Metabolism / Metabolites
In mice, the major metabolic pathway for ... myristicin includes cleavage of the methylenedioxyphenol residue and exhalation of the methylene carbon atom as carbon dioxide.
Myristicin yields 3-methoxycatechol probably in mouse, housefly; yields 1-(3-methoxy-4,5-methylenedioxyphenyl)-3-piperidyl-1-propanone in rat, guinea pig; yields 1-(3-methoxy-4,5-methylenedioxyphenyl)-3-pyrrolidinyl-1-propanone in rat, guinea pig. /From table/
Myristicin was converted into 3-methoxy-4,5-methylenedioxyamphetamine during perfusion of isolated rat liver or incubation with rat liver homogenates.
2 N-containing metabolites of myristicin were excreted in the urine of rats and guinea pigs following oral or ip admin. In the rats the metabolite was 3-piperidyl-1,3-methoxy-4,5-mehtylenedioxyphenyl)-1-propanone while the major metabolite in the guinea pig was 3-pyrrolidinyl-1(3-methoxy-4,5-methylenedioxy-phenyl)-1-propanone.
For more Metabolism/Metabolites (Complete) data for MYRISTICIN (8 total), please visit the HSDB record page.
Myristicin has known human metabolites that include 5-allyl-1-methoxy-2,3-dihydroxybenzene.

Toxicity Summary
Myristicin exerts possible neurotoxic effects on dopaminergic neurons and is a weak inhibitor of monoamine oxidase. (L1271)

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Toxicity Data
LD50: 3000 mg/kg (Oral, Mouse) (L1272)
LD50: 340 mg/kg (Intraperitoneal, Mouse) (L1272)
LD50: 5610 mg/kg (Dermal, Rat) (L1272)
LD50: 1470 mg/kg (Subcutaneous, Mouse) (L1272)
LD50: 8000 mg/kg (Intramuscular, Mouse) (L1272)

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Interactions
Simultaneous topical application of myristicin followed by paraoxon application, caused substantial incr in the toxicity of paraoxon. LD50 values indicated a 10-fold incr in paraoxon toxicity due to a topical application of myristicin at a sublethal dosage of 2 ug/fly.

[1]. Nutmeg as a narcotic. A contribution to the chemistry and pharmacology of nutmeg (Myristica fragrans).Angew Chem Int Ed Engl. 1971 Jun;10(6):370-4.

[2]. Simple and rapid determination of myristicin in human serum.Forensic Toxicol. 2013 Jan;31(1):119-123. Epub 2012 Aug 15.

[3]. Protective effects of myristicin against ulcerative colitis induced by acetic acid in male mice. Food and Agricultural Immunology, 2020, 31(1): 435-446.

[4]. Myristicin Suppresses Gastric Cancer Growth via Targeting the EGFR/ ERK Signaling Pathway. Curr Mol Pharmacol. 2023;16(7):712-724.

Myristicin is an organic molecular entity. It has a role as a metabolite.
Myristicin has been reported in Perilla frutescens, Asarum hypogynum, and other organisms with data available.
Myristicin is found in anise. Myristicin is a constituent of dill, nutmeg, parsley and many other essential oils. May be responsible for psychotic effects of nutmeg at large doses Myristicin, 3-methoxy,4,5-methylendioxy-allylbenzene, is a natural organic compound present in the essential oil of nutmeg and to a lesser extent in other spices such as parsley and dill. Myristicin is a naturally occurring insecticide and acaricide with possible neurotoxic effects on dopaminergic neurons[citation needed]. It has hallucinogenic properties at doses much higher than used in cooking. Myristicin is a weak inhibitor of monoamine oxidase.

Myristicin has been shown to exhibit apoptotic and hepatoprotective functions (A7836, A7837).

Myristicin belongs to the family of Benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole.

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Mechanism of Action
To evaluate the hepatoprotective activity of spices, 21 different spices were fed to rats with liver damage caused by lipopolysaccharide (LPS) plus d-galactosamine (D-GalN). As assessed by plasma aminotranferase activities, nutmeg showed the most potent hepatoprotective activity. Bioassay-guided isolation of the active compound from nutmeg was carried out in mice by a single oral administration of the respective fractions. Myristicin, one of the major essential oils of nutmeg, was found to possess extraordinarily potent hepatoprotective activity. Myristicin markedly suppressed LPS/D-GalN-induced enhancement of serum TNF-alpha concentrations and hepatic DNA fragmentation in mice. These findings suggest that the hepatoprotective activity of myristicin might be, at least in part, due to the inhibition of TNF-alpha release from macrophages. ...
Mouse hepatoma Hepa-1c1c7 (Hepa-1) cells were treated with myristicin to assess the role of myristicin in the process of Cyp1a-1 induction. Treatment of Hepa-1 cells with myristicin increased Cyp1a-1 transcription in a dose-dependent manner as shown by analysis of 7-ethoxyresorufin O-deethylase activity, Cyp1a-1 protein level, and Cyp1a-1 mRNA. Myristicin, however, did not competitively displace [3H]2,3,7,8-tetrachlorodibenzo-p-dioxin from the Hepa-1 cytosolic aryl hydrocarbon (Ah) receptor in a competitive Ah receptor binding analysis using sucrose density gradient sedimentation and did not affect formation of DNA-protein complexes between the Ah receptor and its DRE target in a gel mobility shift assay using oligonucleotides corresponding to DRE 3 of the Cyp1a-1. ...

C11H12O3

192.21

192.078

607-91-0

4276

Colorless to light yellow liquid

1.1±0.1 g/cm3

276.5±0.0 °C at 760 mmHg

<-20ºC

89.8±16.0 °C

0.0±0.5 mmHg at 25°C

1.540

3.26

0

3

3

14

205

0

C=CCC1=CC(=C2C(=C1)OCO2)OC

BNWJOHGLIBDBOB-UHFFFAOYSA-N

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

4-methoxy-6-prop-2-enyl-1,3-benzodioxole

HSDB 3516 HSDB3516Myristicin HSDB-3516

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~520.26 mM)

Solubility in Formulation 1: ≥ 2.5 mg/mL (13.01 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (13.01 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (13.01 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)