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Myristicin: Difference between revisions
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{{SubstanceBox/Myristicin}} | {{SubstanceBox/Myristicin}} | ||
'''Myristicin''' is a [[naturally-occurring]] [[psychoactive class::deliriant]] substance of the [[Chemical class::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]].<ref>http://www.lktlabs.com/products/Myristicin-126-50.html</ref> It | '''Myristicin''' is a [[naturally-occurring]] [[psychoactive class::deliriant]] substance of the [[Chemical class::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]].<ref>http://www.lktlabs.com/products/Myristicin-126-50.html</ref> It has been shown to act on the [[Cannabinoid|endocannabinoid system]].<ref>{{cite journal | vauthors=((El-Alfy, A. T.)), ((Abourashed, E. A.)), ((Patel, C.)), ((Mazhari, N.)), ((An, H.)), ((Jeon, A.)) | journal=Journal of Pharmacy and Pharmacology | title=Phenolic compounds from nutmeg ( Myristica fragrans Houtt.) inhibit the endocannabinoid-modulating enzyme fatty acid amide hydrolase | volume=71 | issue=12 | pages=1879–1889 | date=8 November 2019 | url=https://academic.oup.com/jpp/article/71/12/1879-1889/6122229 | issn=2042-7158 | doi=10.1111/jphp.13174}}</ref> | ||
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}} | 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. | 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. | 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. | ||
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==Pharmacology== | ==Pharmacology== | ||
In 1963, [[Alexander Shulgin]] speculated myristicin could be metabolized to [[MMDA]], a psychoactive drug related to [[MDA]], in the liver.<ref> | In 1963, [[Alexander Shulgin]] speculated myristicin could be metabolized to [[MMDA]], a psychoactive drug related to [[MDA]], in the liver.<ref>{{Citation | title=UNODC - Bulletin on Narcotics - 1966 Issue 4 - 002 | url=//www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1966-01-01_4_page003.html}}</ref> 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 [[deliriant|anticholinergic]], since, in overdose, it produces effects similar to anticholinergics<ref>{{cite journal | vauthors=((McKenna, A.)), ((Nordt, S. P.)), ((Ryan, J.)) | journal=European Journal of Emergency Medicine | title=Acute nutmeg poisoning: | volume=11 | issue=4 | pages=240–241 | date= August 2004 | url=http://journals.lww.com/00063110-200408000-00017 | issn=0969-9546 | doi=10.1097/01.mej.0000127649.69328.a5}}</ref><ref>{{cite journal | vauthors=((Abernethy, M. K.)), ((Becker, L. B.)) | journal=The American Journal of Emergency Medicine | title=Acute nutmeg intoxication | volume=10 | issue=5 | pages=429–430 | date= September 1992 | url=https://linkinghub.elsevier.com/retrieve/pii/073567579290069A | issn=07356757 | doi=10.1016/0735-6757(92)90069-A}}</ref>, 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==== | ||
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}} | 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|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==== | ====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.<ref>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7938946/</ref> | 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.<ref>{{cite journal | vauthors=((El-Alfy, A. T.)), ((Abourashed, E. A.)), ((Patel, C.)), ((Mazhari, N.)), ((An, H.)), ((Jeon, A.)) | journal=The Journal of Pharmacy and Pharmacology | title=Phenolic compounds from nutmeg (Myristica fragrans Houtt.) inhibit the endocannabinoid-modulating enzyme fatty acid amide hydrolase | volume=71 | issue=12 | pages=1879–1889 | date=8 October 2019 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7938946/ | issn=0022-3573 | doi=10.1111/jphp.13174}}</ref> | ||
==Subjective effects== | ==Subjective effects== | ||
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*'''[[Effect::Nausea]]''' - This effect is usually caused by the unpleasurable taste rather than the compounds themselves. | *'''[[Effect::Nausea]]''' - This effect is usually caused by the unpleasurable taste rather than the compounds themselves. | ||
*'''[[Effect::Sedation]]''' - This effect can be extremely strong at higher dosage, leaving the user in a near sleep state during the experience. | *'''[[Effect::Sedation]]''' - This effect can be extremely strong at higher dosage, leaving the user in a near sleep state during the experience. | ||
*'''[[Effect::Stimulation]]''' - | *'''[[Effect::Stimulation]]''' - This effect occurs on lower doses. | ||
*'''[[Effect::Motor control loss]]''' | *'''[[Effect::Motor control loss]]''' | ||
*'''[[Effect::Muscle relaxation]]''' | *'''[[Effect::Muscle relaxation]]''' | ||
*'''[[Effect::Perception of bodily heaviness]]''' | *'''[[Effect::Perception of bodily heaviness]]''' | ||
*'''[[Effect::Photophobia]]''' | *'''[[Effect::Photophobia]]''' | ||
*'''[[Effect::Spontaneous tactile sensations]]''' | *'''[[Effect::Spontaneous tactile sensations]]''' | ||
*'''[[Effect::Tactile enhancement]]''' or '''[[Effect::Tactile suppression]]''' at higher doses. | *'''[[Effect::Tactile enhancement]]''' or '''[[Effect::Tactile suppression]]''' at higher doses. | ||
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*'''[[Effect::Drifting]]''' - Breathing, objects having their size altered | *'''[[Effect::Drifting]]''' - Breathing, objects having their size altered | ||
*'''[[Effect::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 | *'''[[Effect::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 | ||
*'''[[Effect::Tracers]]''' - Tracers can reach up to | *'''[[Effect::Tracers]]''' - Tracers can reach up to 3. level. | ||
*'''[[Effect::Frame rate suppression]]''' - Combined with time distortion nutmeg could make movies and videos feel more dissociative. This effect is similar to DXM | *'''[[Effect::Frame rate suppression]]''' - Combined with time distortion nutmeg could make movies and videos feel more dissociative. This effect is similar to DXM | ||
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*'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::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 [[Internal_hallucinations#Variations|variations]] as delirious in believability, interactive in style, equal in new experiences and memory replays in content, autonomous in controllability and solid in style. | *'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::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 [[Internal_hallucinations#Variations|variations]] as delirious in believability, interactive in style, equal in new experiences and memory replays in content, autonomous in controllability and solid in style. | ||
*'''[[Effect::Peripheral information misinterpretation]] | *'''[[Effect::Peripheral information misinterpretation]] | ||
}} | }} | ||
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*'''[[Effect::Empathy, affection and sociability enhancement]]''' | *'''[[Effect::Empathy, affection and sociability enhancement]]''' | ||
*'''[[Effect::Anxiety]]''' at higher doses or '''[[Effect::Anxiety suppression]]''' on lower doses with a positive setting | *'''[[Effect::Anxiety]]''' at higher doses or '''[[Effect::Anxiety suppression]]''' on lower doses with a positive setting | ||
**'''[[Effect::Paranoia]]''' - This effect is common at high doses. | |||
**'''[[Effect::Feelings of impending doom]] | |||
*'''[[Effect::Confusion]]''' - This effect is more common at higher doses and when the user is dehydrated | *'''[[Effect::Confusion]]''' - This effect is more common at higher doses and when the user is dehydrated | ||
*'''[[Effect::Depersonalization]]]''' and '''[[Effect::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. | *'''[[Effect::Depersonalization]]]''' and '''[[Effect::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. | ||
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*'''[[Effect::Immersion enhancement]]''' - This effect is similar to cannabis and usually does not increase that much as the dose gets higher | *'''[[Effect::Immersion enhancement]]''' - This effect is similar to cannabis and usually does not increase that much as the dose gets higher | ||
*'''[[Effect::Focus suppression]]''' or '''[[Effect::Focus enhancement]]''' - This depends on the dose, user, dehydration and genetic factors. | *'''[[Effect::Focus suppression]]''' or '''[[Effect::Focus enhancement]]''' - This depends on the dose, user, dehydration and genetic factors. | ||
*'''[[Effect::Psychosis]]''' - This effect is common at high or strong doses | *'''[[Effect::Psychosis]]''' - This effect is common at high or strong doses | ||
*'''[[Effect::Sleepiness]]''' - This effect gets stronger as the dose increases | *'''[[Effect::Sleepiness]]''' - This effect gets stronger as the dose increases | ||
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{{toxicity}} | {{toxicity}} | ||
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | {{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | ||
Myristicin [[Toxicity::is neurotoxic]] and [[Toxicity::can be fatal in extremely high doses]].<ref>Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells. | Myristicin [[Toxicity::is neurotoxic]] and [[Toxicity::can be fatal in extremely high doses]].<ref>{{cite journal | vauthors=((Lee, B. K.)), ((Kim, J. H.)), ((Jung, J. W.)), ((Choi, J. W.)), ((Han, E. S.)), ((Lee, S. H.)), ((Ko, K. H.)), ((Ryu, J. H.)) | journal=Toxicology Letters | title=Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells | volume=157 | issue=1 | pages=49–56 | date=16 May 2005 | issn=0378-4274 | doi=10.1016/j.toxlet.2005.01.012}}</ref> Also myristicin causes severe dehydration. It increases side effects of myristicin. | ||
===Dependence and abuse potential=== | ===Dependence and abuse potential=== | ||