Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H12O3 |
Molecular Weight | 192.2112 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(CC=C)=CC2=C1OCO2
InChI
InChIKey=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
Myristicin, a natural product found in nutmeg oil and nutmeg
extract, contains the carbon skeleton for a series of drugs of abuse
related to the 3,4-methylenedioxyamphetamines (MDAs). Myristicin,
1-(3-methoxy-4,5-methylenedioxyphenyl)-2-propene, was identified
as the major component of commercially available nutmeg oil and in
the organic extract of nutmeg powder. Myristicin, or methoxysafrole, is a benzodioxole with slight MAO-inhibiting properties. Myristicin is active at the 5-HT receptors in the brain, and has been shown to have hypotensive, sedative, anti-depressant, anesthetic, hallucinogenic, and serotonergic properties. Large doses generally cause hyper-excitability, followed by CNS depression. 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. Myristicin showed a 31% inhibition of tumor formation in the forestomach of rats. Mice given 5 to 50 mg doses of myristicin, showed 4- to 14-fold increase in liver glutathione S-transferase (GST) activity.
CNS Activity
Curator's Comment: Myristicin is active at the 5-HT receptors in the brain, and has been shown to have hypotensive, sedative, anti-depressant, anesthetic, hallucinogenic, and serotonergic properties. Large doses generally cause hyper-excitability, followed by CNS depression. Myristicin is fairly unique as a hallucinogen (if it may be classified as such), because it lacks a nitrogen atom. It is also rare for a compound lacking a nitrogen group to show activity at the brain's 5-HT receptors.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3722 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9245741 |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Murine Cyp1a-1 induction in mouse hepatoma Hepa-1C1C7 cells by myristicin. | 1997 Apr 28 |
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Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
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[Analysis of volatile constituents of root and rhizome of Asarum heterotropoides Fr. var. mandshuricum (Maxim.) Kitag. by gas chromatography-mass spectrometry]. | 2002 Sep |
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Analysis by gas chromatography-mass spectrometry of the essential oils from the aerial parts of Rutheopsis herbanica (Bolle) Hans. & Kunk., gathered in Fuerteventura (Canary Islands). | 2003 Jan 10 |
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Chemical stimulants of leaf-trenching by cabbage loopers: natural products, neurotransmitters, insecticides, and drugs. | 2003 Sep |
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Enzyme activity in the flesh fly Parasarcophaga dux Thomson influenced by dill compounds, myristicin and apiol. | 2004 Apr |
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[Study on chemical constituents of the essential oil from Myristica fragrans Houtt. by supercritical fluid extraction and steam distillation]. | 2004 Nov |
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Essential oil composition of Piper guineense and its antimicrobial activity. Another chemotype from Nigeria. | 2005 Apr |
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An experimental study of sexual function improving effect of Myristica fragrans Houtt. (nutmeg). | 2005 Jul 20 |
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Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells. | 2005 May 16 |
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Insecticidal activity of the essential oil of Ligusticum mutellina roots. | 2005 May-Jun |
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Nutmeg intoxication in Texas, 1998-2004. | 2005 Nov |
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Abuse of nutmeg (Myristica fragrans Houtt.): studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry. | 2006 Aug |
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Antibacterial principles from Myristica fragrans seeds. | 2006 Fall |
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[Comparing analysis of components in volatile oils of nutmeg and prepared nutmeg by GC-MS]. | 2006 May |
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[GC-MS analysis of essential oil from nutmeg processed by different traditional methods]. | 2007 Aug |
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Ethnoveterinary medicines used for ruminants in British Columbia, Canada. | 2007 Feb 26 |
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Antioxidant activities and volatile constituents of various essential oils. | 2007 Mar 7 |
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Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris. | 2007 May |
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Dillapiol and Apiol as specific inhibitors of the biosynthesis of aflatoxin G1 in Aspergillus parasiticus. | 2007 Sep |
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Perilla frutescens var. frutescens in northern Laos. | 2008 Apr |
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[New neolignan from seed of Myristica fragrans]. | 2008 Feb |
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Variability in essential-oil composition of Piper marginatum sensu lato. | 2008 Jan |
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Metabolism of myristicin by Depressaria pastinacella CYP6AB3v2 and inhibition by its metabolite. | 2008 Jun |
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Ethnopharmacology. | 2008 Oct |
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Chemical composition and antimicrobial activity of the essential oil from Ferula glauca L. (F. communis L. subsp. glauca) growing in Marche (central Italy). | 2009 Jan |
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Distinguishing chinese star anise from Japanese star anise using thermal desorption-gas chromatography-mass spectrometry. | 2009 Jul 8 |
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Preliminary analysis on essential oil composition of Perilla L. cultivated in Lithuania. | 2009 Jul-Aug |
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Chemical composition and antimicrobial activity of Clausena indica (Dalz) Oliv. (Rutaceae) essential oil from Vietnam. | 2009 Jun |
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Antibacterial activity and composition of essential oils from flower, leaf and stem of Chaerophyllum macropodum Boiss. from Iran. | 2009 Jun |
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Flower and root oils of the tunisian Daucus carota L. ssp. maritimus (Apiaceae): integrated analyses by GC, GC/MS, and 13C-NMR spectroscopy, and in vitro antibacterial activity. | 2009 Jun |
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Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components. | 2009 Jun |
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Essential oil composition of three Peperomia species from the Amazon, Brazil. | 2009 Mar |
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Determination of alkenylbenzenes and related flavour compounds in food samples by on-column preconcentration-capillary liquid chromatography. | 2009 Oct 23 |
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Enzyme Inhibition by Molluscicidal Components of Myristica fragrans Houtt. in the Nervous Tissue of Snail Lymnaea acuminata. | 2010 |
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Histological effects of oral administration of nutmeg on the kidneys of adult Wister rats. | 2010 Apr |
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Chemical composition and in vitro evaluation of antioxidant and antibacterial activities of the root oil of Ridolfia segetum (L.) Moris from Tunisia. | 2010 Apr |
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Acaricidal activity of eugenol based compounds against scabies mites. | 2010 Aug 11 |
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Oxidative DNA damage preventive activity and antioxidant potential of plants used in Unani system of medicine. | 2010 Dec 16 |
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Anethum graveolens: An Indian traditional medicinal herb and spice. | 2010 Jul |
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[Analysis of the chemical constituents of volatile oil from Asarum insigne by GC-MS]. | 2010 Jul |
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Essential oil constituents of Illicium griffithii and its antimicrobial activity. | 2010 Jul |
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Histological effects of long term consumption of nutmeg on the medial geniculate body of adult Wistar rats. | 2010 Mar |
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Predicting the hepatocarcinogenic potential of alkenylbenzene flavoring agents using toxicogenomics and machine learning. | 2010 Mar 15 |
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Identification of compounds in the essential oil of nutmeg seeds (Myristica fragrans Houtt.) that inhibit locomotor activity in mice. | 2010 Nov 23 |
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Naturally occurring food toxins. | 2010 Sep |
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Myristicin from nutmeg induces apoptosis via the mitochondrial pathway and down regulates genes of the DNA damage response pathways in human leukaemia K562 cells. | 2014 Jul 25 |
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Protective effect of bioflavonoid myricetin enhances carbohydrate metabolic enzymes and insulin signaling molecules in streptozotocin-cadmium induced diabetic nephrotoxic rats. | 2014 Sep 1 |
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Identification and characterization of reactive metabolites in myristicin-mediated mechanism-based inhibition of CYP1A2. | 2015 Jul 25 |
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Myricitrin exhibits antioxidant, anti-inflammatory and antifibrotic activity in carbon tetrachloride-intoxicated mice. | 2015 Mar 25 |
Patents
Sample Use Guides
Myristicin's psychoactive properties were confirmed by a study on ten human participants. Each of the participants was administered 400 mg of myristicin, or approximately 6-7 mg/kg by body weight. Only four of the participants experienced psychoactive effects, including euphoria, anxiety, and trouble concentrating.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21472076
Myristicin, resulted inactive as antimicrobial agent at the maximum tested concentration of 200 ug/mL, but it induced significant antiproliferative activity on the tested cancer cell lines.
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ACTIVE MOIETY
METABOLITE (PARENT)