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Myristicin is the allylbenzene believed to be primarily responsible for the psychedelic action of nutmeg.
Pharmacology
Type of action: psychedelic
Oral Dosage: approximately 400 mg or more.
Topical Dosage: approximately 40 mg or more.
Duration: approximately 36 hours.
Tests using 1.5 ml of nutmeg oil (an essential oil containing significant quantities of myristicin) in 4 volunteers elicited effects including euphoria lasting 36 hours, heavy-headedness, nausea, restlessness, proneness to laughter, a sense of unreality, heightened awareness, clarity of thought and emotion.[15] Note that individual reactions to nutmeg oil and myristicin vary dramatically. Anecdotal reports indicate that some individuals are very sensitive to nutmeg oil and experience effects from just a few drops of the oil orally or transdermally, while others have ingested as much as 10 ml of nutmeg oil without any noticeable effects.
Myristicin itself is believed to be inactive as a psychedelic even though 400 mg of myristicin orally produces psychedelic activity in approximately 40% of humans tested.[7] It's not generally believed that myristicin itself is responsible for the effects, but rather a metabolite of it is.
The psychedelic activity produced after myristicin ingestion or topical application is believed to be caused by it's piperidine and pyrrolidine alkaloid metabolites created in vivo.[8] It's possible that not all individuals create these alkaloid metabolites in large enough quantities to be effective, which may help explain why 60% of the humans tested did not experience psychedelic effects from 400 mg of myristicin.
Cancer Prevention
Myristicin has been shown to have potent anti-cancer properties. A 65% inhibition of the tumor multiplicity in the lung of rats was observed as the result of treatment of myristicin in rats.[4]
Myristicin showed a 31% inhibition of tumor formation in the forestomach of rats.[4]
Effects on P450 Enzymes in Rats
In rats in vivo myristicin induced CYP1A1, CYP1A2, CYP2B1, CYP2B2, and CYP2E1. Maximum induction was at 12 hours for CYP2E1 and 24 hours for the other enzymes.[5]
Effects on GST in Mice
Mice given 5 to 50 mg doses of myristicin, showed 4- to 14-fold increase in liver glutathione S-transferase (GST) activity.[3]
Natural Sources
| Plant | Origin | Part | Contents of Essential Oil |
|---|---|---|---|
| Bunium Cylindricum (Boiss. et Hohen.) Drude | Fruit | 4.1-67.2% [9] | |
| Mace | 0.2-33.6% [13] | ||
| Nutmeg | 0.3-45.6% [13] |
Non-Alkaloid Metabolites Found in Human Urine
After ingestion of nutmeg the following metabolites of myristicin could be identified:[14]
5-Allyl-1-methoxy-2,3-dihydroxybenzene (demethylenyl myristicin)
Dihydroxy myristicin
Non-Alkaloid Metabolites Created In Vivo
The non-alkaloid metabolites of myristicin are believed to have no psychedelic action in man. The metabolites listed here are created by cytochrome P450 enzymes when myristicin is used orally or topically.
1'-Oxomyristicin
1'-Oxomyristicin is a phenyl vinyl ketone believed to be an intermediate metabolite that forms from 1'-hydroxymyristicin, a metabolite of myristicin.[10]
Corresponding 1'-oxo metabolites have been found for the closely related 1'-hydroxy metabolites of safrole[10][11] and methyl chavicol[12].
5-allyl-1-methoxy-2,3-dihydroxybenzene
5-Allyl-1-methoxy-2,3-dihydroxybenzene is the primary metabolite of myristicin.[6] Like myristicin it is also an allylbenzene. It is possible that this metabolite can be further metabolized into alkaloids. The predicted activity for this compound's theoretical alkaloid metabolites is stimulation without psychedelic action because it lacks a methoxy group on the 3 position (the middle position) on the benzene ring.
In vitro tests show that this metabolite is created primarily by the cytochrome P450 enzyme CYP3A4.[6] The cytochrome P450 enzyme CYP1A2 plays a minor role in its formation in vitro.[6] CYP2A6, CYP2C19, CYP2D6, and CYP2E1 appear to play no role in creating this metabolite in vitro.[6]
See the article on 5-allyl-1-methoxy-2,3-dihydroxybenzene for more detailed information.
1'-hydroxymyristicin
This is a minor metabolite of myristicin.[6]
Alkaloid Metabolites Created In Vivo
1'-Oxomyristicin is believed to be the primary myristicin metabolite that leads to the creation of 2 alkaloids found in vivo after the ingestion of myristicin.[8] These alkaloids are believed to be responsible for the psychedelic activity of myristicin.[8]
3-piperidyl-1-(3'methoxy-4',5'-methylenedioxyphenyl)-1-propanone
This is the piperidine alkaloid metabolite of myristicin. See the article on 3-piperidyl-1-(3'methoxy-4',5'-methylenedioxyphenyl)-1-propanone for more details on this alkaloid metabolite.
3-pyrrolidinyl-1-(3'methoxy-4',5'-methylenedioxyphenyl)-1-propanone
This is the pyrrolidine alkaloid metabolite of myristicin.
Note that dimethylamine alkaloid metabolites of myristicin have not been found, but have been found for several other related allylbenzenes.[8]
Toxicity
Rat oral LD50 = 4260 mg/kg [2]
Cat oral LDLo = 400 mg/kg [2]
Rabbit sc LDLo = 900 mg/kg [2]
Guinea pig LDLo = 2 gm/kg [2]
Chemical Properties
PubChem Compound ID: 4276
Molecular Weight: 192.21118 [g/mol]
Molecular Formula: C11H12O3
Boiling Point: 276.5 deg C[1]
Melting Point: <-20 deg C[1]
Solubility: Insoluble in water, slightly soluble in ethanol, soluble in ether and benzene[1]
XLogP3: 2.9
IUPAC Name: 4-methoxy-6-prop-2-enyl-1,3-benzodioxole
InChI: 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
InChIKey: BNWJOHGLIBDBOB-UHFFFAOYSA-N
Canonical SMILES: COC1=CC(=CC2=C1OCO2)CC=C