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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

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
Asaricin, the main component of Ocotea opifera Mart. essential oil.
2001
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
2001
Nutmeg (myristicin) poisoning--report on a fatal case and a series of cases recorded by a poison information centre.
2001 Apr 15
Effect of leaf essential oil from Piper solmsianum C.DC. in mice behaviour.
2001 Mar
Changes in volatile compounds of carrots (Daucus carota L.) during refrigerated and frozen storage.
2003 Aug 27
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
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
Toxicological efficacy of some indigenous dill compounds against the flesh fly, Parasarcophaga dux Thomson.
2004 Apr
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
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.
2007 Feb 26
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
Variability in essential-oil composition of Piper marginatum sensu lato.
2008 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
Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components.
2009 Jun
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
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:30 GMT 2023
Record UNII
04PD6CT78W
Record Status Validated (UNII)
Record Version
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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
PRIMARY
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
PRIMARY
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
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