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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
Structure of MYRISTICIN

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

HIDE SMILES / InChI

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

PubMed

PubMed

TitleDatePubMed
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
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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on Mon Mar 31 17:47:52 GMT 2025
Edited
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on Mon Mar 31 17:47:52 GMT 2025
Record UNII
04PD6CT78W
Record Status Validated (UNII)
Record Version
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Name Type Language
MYRISTICIN
HSDB   MI  
Common Name English
MYRISTICIN [HSDB]
Preferred Name English
MYRISTICIN [MI]
Common Name English
5-ALLYL-1-METHOXY-2,3-METHYLENEDIOXYBENZENE
Systematic Name English
Code System Code Type Description
HSDB
3516
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
PRIMARY
PUBCHEM
4276
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
PRIMARY
EPA CompTox
DTXSID1025693
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
PRIMARY
WIKIPEDIA
MYRISTICIN
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
PRIMARY
MERCK INDEX
m7690
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
PRIMARY Merck Index
JECFA MONOGRAPH
1769
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
PRIMARY
CAS
607-91-0
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
PRIMARY
FDA UNII
04PD6CT78W
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
PRIMARY
ECHA (EC/EINECS)
210-146-9
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
PRIMARY
MESH
C005246
Created by admin on Mon Mar 31 17:47:52 GMT 2025 , Edited by admin on Mon Mar 31 17:47:52 GMT 2025
PRIMARY
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METABOLITE -> PARENT
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ACTIVE MOIETY