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Activity of terpenes Options
 
hummus
#1 Posted : 6/11/2010 5:48:44 PM

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http://www.omma1998.org/McPartland-Russo-JCANT%201(3-4)-2001.pdf
Found this paper analyzing cannabis and the effects of the different components, but what interests me more is where it looks at other terpenes, notably:
ß-myrcene
Boiling point: 166-168*C / 330.8-334.4 degree Fahrenheit
Properties: Analgesic. Antiinflammatory, Antibiotic, Antimutagenic

d-limonene
Boiling point: 177*C / 350.6 degree Fahrenheit
Properties: Cannabinoid agonist?, Immune potentiator, Antidepressant, Antimutagenic

linalool
Boiling point: 198*C / 388.4 degree Fahrenheit
Properties: Sedative, Antidepressant, Anxiolytic, Immune potentiator

pulegone
Boiling point: 224*C / 435.2 degree Fahrenheit
Properties: Memory booster?, AChE inhibitor, Sedative, Antipyretic

1,8-cineole (eucalyptol)
Boiling point: 176*C / 348.8 degree Fahrenheit
Properties: AChE inhibitor, Increases cerebral, blood flow, Stimulant, Antibiotic, Antiviral, Antiinflammatory, Antinociceptive

a-pinene
Boiling point: 156*C / 312.8 degree Fahrenheit
Properties: Antiinflammatory, Bronchodilator, Stimulant, Antibiotic, Antineoplastic, AChE inhibitor

a-terpineol
Boiling point: 217-218*C / 422.6-424.4 degree Fahrenheit
Properties: Sedative, Antibiotic, AChE inhibitor, Antioxidant, Antimalarial

terpineol-4-ol
Boiling point: 209*C / 408.2 degree Fahrenheit
Properties: AChE inhibitor. Antibiotic

p-cymene
Boiling point: 177*C / 350.6 degree Fahrenheit
Properties: Antibiotic, Anticandidal, AChE inhibitor


First off, d-limonene a cannabinoid agonist?? If so it'd be incredibly cheap, although it might not really be psychoactive, would be interesting to try..

And the fact that all the other common terpenes are AChE inhibitors looks to provide some explanation of the effects of nutmeg, along with some of them being stimulants and some sedative this would provide an explanation for the 'mixed' effects nutmeg provides, and explanation for the dissociation/delerium at very high doses.
Of course each of them will have their own side effects/effective doses but it'd be interesting to assay them for effects.

some random quotes:
The essential oil of
black pepper, Piper nigrum, has a composition of terpenes that is qualitatively
quite similar to that of cannabis

Myrcene is a potent analgesic, acting at central sites that are antagonized by naloxone
Myrcene also works via a peripheral mechanism shared by CBD, CBG, and
CBC – by blocking the inflammatory activity of prostaglandin E2 (Lorenzettiet
al. 1991). This activity is expressed by other terpenoids in cannabis smoke, such as carvacrol, which is more potent than THCor CBG(Burstein et al.
1975).

Limonene may have a low-affinity interaction with cannabinoid receptors
(Meschler and Howlett 1999). Studies of long-term inhalation of lemon fra-
grance (predominately limonene) have demonstrated inhibition of thymic in-
volution in stress-induced immunosuppression in mice(OrtizdeUrbinaetal.
1989).

 

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SnozzleBerry
#2 Posted : 6/11/2010 6:13:39 PM

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Despite being a weird flavor, I found my D-limo extracted hash (which still had d-limo residue in it due to the fact that the BP of d-limo is so high) to be somewhat more potent (or at least a qualitatively different and "better" high) than naptha hash made from the same bud. Other people who smoked it were impressed with its potency, however, no one received a blind comparison of the two, so it's hard to say if this was really anything beyond placebo. Personally, I'm inclined to say it was more than placebo, but who knows as it was not a controlled test. Once I move and set up my new lab, maybe I'll give it another go and try to do some "controlled" subjective testing.
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69ron
#3 Posted : 6/11/2010 7:39:48 PM

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SnozzleBerry, D-limonene will extract more compounds than naphtha, and that alone could explain the increased potency. Naphtha will only extract highly non-polar compounds while D-limonene will extract them along with some moderately non-polar compounds.

To give you some idea of how this works, if you extracted San Pedro cacti with D-limonene, because mescaline is moderately non-polar compounds, it will extract a lot of mescaline. But the same extraction done with naphtha will extract almost no mescaline, but still extract some of the other highly non-polar compounds in the cacti. Using naphtha, you'd end up with an extremely inferior end product.
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Ginkgo
#4 Posted : 6/11/2010 7:50:14 PM

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This is very interesting, thanks a lot for posting this! D-limonene a CB agonist? No way... I have taken 1 gram as a supplement a day for extended periods of times, without any noticeable effect whatsoever.

69ron: In other words, a d-limonene extraction of cacti should be washed with naphtha in order to obtain more or less pure mescaline? Is there any food-safe way to accomplish the same? I now naphtha is close to non-toxic, but nevertheless it does feel very dirty.
 
SnozzleBerry
#5 Posted : 6/11/2010 8:28:19 PM

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69ron wrote:
SnozzleBerry, D-limonene will extract more compounds than naphtha, and that alone could explain the increased potency.

Interesting, I was not formally aware of that, although from the use of d-limo for fullrange dmt extractions and naptha for pure dmt extractions, that makes sense (I'm sure a lot of us are acting along the lines of this knowledge without realizing that we know it Very happy ). Not realizing this in the formal sense, despite the fact that my perception of a "better" high didn't seem to be placebo, I was hesitant to state that it was a legitimate non-placebo effect because I couldn't find any articles or studies showing that smoked terpenes would potentiate cannibinoids. I had read some stuff saying that eating mangos after smoking increased the potency of the experience, but didn't think that would necessarily mean that smoking hash with a little d-limo residue in it would have comparable effects.

Now I guess the question is; is it more potent because of what the limonene pulled, the presence of limonene residue, or both? Any thoughts, speculations, or links to additional resources would be greatly appreciated. Cool

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burnt
#6 Posted : 6/11/2010 9:09:35 PM

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Terpenes are a huge class of compounds. There bioactivity in some cases is known in more detail then in others. Some effects are non-specific and a result of their being lippophillic and thus interfering with membrane permeability and function of membrane bound proteins.

Quote:
D-limonene a CB agonist? No way...


The terpenes of cannabis do not agonize the CB1 receptor at pharmacologically relavent doses.

However beta-caryophyllene, a common sesquiterpene in cannabis, is a reasonably potent CB2 agonist.

Quote:
And the fact that all the other common terpenes are AChE inhibitors looks to provide some explanation of the effects of nutmeg, along with some of them being stimulants and some sedative this would provide an explanation for the 'mixed' effects nutmeg provides, and explanation for the dissociation/delerium at very high doses.
Of course each of them will have their own side effects/effective doses but it'd be interesting to assay them for effects.


This is rather dangerous. Terpenes are safe at low doses but many of them exhibit toxic effects at higher doses.

However inhaling the amounts normally found in plant material is usually a safe way to start dosing. Inhaling or ingesting pure essential oils is risky if the dose is too high, which can be a few mL to a few hundred mL.

One way I think the terpenes in cannabis may be altering the effects is by increasing the absorption at the lungs of THC. If they make the membranes more permeable even if for a brief few moments during smoking or vaporizing it could increase the uptake of the drug making it seem more potent or the effects come on faster.

The only way to know is to do clinical work. The paper the OP cited is a lot of speculation based mostly on in vitro or in vivo animal data some of it quite outdated and some of it at pharmacologically irrelevent doses (>100mg/kg in a mouse!). You would have to look in detail at the papers cited by the authors to notice this.

Regardless there is much work to be done in this area but the real test will be clinical subjects.

 
Ginkgo
#7 Posted : 6/11/2010 9:16:42 PM

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burnt wrote:
Quote:
D-limonene a CB agonist? No way...


The terpenes of cannabis do not agonize the CB1 receptor at pharmacologically relavent doses.

However beta-caryophyllene, a common sesquiterpene in cannabis, is a reasonably potent CB2 agonist.
What? That got to be wrong, or I am misunderstanding something. THC, a terpenoid, is very well established as the main psychoactive compound in cannabis, and that action is from binding to CB1. Are you referring to the fact that it is only a partial agonist, not activating the receptor to its full extent?
 
burnt
#8 Posted : 6/11/2010 9:31:08 PM

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I meant the mono and sesquiterpenes. Not the cannabinoids which are part terpenoid part polyketide.
 
 
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