Myristicin
Encyclopedia
Myristicin is a phenylpropene
, a natural organic compound present in small amounts in the essential oil
of nutmeg
and to a lesser extent in other spices such as parsley
and dill
.
It is insoluble in water, but soluble in ethanol
and acetone
.
.
In case reports raw nutmeg produced anticholinergic
-like symptoms, attributed to myristicin and elemicin
.
In case reports intoxications with nutmeg
had effects that varied from person to person, but were often reported to be an excited and confused state with headaches, nausea and dizziness, dry mouth, bloodshot eyes and memory disturbances. Nutmeg was also reported to induce hallucinogenic effects, such as visual distortions and paranoid ideation. In the reports nutmeg intoxication took several hours before maximum effect was reached. Effects and after-effects lasted up to several days.
Recreational use of nutmeg has caused poisoning, requiring medical treatment, characterized by nausea, vomiting, collapse, tachycardia, dizziness, anxiety, headache, hallucinations and irrational behavior. Blood myristicin concentrations may be measured to confirm a diagnosis of poisoning.
.
While myristicin has been widely accepted as the main psychoactive component of nutmeg (along with elemicin
), both the differences in subjective effects observed between nutmeg and synthetic myristicin, as well as the fact that myristicin is not a major component of the seed (therefore is possibly not present in high enough quantities) suggest it does not fully explain the effects of consuming raw nutmeg.
A 1997 study found data to suggest that myristicin can alter the toxicity and / or metabolic pathway of some compounds.
In a 1963 study preliminary evidence was found, that myristicin may be a weak inhibitor of monoamine oxidase
in mice and rats. The study concluded, that more direct evidence will be required.
Myristicin is a naturally occurring insecticide
and acaricide.
In a 2005 study it showed possible neurotoxic
effects on cultivated human neuroblastoma
(cancer) cells.
In 1963, Alexander Shulgin
speculated myristicin could be metabolized
to MMDA, a psychoactive drug related to MDA
, in the liver
.
This speculation has never been confirmed and studies with the closely related compounds asarone
and safrole
demonstrated that the proposed transamination
reactions did not take place in humans.
However, Alexander Shulgin notes in his book PiHKAL
that
As quoted, this transamination was conducted in vitro, and has yet to be proven to occur in vivo.
in alcohol and the distillate is crystallized upon cooling, colorless needles of isomyristicin are formed.
Phenylpropene
Phenylpropenes, propenylphenols or allylbenzenes are a class of phenylpropanoids, a type of polyphenols.The phenylpropenes, including eugenol, chavicol, safrole and estragole, are derived from the monolignols. These compounds are the primary constituents of various essential oils....
, a natural organic compound present in small amounts in the essential oil
Essential oil
An essential oil is a concentrated hydrophobic liquid containing volatile aroma compounds from plants. Essential oils are also known as volatile oils, ethereal oils or aetherolea, or simply as the "oil of" the plant from which they were extracted, such as oil of clove...
of nutmeg
Nutmeg
The nutmeg tree is any of several species of trees in genus Myristica. The most important commercial species is Myristica fragrans, an evergreen tree indigenous to the Banda Islands in the Moluccas of Indonesia...
and to a lesser extent in other spices such as parsley
Parsley
Parsley is a species of Petroselinum in the family Apiaceae, native to the central Mediterranean region , naturalized elsewhere in Europe, and widely cultivated as an herb, a spice and a vegetable.- Description :Garden parsley is a bright green hairless biennial herbaceous plant in temperate...
and dill
Dill
Dill is a perennial herb. It is the sole species of the genus Anethum, though classified by some botanists in a related genus as Peucedanum graveolens C.B.Clarke.-Growth:...
.
It is insoluble in water, but soluble in ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
and acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
.
Uses
Nutmeg has psychoactive properties at doses much higher than used in cookingCooking
Cooking is the process of preparing food by use of heat. Cooking techniques and ingredients vary widely across the world, reflecting unique environmental, economic, and cultural traditions. Cooks themselves also vary widely in skill and training...
.
In case reports raw nutmeg produced anticholinergic
Anticholinergic
An anticholinergic agent is a substance that blocks the neurotransmitter acetylcholine in the central and the peripheral nervous system. An example of an anticholinergic is dicycloverine, and the classic example is atropine....
-like symptoms, attributed to myristicin and elemicin
Elemicin
Elemicin is a phenylpropene, a natural organic compound, and is a constituent of the essential oil of nutmeg.Elemicin is also a minor constituent of the oleoresin and essential oil of Manila elemi...
.
In case reports intoxications with nutmeg
Nutmeg
The nutmeg tree is any of several species of trees in genus Myristica. The most important commercial species is Myristica fragrans, an evergreen tree indigenous to the Banda Islands in the Moluccas of Indonesia...
had effects that varied from person to person, but were often reported to be an excited and confused state with headaches, nausea and dizziness, dry mouth, bloodshot eyes and memory disturbances. Nutmeg was also reported to induce hallucinogenic effects, such as visual distortions and paranoid ideation. In the reports nutmeg intoxication took several hours before maximum effect was reached. Effects and after-effects lasted up to several days.
Recreational use of nutmeg has caused poisoning, requiring medical treatment, characterized by nausea, vomiting, collapse, tachycardia, dizziness, anxiety, headache, hallucinations and irrational behavior. Blood myristicin concentrations may be measured to confirm a diagnosis of poisoning.
Pharmacology
When consuming raw nutmeg, only 5-15% of the mass consumed is an essential oil fraction, of which at least 4%, at most 8.5% is myristicin, indicating that the amount present overall in the nut varies from 0.2-1.3%. 20 grams of nutmeg would thus on average contain about 150 mg of myristicin. One study found 20 grams of nutmeg to contain 210 mg myristicin, 70 mg elemicin and 39 mg safroleSafrole
Safrole, also known as shikimol, is a phenylpropene. It is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil , or synthesized from other related methylenedioxy...
.
While myristicin has been widely accepted as the main psychoactive component of nutmeg (along with elemicin
Elemicin
Elemicin is a phenylpropene, a natural organic compound, and is a constituent of the essential oil of nutmeg.Elemicin is also a minor constituent of the oleoresin and essential oil of Manila elemi...
), both the differences in subjective effects observed between nutmeg and synthetic myristicin, as well as the fact that myristicin is not a major component of the seed (therefore is possibly not present in high enough quantities) suggest it does not fully explain the effects of consuming raw nutmeg.
A 1997 study found data to suggest that myristicin can alter the toxicity and / or metabolic pathway of some compounds.
In a 1963 study preliminary evidence was found, that myristicin may be a weak inhibitor of monoamine oxidase
Monoamine oxidase
L-Monoamine oxidases are a family of enzymes that catalyze the oxidation of monoamines. They are found bound to the outer membrane of mitochondria in most cell types in the body. The enzyme was originally discovered by Mary Bernheim in the liver and was named tyramine oxidase...
in mice and rats. The study concluded, that more direct evidence will be required.
Myristicin is a naturally occurring insecticide
Insecticide
An insecticide is a pesticide used against insects. They include ovicides and larvicides used against the eggs and larvae of insects respectively. Insecticides are used in agriculture, medicine, industry and the household. The use of insecticides is believed to be one of the major factors behind...
and acaricide.
In a 2005 study it showed possible neurotoxic
Neurotoxin
A neurotoxin is a toxin that acts specifically on nerve cells , usually by interacting with membrane proteins such as ion channels. Some sources are more general, and define the effect of neurotoxins as occurring at nerve tissue...
effects on cultivated human neuroblastoma
Neuroblastoma
Neuroblastoma is the most common extracranial solid cancer in childhood and the most common cancer in infancy, with an annual incidence of about 650 cases per year in the US , and 100 cases per year in the UK . Close to 50 percent of neuroblastoma cases occur in children younger than two years old...
(cancer) cells.
In 1963, Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
speculated myristicin could be metabolized
Metabolism
Metabolism is the set of chemical reactions that happen in the cells of living organisms to sustain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments. Metabolism is usually divided into two categories...
to MMDA, a psychoactive drug related to MDA
3,4-Methylenedioxyamphetamine
3,4-Methylenedioxyamphetamine , also known as tenamfetamine , is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes...
, in the liver
Liver
The liver is a vital organ present in vertebrates and some other animals. It has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...
.
This speculation has never been confirmed and studies with the closely related compounds asarone
Asarone
Asarone, which includes alpha and beta types, is an ether found in certain plants such as acorus and asarum. As a volatile fragrance oil, it is used in killing plant fungal pests and bacteria...
and safrole
Safrole
Safrole, also known as shikimol, is a phenylpropene. It is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil , or synthesized from other related methylenedioxy...
demonstrated that the proposed transamination
Transamination
There are two chemical reactions known as transamination . The first is the reaction between an amino acid and an alpha-keto acid...
reactions did not take place in humans.
However, Alexander Shulgin notes in his book PiHKAL
PiHKAL
PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...
that
Myristicin and the conjugated isomer isomyristicin are also found in parsley oil, and in dill. This was the oil that was actually shown to be converted to MMDA by the addition of ammonia by passage through an in vitro liver preparation.
As quoted, this transamination was conducted in vitro, and has yet to be proven to occur in vivo.
Reactions
When myristicin is heated with potassium hydroxidePotassium hydroxide
Potassium hydroxide is an inorganic compound with the formula KOH, commonly called caustic potash.Along with sodium hydroxide , this colorless solid is a prototypical strong base. It has many industrial and niche applications. Most applications exploit its reactivity toward acids and its corrosive...
in alcohol and the distillate is crystallized upon cooling, colorless needles of isomyristicin are formed.