Nutmeg Extract

a-SalviaLover · eating chemicals

Do you have any idea of an easy way to ectract the alkaloids, found in the nutmeg? I've heard for some sort of vinegar extraction but i couldn't understand how to o it!

loki · guinea pig

nutmeg contains oils, not alkaloids. steam distillation, vacuum fractional distillation and solvent extraction is how it's done

stratosphere · Fri Jun 17, 2005 3:08 pm

i don't know of nutmeg containing any alkaloids which is a phrase meaning naturally occuring amines, like loki said i believe your after the essential oil which is high in eugenol and myristicin.

i think nutmeg essential oil is readily avialable commercially, unless you really need alot, or have a boner to do it yourself, it would probobly save you a great deal of time, effort and money and give you a better result to just order it.

2spun · The Resistor

swiy use'd
IPA to pull the oil out of nutmeg.
evap the ipa a tanish brown wax'e thick oil, swiy understands that there are a few oil's in nutmeg.
Elemicin and Myristicin just to name 2 of the top of my head.
If one can get it commercially maybe a eazie way to go.
But witch oil are ya get'n?
swiy thinks there are 4 types of oils in nutmeg.
Elemicin
Myristicin
Safrole
methyleugenol
maybe even more?
FROM
designer-drugs

------------------------------------------------------------------------------
Nutmeg and its Essential Oil
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From: an89433@anon.penet.fi
Date: Sat, 25 Mar 1995 15:47:09 UTC
Subject: Safrole

After looking up Oil of Nutmeg in the Merck index (10th ed) I came up
with the following :

Oil of nutmeg, constit:

60-80% d-camphene (Bp 158.5-159.5 C), 8% d-pinene; dipentene,
d-borneol (Bp 212 C), l-terpineol, 6% geraniol (Bp 229-230 C),
safrole (Bp 232-234 C), 4% myristicin.

The chemicals of interest here are safrole and myristicin. Temperatures
are in degrees Celsius at 1atm pressure (760mm Hg). My question is :
What is the fraction of safrole in oil of nutmeg. My guess is 4-6% but
a corrected estimate is welcomed...

Oil of sassafras (constit appx 80% of safrole) is of course preferred but
nutmeg is so easily availble that it is at least worth checking this out.

V. Jones

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Author: Daniel R Haney
Email: DrHaney@world.std.com
Date: 1995/10/01

> filter off the crystallized trimyristin.

>Uh... wrong compound.

Crepitance. Trimyristin is CHAFF. You must separate it FIRST
to get at the tiny fraction containing the phenylics of interest.

> The one of interest here is myristicin, not

Yes, I know, ya' yung whippersnapper. The amusing Volatile Oil
Of Nutmeg is the leftover you get with an extraction+crystallization.
Volatile Oil components are less than 5% of the whole nutmeg weight
while the fat trimyristin is at least 25%. That's a lot of crap
to ignore for doctrinaire reasons.

Merck sez enough about the volatile oil to show that it is mostly
terpenes (oboy! let's eat it and belch like bandits) although
containing substantial safrole (hurrah!) and myristicin.

I know you guys want an elegant one-step to snag the oils. So
would I. But ethanol is cheep and this fat extraction requires
less energy than the steam distillation.

Dragging my flu-ridden carcass around the house,
-DrH

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Author: Daniel R Haney
Email: DrHaney@world.std.com
Date: 1995/10/01

I have come perilously close to a chemical prick-waving
match with you and sincerely apologize. As evidence of
earnest good intent, I am passing on the fruits of my
studies on NUTMEG for the edification of all.

On nutmeg, the Encyclopedia Britannica sez:

"Nutmeg and mace contain 7 to 14 percent essential oil,
the principal components of which are pinene, camphene,
and diterpene, all having the empirical formula C10H16.
Nutmeg on expression yeilds about 24 to 30 percent fixed
oil called nutmeg butter, or oil of mace, the principal
component of which is trimyristin..."

On volatile oil of NUTMEG, Merck 11th sez:

(skipping the reference to steam distillation)

"...Constit. 60-80% d-camphene, about 8% d-pinene;
dipentene, d-borneol, l-terpineol, about 6% geraniol,
safrol, about 4% myristicin. The myristicin fraction
with its more than 25% content of elemicin is supposed
to be responsible for the purported hallucinogenic
properties of nutmeg seed: Shulgin, "Nature" 197, 4865,
(1963)"

Sorta figured Shulgin would turn up in there. More later.
The elemicin is not listed or indexed as such in Merck 11th,
but is the 3,4,5 trimethoxy substituted phenylallene.

Neither safrole nor myristicin is there in SUBSTANTIAL amounts,
only SIGNIFICANT amounts. Useless for preparative intents,
useful for scents and flavorings.

100MG OF MYRISTICIN...

4% of 10% (average 7,14) is 0.4%, that is to say, myristicin is .4%
the weight of whole nutmeg. 25 grams of whole nutmeg contains 100 mg
of the myristicin fraction. I'd rather brew beer.

UBER ALCOHOL EXTRACTION:

>...What percentage of oils can be extracted out this way?

Nearly all of them that can be had along with a lot of stuff
you don't want. Solvent extraction is so thorough the the nutmeg
is pale when you are done.

>I was always under the impression that steam
>distillation was much more effective at squeezing the non-miscible
>non-volatiles out.

MY CONJECTURE:
The steam distillation is industrially feasible because of the
mechanical simplicity of equipment and lower physical handling.

The alcohol extraction is fast but requires more handling and so is
better applied to small scale,i.e., benchtop. I guess it depends
on what amount you want to produce.

By example, stearic acid is produced by both methods depending
upon the cheapness of fuel and labor. The results differ
primarily in the last 3% of stuff that is NOT stearic acid such
as proteins, inorganics, unsaturated fats, and funky esters.
Stearic acid is used in vast quantity to make soaps, creams,
and lotions. [end digresssion]

Shulgin's listing of the 10 essential oils follows. I have
renamed them from IUPAC to trivial allylbenzenes to reflect
the ring substitution of a sibling phenalkylamine.

estragole: 4-methoxy allylbenzene
methyleugenol: 3,4-dimethoxy allylbenzene
safrole: 3,4-methylenedioxy allylbenzene
myristicin: 5-methoxy 3,4-methylenedioxy allylbenzene
croweacin: 2-methoxy 3,4-methylenedioxy allylbenzene
elemicin: 3,4,5-trimethoxy allylbenzene
asarone: 2,4,5-trimethoxy propenylbenzene
apiole: 2,5-dimethoxy 3,4-methylenedioxy allylbenzene
dillapiole: 2,3-dimethoxy 4,5-methylenedioxy allylbenzene
???: 2,3,4,5-tetramethoxy allylbenzene

Jason keeps mentioning inorganic salts in nutmeg. While my
first impulse was to ignore that as insignificant, there is
no avoiding inorganic matter entrained in the nutmeg extracts.
All woody/nutty materials contain significant inorganics.

This has been recognized historically -

Rock maple is awfully hard stuff in part because of the silicates
in it. Makes a nice solid body guitar, too. Chews up saw blades.

Stradivari treated wood with brine to leach out the inorganics
as well as the water-soluble rosins and so got a lighter, more
resonant material with extended high frequency response.

I have no exact information as to the disposition of inorganics
in nutmeg or wood so if anyone else knows some figures, speak up.

Good Cheer,
Daniel R. Haney

ps: Hah! The old fart's brain isn't entirely rusted shut.

--------------------------------------------------------------------------------
I got curious enough about nutmeg to do some reading. Nutmeg contains
a variety of allylbenzenes (double bond between beta and gamma carbons),
all very similar to psychedelic amphetamines. I tried drawing the
compounds, but they're difficult in ASCII. The compounds all have the
allylbenzene in common, the differ in their substitutions at the 3,4,5
positions of the benzene ring. The compounds and their concentrations
from (1):

compound substitutions concentration
-------- ------------- -------------
myristicin 3-methoxy, 4,5-methylenedioxy 4.0%
safrole 3,4-methylenedioxy 0.6%
eugenol 3-methoxy, 4-hydroxyl 0.2%
elemicin 3,4,5-trimethoxy *
methyleugenol 3,4-dimethoxy *
----
*-mentioned in (4) and stated as being previously included with
the myristicin portion incorrectly.

Weil's (1) paper gives a broad history of nutmeg use as food and as
narcotic, and gives a summary of research into the pharmacological
effects of nutmeg. Some of the more interesting work cited is that by
Alexander Sulgin (3,4). Unfortunately some of the cited work is from an
unpublished paper, and the library didn't have the journal another
article was in (3) so I only saw excerpts.

The descriptions of the experience mentioned by Weil are consistent
with pyschedelic amphetamine experiences, although the initial phase
of an excitment and distorted perception is often followed by
narcosis, the effects sometimes reported as lasting days. There are a
wide variety of other toxic effects reported (infrequently, death) with
enough frequency to make it clear why this is not a widely abused
substance.

The psychedelic component is examined by Shulgin who concludes that
the hallucinogenic action is mainly from the myristicin and related
components. He notes that only know mechanism of metabolism of any of
the compounds is the detoxification of safrole to piperonylic acid.
This reaction show the capacity to oxidize an olefinic side chain.
He uses this fact to speculate on a possible pharmacologic mechanism
(quoted from Weil):

"Shulte suggests that, if this degradative process is `applicable to
myristicin, or especially to elemicin, a theoretical intermediate, a
vinyl alcohol, could undergo transamination producing the known
psychotomimetic drug, 3,4,5-trimethoxy amphetamine (TMA). The recent
description of the new, synthetic hallucinogen -
3-methoxy-4,5-methylenedioxy amphetamine (MMDA)-which might be
derived by an analogous process from myristicin, itself, is even more
suggestive of a psychotropic function for this component of nutmeg.'"

References
----------
1. Weil, Andrew (1965). Nutmeg as a Narcotic. 19(3), 194-217.

2. Truitt, Edward and others (1961). The Pharmacology of Myristicin; A
Contribution to the Psychoparmacology of Nutmeg. 2(4), 205.

3. Shulgin, Alexander T. (1963). Concerning the pharmacology of nutmeg.
Mind 299-303.

4. Shulgin, Alexander T. (1964). Composition of the myristicin fraction
from oil of nutmeg. Nature, 197:4865, p.379.

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Author: Jacob W Smith
Email: smit0262@gold.tc.umn.edu
Date: 1995/10/02

Myristicin constitutes about two thirds of the aromatic ether
fraction, but it cannot account entirely for the psychoactivity
of nutmeg. Those occurring at more than 10 mg per 20 g are myristicin
(210 mg), elemicin (70 mg), safrole (39 mg), methyleugenol (18 mg),
and methylisoeugenol (11 mg). A 400-mg dose of myristicin, almost twice
the amount present in 20 gm of nutmeg (20 gm being assumed to be the
quantity required to produce psychotropic effects) produces only mild
effects.

Schultes and Hofmann. The Botany and Chemistry of Hallucinogens. p. 121.

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Author: Jason Kennerly
Email: jkenner@cello.gina.calstate.edu
Date: 1995/10/01

Roughly 60g of nutmeg powder was extracted into acetone. The acetone was
allowed to sit like that on a shelf for a few days and...

Something precipitated! white stuff! What is it? I'm *guessing* this has
something to do with the fatty acids, but does it? What the hell is the
stuff. I saved it, i'm pretty damn curious as to what it is.... I know
its not likely to be anything useful, but does this type of thing happen
often?

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Composition of the Myristicin Fraction from Oil of Nutmeg
Alexander T. Shulgin
Nature, Vol. 197, No. 4865, p. 379 (1963)

The aromatic ether fraction of oil of nutmeg has been previously shown to
consist of eugenol (Ia), isoeugenol (IIa) safrole (Ic) and myristicin (Id).
Vacuum distillation yields a fraction (bp 109-112°C @1 mmHg; 60g from
1000g of "W.I." oil of nutmeg (George Lueders and Co)) which consisted of
a substance heretofore accepted both clinically and pharmacologically as
the single compound, myristicin (Id).

3 (I) 3 (II)
\___ \___
/ \ KOH/EtOH / \
4--< O >--CH2--CH==CH2 ==========> 4--< O >--CH2==CH2-CH3
\___/ \___/
/ /
5 5

---------------------------
3 4 5
---------------------------
a OCH3 OH H
b OCH3 OCH3 H
c O--CH2--O H
d O--CH2--O OCH3
e OCH3 OCH3 OCH3
---------------------------

The isomerization of this fraction with alcoholic potassium hydroxide
yielded (trans) isomyristicin (IId), isolated by crystallization of the
distilled reaction mixture. The mother liquors of this isolation.
On analysis by vapour phase chromatography, provided the first indication of
the complexity of the above "myristicin" fraction. Of the four peaks observed,
No. 1 was easily identified as methyl isoeugenol (IIb) by its infra-red
spectrum and direct comparison to a commercial sample. Peak No. 3 was to a
large extent trans-isomyristicin not removed by crystallization. The remaining
two peaks were isolated using a Beckman Megachrome preparative V.P.C.
instrument using a substrate of silicone 710, on firebrick at 220°C.
The presence of a methylenedioxy group (by nuclear magnetic resonance) and the
absence of absorption in the 963-967 cm-1 region of the infra-red spectrum of
peak 2 strongly suggested that the isomer might be cis-isomyristicin. That
trans-propenyl aromatic ethers possess a characteristic absorption band in the
above region (which is transparent for the cis-isomer) has been shown for
isosafrole, anethol, isoeugenol, methylisoeugenol and asarone. Further, it has
been shown recently that the cis-isomer of the stereoisomeric pairs invariably
precedes the trans-isomer during vapour chromatography. This peak was verified
as cis-isomyristicin by its conversion to trans-isomyristicin (IId) and its
synthesis from myristicin, both with alcoholic potassium hydroxide. The fourth
peak was also isolated by preparative chromatography and showed the absence of
a methylenedioxy group, but the presence of a strong band at 957 cm-1.
Isoelemicin (IIe) was synthesized by the potassium hydroxide isomerization of
elemicin and was found to possess an identical infra-red spectrum. Methyl
isoeugenol may be assumed to be in the propenyl form in the original sample of
nutmeg distillate. There is an unresolved peak at this identical time in the
original "myristicin" fraction and a search for the logical precursor methyl
eugenol, has been unsuccessful.

The implied presence of elemicin (Ie) in the original myristicin fraction was
confirmed by the successful separation of it from myristicin by low-temperature
chromatography (108°C, silicone 'SF-96'). Repeated fractional distillation was
ineffective in increasing the myristicin content of this constant boiling
fraction over 70 percent. Consequently in assigning chemical and biological
properties to the substances as isolated from nutmeg, allowance must be made
for this congeneric contaminant.

Much thanks

a-SalviaLover · eating chemicals

I need myristicin. And sorry for my mistake. Myristicyn is not an alkaloid, I was confused from sth i had read, but when I found its structure i realised that it's not true. I am talking about something easy to do and to be capable for direct cnosumation! I'm a fan of myristicin's effects but don't like the taste of nutmeg very much. Therefore I am talking about sth easy. Nutmeg oil is not easily obtainable in my region (or at lest I have no idea where to find it!) 10x in advance!

2spun · The Resistor

a-SalviaLover,

swiy would think one can find better yelds of myristicin.
In Parsley or dill. swiy does not have his ref's wit him right now but will see if he can find a few for ya.

a-SalviaLover · eating chemicals

a-SalviaLover would be grateful to swiy! I don't care if there are some other stuff from the nutmeg, the only hing I want is the chemicals (especially myristicin) to be more concentrated than in the nutmeg so they van be easier to consume! I read some sort of vinegar ectraction from erowid but I don't think I understood it very well! I hope that there would be some good chmists or psychonauts around here who can tell me waht to do!

Vitriodor · Sat Jun 18, 2005 1:44 am

From "Drugs of Natural Origin" by G. Samuelsson:

Nutmeg contains 30-40% fat and 5-15 volatile oil. Terpenes constitute 60-80% of this oil and myristicin about 8%. If taken in large quantities (up to 15 g.....Yuk!) nutmeg has a hallucinogenic effect, which is followed by unpleasant side effects such as reddening of the skins, palpitations and decreased salivation. These reactions are thought to be due to the myristicin contained in the drug.

For an article on "The use of nutmeg as a psychotropic agent" see http://www.unodc.org/unodc/bulletin/bulletin_1966-01-01_4_page003.html

Vit

2spun · The Resistor

off of Rhodium,mirror

Pastinaca sativa -- the parsnip

The most impressive figure from the list above is 662,000 parts per million of myristicin, from the roots of parsnips. The essential oil present in this food is 66.2% myristicin. By comparison, the oil derived from the seeds of nutmegs have much less myristicin than this, for this oil is only about 8% myristicin. If anybody might want to contrive anything like MMDA (3-methoxy-4,5-methylenedioxyphenylisopropylamine, active @ 100-250 mg) for any reason, myristicin would be the starting point.

I have received a report from one party known to us here, that the oil yield from grocery store parsnips was negligible. They are not grown nor sold in my region, so I can't tell you.

Umbillifer foods: condiments, herbs, and spices

All the umbillifer spices have useful phenylpropanoids in their essential oils, period. That's carrots and celery and dill and fennel and parsley and coriander and cardomom and tarragon and so on and so forth. The problem in many cases, is that their phenylpropanoids often contain monomethoxylated (p-methoxy) benzene rings. The main chore is getting rid of the anethole and/or methyl chavicol in fractional vacuum distillation, because PMA isn't stylish any more. These oils are an innocent purchase even in bulk.

Petroselinum crispum -- parsley The star among these is parsley. Parsley seed oil from Eastern Europe and Germany will contain over 50% useful phenylpropanoids, no anethole. A typical Bulgarian seed oil contains 2% elemicin, 34% myristicin, and 16% apiole. The apiole will solidify out of the whole oil below 15 degrees, so it must be even easier to separate once the terpenes have been boiled off below 200 degrees. The leaf oil will also give myristicin and a bit of apiole, but the root oil and especially the seed oil is much better, at a vastly lower cost.

Anethum graveolens -- dill weed

Dill (Anethum graveolens) is opposite of parsley, with respect to where the good phenylpropanoids may be found. American style dill herb oil, is in fact a rich repository of precursor phenylpropanoids, specifically dillapiole. In this case, more so than dill seed oil (which is actually made from the fruits, but it is conventionally called "seed" oil). I am not aware of the details of how "American style dill weed oil", as it is internationally known, is processed, but I expect it may be from all the aerial parts of the plant.
And there's more...

http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/parsnips.html

Synthesis of Myristicin and Elemicin from Eugenol
http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/eugenol2myristicin.html

Composition of
the Myristicin Fraction from Oil of Nutmeg
http://designer-drugs.com/pte/12.162.180.114/dcd/chemistry/nutmeg.myristicin.html

#132 MMDA
http://www.erowid.org/library/books_online/pihkal/pihkal132.shtml

Hope that helps ya a bit
much thanks

a-SalviaLover · eating chemicals

And how exactly would the extract be made?

mrmacgoo4002 · Tue Sep 20, 2005 2:19 pm

Would it be possible to perform a steam distillation on raw nutmeg and use fractionation to extract the safrole content?

Is the method feasible, I've seen a document on lyceaum which states that it would be. However I've found no verification as to whether or not this method would actually work.

Thanks in advance.

loki · guinea pig

there is no real reason why it would not work, given that there is at least 10 degrees difference between the desired product and the rest of the mixture, if the margin is that tight one would need to do fractional vacuum distillation which allows sharper separations. chromatography is another option but perhaps a bit more labour intensive.

I would think that this would be a lotta work for not a lotta result, personally. camphor oil would be a much better option.

hahas · Tue Sep 20, 2005 10:54 pm

Shulgin may have details on the distillation in his 1963 Nature article, i don't recall exactly. i have a feeling that it involved a very good column and strong vacuum. in JCS 2037 (1907) they had a hell of a time getting the very small amount of myristicin (4%) and smaller amount of safrole (.6%) from some kilos of the highest boiling oil. it was a discouraging read, those dudes were prepared for some tough distillation and they got it. everything is simple if you have the right equipment. if not...

mrmacgoo4002 · Wed Sep 21, 2005 7:07 am

Hmm... 0.6%, so you're looking at 6g per kilo, that's no good...

Does anybody know what sorts of yields are expected from distillation of nutmeg essential oil?

What about tiger balm?

http://www.tigerbalm.co.uk/intro.html

http://www.keypharmaceuticals.com.au/analgesicrub.htm

It is said to contain camphor, has anybody looked into this?

loki · guinea pig

that 0.6% figure is actually from the oil

tiger balm is a bloody expensive way to get camphor.