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Myristicin
Systematic (IUPAC) name
6-allyl-4-methoxy-1,3-benzodioxole
Identifiers
CAS number 607-91-0
ATC code  ?
PubChem 4276
ChemSpider 4125
Chemical data
Formula C11H12O3
Mol. mass 192.21 g/mol
SMILES eMolecules & PubChem
Synonyms 3-methoxy,4,5-methylendioxy-allylbenzene
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Uncontrolled
Routes Oral

Myristicin 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 neuroblastoma cells.[1] It has hallucinogenic properties at doses much higher than used in cooking. Myristicin is a weak inhibitor of monoamine oxidase.[2] It also acts as an anticholinergic.[3]

Contents

Uses

In 1963 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 slightly resemble the effects of MDMA, or MMDMA. 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; euphoria is reported and nausea is often experienced, but some report that using cannabis can offset the nausea. Users also report bloodshot eyes and memory disturbances during nutmeg intoxication.[5]

In addition to a semi-conscious state, myristicin also has been known to induce psychoactive effects such as visual distortions. 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 .75 - 1.25g of ground fresh nutmeg for every ten pounds of body weight. This will vary with each nut and person.

Nutmeg intoxication has an extremely long time before peak is reached, sometimes taking up to 7 hours and effects can be felt for up to 24 hours with lingering effects lasting 72 hours. This could be considered unpleasant by some users because the negative effects such as nausea may linger for this period. [6][7]

Overdosage

Excessive usage of nutmeg has caused clinical intoxication, characterized by nausea, vomiting, dizziness, anxiety, headache, hallucinations and irrational behavior. Blood myristicin concentrations may be measured to confirm a diagnosis of poisoning. [8]

See also

References

  1. ^ 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. doi:10.1016/j.toxlet.2005.01.012. PMID 15795093.  
  2. ^ 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.  
  3. ^ McKenna A, Nordt SP, Ryan J (August 2004). "Acute nutmeg poisoning". European Journal of Emergency Medicine : Official Journal of the European Society for Emergency Medicine 11 (4): 240–1. PMID 15249817. http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0969-9546&volume=11&issue=4&spage=240.  
  4. ^ The Use of Nutmeg as a Psychotropic Agent by Andrew Weil at lycaeum.org
  5. ^ See Erowid: Nutmeg for various primary and secondary sources related to nutmeg/myristicin intoxication.
  6. ^ http://www.erowid.org/plants/nutmeg/nutmeg_basics.shtml>
  7. ^ http://www.erowid.org/experiences/subs/exp_Nutmeg.shtml>
  8. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1067-1068.







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