Not all oily substances are difficult to absorb. Look at olive oil or most vegetable oils. They are easily absorbed.

Plus, allylbenzenes are pretty potent. It you consume 28g of nutmeg that is 10% essential oils and the essential oil contains 20% allylbenzenes, then you've only taken .56g of allybenzenes. This is a large dose for most people and most nutmeg is probably weaker than this.

This means that we only need a small amount of the allylbenzenes to be absorbed in order to get the desired effects.

You mention the idea of using emulsions to aid absorbtion. This idea has been been explored before as well. Using lecithin, you can create a very effective emulsion with essential oils. Lecithin might be useful in space booze for this reason. The only slight problem with lecithin is that it has stuff that gets metabolized to dimethylamine.

This compound seems to create weaker shorter lasting effects when taken with allylbenzenes and this is believed to be due to dimethylamine/allylbenzene adducts being more susecptible to MAO. But dimethylamine adducts have been found in in vivo studies. And this does represent a route to the formation of an alkaloid.

There has also been some work done with topical application of allylbenzenes. Topical application ensures absorption and might completely bypass some detrimental enzymes, providing a more direct route to the blood stream. But I doubt this would be helpful for space booze.

Could you expand on this a little? Do you have a reference?


Space embrocation! Space perfume?

Fair enough, what I said doesn't account for regular fat metabolism. I was thinking in terms of drug administration - pills and tinctures need to be manufactured so that a drug delivery matrix ensures as full of an absorption as possible of active compounds. But you're right, many oils/fats are fully digestible. However digestion takes a long time with fats and oils, as they have a tendency to sit in the stomach for a while before they are absorbed, this contributes to a long feeling of being full.

I imagine topical application could work. However without occlusion, it seems unlikely that very much would really be absorbed into the blood. Maybe mix it with vegetable glycerin or coconut oil?

Be that as it may. I was able to obtain the full text of the Peele/Oswald theory on how allylbenzene and related compounds are metabolized. Normally you have to pay a 3rd party about $40(USD) for this research article on the net, hope this helps (you have to be logged in to see it). I've also included a graphic of the proposed pathway if you don't have the time for the whole article. This pathway hasn't been confirmed in man; however, the reaction will occur on its own if everything is present in the environment, so there is reason to believe that it would work in humans.

@downwardsfromzero - the "oilahuasca" theory basically says that just like oral DMT, where it has no effects unless enzymes (MAO) are inhibited in the body, so too with the allylbenzene compounds, which make up an important component of most kitchen spices. The theory is based partially on anecdotal evidence, and partially on nutmeg which is why its coming up here. The active components of nutmeg are allylbenzenes (if you take out the allylbenzene portion of nutmeg, it has no statistically significant effect). In researching the metabolism of allylbenzene in the human body, some people stumbled upon the below article, which describes a possible way that allylbenzene could potentially form an alkaloid. This is what powerfulmedicine is talking about (correct me if I'm wrong).

Image attached. Notice the addition of nitrogen in the last step.

Another thing. People have made nutmeg tea with good results, but they say that if a white precipitate forms on the edge of the cup that you have to redissolve that in the tea. The only piece I can think of that would have this reaction is trimyristin. The trimyristin does not dissolve in water, and if it gets cold, it would form a white/yellow precipitate. Perhaps the allylbenzene portion dissolves in the trimyristin, which is a triglyceride and can be digested (although it would take a while because fats float in the stomach, which can delay absorption by as much as a few hours). If that were true, then the allylbenzene activation would be delayed which is a common time course of nutmeg. The trimyristin would transport the allylbenzenes and possibly protect them from enzymic attack. However trimyristin is NOT in the nutmeg essential oil, which might explain why many people don't get effects from the essential oil . . . ?

I don't have any nutmeg EO, but if someone does AND wants to try an experiment: take coconut oil, melt it, and put 0.5mL of nutmeg EO in the dissolved coconut oil. Drink and report. Coconut oil has 17.5% trimyristin on average, where as nutmeg has 84% trimyristin, so it isn't a perfect example but it may help illustrate if this works.

@powerfulmedicine: I'm so glad you reminded me about fat metabolism! My head is in a spin. I tried an experiment - since trimyristin is a sedative, I figured I'd try a different fatty oil to experiment with, so I picked olive oil. I had actually tried this previously with unground nutmeg kernels (I posted about it a while back, it's in this area of the forum).

This time, to get a much better extraction, I used ground nutmeg, which I first made sure was my preferred red/gold color. I put 2 tablespoons of ground nutmeg into a mason jar and put twice the volume of olive oil in. I stirred every few hours for 2 days. I learned previously that trying to filter nutmeg is very difficult, so I simply took a pipette and drew off the oil from above the ground nutmeg, giving me about 1 volume of product (it ended up being about 1.3 oz). The oil had turned a reddish color, almost identical to space booze.

OK - So I ingested the oil. Whenever I take nutmeg or space paste, I feel effects in 4 hours. This time, I felt effects in TWELVE HOURS and it totally freaked me out, because I had figured it wasn't going to work. I was wrong. I had all the normal effects of nutmeg, but I had almost NO sedation. It actually felt a lot like an amphetamine. It was crazy. It lasted about 12 hours after that. I couldn't sleep.

Now, I did a little research, and olive oil takes a long time to metabolize, but it seems to extract the volatile fraction from the nutmeg. This might lend credence to my theory that trimyristin is transporting the volatile fraction and protecting them from destruction in some way. But maybe not.

My question is, which easily available oil is metabolized much more rapidly? Any that might be metabolized in say an hour?

Wow. What the hell is going on here? I'm starting to have a hard time believing this. It seems like every preparation of nutmeg besides the essential oil works. I really have to start trying to replicate these experiments.

I still don't think that the trimyristin idea is right. It contradicts your water extraction experiment. Water won't extract trimyristin in significant quantities. So it seems like something else that is water soluble is the key to nutmeg's activity.

I wonder if the olive might have extracted trimyristin as well. If you want to continue with the vegetable oil experiment route, I'd suggest trying any oil you can find. Corn, canola, grape seed, sunflower, safflower, etc. See what works best and then work backwards to see what compound(s) is responsible.

I think you should make another thread about vegetable oil extracts of nutmeg.

Thanks for the pdf, oilman!

So, the dimethylamine adduct for, e.g., safrole, would be an isomer of bk-MDDM (DMONE in the Shulgin index)... this would be a relative of homo-MDA, homo-MDMA and their corresponding "beta/-keto" - in this case, actually "gamma-keto" - derivatives. Its systematic name is 1-(1,3-Benzodioxol-5-yl)-3-(dimethylamino)-1-propanone and its CAS number* is 30418-50-9.

From the Shulgin Index: "homo-MDMA substituted for MDMA in MDMA-trained rats; at high levels, it evoked seizure. (Bronson, M.E., Barrios-Zambrano, L., Jiang W., Clark, C. R., DeRuiter, J., Newland, M. C. "Behavioral and developmental effects of two 3,4-methylenedioxymethamphetamine (MDMA) derivatives." Drug Alcohol Dep. 36(3): 161-166 (1994))

homo-MDMA has been sold on the street in Japan under the recognised name MBDB (Matsumoto, T., Kikura-Hanajiri, R., Kamakura, H., Kawahara, N., Goda, Y. "Identification of N-methyl-4-(3,4-methylenedioxyphenyl)butan-2-amine, distibuted as MBDB." J. Health Sci. 52(6): 805-810 (2006))

Human activity of homo-MDMA has not been reported in the scientific literature."

"When compared with MDA in mice, homo-MDA was found to be more toxic and faster-acting. (Davis, B.A., Borne, R.F., "Pharmacologic investigation of compounds related to 3,4-methylenedioxyamphetamine (MDA)." Substance and Alcohol Actions/Misuse 5(2): 105-110 (1984))

Human activity of homo-MDA has not been reported."

So it's certainly a possibility that these phenyl vinyl ketone-amine adducts have some kind of relevance to the activity of nutmeg and the like.

What do we know about the piperidine adducts? Why is it included in the rat allyl benzene metabolite flow chart in the Peele & Oswald paper? The CAS # for the safrole-derived piperidine adduct 1-(1,3-Benzodioxol-5-yl)-3-(1-piperidinyl)-1-propanone is 30418-51-0.

*CAS registry numbers are a trademark of the American Chemical Society.

I agree.

Now, this link is cool!

Human D-3 receptor antagonism - now we're getting somewhere. Some might say

@PowerfulMedicine: Have you seen this (which you'd get to through the previous link but I still think is worth mentioning)?

This may go a long way towards explaining why nutmeg sometimes doesn't work: SUPPLEMENTS AND FOODS TO AVOID
The quercetin thing was mentioned earlier, but I thought it would be good to show some of the detail.

Ya, I've seen all of that. I actually played a small part (really small) in some of the research on that page along with other people. I was thinking about posting that link at some point but wasn't sure since it was made by 69Ron and based off of work done on another forum. That forum is now semi-defunct, but I wasn't sure of the Nexus policy on such things.
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Quercetin might explain why nutmeg doesn't always work. I think I mentioned that earlier without giving much more explanation. But I'm not totally convinced in the case of ground nutmeg. I've seen evidence that quercetin might be part of the reason for the delayed effects of nutmeg.

There were a few oilahuasca experiments back in the day that found that some herbs and supplements could delay and weaken the effects of oilahuasca without totally preventing activation under some circumstances. I remember that black pepper solids was one of them. I think quercetin might have been one of the culprits as well.

Plus, I have a feeling that nutmeg contains quercetin. I still think that quality and regional variation are the reasons that nutmeg doesn't always work.
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The piperidine alkaloids are included because they have been found to form in vivo. I'm pretty sure the paper Oilman posted mentions it. If not, I'll post another paper tomorrow.

Evidence from oilahuasca bioassays have found that supplementing with piperidine from black pepper tea or L-lysine causes the oilahuasca trip to be longer and more intense. This is especially true when sources of dimethylamine are avoided. It's believed to be due to the piperidine alkaloids having higher XlogP values and being less susceptible to MAO.

I'm thinking about your skepticism, and I understand why you feel that way. 2 things: (1) I have gotten effects from oil extract, EtOH extract and water extract; why? And (2) just because it works in ME doesn't mean it will work in YOU. The only way to test the theories is to have lots of people try it! WE NEED MORE DATA! That is the only way to test the theory, and propose methods of activation.

I am going to revive my old thread which was Nutmeg Infused Olive Oil. Thanks for the suggestions on trying different oils. It seems like a worthy cause because the cooking oils are not intoxicating.

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About the the fact that I got effects from all three extractions:

I am trying to understand why this would be, too. First, important to understand is the water extraction. The constituents of nutmeg are mildly soluble in water; the exact solubilities are posted in the other thread, but basically 2 tablespoons of nutmeg and 1L of water when heated will create a tea that can extract all the actives from the nutmeg. In this case, I think the water would just carry the actives to the brain, much in the same way that alcohol gets to the brain even though its XlogP value shouldn't allow it through - it's the Trojan Horse effect (it sneaks in with the water). The solution is perhaps dilute enough (about 300 mg of actives diffused in 1L of water) that destructive enzymes aren't so effective at getting rid of them before they reach the brain.

Another thing about trimyristin and the water extraction is that just because the trimyristin doesn't dissolve in the water doesn't necessarily prohibit that it might be extracted during heating of the tea. One way to make THC infused butter is to throw the cannabis into a pot of boiling water and add some butter to the pot, too. The heat in the solution allows the THC to be extracted, but normally it wouldn't dissolve in the water (it would form a very very thin oily layer above the water which is almost impossible to recover) so we add butter, and then the THC dissolves in the liquid butter, which can easily be recovered. The same thing might happen with trimyristin in this example and it might absorb the allylbenzenes. The trimyristin isn't soluble in water, but it becomes a liquid at temps between 50C and 60C, so it would be ingested WITH the water while not being dissolved in the water.

The ethanol extraction would extract all the water based and oily substances. It makes sense that this would yield an active drink.

The oil though is weird, and why did it take 12 hours to work? The thing I'm thinking is maybe the allylbenzenes are very soluble in vegetable oils (or at least miscible). But olive oil takes a long time to digest, so that delays the time it takes for the allylbenzenes to be "found" by in vivo enzymes. Then they do they're thing, and it takes the normal amount of time after this initial period. Theoretically then, it should in my case take (4-5 hours for nutmeg activation) + (X time it takes for the vegetable oil to be digested) + (delay based on stomach contents) = 12 hours. This link claims it takes 3.25 hours to digest olive oil, which would put the time at 8.25 hours. It isn't crazy to think that since I had eaten before drinking the oil that it took a while for all of the olive oil to be digested, so 12 hours actually doesn't seem that crazy anymore!

What I'm basically saying is that if there is a mechanism of activation in the human body for nutmeg, various extracts could work.

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There is Quercetin in nutmeg. This may partially explain why nutmeg takes so long to start, but is there any way to test this and remove quercetin from the grounds prior to extraction? It's water soluble so you can't really just boil the stuff and then try again.

Also, apparently I didn't think of this! Well, not first anyways. Just found that article, and it lays out basically the exact same procedure that I posted.

I rather had that feeling as soon as I posted! I was hesitant but figured we can't be that po-faced about it. Much of the content in that link is soundly scientific. Just because 69Ron was involved shouldn't automatically disqualify it from all consideration! He has done some good research but made a serious error of judgement leading to his expulsion from this forum. This happens sometimes.
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All of the compounds in nutmeg are present in variable amounts, including quercetin, so... No wonder many people like their amines ready made

It would certainly be worth drafting something on "The Oilahuasca/Spacebooze (-oil,-paste etc.) diet", along with clear caveats about individual enzymological variations for all of this. Although it seems like that's already been done at the site I linked to, if that forum's effectively defunct there's nothing wrong with pinching their data, is there?

Yes it does, I was wondering about where the piperidine came from...


Noted that lysine gives rise to piperidine in vivo - is this really so in humans? Does lysine supplementation enhance the effects of space formulas?
I'm now thinking that gut flora could easily produce piperidine from lysine - does it form in any other way?

Re: dimethylamine - does this mean that choline is best avoided in this regimen? What other sources of dimethylamine are there to avoid? Fish, I suppose, for one.

To tell the truth, I've been putting mace - nutmeg arils - in absinthe for a couple of years now and the effect is very nice!

The link mentions fungi in the nutmeg:

It's probably not significant and merely due to his use of cheap nutmeg in China but endophytic fungi have been shown to play an important role in more than one psychoactive plant. One for the mycologists or just a(nother) blind alley?


Note pharmacological data!
(from here)

I don't question the validity of the research and I honestly think 69Ron is a standup guy. I really don't care about what happened with his expulsion from the Nexus. I just wasn't sure of the exact rules on the Nexus.

That website is truly a treasure trove of information with a lot of interesting avenues of research that are totally unexplored elsewhere.


Even if the forum was thriving, there would be no complaints from them with using that forum's data as far as I know. 69Ron actually tried to actively disseminate updated oilahuasca theories on other forums back in the day. As long as it doesn't go against any Nexus rules I see no problem.



I'm not sure if L-lysine is confirmed to produce piperidine in humans, but the idea was that gut flora would catalyze the reaction. Lysine supplementation was done over the course of a few days to ensure maximum piperidine levels.

I don't know if it helps with space preparations. I'm not aware that anyone has specifically tested this. But space preparations do contain black pepper, a source of piperidine.

Choline should be avoided in general. Especially for some allylbenzenes whose dimethylamine versions were pretty much inactive. I think that methyleugenol's dimethylamine version was inactive according to some tests.

Fish are best avoided as well as sources of trimethylglycine (betaine). Although choline supplementation will ensure that there is at least some sort of free amine that can condense with allylbenzene phenylvinyl ketones or aldehydes.

@PowerfulMedicine: have you had any success with this formula yet?

There are so many variables to take into account, it casts new light on shamanic dieting as well, perhaps.

It most certainly is! So much so that I only just read this section:
I feel a teeny bit silly (again) now But I will add that carnitine is another source of trimethylamine in vivo, so red meat, it seems, is also best avoided when working with phenylpropenes.

The paper I've attached to this post is priceless. It is some of the first published work on nutmeg intoxication in modern literature. One of the authors takes nutmeg for the first time and it describes the experience.

The first part is where 10 people get straight myristicin, but only 4 of them get effects.

Great stuff. I found these bits rather amusing:
Just another day at the office

Part of each page appears to be truncated, which is a bit annoying. Is there a better version somewhere (or is my pdf reader defective?)

I've also trawled through the Shulgin Index a bit. There are a few compounds listed which may be of interest, conveniently tabulated on p.358 as "Table 10. Phenethylamine-like molecules with three-carbon chains between the benzene ring and nitrogen." Shulgin glosses these with a "homo-" prefix, as though a methylene group has been inserted into the sidechain next to the benzene ring.

None of the 23 compounds mentioned has the gamma-keto functional group and many of them are 4-carbon chain amphetamine homologues, with a methyl group alpha to the nitrogen.

Starting with what are probably the more relevant gamma-phenyl-n-propylamines (3-phenyl-1-aminopropanes):

*homo-PEA [2038-57-5]
(Glennon, R.A., Liebowitz, S.M., Anderson, G. Serotonin receptor affinities of psychoactive phenalkylamine analogs. J.Med.Chem. 23(9): 990-994 (1980); van der Schoot, J.B., Ariens, E.J., van Rossum, J.M., Hurkmans, J.A. Phenylisopropylamine derivatives, structure and action. Arzneimittel Forsch. 12: 902-907 (1962))

*homo-beta,N-MePEA [104178-02-1]
(Clark, L.C., Jr., Fox, R.P., Morin, R., Benington, F. Effects of psychotomimetic compounds on certain oxidative and hydrolytic enzymes in mammalian brain. J.Nerv.Mental Dis. 124: 466-472 (1956))

*homo-N-Et-3-MPEA [71250-30-1] and
*homo-N,N-Et-3-MPEA [71250-28-7]
(Griffith, R.C., Gentile, R.J., Davidson, T.A., Scott, F.L. convenient one-step synthesis of N-substituted alpha-methylphenethylamines via aminomercuration-demercuration. J.Org.Chem. 44(20): 3580-3583 (1979))

*homo-Dopamine [52336-30-8] (Winn, M., Rasmussen, R., Minard, F., Kyncl, J., Plotnikoff, N. Homologs of dopa, alpha-methyldopa, and dopamine as potential cardiovascular drugs. J.Med.Chem. 18(4): 434-437 (1975))

*homo-MDPEA [33543-11-2] (Dallaker, F., Bernabei, D., Katzke, R., Benders, P.H. Derivatives of (methylenedioxy)benzene. 32, N-methyl[3,4-(methylenedioxy)-phenyl]alkylamines. Chem.Berichte 104(8 ): 2517-2525 (1971))

*homo-N-Me-2,5-DMPEA (homo-N-Me-2C-H) [66997-06-6] (Glennon, R.A., Liebowitz, S.M., Mack, E.C. Serotonin receptor binding affinities of several psychoactive phenylalkylamine and N,N-dimethyltryptamine analogs. J.Med.Chem. 21(8 ): 822-825 (1978 ))

*homo-N,N-Me-2,5-DMPEA (homo-N,N-diMe-2C-H) [64057-69-8] (Baltzly, R., Buck, J.S. Amines related to 2,5-dimethoxyphenethylamine. I. J.A.C.S. 62: 161-164 (1940a))

*homo-Mescaline [3166-94-7] (Clark et al., 1956; Clark, L.C., Jr., Benington, F., Morin, R.D. The enzymatic oxidative deamination and effects on cat behavior of mescaline and structurally-related phenethylamines. J.Med.Chem. 8(3): 353-355 (1964))

Of these nine compounds, homo-mescaline and homo-MDPEA are probably the most relevant (as they correspond fairly directly to elemicin and safrole). The latter is also mentioned as a synthetic intermediate in J. Med. Chem., 1986, 29 (2), pp 181–185.

Well, it's been a while and I've had a chance to try a couple of experiments using nutmeg tincture.

The tincture was prepared from 11 nutmegs, ground to a powder and soaked in twice their volume of high-proof alcohol. The mixture was shaken a few times over the couple of weeks it stood before the liquid - now a rich brownish red colour - was carefully decanted off the solids. This provided 100mL of tincture to work with.

Tests proved the tincture to be psychoactive in a not wholly "psychedelic" way at doses of 5 - 10 mL (which, for once, were measured reasonably accurately!) Black coffee was used as the medium of administration, where a strong 'ouzo effect' was visible upon addition of the tincture. The onset of effects typically occurred over 2-3 hours and continued to build for 6 hours or more. Split dosing also proved to be effective.

Subjective effects included varying degrees of euphoria, feelings of relaxation, improved socialiability, paraesthesias, colour and sound enhancement and, later on, mild closed-eye visuals. Sexual enjoyment was found to be enhanced.

Cognition and ability to focus on tasks were significantly impaired. These cognitive effects were at times felt to be akin to those of mild concussion. Mild incoordination occurred at times.

There was little nausea during two experiences except on two occasions which appeared to closely follow the eating of lettuce. Otherwise, appreciation of food was normal or slightly enhanced.

There appeared to be no difficulty in sleeping although the sexual enhancement did on occasion delay its onset. Dreaming was clear, colourful and positive - at least mildly more so than usual. Effects overall lasted 18 to 30 hours and could apparently be rekindled by a small amount of cannabis.


Perhaps next on the cards will be the other space booze components as individual tinctures, combined and permutated.