matter of speculation, the contribution of terpenes, flavanoids are other volatiles, to the effects of a certain member of the Cannabaceae family (only mentioning it here because its _directly_ relevant - I hope this is okay, but a vast majority of the second part of this post/information would disappear if I were not able to make this reference. It is only informational, and I dont condone use of this plant - hope this is okay!).

Terpenes like 3. myrcene, limonene, alpha-Pinene & Eucaluptol are thought to contribute to the effects and the smell of this plant. There are at least a dozen suspects, and its likely more complex than that.

But I mention these four specifically for a reason: they are all in tobacco.

Limonene for example smells like orange peel - its also found in orange peels, and is medically active in them. Pinene smells like pine, and is medically active there. beta-Myrcene occurs in mangos, and is medically active there. And so on.

When the terepenes and other volitiles occur in high concentration, along with alkaloids, it seems reasonable to speculate they make some kind of interactive contribution. There contribution could even be significant.

There is one internet individual (well leave him out of this, but the information is relevant), who investigated this personally with a large group of freinds and swears that the volitiles make a major contribution to the relaxing nature of that unnamed plant. (I dont condone or advise such experimentation either obviously!)

I imagine this scenario is not that terrible unfamiliar to the vaping community (for example wta's). Ie one active being overemphasized to the detriment of the whole plant matrix.

The point I am getting to, all of those four mentioned terpenes, as well as the sedative terpene in lavender, also occur in tobacco.

Flavanoids are also often bioactive.

There are a very large number of volitiles in tobacco. In fact heres a list of one analysis (which of course mentions all the ones I bring up!):

http://leffingwell.com/download/Volatile Constituents of Perique Tobacco4.pdf






So, back to the start:

"What is the contribution of volitiles like terpenes to the effects of trade tobacco?

And possibly just as fun to talk about- if a more effective means were established for extracting these, as isolated components, and storing them, is it possible to entirely replicate the smell and taste of tobacco? (the plant, not the yucky burning qualities)."



This would of course have limitations - volatiles by nature degrade.

They would need to be stored in opaque containers, be totally vacuum sealed, out of heat, and they would degrade once opened in a limited time period, like say, a saffron absolute does.

Regarding the smell/taste: Of course existing extracts, like simple ethanol extracts, and whole co2 absolutes, may end up not smelling/tasting right for exactly this reason, degradation due to improper storage (because they are well volitile, like the name implies - all these key ingredients degrade ultra easily).

It takes very little exposure to air for say, something like the key volitiles in saffron to degrade. A pure absolute of saffron is useless about one week of having its vacuum seal broken, whereas the whole plant, the volitiles can survive much longer (although they are still somewhat sealed, and kept fresh, and still degrade reasonably fast)

So the first step in a real flavour/smell extraction, is to only extract the volitiles, the flavanoids, flavanols, terpenes, terpenoids etc. The second step would be to actually store, and treat it properly (ie as a volitile). Hard to say if the e-liquid business is anywhere near being able to provide that sort of thing, but its fun to speculate on. Plus it would be expensive! :p

Regarding the effects: We know about wta's now. We know about the combustion generated mao-inhibitors. What about the volitiles?

Thoughts?
 
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haiqu

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Limonine and eucalyptol are oils and won't vape well, possibly contaminating the atty fairly quickly. I didn't check any of the other ingredients you mention but I suspect they're additives rather than part of natural tobacco.

Do you really want to vape that crap? If so just get hold of some tobacco absolute and add it to your mixes.
 

Drael

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Limonine and eucalyptol are oils and won't vape well, possibly contaminating the atty fairly quickly. I didn't check any of the other ingredients you mention but I suspect they're additives rather than part of natural tobacco.

Do you really want to vape that crap? If so just get hold of some tobacco absolute and add it to your mixes.

Oils? Not at all. They are all super thin. Oils _contain_ them, but they are not oils. Many of them are used as solvents.

Isovaleric acid is added sometimes, but all of the others are naturally occuring. Isovaleric may be naturally occuring too, as well, I suspect.

Terpenes are the strong aromatic principles. Very common in aromatic plants.

In a tobacco absolute, they are volitile (they break down quickly), so they would break down in a liquid form, unless stored in an opaque container that is vacuum sealed. A poorly stored and transported tobacco absolute, would be a degraded diluted muddle of terpenes.

This is exactly why absolute of saffron (the colour and taste are two different terpenes), is considered useless one week after the vacuum seal is broken. Those are more volitile than most terpenes, but it gives you an idea. Freshness = purity and potency with terpenes.

There still might be some benefit in me trying some absolutes, but Id rather try something with a higher freshness, or stronger purity. In that Id prefer something with added linalool, or an absolute that at minimum is well sealed and in an opaque container.

Would I like to vape them? Yes in a natural proportion, yes im totally curious.

Terpenes arent unhealthy, as I said, they occur in lavender, orange peels etc. Linalool, especially, I am very curious about.

I didnt just post this after a few googles, lol.

I have spent YEARS studying plants and bioactive compounds, and in particular these type of terpenes are very familiar to me. The general area is part of a sort of an hobbyist academic specialty of mine.

When I realised they were in tobacco, I had a real "aha" moment. I was like, wow linalool. That makes _so_ much sense XD

I have seen, and smelt the pure liquid forms of beta-myrcene, d-limonene and linalool. They all occur in natural places, like mango's, orange peels, and lavender. They are so thin, and so easy evapourating they virtually "vape" themselves, when you open the bottle.

Thats why they are effective in aromatherapy oils (though again, pure they are not oils are all, they are merely contained in some natural oils).

I can attest to the fact the myrcene and linalool are indeed sedative, particularly the later.

Just smoking a bit of lavender, like I did when I was a teen, or even just smelling a bottle of lavender oil, is enough to get the molecules enough into your body to produce a measurable reaction (and feel pretty chilled).

TBH your casual internet skepticism is a little lol :D

You've clearly, never seen, handled, smelt, or even read much about, pure limonene, or any other pure terpene :p

Alot of them are considered very health promoting.

You can get limonene (not 100% pure, as an orange extract) as a high dose supplement (1000mgs per cap I beleive). Its used for heartburn and reflux.

Linalool is in lots of cosmetic products (and it absorbs through the skin, and through inhalation), and its GRAS in food. Well, orange peels, mangos, and lavender are also directly eaten in recipes too.

Take a look at the back of a few bottles of shampoo, or face creame, whatever - its not in every product, but you find at least one cosmetic product in your supermarket/corner store for sure. For awhile I was looking and it seems like it was in everything, but a quick scour of my shared bathroom only reveals a few hits.

And youll also find other terpenes, like limonene, in cosmetic products.
 
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Drael

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Okay, not so much speculation now! :p

Reading the joyetech website, it would seem like _all_ of their e-liquids have linalool

(which i speculated would add to the relaxing effects, its one of the terpenes I speculated about above)

To recap, its the principle sedative responsible for the effects of lavender, so it IS sedative, and its in tobacco naturally (and also that other relaxing plant we shall not name). Its also aromatic.

Joyetech TOBACCO

Its the forth base ingredient.

And its the strongest sedative terpene, one I know from personal experience has effects, that I was most curious about.

Not too surprising its already in a blend, as its GRAS, and already made in food grade (despite being a very dose potent sedative).

The plot thickens :p

To recap:

Linalool study for mice: http://www.ncbi.nlm.nih.gov/pubmed/18824339

Linalool study for humans: http://www.ncbi.nlm.nih.gov/pubmed/15238993

So....anyone tried the joyetech e-fluids?

"Do you really want to vape that crap?"

Seems like people already are :D

:2cool:
 
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Drael

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This is very interesting and you seem quite knowledgable. Drael can you make some suggestions as to the implementation of this in DIY? New things are always demonized. Open minds are few and far between.
Peace!:D

Well hmm. I suspect the terpenes would extract well in an absolute (and most terpenes are alcohol soluble), or even ethanol extraction of tobacco - provided said extract was sealed fresh, vacuumed packaged, and in a dark bottle (basically like saffron extract is packaged - thats the big if).

Because terpenes are volitile, how it was stored, handled, packaged etc is totally key. So it might be possible to get a terpene effect from a good source of extract, or absolute - if one could find such a good source, or do such an extract ones self (and either use immediately, or store correctly, using preserving type techniques above - fresh vaccuum sealing, refrigerating, keeping out of sunlight, storing in smaller bottles so after opening they dont degrade etc - about a week or more of air exposure after opening would probably be enough to spoil).

This is probably the most immediately practical solution.

Linalool, and limonene can both be acquired in a pure food grade, and limonene is fairly benign at any dosage (people use it orally for heart burn - it also imparts an orange peel smell)

Linalool I think would be the total key terpene however, being the most obviously active relaxant/sedative, and while its benign, it is very dose potent (you need very little of it for an effect, and youd not want alot of it). Even though its in lavender, tobacco and other places, thats in small amounts. Its very safe as naturally present.

Basically I wouldnt know exactly how much to put in.

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I think thats a real caveat, I strongly advise people not to just chuck in linalool in your e-liquid at random/high dosages and see what happens!
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Clearly a few e-liquid manufacturers put it in already, but again how much I dont know. Hard to know where one would get the dosage information for linalool in e-liquid, and what is an ideal starting point.

Thats what wed need to know, what dose/amount is advised for this use, or currently used by manufacturers. One could also probably extrapolate from how much is in tobacco, but that would be rough science, and its nothing id advise.

Basically the risk is, that you have too much linalool, and it over sedates you (obviously being overly sedated can be harmful)

If we knew how much to use as a starting point, with some certainty, then it would be a simple matter.

Again, I think probably the tobacco extract/absolute is the most practical/easy starting point, but the trouble would in finding an extract where the terpenes had not degraded as they are inclined to do.

Hope thats some help...
 
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