Myristicin

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Summary sheet: Myristicin
Myristicin
Myristicin.svg
Nutmeg.jpg
Chemical Nomenclature
Common names Nutmeg
Substitutive name Myristicin, 3-methoxy,4,5-methylenedioxy-allylbenzene
Systematic name 6-allyl-4-methoxy-1,3-benzodioxole
Class Membership
Psychoactive class Deliriant
Chemical class Phenylpropene / MDxx
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.



⇣ Oral
Dosage
Light 50 - 200 mg
Common 200 - 500 mg
Strong 500 - 800 mg
Heavy 800 mg +
Duration
Total 12 - 72 hours
Onset 3 - 8 hours
Come up 1 - 4 hours
Peak 9 - 12 hours
Offset 12 - 48 hours
After effects 24 - 72 hours









DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.

Interactions
Benzodiazepines
Depressants
Stimulants
Alcohol
Serotonin releasers
Opioids
DXM
DPH

Myristicin is a naturally-occurring deliriant substance of the phenylpropene class. It is present in small amounts in the essential oil of nutmeg and, to a lesser extent, in other spices such as parsley and dill.[1] It has been shown to act on the endocannabinoid system.[2]

Myristicin, along with elemicin, is thought to be the main psychoactive constituent of nutmeg.[citation needed] When oxidized with Potassium permanganate, Myristicin can be converted into Myristicinaldehyde, which can then be used to synthesize MMDPEA (Lophophine) via reductive amination.[citation needed] Additionally, myristicin is the traditional precursor for the psychedelic and empathogenic drug MMDA.[citation needed]

Nutmeg is 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. 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.

It should be noted that the dosage listed on this page assumes that one is using nutmeg powder and not pure myristicin, as this is extremely uncommon. It is highly advised to use harm reduction practices if using this substance.

Chemistry

Myristicin, also known as 3-methoxy,4,5-methylenedioxyallylbenzene, is a naturally occurring substance that belongs to a chemical class known as the phenylpropenes. It features a methylenedioxy ring at carbons R4 and R5 of the benzene ring. The benzene ring is also substituted with a separate methoxy group at the R3 carbon, and an allyl chain at R6 to make the main phenylpropene group.

Pharmacology

In 1963, Alexander Shulgin speculated myristicin could be metabolized to MMDA, a psychoactive drug related to MDA, in the liver.[3] This, however, is unlikely due to the fact that no amphetamine metabolites were found in urine after the ingestion of myristicin. It is believed that myristicin is an anticholinergic, since, in overdose, it produces effects similar to anticholinergics[4][5], but the exact mechanism of action has not been established. Myristicin is also found to be a serotonin receptor antagonist, while simultaneously acting as a weak MAO inhibitor.[citation needed]

Elemicin

Elemicin is found in nutmeg alongside myristicin and contributes to its hallucinogenic effects. Elemicin is likely to have similar effects to myristicin. It is also the traditional precursor in synthesizing the alkaloid mescaline.[citation needed]

people who have ingested Elemi oil, (a source of elemicin that exists without high amounts of Myristicin) have claimed the visual effects the oil produce seem to be more similar to classical hallucinogens than the visual effects of nutmeg oil, (which seem to be more delirious and sedating in nature)

This distinction seems to paint Myristicin as a more sedating and mind-dulling drug, while Elemicin seems to be more-visually active and stimulating. this assumption is further supported by the fact that while Elemicin has direct structural ties to Mescaline, Myristicin has ties to MDXX compounds such as MDMA.

The chemical structure of Elemicin appears to be a carbon-based analogue of Mescaline while Myristicin itself appears to be a carbon analogue of Lophophine, these structural differences may be indicators of the slightly different psychoactive effects both Elemicin and Myristicin have.

Cannabinoids

No compound has been found in nutmeg to directly bind to CB1 or CB2 receptors. Three compounds in nutmeg (Malabaricone C, Licarin A, 5-Methoxylicarin A) have been shown to act as endo-cannabinoid modulating agents by inhibiting the enzymes FAAH and MAGL.[6]

Subjective effects

In comparison to datura or diphenhydramine, myristicin's effects tend to be milder and can be pleasant and euphoric depending on dose. It has unique effects compared to other deliriants or hallucinogens. It also has a long, smooth, and enjoyable come-up, where the effects build in a similar manner to cannabis. In addition to this, cannabis like effects throughout the duration have been reported among users of the substance which is possibly due to its activity on cannabinoid receptors. With higher doses, however, the deliriant effects become more pronounced. Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.


Physical effects
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  • The physical effects of myristicin are usually described as mild and tolerable, which makes them different from other deliriants. They can be uncomfortable or pleasurable, depending on the dosage. They generally include:

Visual effects
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Cognitive effects
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Auditory effects
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    • Hallucinations - One might hear tinnitus, noises, voices, or a static humming sound in the background while intoxicated.
    • Suppression - Sound can sound more distorted at higher doses with a bad setting or even more deep and angelic/ghost- like at lower doses.

After effects
Aftereffects (3).svg

Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include:

Additional experience reports can be found here:

Forms

Myristicin is found in nutmeg, nutmeg essential oil, and to a lesser extent in parsley, dill, and other plants.

Ground nutmeg powder

Ground nutmeg powder

This is the most common form in which myristicin is sold, and it can be found in almost any supermarket as a spice.

It is worth noting that anecdotal reports suggest no clear guide on dosaging in this form. Myristicin degrades once it has been ground up, therefore it is impossible to know the potency of the powder, and the longer that the nutmeg stays as a powder, the weaker the myristicin content. When using store-bought nutmeg, the dose for oral consumption is generally considered to be:

  • Light: 5 - 15g
  • Common: 15 - 20g
  • Strong: 20 - 30g
  • Heavy: 30g+

Whole nutmeg

Whole nutmeg is also sold in most places as a spice.

  • Light: 2 - 5g
  • Common: 5 - 15g
  • Strong: 15 - 20g
  • Heavy: 20g+

Pure myristicin

Myristicin can be extracted from nutmeg powder by fractional distillation. When using pure myristicin, the dose for oral consumption is generally considered to be:

  • Light: 50 - 200mg
  • Common: 200 - 500mg
  • Strong: 500 - 800mg
  • Heavy: 800mg+

Toxicity and harm potential

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This toxicity and harm potential section is a stub.

As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it.
Note: Always conduct independent research and use harm reduction practices if using this substance.

Further information: Research chemicals § Toxicity and harm potential, and Responsible use § Hallucinogens

Myristicin is neurotoxic and can be fatal in extremely high doses.[7] Also myristicin causes severe dehydration. It increases side effects of myristicin.

Dependence and abuse potential

Myristicin is not known to be addictive and the desire to use it can actually decrease with use.

Information regarding tolerance is unknown.

Dangerous Interactions

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

  • Stimulants - Nutmeg puts a fair amount of strain on the cardiovascular system, adding stimulant drugs to the mix would increase side effects.
  • Alcohol - Anecdotal reports suggest that small/medium amounts of alcohol can create some positive effects, however respiratory depression is a risk. Large amounts of alcohol should not be combined with myristicin in any circumstance.
  • Opioids - Large amounts of opioids can lead to respiratory depression when taken with myristicin.
  • Benzodiazepines[citation needed]
  • DXM - While it is possible to take a very small dose of DXM with myristicin, it is highly risky and is generally seen to be dangerous.
  • DPH - DPH is cardio toxic, combining it with myristicin could be fatal.
  • Depressants - Respiratory depression is a risk when combining with depressant drugs, while a few anecdotal reports have shown few side effects, it is generally recommended against.
  • Serotonin releasers such as MDMA, 4-FA, methamphetamine, methylone and αMT will cause serotonin syndrome. If planning to combine these two, proceed with great caution.

Legal status

Myristicin and nutmeg are both unscheduled in nearly all parts of the world and are commonly bought in form of either ground spice, essential oil, or whole nuts.

  • United Kingdom: Nutmeg is legal to purchase as a spice in the United Kingdom, however, using it recreationally or extracting the myristicin is against the law.

See also

External links

References

  1. ↑ http://www.lktlabs.com/products/Myristicin-126-50.html
  2. ↑ El-Alfy, A. T., Abourashed, E. A., Patel, C., Mazhari, N., An, H., Jeon, A. (8 November 2019). "Phenolic compounds from nutmeg ( Myristica fragrans Houtt.) inhibit the endocannabinoid-modulating enzyme fatty acid amide hydrolase". Journal of Pharmacy and Pharmacology. 71 (12): 1879–1889. doi:10.1111/jphp.13174. ISSN 2042-7158. 
  3. ↑ UNODC - Bulletin on Narcotics - 1966 Issue 4 - 002 
  4. ↑ McKenna, A., Nordt, S. P., Ryan, J. (August 2004). "Acute nutmeg poisoning:". European Journal of Emergency Medicine. 11 (4): 240–241. doi:10.1097/01.mej.0000127649.69328.a5. ISSN 0969-9546. 
  5. ↑ Abernethy, M. K., Becker, L. B. (September 1992). "Acute nutmeg intoxication". The American Journal of Emergency Medicine. 10 (5): 429–430. doi:10.1016/0735-6757(92)90069-A. ISSN 0735-6757. 
  6. ↑ El-Alfy, A. T., Abourashed, E. A., Patel, C., Mazhari, N., An, H., Jeon, A. (8 October 2019). "Phenolic compounds from nutmeg (Myristica fragrans Houtt.) inhibit the endocannabinoid-modulating enzyme fatty acid amide hydrolase". The Journal of Pharmacy and Pharmacology. 71 (12): 1879–1889. doi:10.1111/jphp.13174. ISSN 0022-3573. 
  7. ↑ Lee, B. K., Kim, J. H., Jung, J. W., Choi, J. W., Han, E. S., Lee, S. H., Ko, K. H., Ryu, J. H. (16 May 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. ISSN 0378-4274. 
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