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=C2OCOC2=CC(CC=C)=C1
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 |
|---|---|---|---|
Target ID: CHEMBL3722 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9245741 |
|||
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Identification and characterization of reactive metabolites in myristicin-mediated mechanism-based inhibition of CYP1A2. | 2015-07-25 |
|
| Myricitrin exhibits antioxidant, anti-inflammatory and antifibrotic activity in carbon tetrachloride-intoxicated mice. | 2015-03-25 |
|
| Protective effect of bioflavonoid myricetin enhances carbohydrate metabolic enzymes and insulin signaling molecules in streptozotocin-cadmium induced diabetic nephrotoxic rats. | 2014-09-01 |
|
| Myristicin from nutmeg induces apoptosis via the mitochondrial pathway and down regulates genes of the DNA damage response pathways in human leukaemia K562 cells. | 2014-07-25 |
|
| Oxidative DNA damage preventive activity and antioxidant potential of plants used in Unani system of medicine. | 2010-12-16 |
|
| Identification of compounds in the essential oil of nutmeg seeds (Myristica fragrans Houtt.) that inhibit locomotor activity in mice. | 2010-11-23 |
|
| Naturally occurring food toxins. | 2010-09 |
|
| Acaricidal activity of eugenol based compounds against scabies mites. | 2010-08-11 |
|
| Anethum graveolens: An Indian traditional medicinal herb and spice. | 2010-07 |
|
| [Analysis of the chemical constituents of volatile oil from Asarum insigne by GC-MS]. | 2010-07 |
|
| Essential oil constituents of Illicium griffithii and its antimicrobial activity. | 2010-07 |
|
| Histological effects of oral administration of nutmeg on the kidneys of adult Wister rats. | 2010-04 |
|
| Chemical composition and in vitro evaluation of antioxidant and antibacterial activities of the root oil of Ridolfia segetum (L.) Moris from Tunisia. | 2010-04 |
|
| Predicting the hepatocarcinogenic potential of alkenylbenzene flavoring agents using toxicogenomics and machine learning. | 2010-03-15 |
|
| Histological effects of long term consumption of nutmeg on the medial geniculate body of adult Wistar rats. | 2010-03 |
|
| Enzyme Inhibition by Molluscicidal Components of Myristica fragrans Houtt. in the Nervous Tissue of Snail Lymnaea acuminata. | 2010 |
|
| Determination of alkenylbenzenes and related flavour compounds in food samples by on-column preconcentration-capillary liquid chromatography. | 2009-10-23 |
|
| Preliminary analysis on essential oil composition of Perilla L. cultivated in Lithuania. | 2009-08-26 |
|
| Distinguishing chinese star anise from Japanese star anise using thermal desorption-gas chromatography-mass spectrometry. | 2009-07-08 |
|
| Chemical composition and antimicrobial activity of Clausena indica (Dalz) Oliv. (Rutaceae) essential oil from Vietnam. | 2009-06 |
|
| Antibacterial activity and composition of essential oils from flower, leaf and stem of Chaerophyllum macropodum Boiss. from Iran. | 2009-06 |
|
| 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. | 2009-06 |
|
| Nutmeg (Myristica fragrans Houtt.). | 2009-06 |
|
| Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components. | 2009-06 |
|
| Essential oil composition of three Peperomia species from the Amazon, Brazil. | 2009-03 |
|
| Chemical composition and antimicrobial activity of the essential oil from Ferula glauca L. (F. communis L. subsp. glauca) growing in Marche (central Italy). | 2009-01 |
|
| Ethnopharmacology. | 2008-10 |
|
| Metabolism of myristicin by Depressaria pastinacella CYP6AB3v2 and inhibition by its metabolite. | 2008-06 |
|
| Perilla frutescens var. frutescens in northern Laos. | 2008-04 |
|
| [New neolignan from seed of Myristica fragrans]. | 2008-02 |
|
| Variability in essential-oil composition of Piper marginatum sensu lato. | 2008-01 |
|
| Dillapiol and Apiol as specific inhibitors of the biosynthesis of aflatoxin G1 in Aspergillus parasiticus. | 2007-09 |
|
| [GC-MS analysis of essential oil from nutmeg processed by different traditional methods]. | 2007-08 |
|
| Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris. | 2007-05 |
|
| Antioxidant activities and volatile constituents of various essential oils. | 2007-03-07 |
|
| Ethnoveterinary medicines used for ruminants in British Columbia, Canada. | 2007-02-26 |
|
| 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. | 2006-08 |
|
| [Comparing analysis of components in volatile oils of nutmeg and prepared nutmeg by GC-MS]. | 2006-05 |
|
| Antibacterial principles from Myristica fragrans seeds. | 2006 |
|
| Nutmeg intoxication in Texas, 1998-2004. | 2005-11 |
|
| Insecticidal activity of the essential oil of Ligusticum mutellina roots. | 2005-07-27 |
|
| An experimental study of sexual function improving effect of Myristica fragrans Houtt. (nutmeg). | 2005-07-20 |
|
| Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells. | 2005-05-16 |
|
| Essential oil composition of Piper guineense and its antimicrobial activity. Another chemotype from Nigeria. | 2005-04 |
|
| [Study on chemical constituents of the essential oil from Myristica fragrans Houtt. by supercritical fluid extraction and steam distillation]. | 2004-11 |
|
| [GC-MS analysis of essential oils from seeds of Myristica fragrans in Chinese market]. | 2004-04 |
|
| Enzyme activity in the flesh fly Parasarcophaga dux Thomson influenced by dill compounds, myristicin and apiol. | 2004-04 |
|
| Toxicological efficacy of some indigenous dill compounds against the flesh fly, Parasarcophaga dux Thomson. | 2004-04 |
|
| [Analysis of volatile constituents of root and rhizome of Asarum heterotropoides Fr. var. mandshuricum (Maxim.) Kitag. by gas chromatography-mass spectrometry]. | 2002-09 |
|
| Murine Cyp1a-1 induction in mouse hepatoma Hepa-1C1C7 cells by myristicin. | 1997-04-28 |
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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| Record UNII |
04PD6CT78W
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| Record Status |
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