Myristicin

Myristicin

Systematic (IUPAC) name
6-allyl-4-methoxy-1,3-benzodioxole
Clinical data
Legal status	Uncontrolled
Routes of administration	Oral
Identifiers
CAS Number	607-91-0 Y
PubChem	CID 4276
ChemSpider	4125 Y
KEGG	C10480 Y
ChEMBL	CHEMBL481044 Y
Synonyms	3-methoxy,4,5-methylenedioxy-allylbenzene
Chemical data
Formula	C11H12O3
Molar mass	192.21 g/mol
SMILES O1c2cc(cc(OC)c2OC1)C\C=C
InChI InChI=1S/C11H12O3/c1-3-4-8-5-9(12-2)11-10(6-8)13-7-14-11/h3,5-6H,1,4,7H2,2H3 Y Key:BNWJOHGLIBDBOB-UHFFFAOYSA-N Y
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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.^[1]

Myristicin is a psychoactive drug, acting as an anticholinergic, and is the traditional precursor for the psychedelic and empathogenic drug MMDA.

Uses

Nutmeg has psychoactive properties at doses much higher than used in cooking.

In case reports, raw nutmeg produced anticholinergic-like symptoms, attributed to myristicin and elemicin.^[2][3][4]

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.^{[5][6][7][8][9][10][11][12][13][14]}

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.^[15]

Pharmacology

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.^[16][2] One study found 20 grams of nutmeg to contain 210 mg myristicin, 70 mg elemicin and 39 mg safrole.^[2][17]

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.^[3]

A 1997 study found data to suggest that myristicin can alter the toxicity and / or metabolic pathway of some compounds.^[18] 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.^[19] Myristicin is a naturally occurring insecticide and acaricide. In a 2005 study it showed possible neurotoxic effects on cultivated human neuroblastoma (cancer) cells.^[20]

In 1963, Alexander Shulgin speculated myristicin could be metabolized to MMDA, a psychoactive drug related to MDA, in the liver.^[3]

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.^[21] However, Alexander Shulgin notes in his book PiHKAL 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."^[22]

As quoted, this transamination was conducted in vitro, and has yet to be proven to occur in vivo.^[17]

Reactions

When myristicin is heated with potassium hydroxide in alcohol and the distillate is crystallized upon cooling, colorless needles of isomyristicin are formed. ^[23]

See also

• Elemicin

References