Myristicin is a naturally occurring compound (an allylbenzene) found in common herbs and spices such as nutmeg.
When ingested in high doses, myristicin may produce hallucinogen,[
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Uses
Isolated myristicin has proven an effective insecticide against many agricultural pests, including Aedes aegypti mosquito larvae, Spilosoma obliqua (hairy caterpillars),
The chemical structure of myristicin is similar to some amphetamine compounds, and it may be capable of producing psychotropic effects.[ Normal levels of intake of myristicin from spices in food is unlikely to cause these effects.][ Myristicin can be used in the chemical synthesis of amphetamine derivatives such as the designer drug MMDMA that is similar in structure and effect to MDMA.][ and therefore is used to exploit the effects of myristicin.][
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Furthermore, myristicin interferes with multiple signaling pathways and enzyme processes in the body.
Sources of myristicin
Myristicin can be found in the essential oil of nutmeg, black pepper, Piper excelsum,
Trace amounts have also been isolated from a variety of plant species including Ridolfia segetum (harvest fennel), species of the Oenanthe genus (water dropworts), some species of the Lamiaceae family (mint family), Cinnamomum glanduliferum (Nepal camphor tree),
Depending on the conditions of growth and storage of the plant, a high quality nutmeg ( Myristica fragrans) seed can contain up to 13 mg of myristicin per 1 gram.
Physiological effects
Psychoactive effects
At a minimum dose of about 5 grams of nutmeg powder, symptoms of nutmeg intoxication can begin to emerge.
Pharmacology
Myristicin is additionally known to be a weak inhibitor of monoamine oxidase (MAO), an enzyme in humans that metabolizes neurotransmitters (for example, serotonin, dopamine, epinephrine, and norepinephrine). It lacks the basic nitrogen atom that is typical of monoamine oxidase inhibitors (MAOIs), potentially explaining a weaker inhibitory effect.
While smaller concentrations of MAOIs may not cause problems, there are additional warnings regarding drug interactions. Those taking antidepressants that are MAOIs (such as phenelzine, isocarboxazid, tranylcypromine or selegiline
The pharmacology of myristicin and other nutmeg constituents has been reviewed.
Metabolites
Metabolism of myristicin yields 3-methoxycatechol[ and enzymatically forms 5-allyl-1-methoxy-2,3-dihydroxybenzene (oxidation of the methylenedioxy group). Myristicin is also transformed into demethylenylmyristicin, dihydroxymyristicin, and elemicin is transformed into O-demethylelemicin, O-demethyldihydroxyelemicin, and safrole.][
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There has been speculation that myristicin might be converted into the psychedelic MMDA, but this has not been demonstrated in humans.
Chemistry
With a chemical structure resembling amphetamines and other precursors, myristicin can also be used to synthesize illicit hallucinogenic drugs. Under controlled conditions, myristicin isolated from nutmeg oil can be converted into MMDMA, a synthetic "designer drug" amphetamine derivative that is less potent than MDMA but produces comparable stimulant and hallucinogenic effects.
Myristicin is insoluble in water, and soluble in ethanol, ether, and benzene.[
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Toxicity
In laboratory studies, myristicin is Cytotoxicity. Specifically, it stimulates cytochrome c release, which activates caspase cascades and induces early apoptosis in the cells.
The effects of nutmeg consumed in large doses are attributed mostly to myristicin: 1–7 hours following ingestion, symptoms include disorientation, giddiness, stupor, and stimulation of the central nervous system leading to euphoria.[ Also occurring are mild to intense (similar to those induced by deliriants: walls and ceiling glitching or breathing), disorientation to time and surroundings, dissociation, feelings of levitation, loss of consciousness, tachycardia, weak pulse, anxiety, and hypertension.][ Symptoms of nutmeg intoxication further include nausea, abdominal pain, vomiting, minor to severe muscle spasms (severe in extreme overdose), headache, dryness of mouth, mydriasis or miosis, hypotension, shock, and potentially death.][
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Myristicin poisoning can be detected by testing levels of myristicin in the blood.
