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
Nutmeg (myristicin) poisoning--report on a fatal case and a series of cases recorded by a poison information centre.
2001 Apr 15
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
[GC-MS analysis of essential oils from seeds of Myristica fragrans in Chinese market].
2004 Apr
Insecticidal activity of the essential oil of Ligusticum mutellina roots.
2005 May-Jun
[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
[New neolignan from seed of Myristica fragrans].
2008 Feb
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
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
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
Acaricidal activity of eugenol based compounds against scabies mites.
2010 Aug 11
Anethum graveolens: An Indian traditional medicinal herb and spice.
2010 Jul
Identification of compounds in the essential oil of nutmeg seeds (Myristica fragrans Houtt.) that inhibit locomotor activity in mice.
2010 Nov 23
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 16 16:17:59 UTC 2022
Edited
by admin
on Fri Dec 16 16:17:59 UTC 2022
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 16 16:17:59 UTC 2022 , Edited by admin on Fri Dec 16 16:17:59 UTC 2022
PRIMARY
PUBCHEM
4276
Created by admin on Fri Dec 16 16:17:59 UTC 2022 , Edited by admin on Fri Dec 16 16:17:59 UTC 2022
PRIMARY
EPA CompTox
DTXSID1025693
Created by admin on Fri Dec 16 16:17:59 UTC 2022 , Edited by admin on Fri Dec 16 16:17:59 UTC 2022
PRIMARY
WIKIPEDIA
MYRISTICIN
Created by admin on Fri Dec 16 16:17:59 UTC 2022 , Edited by admin on Fri Dec 16 16:17:59 UTC 2022
PRIMARY
MERCK INDEX
M7690
Created by admin on Fri Dec 16 16:17:59 UTC 2022 , Edited by admin on Fri Dec 16 16:17:59 UTC 2022
PRIMARY Merck Index
CAS
607-91-0
Created by admin on Fri Dec 16 16:17:59 UTC 2022 , Edited by admin on Fri Dec 16 16:17:59 UTC 2022
PRIMARY
FDA UNII
04PD6CT78W
Created by admin on Fri Dec 16 16:17:59 UTC 2022 , Edited by admin on Fri Dec 16 16:17:59 UTC 2022
PRIMARY
ECHA (EC/EINECS)
210-146-9
Created by admin on Fri Dec 16 16:17:59 UTC 2022 , Edited by admin on Fri Dec 16 16:17:59 UTC 2022
PRIMARY
MESH
C005246
Created by admin on Fri Dec 16 16:17:59 UTC 2022 , Edited by admin on Fri Dec 16 16:17:59 UTC 2022
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY