|Chemical and physical data|
|Molar mass||192.21 g/mol|
|3D model (Jmol)||Interactive image|
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.
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.
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.
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. One study found 20 grams of nutmeg to contain 210 mg myristicin, 70 mg elemicin and 39 mg safrole.
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.
A 1997 study found data to suggest that myristicin can alter the toxicity and / or metabolic pathway of some compounds. 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. Myristicin is a naturally occurring insecticide and acaricide. In a 2005 study it showed possible neurotoxic effects on cultivated human neuroblastoma (cancer) cells.
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. 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."
- "Myristicin". Carcinogens and Tumor Promoters. LKT Laboratories. Retrieved 8 August 2011.
- 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.
- Weil, Andrew (1966). "The Use of Nutmeg as a Psychotropic Agent". Bulletin on Narcotics. UNODC. 1966 (4): 15–23.
- 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.
- 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.
- 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 . PMID 15735280.
- 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 . PMID 9681323.
- Brenner, N.; Frank, O. S.; Knight, E. (1993). "Chronic Nutmeg Psychosis" (pdf). Journal of the Royal Society of Medicine. 86 (3): 179–180. PMC . PMID 8459391.
- 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 . PMID 3730084.
- 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 . PMID 942686.
- 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 . PMID 5440555.
- 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 . PMID 5661198.
- Dale, H. H. (1909). "Note on Nutmeg-Poisoning" (pdf). Proceedings of the Royal Society of Medicine. 2 (Therapeutical and Pharmacological Section): 69–74. PMC . PMID 19974070.
- Cushny, A. R. (1908). "Nutmeg Poisoning" (pdf). Proceedings of the Royal Society of Medicine. 1 (Therapeutical and Pharmacological Section): 39–44. PMC . PMID 19973353.
- 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.
- "Description of components of nutmeg". Nutmeg and Derivatives - Working paper FO-V4084. UN / FAO Forest Department.
- Stafford, P. G.; Bigwood, J. (1992). Psychedelics Encyclopedia. Berkeley CA: Ronin Publishing. p. 292. ISBN 0-914171-51-8.
- "Myristicin / CAS No. 607-91-0" (pdf). Summary of data for chemical selection. NIH - National Toxicology Program / CSWG. 1997.
- 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.
- 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.
- 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.
- Shulgin, A. T. "TMA: 3,4,5-Trimethoxyamphetamine". Pihkal. Isomerdesign. #157.
- Shulgin, A. T. "MMDA: 3-Methoxy-4,5-methylenedioxyamphetamine". Pihkal. Isomerdesign. #157.