Myristicin is a naturally occurring compound (an allylbenzene) found in common herbs and spices such as nutmeg. It is an insecticide, and has been shown to enhance the effectiveness of other insecticides.
When ingested in high doses, myristicin may produce hallucinogenic effects, and can be converted to MMDMA in controlled chemical synthesis. It interacts with many enzymes and signaling pathways in the body, and may have dose-dependent cytotoxicity in living cells. and many members of the Umbelliferae family, including anise, carrots, parsley, celery, dill, and parsnip. and Piper mullesua ("Hill Pepper").
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) or taking selective serotonin reuptake inhibiting (SSRI) antidepressants should avoid essential oils rich in myristicin, such as that of nutmeg and anise.
Myristicin does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.
The pharmacology of myristicin and other nutmeg constituents has been reviewed.
Metabolites
Metabolism of myristicin yields 3-methoxycatechol
However, two nitrogen-containing metabolites of myristicin have been identified in the urine of rats and guinea pigs following oral or intraperitoneal administration. The major basic ninhydrin-positive urinary metabolite of myristicin in the rat is 3-piperidyl-1-(3′methoxy-4′,5′-methylenedioxyphenyl)-1-propanone, while the major basic ninhydrin-positive urinary metabolite of the guinea pig is 3-pyrrolidinyl-1-(3′methoxy-4′,5′-methylenedioxyphenyl)-1-propanone. Equivalent nitrogen-containing metabolites have also been identified for safrole and elemicin, including the dimethylamine, piperidine and pyrrolidine forms. Whether these aminated metabolites are responsible for the reported psychoactive & psychedelic effects from botanical sources of these allylbenzenes is not known.
Chemistry
thumb|class=skin-invert-image|Synthesis of MMDMA from myristicin There are no known antidotes for myristicin poisoning, and treatment focuses on symptom management and potential sedation in cases of extreme [[delirium or aggravation.