Myristicin
| Summary sheet: Myristicin |
| Myristicin | |||||||||||||||||||||||||||||||
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| 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 | ||||||||||||||||||||||||||||||
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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] 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]
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:
- Difficulty urinating or / and Frequent urination - This can be described as a feeling of concrete blocking the urethra, painfully conflicting with a frequent need to urinate. However, some users report urinating perfectly fine. This effect might be dose-dependent.
- Dry mouth - This effect is usually stronger than cannabis but much weaker than other deliriants like Datura.
- Dehydration - Nutmeg causes a lot of dehydration and dehydration is proven to cause deliriant effects and delirium. Staying hydrated can decrease deliriant and negative effects.
- Dizziness - This effect can be decreased by going for a walk or drinking ginger tea.
- Nausea - This effect is usually caused by the unpleasurable taste rather than the compounds themselves.
- Sedation - This effect can be extremely strong at higher dosage, leaving the user in a near sleep state during the experience.
- Stimulation - This effect occurs on lower doses.
- Motor control loss
- Muscle relaxation
- Perception of bodily heaviness
- Photophobia
- Spontaneous tactile sensations
- Tactile enhancement or Tactile suppression at higher doses.
- Tactile hallucination - This effect is reported only at heavy doses.
- Gustatory enhancement - This effect is very similar to cannabis.
- Appetite enhancement - This effect is similar to cannabis, and due to food tasting better users will usually eat more.
- Physical euphoria - This effect can be described as warm, calming sensations over the body which can be compared to alcohol.
- Vasodilation - This effect increases with the dosage and can cause bloodshot eyes.
- Decreased blood pressure This effect is due to vasodilation and can result in dizziness.
Visual effects 
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Myristicin can both enhance and suppress visual stimuli depending on many factors that include but are not limited to; age, genetic factors, dehydration, combining nutmeg with other spices, sleep deprivation, and placebo. Some of the visual effects of nutmeg include:
Suppression
- Visual acuity suppression - This effect can result in blurry vision. It sometimes can last for days after the trip itself.[citation needed]
- Double vision
- Pattern recognition suppression
- After images
- Drifting - Breathing, objects having their size altered
- Environmental patterning - You may see lines around and inside objects, essentially everything will have structure - You may see eyes like you would on psilocybin but to a lesser intensity
- Tracers - Tracers can reach up to 3. level.
- Frame rate suppression - Combined with time distortion nutmeg could make movies and videos feel more dissociative. This effect is similar to DXM
Enhancements
- Colour enhancement - Visuals might be slightly more vibrant and objects might have a glow around them
Hallucinatory states
Myristicin is moderately efficient at inducing delirious hallucinations which can be broken into the categories described below:
- External hallucination (autonomous entities; settings, sceneries, and landscapes; perspective hallucinations and scenarios and plots) - In comparison to other classes of hallucinogen, this effect occurs more frequently than that of any other at moderate to heavy doses and is the defining feature of the experience. It can be comprehensively described through its variations as delirious in believability, autonomous in controllability, and solid in style. The most common themes for these hallucinations include those of everyday occurrences such as smoking phantom cigarettes, talking to people who are not there, insects, and sinister, nightmarish experiences.
- Internal hallucination (autonomous entities; settings, sceneries, and landscapes; perspective hallucinations and scenarios and plots) - In comparison to other classes of hallucinogen, this effect occurs briefly and spontaneously at moderate doses but becomes progressively extended in its occurrence and duration proportional to dosage before eventually becoming all-encompassing. It can be comprehensively described through its variations as delirious in believability, interactive in style, equal in new experiences and memory replays in content, autonomous in controllability and solid in style.
- Peripheral information misinterpretation
Cognitive effects 
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The cognitive effects of myristicin are described by many as mildly euphoric, but can also be dysphoric throughout the trip, primarily consisting of moderate paranoia. It can also be confusing and disorienting. Myristicin contains unique cognitive effects found almost exclusively in the deliriant class.
The most prominent of these effects include:
- Amnesia
- Empathy, affection and sociability enhancement
- Anxiety at higher doses or Anxiety suppression on lower doses with a positive setting
- Paranoia - This effect is common at high doses.
- Feelings of impending doom
- Confusion - This effect is more common at higher doses and when the user is dehydrated
- Depersonalization and Derealization - This effect differs from classic disscoatives and tends to be more dream like and results more often in anxiety due to the unpleasant body load nutmeg offers. This effect appears at higher doses only and is similar to the DPDR produced by THC and synthetic cannabinoids.
- Emotion enhancement - This effect can enhance both negative and positive feelings, which means set and setting can alter the nutmeg experience
- Euphoria
- Analysis suppression
- Language suppression
- Increased music appreciation
- Laughter - This effect is similar to cannabis
- Immersion enhancement - This effect is similar to cannabis and usually does not increase that much as the dose gets higher
- Focus suppression or Focus enhancement - This depends on the dose, user, dehydration and genetic factors.
- Psychosis - This effect is common at high or strong doses
- Sleepiness - This effect gets stronger as the dose increases
- Suggestibility enhancement
- Time distortion - This effect is mainly in the form of time expansion.
- Thought deceleration - This effect is more similar to cannabis than alcohol
- Thought disorganization - This effect is similar to alcohol
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 
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The hangover of nutmeg is generally described as more intense alcohol hangover. The main cause of the hangover is dehydration.
- Appetite suppression - This effect can be very intense if the dose was high.
- Motivation enhancement or *Motivation suppression
- Increased bodily temperature - This effect is more similar to alcohol than other deliriants like DPH and Datura.
- Constipation This effect can be reduced by using oil extraction preparation method
- Dry mouth
- Nausea
- Bodily pressures
- Photophobia
- Darker urine
- Physical fatigue
- Cognitive fatigue
- Analysis suppression
- Thought deceleration
- Dehydration This effect is the main cause of the hangover
- Anxiety
- Stomach bloating This effect can be decreased by using oil extraction method
- Stomach cramp This effect can be decreased by using oil extraction method
Experience reports
Anecdotal reports which describe the effects of this compound within our experience index include:
- Experience:3 drops of cinnamon bark oil/ 5 drops of german chamomile oil/ 2mL of nutmeg oil in lecithin - experiments with nutmeg oil
- Experience:4 tablespoons of Nutmeg
- Experience:Nutmeg (8 teaspoons) - My Mom Introduces Me To Genesis and Other Things
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
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. |
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
- ↑ http://www.lktlabs.com/products/Myristicin-126-50.html
- ↑ 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.
- ↑ UNODC - Bulletin on Narcotics - 1966 Issue 4 - 002
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.