Author Topic: List of compounds in Myristica Fragrans oil? (searching for myristicin) (Read 312 times)

NeilPatrickHarris · « **on:** February 03, 2011, 12:31:26 AM »

Does anyone have a breakdown of all the compounds on Myristica Fragrans oil? The compound I'm chasing after is myristicin. I'm aware that the best place to find myristicin is in french parsley oil, however that is difficult to find and i've heard stories of vendors selling regular parsley oil and claiming it's french parsley oil. So i thought perhaps it would be a better idea to get it from nutmeg (Myristica Fragrans) oil instead where it is present in low concentrations but you know if you get enough of it then you'll get at least 3-6% myristicin supposedly. I'm curious what the compounds in Myristica Fragrans oil is though to make sure that the myristicin can be fractionally distilled from everything else and that there isn't anything else with a bp too close to myristicin... otherwise i should probably try to roll the dice at different vendors for french parsley oil in hopes of getting the real deal - french parsley oil with high myristicin content.

Oerlikon · « **Reply #1 on:** February 03, 2011, 02:18:56 AM »

Second approach is highly recommended!
I am allmost 100% sure that any Nutmeg essential oil has lower concentration of
myristicin than ANY parsley oil.
(cca. <5% vs. >5-90% in favour of parsley oil)

psychexplorer · « **Reply #2 on:** February 03, 2011, 02:55:41 AM »

Strike's Sources notes:

Dill root oil: 17.9%
Mature fennel root oil: 24.7%

in addition to the parsley and nutmeg sources mentioned above.

Personally, I'd forget about the nutmeg. It isn't so overly abundant in your desired precursor to make a lightly watched oil worth it.

Finding an honest vendor for the exact parsley oil which you want should not be too difficult. Rather than asking the direct question in re: myristicin content, you can easily blend in with the rest of the aromatherapy/hippie/natural/new age/organic crowd by asking if they have a certificate of analysis, if they can document where it was grown, fair trade, organic, superstition, homeopathic, etc.

Fortunately for us, the nature of the oils trade makes it very easy to determine either contents or sources, thanks to all the superstition and hearsay in the typical customer base, as well as the strong interest in ethical/sourcing/organic concerns. Essentially, if your faith healer recommended french parsley seed oil, then it should be no problem asking a few vendors for exactly that. They get that question all the time, it isn't suspicious, and the better (and longer lived) vendors have adapted to needing to answer all sorts of quirky questions if they want business from oils connoisseurs.

There is no shortage of vendors for essentials. Create a throwaway email account, shotgun out your questions to the vendors, then look through the replies. Order with another name and email like a week later. With enough questions going out, you should be able to find someone who can answer them in the way you need.

The larger oils vendors didn't get that way by shortchanging customers and intentionally mislabeling oils. Many of the online vendors are run by enthusiasts from that field doing something they know from their home.

Change into a super-hippie mentality and put the law of large numbers on your side. It's out there. No need to bother with an inferior and more suspicious nutmeg oil.

What you're looking for is rather variable in its concentration in various oils, so after finding a few vendors, order small batches from which you can determine actual myristicin content through purification. Once you've found the right batch, order enough so you don't have to repeat the shopping/testing/ordering process any time soon.

NeilPatrickHarris · « **Reply #3 on:** February 03, 2011, 03:22:54 AM »

ok, so i see there are only 2 species within the genus Petroselinum (parsley) per wikipedia. the first is Petroselinum crispum from southern europe and africa. the second is Petroselinum segetum and is from western europe and southern europe. but after reading some hive posts i saw references to a type of Indian parsley which is Petroselinum Sativum.

i found this:

Quote

Curly parsley is usually dominated by myristicin race

^ h**p://translate.google.com/translate?hl=en&sl=tr&u=http://www.dogaltedavi.net/f92/maydanoz_petesilie_petroselinum_crispum-3989.html&ei=ARhKTcPGEJDVgAeOnfTWDw&sa=X&oi=translate&ct=result&resnum=10&ved=0CF4Q7gEwCQ&prev=/search%3Fq%3DPetroselinum%2Bcrispum%2BPetroselinum%2Bsegetum%2Bmyristicin%2Bapiol%26hl%3Den%26biw%3D1280%26bih%3D607%26prmd%3Divns

apparently flat leaf parsley is P. crispum var. neapolitanum and curly parsley is P. crispum var. crispum.

i found this hive post:

Quote

Allow me to give you some information which can save you some frustration in the future when purchasing oil of parsley.

You have to keep in mind that parsley has three chemotypes: fruits in which the predominant constituents of the fruit oil is myristicin, apiole, or more rarely allyltetramethoxybenzene. As a rule of the thumb, oils rich in myristicin (70-90%) only contain traces of apiole and/or allyltetramethoxybenzene; oils predominantly consisting of apiole (70-90%) usually have traces of the allyltetramethoxybenzene but always seem to contain myristicin (5-15%) - important for your fractional distillation; oils rich in allyltetramethoxybenzene (ca 55%) usually have smaller fractions of both myristicin and apiole (5-20%). This, however, is for the seeds. It can happen that your parsley seed oil doesn't contain apiole, myristicin or allyltetramethoxybenzene at all! To avoid this frustrating situation, you should (a) always ask for a analysis certificate (especially since oil of parsley isn't the cheapest around) and (b) ask for a sample to check the quality.
How check the quality? TLC is the easiest and most OTC method. Back in the days, I had some nice labs to do this for me, but ... *siiigh* . Anyway, this is a method I have always used and has served me well:

solvent system: toluene-ethyl acetate (97:3)
detection: vanillin-sulfuric acid reagent

Vanillin-sulfuric acid reagent:
solution I: 5% EtOH sulfuric acid
solution II: 1% EtOH vanillin
The plate is sprayed vigorously with 10 mL solution I, followed immediately by 5-10 mL solution II. After hetating at 110°C for 5-10 min under observation, the plate is evaluated in vis.

This method is commonly applied to screen the components of essential oils via TLC. Apiole (Rf 0.75) and myristicin (Rf 0. are coloured brown-violet. Allyltetramethoxybenzene gives weaker coloured bands.

Ref: H Wagner. Plant Drug Analysis, p 82.

Additional note: the chemotypes are region INdependant! Parsley seed oil from Hungary can be rich in myristicin, apiole or allyltetramethoxybenzene, just as seed oil from France, Pakistan or Australia. Trusting on the region of origin is impossible.

^ hiveboard/chemistrydiscourse/000429807.html

Quote

As a natural part of the essential oil of garden parsley, Petroselinum crispum (Mill.) NYM. ex A.W. HILL. It is at this plant different "chemical races ", and indeed a myristicin breed with up to 77% Myristicin (Apiol: 0-3%) remains a Apiol-race with about 58 to 80% Apiol (Myristicin 90-30 %) and a Allyltetramethoxybenzol-race with 50 to 60% ATMOB that contains only traces of Petersilienapiol. The data refer to the see of the ripe fruit steam distilled oil, Table 1. Apiol myristicin and are responsible for the spasmolytic (antispasmodic), mild diuretic and strong uterine stimulant effect of parsley fruits. The substance is attributed to an allergenic

^ HUNNIUS Pharmazeutisches Wörterbuch 7. Aufl., S. 953 (Walter de Gruyter, Berlin New York 1993), translated from German

according to "Who Eats Parsnips?" h**p://www.erowid.org/archive/rhodium/chemistry/parsnips.html
it shows the following 3 as the best sources for myristicin:
*Pastinaca sativa -- Parsnip; 183,000 - 662,000 ppm in Root Essential Oil;
*Petroselinum crispum -- Parsley; 14,785 - 19,800 ppm in Seed;
*Myristica fragrans -- Mace, Muskatnussbaum (Ger.), Nutmeg, nogal moscado (Sp.), nuez moscada (Sp.); 800 - 12,800 ppm in Seed;

I can't find Pastinaca Sativa root oil anywhere. Petroselinum Crispum seed oil can be found but from what i've read you can't rely on the country of origin as an absolute answer to know for sure that it will have a large amount of myristicin content. It seems like trying to find myristicin from Petroselinum Crispum is a wild goose chase... and what about the other parsley (petroselinum) species? It seems to me that nutmeg oil will have a guaranteed amount of myristicin ranging from 3-6% from what i've read, whereas parsley seed oils may not have any myristicin at all and finding the right parsley seed oil is.... well... confusing the living hell out of me

NeilPatrickHarris · « **Reply #4 on:** February 03, 2011, 03:25:41 AM »

psychexplorer thanks for that reply, i think your approach makes the most sense. shop around for parsley seed oil, ask for a certificate of analysis and just keep doing that until i find a vendor with a satisfactory amount of myristicin. thanks!

salat · « **Reply #5 on:** February 03, 2011, 04:57:38 AM »

You can also check out Dr Dukes Phytochemical Database too which is where Strike probably got the info - you never know when you might want to look for something new.

This is the page for searching for a particular chemical.
http://www.ars-grin.gov/duke/highchem.html

This is the page for searching a plant, this can be especially handy if you are doing plant extractions in which case you need to get a feel for what is in the mix.
http://www.ars-grin.gov/duke/plants.html

Salat

Inonotuus · « **Reply #6 on:** December 09, 2011, 02:00:42 AM »

I don't have access to the full text, but this paper might answer your question in detail:

Quote

Study on chemical constituents of the essential oil from Myristica fragrans Houtt. by supercritical fluid extraction and steam distillation].
[Article in Chinese]
Qiu Q, Zhang G, Sun X, Liu X.
Source

School of Environmental Science and Engineering, Shandong University, Jinan.
Abstract

Essential oils were extracted from Myristica fragrans Houtt. by supercritical fluid extraction (SFE) and steam distillation (SD). Their components were analyzed by gas chromatography-mass spectrometry and compared. 48 compounds were identified for the essential oil extracted by supercritical carbon dioxide, and its main components have been found to be myristic acid, myristicin, terpinen-4-ol, alpha-pinene and safrole. 38 compounds were identified for the essential oil obtained by SD, and its main components have been found to be beta-pinene, terpinen-4-ol, alpha-pinene, gamma-terpinene and beta-phellandrene.

Source:
http://www.ncbi.nlm.nih.gov/pubmed/15810588

Also, if you contact a quality distributor of essential oils, they almost always have the chemical breakdown of their particular product available upon request.

Baba_McKensey · « **Reply #7 on:** December 09, 2011, 11:30:25 PM »

http://milkmandan.webs.com/MyrApiole.htm

Dr. Tox · « **Reply #8 on:** December 10, 2011, 12:13:28 AM »

Not to forget: http://www.erowid.org/archive/rhodium/chemistry/parsnips.html

Myristicin:
Pastinaca sativa -- Parsnip; 183,000 - 662,000 ppm in Root Essential Oil;
Petroselinum crispum -- Parsley; 14,785 - 19,800 ppm in Seed;
Myristica fragrans -- Mace, Muskatnussbaum (Ger.), Nutmeg, nogal moscado (Sp.), nuez moscada (Sp.); 800 - 12,800 ppm in Seed;
Perilla frutescens -- Perilla; 300 - 3,800 ppm in Leaf;
Petroselinum crispum -- Parsley; 425 - 2,550 ppm in Plant;
Myristica fragrans -- Mace, Muskatnussbaum (Ger.), Nutmeg, nogal moscado (Sp.), nuez moscada (Sp.); 410 - 620 ppm in Leaf;
Carum carvi -- Caraway, Carum, Comino (Sp.), Comino de prado (Sp.), Kummel (Ger.); 60 - 420 ppm in Fruit;
Petroselinum crispum -- Parsley; 131 ppm in Leaf;
Carum carvi -- Caraway, Carum, Comino (Sp.), Comino de prado (Sp.), Kummel (Ger.); 120 ppm in Plant;
Daucus carota -- Carrot; 0.5 - 34 ppm in Root; Anethum graveolens -- Dill, Garden Dill; in Fruit; in Root;
Apium graveolens -- Celery; in Plant;
Coriandrum sativum -- Chinese Parsley, Cilantro, Coriander; in Fruit;
Foeniculum vulgare -- Fennel; in Fruit;
Levisticum officinale -- Lovage; in Seed;
Oenanthe aquatica -- Water Fennel, Water Hemlock; in Fruit;
Oenanthe crocata -- Water Dropwort; in Plant;
Oenanthe javanica -- Javan Water Dropwort; in Fruit;
Pimpinella anisum -- Anise, Sweet Cumin; in Plant;
Piper nigrum -- Black Pepper, Pepper, White Pepper; in Fruit;
Sassafras albidum -- Sassafras; in Root;
Vaccinium corymbosum -- Blueberry; in Fruit;

Vesp · « **Reply #9 on:** December 10, 2011, 01:49:38 PM »

Is Pastinaca sativa a viable option? It seems to me that it would be easy enough to get large amounts of... considering it is essentially an invasive species that grows all over the USA.

If it so happens to be 18 to 66% Myristicin -- that is pretty good. Esp if it can be easily extracted from the roots?

Inonotuus · « **Reply #10 on:** December 16, 2011, 01:53:39 AM »

Quote from: Dr. Tox on December 10, 2011, 12:13:28 AM

Oenanthe aquatica -- Water Fennel, Water Hemlock; in Fruit;
Oenanthe crocata -- Water Dropwort; in Plant;
Oenanthe javanica -- Javan Water Dropwort; in Fruit;

Be careful if handling these guys, as they are also virulently poisonous. Gloves would be a good idea, as you can absorb the poisons directly through your skin with too much handling.

Baba_McKensey · « **Reply #11 on:** December 16, 2011, 11:35:10 PM »

The Merck Index lists typical consituents of nutmeg oil. It can vary depending on strain and growing conditions.

fresh1 · « **Reply #12 on:** December 17, 2011, 02:58:25 AM »

Quote

Is Pastinaca sativa a viable option

More than likely, however, like oil from Camphors, it varies HEAPS depending on what plant, which part, and at what time of year......

Its been found that the seedlings <10cm high (which sprout everywhere under the tree) can be most juicy, but again, much depends on the actual plant, and where its growing IME.

Baba_McKensey · « **Reply #13 on:** December 24, 2011, 05:17:51 PM »

https://www.hyperlab.info/inv/index.php?s=&act=ST&f=17&t=28793&hl=parsley

Baba_McKensey · « **Reply #14 on:** December 24, 2011, 05:20:47 PM »

See also Chem. Abs. 2 page 1007

Vesp · « **Reply #15 on:** December 24, 2011, 10:10:19 PM »

@Fresh1 --- any data on that <10cm high stuff? or is that just your observations?

antibody2 · « **Reply #16 on:** September 04, 2012, 09:59:14 PM »

Neil - here is a link with the constituents of EO of Nutmeg
http://www.erowid.org/archive/rhodium/pdf/nutmeg.oil.analysis.pdf

Another analysis Antibody has seen states EO of nutmeg has the following: myristicin, elemicin, safrol, eugenol. With a total phenylpropanoid content of 20%. This is going to be a very tedious fractional distillation of an oil that costs 1.5 - 2X as much as parsley oil

IMHO - you would be much better of working with parsley seed oil, the upside being that the other major constituent is apiol (30-50%) while myricticin content is (10-30%) not to mention some elemicin and tetramethoxyallybenzene. This fractional distillation will still be challenging, but your fractions will be twice the size, so it should be somewhat easier than with EO of nutmeg.

The other thing to consider, DMMDA (from apiol) is completely out of this world

(it has the classic 2,5 methoxy structure after all) while MMDA is in my opinion little better than MDA, yawn. Done em both. My most euphoric experience ever was with DMMDA.

PM me if you need a source of parsley oil with the goods.

Assyl Fartrate · « **Reply #17 on:** September 22, 2012, 02:43:43 AM »

Were those euphoric experiences with DMMDA repeatable?

You're one of a very small number of people who has used this drug (odds are most of the few reports out there are MDA, 2C-B, MMDA in the case of misidentified oils, or something similar), and you're a lot more articulate than the average person - could you provide a detailed summary of the effects, potency, dosage, and any tips from the synthesis? Your enthusiasm and experience with psychedelics makes this exceptionally interesting.

Will we witness the arrival of camphor's taller, slimmer twin sister? There's zero restrictions whatsoever on this stuff, and parsley is a joke to grow... it doesn't even require full sun.

Tsathoggua · « **Reply #18 on:** October 02, 2012, 12:47:44 PM »

Inonotuus, you ninja'ed me. Good one providing the warning. These guys aren't just lethal, they are downright nasty too, oenanthetoxin, and the related circutoxin, are both a potent noncompetitive GABAa antagonists. Nasty, painful way to go.

Most likely volatile, being just a fairly simply polyyene alcohol, and I would very much imagine it is indeed capable of transdermal absorption.

One slip, and you are fucked. These are probably THE deadliest plants found in the UK, the water hemlock, hemlock water dropwort and close allies. Maybe aconite is more so, or some of the Veratrum spp. hellebores, but the hemlock water dropworts are very much in the running for the top spot.

Quite capable of killing, from just a one bite of plant material by people who mistake it for edible umbellifers such as parsnip etc. I've read of a single bite of leaf in a sandwich producing fatality, the roots are even more toxic AFAIK.

Don't fuck with those Oenanthe spp.

I sure as hell wouldn't want to be the poor bastard who has to distill essential oils from any of them, put it that way.

antibody2 · « **Reply #19 on:** November 29, 2012, 11:28:17 PM »

Quote from: Assyl Fartrate on September 22, 2012, 02:43:43 AM

Were those euphoric experiences with DMMDA repeatable?

You're one of a very small number of people who has used this drug (odds are most of the few reports out there are MDA, 2C-B, MMDA in the case of misidentified oils, or something similar), and you're a lot more articulate than the average person - could you provide a detailed summary of the effects, potency, dosage, and any tips from the synthesis? Your enthusiasm and experience with psychedelics makes this exceptionally interesting.

Hi Assyl Fartrate - Sorry for the delay in replying. I only just noticed your query. Yes, DMMDA was bioassayed several times, each time with utterly heavenly results. This was about ten years ago so some of the details are foggy. But it was DMMDA, without question, as it came from my lab. The apiol was identified based on its BP and the order it came off the still relative to the other constituents expected in that oil. Even with a litre of oil to start the fractions were not sharp, meaning the temperature more or less rose steadily and it was up to me to decide what a fraction was. Colour was some help in sorting out the fractions. I posted a detailed blow by blow of that distillation on the hive at the time, if anyone still has access to that board or its database. Keyword searchs like "parsley oil" "distillation" would probably turn it up. It detailed the BPs of teh fractions as well as their sizes.

As far as effects and potency go, it is much stronger than MDA, I was dosing between 100-120mgs and at that dose it was obvious to people at parties that I had gone pretty deep. I was able to function, but often lost my train of thought mid sentence. Duration was similar to MDA. It had many of the empathogenic qualities of MDMA which are completely absent in MDA. I would also describe the experience as being mildly psychedelic, in so far as it enhanced colour and gave a sparkle to the day that I haven't experienced with other substituted amphetamines except TMA, which is also psychedelic but is entirely without the bliss/empathogenic qualities of DMMDA. I also remember sitting on a boat at the sailing club being so totally blissed out that I sat there by myself doing nothing for several hours, happy to just be.

It was made by isomerizing apiole under vacuum with 1% KOH >> modified performic rxn with DCM at reflux >> hydrolysis in dilute H2SO4 >> the ketone was distilled and converted to its oxime with hydroxylamine in MeOH >> which was then reduced with acidic Al/Hg in EtOH. There was no special treatment required. Everything was run as though MDA were being produced. Apiole is much less prone to cyclization that asarone or dill apiole.

If I were ever to go to the trouble of producing another amphetamine it would be DMMDA without question.

Author Topic: List of compounds in Myristica Fragrans oil? (searching for myristicin) (Read 312 times)

NeilPatrickHarris

List of compounds in Myristica Fragrans oil? (searching for myristicin)

Oerlikon

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

psychexplorer

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

NeilPatrickHarris

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

NeilPatrickHarris

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

salat

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

Inonotuus

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

Baba_McKensey

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

Dr. Tox

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

Vesp

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

Inonotuus

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

Baba_McKensey

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

fresh1

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

Baba_McKensey

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

Baba_McKensey

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

Vesp

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

antibody2

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

Assyl Fartrate

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

Tsathoggua

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)

antibody2

Re: List of compounds in Myristica Fragrans oil? (searching for myristicin)