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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
Murine Cyp1a-1 induction in mouse hepatoma Hepa-1C1C7 cells by myristicin.
1997 Apr 28
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
Chemical stimulants of leaf-trenching by cabbage loopers: natural products, neurotransmitters, insecticides, and drugs.
2003 Sep
Toxicological efficacy of some indigenous dill compounds against the flesh fly, Parasarcophaga dux Thomson.
2004 Apr
[Study on chemical constituents of the essential oil from Myristica fragrans Houtt. by supercritical fluid extraction and steam distillation].
2004 Nov
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
[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
Variability in essential-oil composition of Piper marginatum sensu lato.
2008 Jan
Ethnopharmacology.
2008 Oct
Preliminary analysis on essential oil composition of Perilla L. cultivated in Lithuania.
2009 Jul-Aug
Antibacterial activity and composition of essential oils from flower, leaf and stem of Chaerophyllum macropodum Boiss. from Iran.
2009 Jun
Determination of alkenylbenzenes and related flavour compounds in food samples by on-column preconcentration-capillary liquid chromatography.
2009 Oct 23
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
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
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 Mon Mar 31 17:47:52 GMT 2025
Edited
by admin
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