U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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
Murine Cyp1a-1 induction in mouse hepatoma Hepa-1C1C7 cells by myristicin.
1997 Apr 28
[Analysis of volatile constituents of root and rhizome of Asarum heterotropoides Fr. var. mandshuricum (Maxim.) Kitag. by gas chromatography-mass spectrometry].
2002 Sep
Roles of human liver cytochrome P450 3A4 and 1A2 enzymes in the oxidation of myristicin.
2003 Feb 3
[An inaugural generalized tonic-clonic convulsive crisis following ingestion of Japanese star anise].
2003 Jan 11
Hepatoprotective effect of myristicin from nutmeg (Myristica fragrans) on lipopolysaccharide/d-galactosamine-induced liver injury.
2003 Mar 12
An experimental study of sexual function improving effect of Myristica fragrans Houtt. (nutmeg).
2005 Jul 20
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
Perilla frutescens var. frutescens in northern Laos.
2008 Apr
Metabolism of myristicin by Depressaria pastinacella CYP6AB3v2 and inhibition by its metabolite.
2008 Jun
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
Antibacterial activity and composition of essential oils from flower, leaf and stem of Chaerophyllum macropodum Boiss. from Iran.
2009 Jun
Nutmeg (Myristica fragrans Houtt.).
2009 Jun
Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components.
2009 Jun
Chemical composition and in vitro evaluation of antioxidant and antibacterial activities of the root oil of Ridolfia segetum (L.) Moris from Tunisia.
2010 Apr
Identification of compounds in the essential oil of nutmeg seeds (Myristica fragrans Houtt.) that inhibit locomotor activity in mice.
2010 Nov 23
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:08:30 UTC 2023
Edited
by admin
on Fri Dec 15 15:08:30 UTC 2023
Record UNII
04PD6CT78W
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 15:08:30 UTC 2023
PRIMARY
PUBCHEM
4276
Created by admin on Fri Dec 15 15:08:31 UTC 2023 , Edited by admin on Fri Dec 15 15:08:31 UTC 2023
PRIMARY
EPA CompTox
DTXSID1025693
Created by admin on Fri Dec 15 15:08:30 UTC 2023 , Edited by admin on Fri Dec 15 15:08:30 UTC 2023
PRIMARY
WIKIPEDIA
MYRISTICIN
Created by admin on Fri Dec 15 15:08:31 UTC 2023 , Edited by admin on Fri Dec 15 15:08:31 UTC 2023
PRIMARY
MERCK INDEX
m7690
Created by admin on Fri Dec 15 15:08:31 UTC 2023 , Edited by admin on Fri Dec 15 15:08:31 UTC 2023
PRIMARY Merck Index
JECFA MONOGRAPH
1769
Created by admin on Fri Dec 15 15:08:30 UTC 2023 , Edited by admin on Fri Dec 15 15:08:30 UTC 2023
PRIMARY
CAS
607-91-0
Created by admin on Fri Dec 15 15:08:30 UTC 2023 , Edited by admin on Fri Dec 15 15:08:30 UTC 2023
PRIMARY
FDA UNII
04PD6CT78W
Created by admin on Fri Dec 15 15:08:30 UTC 2023 , Edited by admin on Fri Dec 15 15:08:30 UTC 2023
PRIMARY
ECHA (EC/EINECS)
210-146-9
Created by admin on Fri Dec 15 15:08:30 UTC 2023 , Edited by admin on Fri Dec 15 15:08:30 UTC 2023
PRIMARY
MESH
C005246
Created by admin on Fri Dec 15 15:08:31 UTC 2023 , Edited by admin on Fri Dec 15 15:08:31 UTC 2023
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY