Myristicin

Myristicin
Myristicin
Systematic (IUPAC) name
6-allyl-4-methoxy-1,3-benzodioxole
Clinical data
Pregnancy cat.  ?
Legal status Uncontrolled
Routes Oral
Identifiers
CAS number 607-91-0 YesY
ATC code  ?
PubChem CID 4276
ChemSpider 4125 YesY
KEGG C10480 YesY
ChEMBL CHEMBL481044 YesY
Synonyms 3-methoxy,4,5-methylenedioxy-allylbenzene
Chemical data
Formula C11H12O3
Mol. mass 192.21 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (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]

Contents

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

When consuming raw nutmeg, only 5-15% of the mass consumed is an essential oil fraction, of which at least 4%,[16] at most 8.5% [2] is myristicin, indicating that the amount present overall in the nut varies from 0.2-1.3%. 20 grams of nutmeg would thus on average contain about 150 mg of myristicin. One study found 20 grams of nutmeg to contain 210 mg myristicin, 70 mg elemicin and 39 mg safrole.[17][2]

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] In a 1963 study preliminary evidence was found, that myristicin may be a weak inhibitor of monoamine oxidase 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.[citation needed]

See also

References

  1. ^ "Myristicin". Carcinogens and Tumor Promoters. LKT Laboratories. http://www.lktlabs.com/products/Myristicin-126-50.html. 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. http://bitnest.ca/external.php?id=%250E%253D9%250F%2524G%252F%2518B%255B%255B4%2522.FXQ%255CO%2500TK.  edit
  3. ^ a b c Weil, Andrew (1966). "The Use of Nutmeg as a Psychotropic Agent". Bulletin on Narcotics (UNODC) (4): 15–23. http://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1966-01-01_4_page003.html. 
  4. ^ McKenna, A.; Nordt, S. P.; Ryan, J. (2004). "Acute nutmeg poisoning". European journal of emergency medicine 11 (4): 240–241. PMID 15249817.  edit
  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.  edit
  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. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1726685/pdf/v022p00223.pdf.  edit
  7. ^ Quin, G. I.; Fanning, N. F.; Plunkett, P. K. (1998). "Letter: Nutmeg intoxication" (pdf). Journal of accident & emergency medicine 15 (4): 287–288. PMC 1343156. PMID 9681323. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1343156/pdf/jaccidem00025-0077e.pdf.  edit
  8. ^ Brenner, N.; Frank, O. S.; Knight, E. (1993). "Chronic nutmeg psychosis". Journal of the Royal Society of Medicine 86 (3): 179–180. PMC 1293919. PMID 8459391. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1293919.  edit
  9. ^ Scholefield, J. H. (1986). "Letter: Nutmeg--an unusual overdose". Archives of emergency medicine 3 (2): 154–155. PMC 1285340. PMID 3730084. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1285340.  edit
  10. ^ Venables, G. S.; Evered, D.; Hall, R. (1976). "Letter: Nutmeg poisoning". British medical journal 1 (6001): 96. PMC 1638356. PMID 942686. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1638356.  edit
  11. ^ Panayotopoulos, D. J.; Chisholm, D. D. (1970). "Correspondence: Hallucinogenic effect of nutmeg" (pdf). British medical journal 1 (5698): 754. PMC 1699804. PMID 5440555. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1699804/pdf/brmedj02279-0080c.pdf.  edit
  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. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2611568/pdf/jnma00524-0033.pdf.  edit
  13. ^ Dale, H. H. (1909). "Note on Nutmeg-Poisoning". Proceedings of the Royal Society of Medicine 2 (Ther Pharmacol Sect): 69–74. PMC 2046458. PMID 19974070. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2046458.  edit
  14. ^ Cushny, A. R. (1908). "Nutmeg Poisoning". Proceedings of the Royal Society of Medicine 1 (Ther Pharmacol Sect): 39–44. PMC 2045778. PMID 19973353. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2045778.  edit
  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. http://www.fao.org/docrep/v4084e/v4084e04.htm. 
  17. ^ a b Stafford, P.G.; Bigwood, J. (1992). Psychedelics encyclopedia. Berkeley CA: Ronin Publishing. p. 292. ISBN 0-914171-51-8. http://books.google.com/books?id=o4_pLqCOyDsC&pg=PA292. 
  18. ^ "Myristicin / CAS No. 607-91-0" (pdf). Summary of data for chemical selection. NIH - National Toxicology Program / CSWG. 1997. http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/Myristicin.pdf. 
  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. http://ebm.rsmjournals.com/content/112/3/647.abstract.  edit
  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.  edit
  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. PMID 20040135.  edit
  22. ^ Shulgin, A. T.. "TMA: 3,4,5-Trimethoxyamphetamine". Pihkal. Isomerdesign. #157. http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=157. 
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Look at other dictionaries:

  • Myristicīn — Myristicīn, die aus lange gestandenem ätherischen Muskatnußöl als eine krystallinische Kruste sich ansetzende atlasglänzende Fettsubstanz; riecht u. schmeckt wie Muskatnuß, löst sich in 10 Theilen kochendem Wasser u. schießt beim langsamen… …   Pierer's Universal-Lexikon

  • Myristicin — Strukturformel Allgemeines Name Myristicin Andere Namen …   Deutsch Wikipedia

  • myristicin — noun 3 methoxy,4,5 methylendioxy allylbenzene, a natural organic compound found in the essential oil of nutmeg and to a lesser extent in other spices; it can be used as an insecticide and acaricide and has hallucinogenic properties at high doses …   Wiktionary

  • myristicin — A constituent of nutmeg thought to be responsible, at least in part, for the bizarre central nervous system symptoms produced by the ingestion of large amounts of nutmeg. * * * my·ris·ti·cin mi ris tə sən n a crystalline phenolic ether C11H12O3… …   Medical dictionary

  • myristicin — my·ris·ti·cin …   English syllables

  • myristicin — mə̇ˈristəsə̇n noun ( s) Etymology: International Scientific Vocabulary myristic + in : a crystalline phenolic ether C11H12O3 that has a strong odor and occurs in various essential oils (as nutmeg oil, mace oil, parsley oil) …   Useful english dictionary

  • Muskat — Muskatnussbaum Muskatnussbaum mit aufgesprungener Frucht Systematik Klasse: Einfurchenpollen Zweikeimblättrige (Magnoliopsida) …   Deutsch Wikipedia

  • Muskatbutter — Muskatnussbaum Muskatnussbaum mit aufgesprungener Frucht Systematik Klasse: Einfurchenpollen Zweikeimblättrige (Magnoliopsida) …   Deutsch Wikipedia

  • Muskatnuss — Muskatnussbaum Muskatnussbaum mit aufgesprungener Frucht Systematik Klasse: Einfurchenpollen Zweikeimblättrige (Magnoliopsida) …   Deutsch Wikipedia

  • Muskatnussbutter — Muskatnussbaum Muskatnussbaum mit aufgesprungener Frucht Systematik Klasse: Einfurchenpollen Zweikeimblättrige (Magnoliopsida) …   Deutsch Wikipedia

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