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Myristicin

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Myristicin
Clinical data
Other names3-methoxy,4,5-methylenedioxy-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
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.009.225 Edit this at Wikidata
Chemical and physical data
FormulaC11H12O3
Molar mass192.21 g/mol g·mol−1
3D model (JSmol)
  • O1c2cc(cc(OC)c2OC1)C\C=C
  • 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 checkY
  • Key:BNWJOHGLIBDBOB-UHFFFAOYSA-N checkY
  (verify)

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]

References

  1. ^ "Myristicin". Carcinogens and Tumor Promoters. LKT Laboratories. Retrieved 8 August 2011.
  2. ^ a b c Shulgin, A. T.; Sargent, T.; Naranjo, C. (1967). "The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines" (pdf). Psychopharmacology Bulletin. 4 (3): 13. PMID 5615546.
  3. ^ a b c Weil, Andrew (1966). "The Use of Nutmeg as a Psychotropic Agent". Bulletin on Narcotics. 1966 (4). UNODC: 15–23.
  4. ^ McKenna, A.; Nordt, S. P.; Ryan, J. (2004). "Acute Nutmeg Poisoning". European Journal of Emergency Medicine. 11 (4): 240–241. doi:10.1097/01.mej.0000127649.69328.a5. PMID 15249817.
  5. ^ Burroughs, William S. (1957). "Letter from a Master Addict to Dangerous Drugs". British Journal of Addiction to Alcohol & Other Drugs. 53 (2): 119–132. doi:10.1111/j.1360-0443.1957.tb05093.x.
  6. ^ Demetriades, A. K.; Wallman, P. D.; McGuiness, A.; Gavalas, M. C. (2005). "Low Cost, High Risk: Accidental Nutmeg Intoxication" (pdf). Emergency Medicine Journal. 22 (3): 223–225. doi:10.1136/emj.2002.004168. PMC 1726685. PMID 15735280.
  7. ^ Quin, G. I.; Fanning, N. F.; Plunkett, P. K. (1998). "Letter: Nutmeg Intoxication" (pdf). Journal of Accident & Emergency Medicine. 15 (4): 287–288. doi:10.1136/emj.15.4.287-d. PMC 1343156. PMID 9681323.
  8. ^ Brenner, N.; Frank, O. S.; Knight, E. (1993). "Chronic Nutmeg Psychosis" (pdf). Journal of the Royal Society of Medicine. 86 (3): 179–180. PMC 1293919. PMID 8459391.
  9. ^ Scholefield, J. H. (1986). "Letter: Nutmeg--an Unusual Overdose" (pdf). Archives of Emergency Medicine. 3 (2): 154–155. doi:10.1136/emj.3.2.154. PMC 1285340. PMID 3730084.
  10. ^ Venables, G. S.; Evered, D.; Hall, R. (1976). "Letter: Nutmeg Poisoning" (pdf). British Medical Journal. 1 (6001): 96. doi:10.1136/bmj.1.6001.96-c. PMC 1638356. PMID 942686.
  11. ^ Panayotopoulos, D. J.; Chisholm, D. D. (1970). "Correspondence: Hallucinogenic Effect of Nutmeg" (pdf). British Medical Journal. 1 (5698): 754. doi:10.1136/bmj.1.5698.754-b. PMC 1699804. PMID 5440555.
  12. ^ Williams, E. Y.; West, F. (1968). "The Use of Nutmeg as a Psychotropic Drug. Report of two Cases" (pdf). Journal of the National Medical Association. 60 (4): 289–290. PMC 2611568. PMID 5661198.
  13. ^ Dale, H. H. (1909). "Note on Nutmeg-Poisoning" (pdf). Proceedings of the Royal Society of Medicine. 2 (Therapeutical and Pharmacological Section): 69–74. PMC 2046458. PMID 19974070.
  14. ^ Cushny, A. R. (1908). "Nutmeg Poisoning" (pdf). Proceedings of the Royal Society of Medicine. 1 (Therapeutical and Pharmacological Section): 39–44. PMC 2045778. PMID 19973353.
  15. ^ Baselt, R. (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 1067–1068. ISBN 978-0- 9626523-7-0.
  16. ^ "Description of components of nutmeg". Nutmeg and Derivatives - Working paper FO-V4084. UN / FAO Forest Department. {{cite web}}: |chapter= ignored (help)
  17. ^ a b Stafford, P. G.; Bigwood, J. (1992). Psychedelics Encyclopedia. Berkeley CA: Ronin Publishing. p. 292. ISBN 0-914171-51-8.
  18. ^ "Myristicin / CAS No. 607-91-0" (pdf). Summary of data for chemical selection. NIH - National Toxicology Program / CSWG. 1997.
  19. ^ Truitt Jr, E. B.; Duritz, G.; Ebersberger, E. M. (1963). "Evidence of Monoamine Oxidase Inhibition by Myristicin and Nutmeg". Proceedings of the Society for Experimental Biology and Medicine. 112: 647–650. PMID 13994372.
  20. ^ Lee, B. K.; Kim, J. H.; Jung, J. W.; Choi, J. W.; Han, E. S.; Lee, S. H.; Ko, K. H.; Ryu, J. H. (2005). "Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells". Toxicology Letters. 157 (1): 49–56. doi:10.1016/j.toxlet.2005.01.012. PMID 15795093.
  21. ^ Björnstad, K.; Helander, A.; Hultén, P.; Beck, O. (2009). "Bioanalytical Investigation of Asarone in Connection with Acorus calamus Oil Intoxications". Journal of Analytical Toxicology. 33 (9): 604–609. doi:10.1093/jat/33.9.604. PMID 20040135.
  22. ^ Shulgin, A. T. "TMA: 3,4,5-Trimethoxyamphetamine". Pihkal. Isomerdesign. #157.
  23. ^ Shulgin, A. T. "MMDA: 3-Methoxy-4,5-methylenedioxyamphetamine". Pihkal. Isomerdesign. #157.
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