|Other names||3-methoxy-4,5-methylenedioxy-allylbenzene; 5-methoxy-3,4-methylenedioxy-allylbenzene|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||192.214 g·mol−1|
|3D model (JSmol)|
Myristicin (or methoxysafrole) is a phenylpropene, a natural organic compound present in small amounts in the essential oil of nutmeg and anise,[not verified in body] in several members of the carrot family,[not verified in body] and to a lesser extent in other spices/herbs such as parsley and dill.[not verified in body] In such plants, it acts as a natural bioactive agent, specifically as an insecticide or acaricide.[better source needed]
Myristicin is a naturally occurring acaricide (agent that kill members of the arachnid subclass Acari, which includes ticks and mites)[better source needed] as well as an apprent general insecticide.
Widelski and Kukula-Koch note in a textbook chapter in their 2017 Pharmacognosy that myristicin, "present in the volatile oil of M. fragrans, is a potential chemopreventive agent, by way of its ability to induce the activity of the detoxifying enzyme system, glutathione S-transferase",[full citation needed] an activity that is widely discussed[full citation needed] alongside a variety of apoptotic, anticancer, and other activities.
Myristicin is also known to be a weak inhibitor of monoamine oxidase, a liver enzyme in humans that metabolizes neurotransmitters (e.g., serotonin, dopamine, epinephrine, and norepinephrine), and its action, alone and in combination with other drugs, may contribute to circulatory disorders upon its ingestion.
Consumption of nutmeg in large quantities is known to cause hallucinations "followed by unpleasant side effects"; as Widelski and Kukula-Koch further note,
For the psychoactivity of nutmeg to be experienced, the metabolic conversion of the two components of nutmeg essential oil, myristicin and elmicin into compounds similar to amphetamine has to take place... [where] metabolism of myristicin leads to 3-methoxy-4,5-methylenedioxy amphetamine...
The primary literature reports various cases of nutmeg ingestion, including attempts by adolescents trying to achieve a "low cost" high. Such recreational uses of nutmeg as a psychoactive agent have caused acute poisoning that required medical treatment, with symptoms including dry mouth, facial flushing, nausea, vomiting, hypertension, tachycardia, dizziness, anxiety, headache, as well as hallucinations, feelings of euphoria and unreality, delirium, irrational behavior, and collapse. Blood myristicin concentrations may be measured to confirm a diagnosis of poisoning.
Specifically, possible neurotoxic effects on dopaminergic neurons have been reported; more widely, as presented in case reports, raw nutmeg consumption has produced poisoning symptoms where an anticholinergic mechansim attributed to myristicin and elemicin was invoked.[non-primary source needed]
Raw nutmeg consists of 5-15% essential oil by mass. 4-8.5% of nutmeg essential oil, or 0.2-1.3% of raw nutmeg, is myristicin. One study found 20 grams of nutmeg to contain 210 mg myristicin, 70 mg elemicin and 39 mg safrole.
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. A 1963 study found preliminary evidence that myristicin may be a weak monoamine oxidase inhibitor in mice and rats. The study concluded that more direct evidence will be required. In a 2005 study it showed possible neurotoxic effects on cultivated human neuroblastoma cells.
In 1963, Alexander Shulgin speculated myristicin could be metabolized to MMDA, a psychoactive drug related to MDA, in the liver. This speculation remains unconfirmed as of 2009; studies with the closely related compounds asarone and safrole support the conclusion that the proposed transamination reactions do not take place in humans.[non-primary source needed]