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Myristicin

Myristicin^[1]

IUPAC name	4-Methoxy-6-prop-2-enyl-benzo[1,3]dioxole
Other names	5-Allyl-1-methoxy-2,3-(methylenedioxy)benzene
Identifiers
CAS number	607-91-0
PubChem	4276
EINECS number	210-146-9
SMILES	COC1=CC(=CC2=C1OCO2)CC=C
Properties
Molecular formula	C₁₁H₁₂O₃
Molar mass	192.211 g/mol
Appearance	Colorless oil
Density	1.1437 g/cm³ at 20 °C
Melting point	<25 °C
Boiling point	173 °C (40 mmHg)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Myristicin, 3-methoxy,4,5-methylendioxy-allylbenzene, is a natural organic compound present in the essential oil of nutmeg and to a lesser extent in other spices such as parsley and dill. Myristicin is a naturally occurring insecticide and acaricide with possible neurotoxic effects on dopaminergic neurons. It has hallucinogenic properties at doses much higher than used in cooking. Myristicin is a weak inhibitor of monoamine oxidase.^[2]^[3]

Additional recommended knowledge

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Uses

In 1963 by Alexander Shulgin speculated that myristicin could be converted to an amphetamine metabolite in the liver by transamination.^[4] This may never be verified and seems unlikely from what is known about the metabolism of the related compound safrole to piperonylic acid.

Intoxications with myristicin or nutmeg essential oil do not resemble the effects of MDMA, MMDA, or of psychedelic drugs. Myristicin can, however, be converted into MMDA using a reaction similar to the one used to convert safrole into MDMA. Effects vary from person to person, but are often reported to be a state somewhere between waking and dreaming; nausea is often experienced, but some report that using cannabis can offset the nausea.^[5]

In addition to a semi-conscious state, myristicin also has been known to induce psychoactive or hallucinogenic effects.^{[citation needed]} The dosage required to achieve such an effect varies from person to person and from source to source. The average dosage required to obtain these effects are somewhere in the region of 15 to 25 g of ground fresh nutmeg. This will vary with each nut.

References

^ Merck Index, 12th Edition, 6417.
^ Truitt EB, Duritz G, Ebersberger EM (1963). "Evidence of monoamine oxidase inhibition by myristicin and nutmeg". Proc. Soc. Exp. Biol. Med. 112: 647-50. PMID 13994372.
^ Lee BK, Kim JH, Jung JW, Choi JW, Han ES, Lee SH, Ko KH, Ryu JH (2005). "Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells". Toxicol. Lett. 157 (1): 49-56. PMID 15795093.
^ The Use of Nutmeg as a Psychotropic Agent by Andrew Weil at lycaeum.org
^ See Erowid: Nutmeg for various primary and secondary sources related to nutmeg/myristicin intoxication.

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