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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=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

HIDE SMILES / InChI
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
Murine Cyp1a-1 induction in mouse hepatoma Hepa-1C1C7 cells by myristicin.
1997 Apr 28
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
2001
[Analysis of volatile constituents of root and rhizome of Asarum heterotropoides Fr. var. mandshuricum (Maxim.) Kitag. by gas chromatography-mass spectrometry].
2002 Sep
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
Chemical stimulants of leaf-trenching by cabbage loopers: natural products, neurotransmitters, insecticides, and drugs.
2003 Sep
Enzyme activity in the flesh fly Parasarcophaga dux Thomson influenced by dill compounds, myristicin and apiol.
2004 Apr
[Study on chemical constituents of the essential oil from Myristica fragrans Houtt. by supercritical fluid extraction and steam distillation].
2004 Nov
Essential oil composition of Piper guineense and its antimicrobial activity. Another chemotype from Nigeria.
2005 Apr
An experimental study of sexual function improving effect of Myristica fragrans Houtt. (nutmeg).
2005 Jul 20
Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells.
2005 May 16
Insecticidal activity of the essential oil of Ligusticum mutellina roots.
2005 May-Jun
Nutmeg intoxication in Texas, 1998-2004.
2005 Nov
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
Antibacterial principles from Myristica fragrans seeds.
2006 Fall
[Comparing analysis of components in volatile oils of nutmeg and prepared nutmeg by GC-MS].
2006 May
[GC-MS analysis of essential oil from nutmeg processed by different traditional methods].
2007 Aug
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.
2007 Feb 26
Antioxidant activities and volatile constituents of various essential oils.
2007 Mar 7
Comparative analysis of the oil and supercritical CO2 extract of Ridolfia segetum (L.) Moris.
2007 May
Dillapiol and Apiol as specific inhibitors of the biosynthesis of aflatoxin G1 in Aspergillus parasiticus.
2007 Sep
Perilla frutescens var. frutescens in northern Laos.
2008 Apr
[New neolignan from seed of Myristica fragrans].
2008 Feb
Variability in essential-oil composition of Piper marginatum sensu lato.
2008 Jan
Metabolism of myristicin by Depressaria pastinacella CYP6AB3v2 and inhibition by its metabolite.
2008 Jun
Ethnopharmacology.
2008 Oct
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
Distinguishing chinese star anise from Japanese star anise using thermal desorption-gas chromatography-mass spectrometry.
2009 Jul 8
Preliminary analysis on essential oil composition of Perilla L. cultivated in Lithuania.
2009 Jul-Aug
Chemical composition and antimicrobial activity of Clausena indica (Dalz) Oliv. (Rutaceae) essential oil from Vietnam.
2009 Jun
Antibacterial activity and composition of essential oils from flower, leaf and stem of Chaerophyllum macropodum Boiss. from Iran.
2009 Jun
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
Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components.
2009 Jun
Essential oil composition of three Peperomia species from the Amazon, Brazil.
2009 Mar
Determination of alkenylbenzenes and related flavour compounds in food samples by on-column preconcentration-capillary liquid chromatography.
2009 Oct 23
Enzyme Inhibition by Molluscicidal Components of Myristica fragrans Houtt. in the Nervous Tissue of Snail Lymnaea acuminata.
2010
Histological effects of oral administration of nutmeg on the kidneys of adult Wister rats.
2010 Apr
Chemical composition and in vitro evaluation of antioxidant and antibacterial activities of the root oil of Ridolfia segetum (L.) Moris from Tunisia.
2010 Apr
Acaricidal activity of eugenol based compounds against scabies mites.
2010 Aug 11
Oxidative DNA damage preventive activity and antioxidant potential of plants used in Unani system of medicine.
2010 Dec 16
Anethum graveolens: An Indian traditional medicinal herb and spice.
2010 Jul
[Analysis of the chemical constituents of volatile oil from Asarum insigne by GC-MS].
2010 Jul
Essential oil constituents of Illicium griffithii and its antimicrobial activity.
2010 Jul
Histological effects of long term consumption of nutmeg on the medial geniculate body of adult Wistar rats.
2010 Mar
Predicting the hepatocarcinogenic potential of alkenylbenzene flavoring agents using toxicogenomics and machine learning.
2010 Mar 15
Identification of compounds in the essential oil of nutmeg seeds (Myristica fragrans Houtt.) that inhibit locomotor activity in mice.
2010 Nov 23
Naturally occurring food toxins.
2010 Sep
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
Protective effect of bioflavonoid myricetin enhances carbohydrate metabolic enzymes and insulin signaling molecules in streptozotocin-cadmium induced diabetic nephrotoxic rats.
2014 Sep 1
Identification and characterization of reactive metabolites in myristicin-mediated mechanism-based inhibition of CYP1A2.
2015 Jul 25
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
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.
Name Type Language
MYRISTICIN
HSDB   MI  
Common Name English
MYRISTICIN [MI]
Common Name English
5-ALLYL-1-METHOXY-2,3-METHYLENEDIOXYBENZENE
Systematic Name English
MYRISTICIN [HSDB]
Common Name English
Code System Code Type Description
HSDB
3516
Created by admin on Fri Dec 15 15:08:30 GMT 2023 , Edited by admin on Fri Dec 15 15:08:30 GMT 2023
PRIMARY
PUBCHEM
4276
Created by admin on Fri Dec 15 15:08:31 GMT 2023 , Edited by admin on Fri Dec 15 15:08:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID1025693
Created by admin on Fri Dec 15 15:08:30 GMT 2023 , Edited by admin on Fri Dec 15 15:08:30 GMT 2023
PRIMARY
WIKIPEDIA
MYRISTICIN
Created by admin on Fri Dec 15 15:08:31 GMT 2023 , Edited by admin on Fri Dec 15 15:08:31 GMT 2023
PRIMARY
MERCK INDEX
m7690
Created by admin on Fri Dec 15 15:08:31 GMT 2023 , Edited by admin on Fri Dec 15 15:08:31 GMT 2023
PRIMARY Merck Index
JECFA MONOGRAPH
1769
Created by admin on Fri Dec 15 15:08:30 GMT 2023 , Edited by admin on Fri Dec 15 15:08:30 GMT 2023
PRIMARY
CAS
607-91-0
Created by admin on Fri Dec 15 15:08:30 GMT 2023 , Edited by admin on Fri Dec 15 15:08:30 GMT 2023
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FDA UNII
04PD6CT78W
Created by admin on Fri Dec 15 15:08:30 GMT 2023 , Edited by admin on Fri Dec 15 15:08:30 GMT 2023
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ECHA (EC/EINECS)
210-146-9
Created by admin on Fri Dec 15 15:08:30 GMT 2023 , Edited by admin on Fri Dec 15 15:08:30 GMT 2023
PRIMARY
MESH
C005246
Created by admin on Fri Dec 15 15:08:31 GMT 2023 , Edited by admin on Fri Dec 15 15:08:31 GMT 2023
PRIMARY