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).
Merck sez enough about the volatile oil to show that it is mostly
terpenes although containing substantial safrole (hurrah!) and myristicin.
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:
"...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)"
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.
______________________________________________________
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.
Nutmeg contains a variety of allylbenzenes (double bond between beta and gamma carbons),
all very similar to psychedelic amphetamines.
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.
"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.'"
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.
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.
