Myristicin: Difference between revisions

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Nutmeg has [[psychoactive]] properties at doses much higher than used in [[cooking]].
Nutmeg has [[psychoactive]] properties at doses much higher than used in [[cooking]].


In case reports, rawrtyrty5frgrhui
⚫
In case reports, raw nutmeg produced [[anticholinergic]]-like symptoms, attributed to myristicin and [[elemicin]].<ref name="Shulgin">{{ cite pmid | 5615546 }}</ref><ref name=Weil>{{ 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 | publisher = UNODC | url = http://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1966-01-01_4_page003.html }}</ref><ref>{{ cite pmid | 15249817 }}</ref>
tuiop
⚫
iti[ nutmeg produced [[anticholinergic]]-like symptoms, attributed to myristicin and [[elemicin]].<ref name="Shulgin">{{ cite pmid | 5615546 }}</ref><ref name=Weil>{{ 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 | publisher = UNODC | url = http://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1966-01-01_4_page003.html }}</ref><ref>{{ cite pmid | 15249817 }}</ref>


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.<ref>
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.<ref>

Revision as of 14:05, 25 June 2014

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, rawrtyrty5frgrhui tuiop iti[ 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 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. Retrieved 8 August 2011.
  2. ^ a b c Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 5615546 , please use {{cite journal}} with |pmid= 5615546 instead.
  3. ^ a b c Weil, Andrew (1966). "The Use of Nutmeg as a Psychotropic Agent". Bulletin on Narcotics. 1966 (4). UNODC: 15–23.
  4. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 15249817 , please use {{cite journal}} with |pmid= 15249817 instead.
  5. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi: 10.1111/j.1360-0443.1957.tb05093.x , please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi= 10.1111/j.1360-0443.1957.tb05093.x instead.
  6. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 15735280 , please use {{cite journal}} with |pmid= 15735280 instead.
  7. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 9681323 , please use {{cite journal}} with |pmid= 9681323 instead.
  8. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 8459391 , please use {{cite journal}} with |pmid= 8459391 instead.
  9. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 3730084 , please use {{cite journal}} with |pmid= 3730084 instead.
  10. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 942686 , please use {{cite journal}} with |pmid= 942686 instead.
  11. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 5440555 , please use {{cite journal}} with |pmid= 5440555 instead.
  12. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 5661198 , please use {{cite journal}} with |pmid= 5661198 instead.
  13. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 19974070 , please use {{cite journal}} with |pmid= 19974070 instead.
  14. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 19973353 , please use {{cite journal}} with |pmid= 19973353 instead.
  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. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 13994372 , please use {{cite journal}} with |pmid= 13994372 instead.
  20. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 15795093 , please use {{cite journal}} with |pmid= 15795093 instead.
  21. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 20040135 , please use {{cite journal}} with |pmid= 20040135 instead.
  22. ^ Shulgin, A. T. "TMA: 3,4,5-Trimethoxyamphetamine". Pihkal. Isomerdesign. #157.
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