Jump to content

Myristicin

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by 92.234.50.57 (talk) at 18:37, 2 February 2010 (Uses: Give weight in SI units along with original imperial measurement.). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Myristicin
Clinical data
Other names3-methoxy,4,5-methylendioxy-allylbenzene
Routes of
administration
Oral
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 6-allyl-4-methoxy-1,3-benzodioxole
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.009.225 Edit this at Wikidata
Chemical and physical data
FormulaC11H12O3
Molar mass192.21 g/mol
3D model (JSmol)
  • COC1=CC(=CC2=C1OCO2)CC=C

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]

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.[citation needed] 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 4.54kg (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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ McKenna A, Nordt SP, Ryan J (2004). "Acute nutmeg poisoning". European Journal of Emergency Medicine : Official Journal of the European Society for Emergency Medicine. 11 (4): 240–1. PMID 15249817. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
  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.