Nutmeg rocks my world

[Fractalhead]

Torsten, I just ran some of the nutmeg oil you gave me at EB03 (for the TLC workshops) through a GC/MS and myristicin is definitely a major component (the myristicin peak area was about 40% of the total ion chromatogram). I should point out however that this doesn't mean that the oil is 40% myristicin. We won't know the accurate % makeup until we run these oils through a GC fitted with an FID detector. Elemicin, safrol, eugenol, isoeugenol, methyl eugenol and methyl isoeugenol were also present albeit at much lower concentrations than the myristicin. Can you remember if this was the good oil that has been used successfully in massage experiments? BTW, I also ran some 'Gumleaf Essentials' nutmeg oil using the same program and got almost the same amount of myristicin and very similar overall profile.

The parsley oil you also gave me for the workshops was virtually devoid of myristicin compared to the nutmeg oils. I'm guessing this oil was distilled from parsley foliage rather than the seeds.

All in all a very interesting day in the lab If you can get me a sample of this new putatively good oil(s) by early next week I might be able to run them through aswell for a comparison.

[ 06. May 2005, 13:25: Message edited by: Fractalhead ]

[Benzedrine]

The muscle activity relation's to effects really interest me.

Now for something truly embarassing. When I was young there was a recipe that I still partially remember. It involved huge amounts of sugar, coffee and nutmeg mixed with water into a thick stew. Afterwards bread was dipped into it and then cooked in a microwave. This would in slabs of a foul smelling brown sponge. The taste and texture made it very difficult to get down.

This incredibly dodgy stuff was often a surprisingly enjoyable intoxicant. Much better then nutmeg on its own, I wonder now if the large amount of sugar and coffee were just to boost body activity.

[Torsten]

Great work fractal!!

Sadly, I don't recall which nutmeg oil you had, however, I still have all that EB3 TLC stuff in one crate somewhere and the oil may well be there.

I can send you some of the new oil if you like. please email me your addy.

The parsley oil was supposed to be seed oil. Some chemovars don't have myristicin, but plenty of apiol etc.

How difficult would it be to get a myristicin ref sample?

[Fractalhead]

Torsten I just emailed the details to you via the little 'Email Torsten' button above your post. It says you kept your email address private but let me type the email into a message box. I hope this works. I'm sure it can't be too hard to get a pure myristicin standard from one of the chem supply companies. But I don't think it is really neccessary for GCMS especially if you run a few myristicin containing plants through and compare retention times aswell as spectra. I didn't get any apiol hits in the parsley oil but I will check the data again to see if it could have been missed for some reason.

[Entheo]

Hi Rev

 

Rev:

There are several other souces of myristicin as well

theres plant in NZ (name???)

Might you be talking about Maori kava?

http://www.entheology.org/edoto/anmviewer.asp?a=67&z=5

The plant contains about 0.1% essential oil by steamed distillation which is composed of up to 41.3% myristicin and about 3.1% elemicin (Briggs et al., 1975)

also The Rose-leaves Anise, Scandia rosaefolia of New Zealand has up 0.2% dry weight essential oil in its leaves composed of up to 47% myristicin (Briggs et al., 1975).

the best of the Australian plants is

Zieria covengi with 2% dry weight essential oil in its leaves composed of up to 23.4% myristicin, and also small amounts of safrole, methyl eugenol & elemicin.

hope that helps

[Fractalhead]

Thanks for that info Entheo. I'd love to get my horticultural hands on a lot of those Zieria chemotypes. There certainly are some nice smelling ones

I checked back over the raw gcms data for the parsley oil and interestingly, there was a decent peak with about the right retention time for apiol and only gave a pretty poor match with anything in the ms library (i think it was a really old nist(98) library). So that peak could well have been apiol if apiol wasn't in the library (didn't have time to check). I need to search against a more comprehensive library.

Checked some Melaleuca bracteata oil as well and found both a litle bit of anethole and fair bit of methyl eugenol. Definitely no elemicin . So the search is still on for the elemicin rich M. bracteata.

[Rev]

Scandia was the species i wanted...

I have Zieria prostrata and Zieria smithii

can strike you some cuttings in time fractal

you have any cuttings of those other rutaceaous aromatics still?

Also i think your after Melaleuca squamiphloia with the elemicin

but u should try the more common M stypheloides first (of which squam was divided off from)

(its on the darling downs BTW - next time ur in SE qld lets go find it)

I have a hedge of it getting going

HM do you need to test?

also found a related species (unknown but myrtaceaous) that reeks of nutmeg

i take it thats a good sign

dont have a still so can i use a solvent to extract?

if so plz divulge..

alos please H.M ml extract for testing?

ta

rev

[ 09. May 2005, 15:42: Message edited by: Rev ]

[Fractalhead]

Hi Rev,

Yeah we have managed to keep a few cuttings going but we seem to have a problem with our rutaceae going nuts for a while before suddenly going brown and then dead all within the space of a couple of days. Unfortunately I think this happened to the ones you wanted but we will try again from new plants.

You can do a solvent extract if you just want to get a feel for the likely profile of the steam distilled oil. However, you should bear in mind that you may extract some of the more non-volatile stuff and hence the mixture may be a bit more complex. I would recommend a low polarity solvent like hexane.

For pure oils, you need less than a few ul diluted into 1 or 2 ml of solvent to do heaps of analyses. For the solvent extraction its harder to say (not having done it) but I would guess a few hundred mg of tissue ground in a couple of ml of hexane and filtered would be a good starting point. It would probably be a good idea to centrifuge this prior to injection to avoid injecting particulates into the instrument. I know of people using this kind of method to analyse oil plants. I will check their protocol and get back to you. The actual injected sample is usually only about 1 ul.

Sounds like we have no shortage of things to grow and analyse

[ergoamide]

Has anyone tried the mace from sab here and had a positive bioassay from and does anyone know about the mace oil sab is also sellin hows that.

[Fractalhead]

Hi Tort,

I've analysed those Myristica sp. ois of yours on a gc/ms. Am I right in guessing that one of them was mace and one of them nutmeg oil. You were very cryptic with your M and N labelling I guess it was a nice example of a blind study...

I'll post the library search qualitative reports below:

HERE is the 'N' oil data:

Pk# RT Area% Library/ID Ref# CAS# Qual

_____________________________________________________________________________

1 5.98 15.63 D:DatabaseNIST02.L

1R-.alpha.-Pinene 15161 007785-70-8 90

1S-.alpha.-Pinene 15160 007785-26-4 87

Cyclohexene, 4-methylene-1-(1-meth 15299 000099-84-3 81

ylethyl)-

2 6.04 26.91 D:DatabaseNIST02.L

1R-.alpha.-Pinene 15163 007785-70-8 95

1R-.alpha.-Pinene 15161 007785-70-8 95

Bicyclo[3.1.1]hept-2-ene, 2,6,6-tr 15351 002437-95-8 93

imethyl-, (.+/-.)-

3 6.36 6.02 D:DatabaseNIST02.L

Bicyclo[3.1.0]hex-2-ene, 4-methyl- 15349 028634-89-1 91

1-(1-methylethyl)-

Bicyclo[3.1.0]hexane, 4-methylene- 15348 003387-41-5 91

1-(1-methylethyl)-

Bicyclo[3.1.0]hexane, 4-methylene- 15354 003387-41-5 91

1-(1-methylethyl)-

4 6.46 19.40 D:DatabaseNIST02.L

.beta.-Phellandrene 15173 000555-10-2 90

.beta.-Pinene 15150 000127-91-3 81

Cyclohexane, 1-methylene-4-(1-meth 15307 000499-97-8 80

ylethenyl)-

5 6.97 11.07 D:DatabaseNIST02.L

Limonene 15127 000138-86-3 52

Cyclohexanol, 2-methyl-5-(1-methyl 25625 000619-01-2 38

ethenyl)-

1,3,7-Octatriene, 3,7-dimethyl- 15218 000502-99-8 38

6 7.18 2.86 D:DatabaseNIST02.L

3-Carene 15131 013466-78-9 42

1,4-Cyclohexadiene, 1-methyl-4-(1- 15330 000099-85-4 42

methylethyl)-

Cyclohexene, 1-methyl-5-(1-methyle 15336 001461-27-4 42

thenyl)-, ®-

7 7.77 1.29 D:DatabaseNIST02.L

Pentafluoropropionic acid, pentade 149597 1000280-07-5 58

cyl ester

Pentafluoropropionic acid, octadec 159526 1000280-07-7 49

yl ester

1-Dodecanol, 3,7,11-trimethyl- 75210 006750-34-1 49

8 8.30 4.28 D:DatabaseNIST02.L

3-Cyclohexen-1-ol, 4-methyl-1-(1-m 25652 000562-74-3 90

ethylethyl)-

3-Cyclohexen-1-ol, 4-methyl-1-(1-m 25686 020126-76-5 87

ethylethyl)-, ®-

3-Cyclohexen-1-ol, 4-methyl-1-(1-m 25683 020126-76-5 76

ethylethyl)-, ®-

9 9.16 1.69 D:DatabaseNIST02.L

1,3-Benzodioxole, 5-(2-propenyl)- 30384 000094-59-7 92

1,3-Benzodioxole, 5-(1-propenyl)- 30379 000120-58-1 91

1,3-Benzodioxole, 5-(1-propenyl)- 30382 000120-58-1 91

10 10.68 10.85 D:DatabaseNIST02.L

1,3-Benzodioxole, 4-methoxy-6-(2-p 50186 000607-91-0 92

ropenyl)-

1,3-Benzodioxole, 4-methoxy-6-(2-p 50187 000607-91-0 91

ropenyl)-

1,3-Benzodioxole, 4-methoxy-6-(2-p 50188 000607-91-0 89

ropenyl)-

and here id the 'M' oil:

Pk# RT Area% Library/ID Ref# CAS# Qual

_____________________________________________________________________________

1 5.98 20.45 D:DatabaseNIST02.L

1R-.alpha.-Pinene 15161 007785-70-8 95

1S-.alpha.-Pinene 15160 007785-26-4 94

Bicyclo[3.1.1]hept-2-ene, 3,6,6-tr 15289 004889-83-2 91

imethyl-

2 6.37 4.57 D:DatabaseNIST02.L

Bicyclo[3.1.0]hex-2-ene, 4-methyl- 15349 028634-89-1 87

1-(1-methylethyl)-

Bicyclo[3.1.0]hexane, 4-methylene- 15354 003387-41-5 87

1-(1-methylethyl)-

1S-.alpha.-Pinene 15160 007785-26-4 83

3 6.46 21.75 D:DatabaseNIST02.L

.beta.-Pinene 15146 000127-91-3 91

Cyclohexene, 4-methylene-1-(1-meth 15299 000099-84-3 91

ylethyl)-

1R-.alpha.-Pinene 15161 007785-70-8 86

4 6.79 3.10 D:DatabaseNIST02.L

1,4-Cyclohexadiene, 1-methyl-4-(1- 15330 000099-85-4 87

methylethyl)-

Cyclohexene, 4-methyl-3-(1-methyle 15308 099805-90-0 86

thylidene)-

Bicyclo[4.1.0]hept-3-ene, 3,7,7-tr 15344 000498-15-7 60

imethyl-, (1S)-

5 6.87 2.21 D:DatabaseNIST02.L

Benzene, 4-ethyl-1,2-dimethyl- 14364 000934-80-5 42

Benzene, 1-methyl-2-(1-methylethyl 14406 000527-84-4 38

)-

Benzene, 1-methyl-4-(1-methylethyl 14401 000099-87-6 38

)-

6 6.91 3.36 D:DatabaseNIST02.L

Cyclohexene, 1-methyl-4-(1-methyle 15340 005989-54-8 49

thenyl)-, (S)-

Limonene 15128 000138-86-3 46

D-Limonene 15136 005989-27-5 41

7 6.95 8.88 D:DatabaseNIST02.L

Cyclohexene, 1-methyl-5-(1-methyle 15288 013898-73-2 55

thenyl)-

1,3,7-Octatriene, 3,7-dimethyl- 15218 000502-99-8 45

1S-.alpha.-Pinene 15160 007785-26-4 38

8 7.18 4.23 D:DatabaseNIST02.L

Bicyclo[4.1.0]hept-3-ene, 3,7,7-tr 15344 000498-15-7 55

imethyl-, (1S)-

1,4-Cyclohexadiene, 1-methyl-4-(1- 15329 000099-85-4 55

methylethyl)-

1,4-Cyclohexadiene, 1-methyl-4-(1- 15330 000099-85-4 55

methylethyl)-

9 7.44 3.49 D:DatabaseNIST02.L

Silane, trichlorodocosyl- 163388 007325-84-0 30

3-Hexadecyloxycarbonyl-5-(2-hydrox 158227 1000222-82-8 22

yethyl)-4-methylimidazolium ion

Pentadecane, 1-bromo- 111968 000629-72-1 18

10 8.30 6.48 D:DatabaseNIST02.L

3-Cyclohexen-1-ol, 4-methyl-1-(1-m 25686 020126-76-5 87

ethylethyl)-, ®-

3-Cyclohexen-1-ol, 4-methyl-1-(1-m 25683 020126-76-5 87

ethylethyl)-, ®-

3-Cyclohexen-1-ol, 4-methyl-1-(1-m 25654 000562-74-3 87

ethylethyl)-

11 8.40 1.19 D:DatabaseNIST02.L

5-Dodecene, (E)- 34726 007206-16-8 25

Heptafluorobutyric acid,n-tridecyl 155417 1000216-78-9 25

ester

Heptafluorobutyric acid, n-tetrade 158317 007365-36-8 25

cyl ester

12 9.16 2.38 D:DatabaseNIST02.L

1,3-Benzodioxole, 5-(1-propenyl)- 30379 000120-58-1 94

1,3-Benzodioxole, 5-(1-propenyl)- 30382 000120-58-1 94

1,3-Benzodioxole, 5-(2-propenyl)- 30384 000094-59-7 93

13 10.22 1.18 D:DatabaseNIST02.L

Decane 18419 000124-18-5 30

1,4-Benzenediamine, N,N'-diethyl- 31788 003010-30-8 30

Benzenemethanol, 4-(1,1-dimethylet 31873 000877-65-6 30

hyl)-

14 10.69 15.58 D:DatabaseNIST02.L

1,3-Benzodioxole, 4-methoxy-6-(2-p 50186 000607-91-0 96

ropenyl)-

1,3-Benzodioxole, 4-methoxy-6-(2-p 50187 000607-91-0 96

ropenyl)-

1,3-Benzodioxole, 4-methoxy-6-(2-p 50188 000607-91-0 90

ropenyl)-

15 11.10 1.15 D:DatabaseNIST02.L

Cyclopropane, 1-butyl-2-pentyl-, t 34843 074663-87-9 42

rans-

4-Heptafluorobutyryloxyhexadecane 162900 1000282-97-2 38

5-Undecene, (E)- 25825 000764-97-6 38

I hope you can all make sense of that. Please people note that % in this case relates to a percentage of a particular peak means the percentage of the total area under the total ion chromatogram (TIC) not the percentage makeup of the oil in % mass. Anyone who wants to view the raw data is welcome to email me and I'll email you the raw data file so you can scan the data files with your own personal library. There are definitely a few peaks in there that don't match anything on the standard library. Check out the low match scores out of 100. So if you have any ideas what these unknowns might be you could run some standards and add the mass spectra to your library. I've discovered much to my disappointment that NIST02 doesn't contain croweacin. However, it does have croweacic acid. I think croweacin matches myristicin to some degree. We might get a strong hit to croweacic acid if we pre-oxidise our oil with permanganate...

[Rev]

Hey fractal did u get achance to run those oil vials i sent over?

[Torsten]

Originally posted by Fractalhead:

I've analysed those Myristica sp. ois of yours on a gc/ms. Am I right in guessing that one of them was mace and one of them nutmeg oil. You were very cryptic with your M and N labelling

I scratched the letters into the lid before I read that the nutmeg oil was in fact also a mace oil. Someone sent me this 'nutmeg' from perth because it had such promising aroma. It says nutmeg on the front of the bottle, but the contents listing actually states mace essential oil.

As far as area of the peaks goes, is it safe to assume that myristicin and safrole have the same signature or whatever you call it (ie equivalent amounts of each would show up as equivalent peak percentages)? Assuming this, then

the 'N' oil data:

Safrole 1.69

Myristicin 10.85

Total 12.54

'M' oil data:

safrole 2.38

Myristicin 15.50

Total 17.88

This would mean the mace oil is about 40% stronger than the nutmeg (ie perth mace) oil.

So if we could distill all the other crap off these oils we should be able to work out percentages of w/v.

Can we also assume from this that there is no elemicin in either of these samples? Elemicin is often cited as the likely psychoactive in nutmeg oil due to its structural relationship with mescaline (ie TMA), but I have always doubted this as there is no such visual component.

Excellent work fractal!!

[incognito]

so what are the effects of nutmeg? i believed it to be urban myth!

[mr toodly]

Nausea, sedation, local anesthesia, festive evergreen scent.

[Torsten]

Low myristicin oil gives the effects as described by r jackson. High myristicin oil gives effects quite similar to MDA. If you have to take more than a few ml then your oil is crap and chances are once you reach an active dose then you will also get very sick. Good oil will be quite active at low doses.

What exactly makes an oil a good oil is still up for discussion, but preliminary experiments indicate that it needs to have a high allylbenzene content. These analyses are designed to elucidate which allylbenzenes. It is now clear that we only need to look at safrole and myristicin. Given the lower potency of MMDA it may turn out to be mostly a matter of safrole.

There are other actives in nutmeg oil, but these can be quite toxic - even fatal. Their activity is mostly that of sedation, inebriation and nausea.

The effect of sassafras oil and good nutmeg oil is quite similar, but with major dosage differences. Flavour/aroma is the main reason why sassafras is not as desirable.

Also, before anyone rants on about the carcinogenicity of safrole, please do some research (incl on these forums). And anyone wanting to know more about the good nutmeg effects UTSE.

[ergoamide]

So T, is either of the oils above (N&M) the mace oil in the sab store.

[Torsten]

The M oil is the one in the webstore. It is also the one I bioassayed with a satisfactory result (but nothing to rave about). Still looking for something better.

[incognito]

btw r jackson, ur avatar looks kinda like a cacti-angel with wings spread, or am i drinkin to much coffee??

[Fractalhead]

Torsten, just glancing over your analysis it looks like you came to the same conclusions I did... except for the bit about their being no elemicin. The mace oil definitely had 'some' elemicin. Unfortunately, at the threshold settings I ran that nist search on, there wasn't quite enough signal from elemicin to be included in the search. I actually injected a very dilute solution of the oil in methanol. If I'd changed the settings or upped the sample concentration elemicin would have turned up for sure. I found a peak after myristicin that was very small and did a manual search that hit elemicin with a high match score. This same peak has turned up in just about every myristica oil analysed so far. There are def differences in the ratios of the three main allylbenzenes (s, m and e) in different oils but every oil i've tested now (about 5 or six), the myristicin peak is about 5-10 fold larger than the S peak. When I have time I'll collate all the data and post it up.

So if there were some Myrista sp. essential oil 'high boiling fraction' available, who might be interested? Who knows, maybe you can get some cash back when you send your 'mid-party' urine sample back to me so I can analyse it for metabolites that might provide some clues as to the metabolic pathways going on.

No seriously, if i get some refined oils together, would anyone be interested in being involved in a big community science experiment? I'm thinking if people each pay a certain amount of money to take part and then I send out a sample of refined nutmeg oil (with all the nasty lighter boiling crap like pinene etc removed). To encourage everyone to send back a urine sample, I could send back some extra treats when I receive the urine sample (no rude practical jokes please . Some of the money will go towards buying the disposable solid phase liquid extractors that will concentrate all the basic metabolites prior to analysis.

If we all work together we could really nail this metabolic nutmeg madness once and for all

[dracos6]

yeah id love to take part, just lemme know when

 

Fractalhead:

when I receive the urine sample (no rude practical jokes please

[teonanacatl]

im in

[Torsten]

It would be really good to get some absolute numbers on these oils rather than just relative. I'll email you about that later today.

I think the urine test is a great idea. I'm in.

[ergoamide]

I'm up for anything of the like, spunds like a great idea 2 me. My guess is though that pl will have 2 abstain from any other mind altering substance for a peroid b4 and after ingestion 2 make sure we arent gettin confused here.

[AndyAmine.]

Sign me up chief!

[Fractalhead]

Hehe. Wow!! so many willing participants... Yes I think that absta(i?)nence would be a good scientifically responsible thing to maintain in the week or so prior to the experiment. Maybe the more energetically inclined lab rats could even do some vigorous muscular exercise and we can compare their stats with the couch cruisers' Who knows, we might even come up with some novel mass spectra...

So Tort, do you reckon refined parsley would be a satisfactory substitute? I remember you saying something about vertigo after some refined dill oil. Something about the tetra-subs?

Also T, what kind of dose do you think would be a good starting point in terms of dose if we're assuming a 90% w/v myristicin oil? I've got that paper from Sasha where they achieve a mild effect from 400mg myristicin but I'm not sure whether they knew about your exercise theory in those days Maybe we can do two experiments with different doses.

This is going to be fun!

Fractal