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
Molecular Formula | C11H12O3 |
Molecular Weight | 192.2112 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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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Nutmeg (myristicin) poisoning--report on a fatal case and a series of cases recorded by a poison information centre. | 2001 Apr 15 |
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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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[GC-MS analysis of essential oils from seeds of Myristica fragrans in Chinese market]. | 2004 Apr |
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Insecticidal activity of the essential oil of Ligusticum mutellina roots. | 2005 May-Jun |
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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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[New neolignan from seed of Myristica fragrans]. | 2008 Feb |
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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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Nutmeg (Myristica fragrans Houtt.). | 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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Acaricidal activity of eugenol based compounds against scabies mites. | 2010 Aug 11 |
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Anethum graveolens: An Indian traditional medicinal herb and spice. | 2010 Jul |
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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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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.
Substance Class |
Chemical
Created
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admin
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Edited
Fri Dec 16 16:17:59 UTC 2022
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Fri Dec 16 16:17:59 UTC 2022
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Record UNII |
04PD6CT78W
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Record Status |
Validated (UNII)
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MYRISTICIN
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