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词条 Myristicin
释义

  1. Uses

  2. Pharmacology

  3. Reactions

  4. References

{{Drugbox
| Watchedfields = changed
| verifiedrevid = 408765419
| IUPAC_name = 6-Allyl-4-methoxy-1,3-benzodioxole
| image = Myristicin.svg
| width = 200
| image2 = Myristicin-3D-balls.png
| legal_status = Uncontrolled
| routes_of_administration = Oral
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 607-91-0
| PubChem = 4276
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4125
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10480
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 481044
| C=11 | H=12 | O=3
| smiles = O1c2cc(cc(OC)c2OC1)C\\C=C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BNWJOHGLIBDBOB-UHFFFAOYSA-N
| synonyms = 3-methoxy,4,5-methylenedioxy-allylbenzene
}}

Myristicin (or methoxysafrole) is a phenylpropene, a natural organic compound present in small amounts in the essential oil of nutmeg and anise and to a lesser extent in other spices/herbs such as parsley and dill; also found in several members of the carrot family (Apiaceae). It acts as a naturally occurring insecticide & acaricide.

It is insoluble in water, but soluble in ethanol and acetone.[1]

Myristicin is also a psychoactive drug, acting as an anticholinergic, and is the traditional precursor for the synthesis of the psychedelic and empathogenic drug MMDA.

Uses

Nutmeg has psychoactive properties at doses much higher than used in cooking. Although these intoxications may be ascribed to the actions of myristicin, it is likely that other components of nutmeg may also be involved, as ingestion of pure myristicin has been found not to produce the same results obtained from ingestion of the entire nutmeg.

In case reports, raw nutmeg produced anticholinergic-like symptoms, attributed to myristicin and elemicin.[2][3][4]

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. Most patients with accidental nutmeg intoxication experience high anxiety and an impending sense of doom after the initial excitation. 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]

In a 2005 study it showed possible neurotoxic effects on cultivated human neuroblastoma 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]

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. ^{{ cite web |url = http://www.lktlabs.com/products/Myristicin-126-50.html |title = Myristicin |website = Carcinogens and Tumor Promoters |publisher = LKT Laboratories |accessdate = 8 August 2011 |deadurl = yes |archiveurl = https://web.archive.org/web/20120328162245/http://www.lktlabs.com/products/Myristicin-126-50.html |archivedate = 28 March 2012 |df = }}
2. ^1 2 {{Cite journal | last1 = Shulgin | first1 = A. T. | last2 = Sargent | first2 = T. | last3 = Naranjo | first3 = C. | title = The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines | journal = Psychopharmacology Bulletin | volume = 4 | issue = 3 | pages = 13 | year = 1967 | pmid = 5615546 | url = http://bitnest.ca/external.php?id=%250E%253D9%250F%2524G%252F%2518B%255B%255B4%2522.FXQ%255CO%2500TK | format = pdf}}
3. ^1 2 {{ cite journal | last = Weil | first = Andrew | title = The Use of Nutmeg as a Psychotropic Agent | journal = Bulletin on Narcotics | year = 1966 | volume = 1966 | issue = 4 | pages = 15–23 | url = http://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1966-01-01_4_page003.html }}
4. ^{{Cite journal | last1 = McKenna | first1 = A. | last2 = Nordt | first2 = S. P. | last3 = Ryan | first3 = J. | title = Acute Nutmeg Poisoning | journal = European Journal of Emergency Medicine| volume = 11 | issue = 4 | pages = 240–241 | year = 2004 | pmid = 15249817 | doi=10.1097/01.mej.0000127649.69328.a5}}
5. ^{{Cite journal | last1 = Burroughs | first1 = William S. | title = Letter from a Master Addict to Dangerous Drugs | doi = 10.1111/j.1360-0443.1957.tb05093.x | journal = British Journal of Addiction to Alcohol & Other Drugs| volume = 53 | issue = 2 | pages = 119–132 | year = 1957 | pmid = | pmc = }}
6. ^{{Cite journal | last1 = Demetriades | first1 = A. K. | last2 = Wallman | first2 = P. D. | last3 = McGuiness | first3 = A. | last4 = Gavalas | first4 = M. C. | title = Low Cost, High Risk: Accidental Nutmeg Intoxication | doi = 10.1136/emj.2002.004168 | journal = Emergency Medicine Journal | volume = 22 | issue = 3 | pages = 223–225 | year = 2005 | pmid = 15735280 | pmc = 1726685 }}
7. ^{{Cite journal | doi = 10.1136/emj.15.4.287-d | last1 = Quin | first1 = G. I. | last2 = Fanning | first2 = N. F. | last3 = Plunkett | first3 = P. K. | title = Letter: Nutmeg Intoxication | journal = Journal of Accident & Emergency Medicine | volume = 15 | issue = 4 | pages = 287–288 | year = 1998 | pmid = 9681323 | pmc = 1343156}}
8. ^{{Cite journal | last1 = Brenner | first1 = N. | last2 = Frank | first2 = O. S. | last3 = Knight | first3 = E. | title = Chronic Nutmeg Psychosis | journal = Journal of the Royal Society of Medicine | volume = 86 | issue = 3 | pages = 179–180 | year = 1993 | pmid = 8459391 | pmc = 1293919}}
9. ^{{Cite journal | doi = 10.1136/emj.3.2.154 | last1 = Scholefield | first1 = J. H. | title = Letter: Nutmeg--an Unusual Overdose | journal = Archives of Emergency Medicine | volume = 3 | issue = 2 | pages = 154–155 | year = 1986 | pmid = 3730084 | pmc = 1285340}}
10. ^{{Cite journal | last1 = Venables | first1 = G. S. | last2 = Evered | first2 = D. | last3 = Hall | first3 = R. | title = Letter: Nutmeg Poisoning | journal = British Medical Journal | volume = 1 | issue = 6001 | pages = 96 | year = 1976 | pmid = 942686 | pmc = 1638356 | doi = 10.1136/bmj.1.6001.96-c}}
11. ^{{Cite journal | last1 = Panayotopoulos | first1 = D. J. | last2 = Chisholm | first2 = D. D. | title = Correspondence: Hallucinogenic Effect of Nutmeg | journal = British Medical Journal | volume = 1 | issue = 5698 | pages = 754 | year = 1970 | pmid = 5440555 | pmc = 1699804| doi=10.1136/bmj.1.5698.754-b}}
12. ^{{Cite journal | last1 = Williams | first1 = E. Y. | last2 = West | first2 = F. | title = The Use of Nutmeg as a Psychotropic Drug. Report of two Cases | journal = Journal of the National Medical Association | volume = 60 | issue = 4 | pages = 289–290 | year = 1968 | pmid = 5661198 | pmc = 2611568}}
13. ^{{Cite journal | last1 = Dale | first1 = H. H. | title = Note on Nutmeg-Poisoning | journal = Proceedings of the Royal Society of Medicine | volume = 2 | issue = Therapeutical and Pharmacological Section | pages = 69–74 | year = 1909 | pmid = 19974070 | pmc = 2046458}}
14. ^{{Cite journal | last1 = Cushny | first1 = A. R. | title = Nutmeg Poisoning | journal = Proceedings of the Royal Society of Medicine | volume = 1 | issue = Therapeutical and Pharmacological Section | pages = 39–44 | year = 1908 | pmid = 19973353 | pmc = 2045778}}
15. ^{{ cite book | last = Baselt | first = R. | title = Disposition of Toxic Drugs and Chemicals in Man | edition = 8th | publisher = Biomedical Publications | location = Foster City, CA | year = 2008 | pages = 1067–1068 | isbn = 978-0- 9626523-7-0 }}
16. ^{{Cite book| url = http://www.fao.org/docrep/v4084e/v4084e04.htm | website = Nutmeg and Derivatives - Working paper FO-V4084 | title = Description of components of nutmeg | chapter = 5 | publisher = UN / FAO Forest Department }}
17. ^{{ cite book | last1 = Stafford | first1 = P. G. | last2 = Bigwood | first2 = J. | title = Psychedelics Encyclopedia | page = 292 | year = 1992 | publisher = Ronin Publishing | location = Berkeley CA | isbn = 978-0-914171-51-5 | url = https://books.google.com/books?id=o4_pLqCOyDsC&pg=PA292 }}
18. ^{{ cite web | url = https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/myristicin_508.pdf | format = pdf | year = 1997 | title = Myristicin / CAS No. 607-91-0 | website = Summary of data for chemical selection | publisher = NIH - National Toxicology Program / CSWG | archiveurl = https://web.archive.org/web/20120716213845/http://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/Myristicin.pdf | archivedate = 2012-07-16 | df = }}
19. ^{{Cite journal | last1 = Truitt Jr | first1 = E. B. | last2 = Duritz | first2 = G. | last3 = Ebersberger | first3 = E. M. | title = Evidence of Monoamine Oxidase Inhibition by Myristicin and Nutmeg | journal = Proceedings of the Society for Experimental Biology and Medicine | volume = 112 | pages = 647–650 | year = 1963 | pmid = 13994372| doi = | url = http://ebm.rsmjournals.com/content/112/3/647.abstract}}
20. ^{{Cite journal | last1 = Lee | first1 = B. K. | last2 = Kim | first2 = J. H. | last3 = Jung | first3 = J. W. | last4 = Choi | first4 = J. W. | last5 = Han | first5 = E. S. | last6 = Lee | first6 = S. H. | last7 = Ko | first7 = K. H. | last8 = Ryu | first8 = J. H. | doi = 10.1016/j.toxlet.2005.01.012 | title = Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells | journal = Toxicology Letters | volume = 157 | issue = 1 | pages = 49–56 | year = 2005 | pmid = 15795093 | pmc = }}
21. ^{{Cite journal | last1 = Björnstad | first1 = K. | last2 = Helander | first2 = A. | last3 = Hultén | first3 = P. | last4 = Beck | first4 = O. | title = Bioanalytical Investigation of Asarone in Connection with Acorus calamus Oil Intoxications | journal = Journal of Analytical Toxicology | volume = 33 | issue = 9 | pages = 604–609 | year = 2009 | pmid = 20040135 | doi=10.1093/jat/33.9.604}}
22. ^{{ cite web | last = Shulgin | first = A. T. | url = http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=157 | website = Pihkal | title = TMA: 3,4,5-Trimethoxyamphetamine | at = #157 | publisher = Isomerdesign }}
23. ^{{ cite web | last = Shulgin | first = A. T. | url = http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=132 | website = Pihkal | title = MMDA: 3-Methoxy-4,5-methylenedioxyamphetamine | at = #157 | publisher = Isomerdesign }}
{{Hallucinogens}}{{phenylpropene}}

7 : Plant toxin insecticides|Monoamine oxidase inhibitors|Phenylpropenes|O-Methylated phenylpropanoids|O-Methylated natural phenols|Benzodioxoles|Allyl compounds
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