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Myristicin

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Title: Myristicin  
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Subject: Elemicin, MMDA (drug), PiHKAL, Nutmeg, Magnoliids
Collection: Alkenes, Benzodioxoles, Monoamine Oxidase Inhibitors, O-Methylated Phenylpropanoids, Phenylpropenes, Plant Toxin Insecticides
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Myristicin

Myristicin
Systematic (IUPAC) name
6-allyl-4-methoxy-1,3-benzodioxole
Clinical data
Legal status
  • Uncontrolled
Routes of
administration
Oral
Identifiers
CAS Registry Number  YesY
PubChem CID:
ChemSpider  YesY
KEGG  YesY
ChEMBL  YesY
Synonyms 3-methoxy,4,5-methylenedioxy-allylbenzene
Chemical data
Formula C11H12O3
Molecular mass 192.21 g/mol
 YesY   

Myristicin is a 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.

Contents

  • Uses 1
  • Pharmacology 2
  • Reactions 3
  • See also 4
  • References 5

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

References

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  17. ^ a b
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