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 acts as an [[Deliriant|anticholinergic]] in high doses{{citation needed}}, and has been shown to act on the [[Cannabinoid|endocannabinoid system]].<ref>https:// | '''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 acts as an [[Deliriant|anticholinergic]] in high doses{{citation needed}}, and 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}} 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==== | ||
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====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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{{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=== |