Myristicin (CHEM002443)

Record Information
Version1.0
Creation Date2009-07-23 18:26:23 UTC
Update Date2026-04-03 04:19:38 UTC
Accession NumberCHEM002443
Identification
Common NameMyristicin
ClassSmall Molecule
Description
Myristicin is found in anise. Myristicin is a constituent of dill, nutmeg, parsley and many other essential oils. May be responsible for psychotic effects of nutmeg at large doses Myristicin, 3-methoxy,4,5-methylendioxy-allylbenzene, is a natural organic compound present in the essential oil of nutmeg and to a lesser extent in other spices such as parsley and dill. Myristicin is a naturally occurring insecticide and acaricide with possible neurotoxic effects on dopaminergic neurons[citation needed]. It has hallucinogenic properties at doses much higher than used in cooking. Myristicin is a weak inhibitor of monoamine oxidase. Myristicin has been shown to exhibit apoptotic and hepatoprotective functions (1, 2). Myristicin belongs to the family of Benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole.
Contaminant Sources
  • FooDB Chemicals
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ether
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • PFAS
  • Pesticide
  • Phytotoxin
  • Plant Toxin
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Allyl-1-methoxy-2,3-(methylenedioxy)benzeneMeSH
AsaricinMeSH
1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)- (9ci)HMDB
1-Allyl-3-methoxy-4,5-methylenedioxybenzeneHMDB
1-Methoxy-2,3-methylenedioxy-5-(2-propenyl)benzeneHMDB
4-Methoxy-6-(2-propenyl)-1,3-benzodioxoleHMDB
4-Methoxy-6-(2-propenyl)-1,3-benzodioxole, 9ciHMDB
4-Methoxy-6-[2-propenyl]-1,3-benzodioxoleHMDB
5-Allyl-1-methoxy-2,3-(methylenedioxy)-benzeneHMDB
5-Allyl-2,3-(methylendioxy)anisoleHMDB
6-Allyl-4-methoxy-1,3-benzodioxoleHMDB
Myristicin (6ci)HMDB
Myristicin from parsley leaf oilHMDB
MyristicineHMDB
Chemical FormulaC11H12O3
Average Molecular Mass192.211 g/mol
Monoisotopic Mass192.079 g/mol
CAS Registry Number607-91-0
IUPAC Name4-methoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole
Traditional Namemyristicin
SMILESCOC1=C2OCOC2=CC(CC=C)=C1
InChI IdentifierInChI=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
InChI KeyBNWJOHGLIBDBOB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Ether
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point< -20°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.83 g/LALOGPS
logP2.47ALOGPS
logP2.54ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.58 m³·mol⁻¹ChemAxon
Polarizability20.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral (ingestion) (5) ; dermal (5)
Mechanism of ToxicityMyristicin exerts possible neurotoxic effects on dopaminergic neurons and is a weak inhibitor of monoamine oxidase. (3)
MetabolismNot Available
Toxicity ValuesLD50: 3000 mg/kg (Oral, Mouse) (4) LD50: 340 mg/kg (Intraperitoneal, Mouse) (4) LD50: 5610 mg/kg (Dermal, Rat) (4) LD50: 1470 mg/kg (Subcutaneous, Mouse) (4) LD50: 8000 mg/kg (Intramuscular, Mouse) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMyristicin is a plant toxin found in the essential oil of nutmeg and to a lesser extent in other spices such as parsley and dill. It is a naturally occurring insecticide and acaricide. (3)
Minimum Risk LevelNot Available
Health EffectsMyristicin has neurotoxic effects and hallucinogenic properties. (3)
SymptomsMyristicin produces a semi-conscious state, and may also cause euphoria, bloodshot eyes, and memory disturbances. It is also known to induce psychoactive effects such as visual distortions. (3)
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0035873
FooDB IDFDB014654
Phenol Explorer IDNot Available
KNApSAcK IDC00002762
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMyristicin
Chemspider ID4125
ChEBI IDNot Available
PubChem Compound ID4276
Kegg Compound IDC10480
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Lee BK, Kim JH, Jung JW, Choi JW, Han ES, Lee SH, Ko KH, Ryu JH: Myristicin-induced neurotoxicity in human neuroblastoma SK-N-SH cells. Toxicol Lett. 2005 May 16;157(1):49-56.
2. Morita T, Jinno K, Kawagishi H, Arimoto Y, Suganuma H, Inakuma T, Sugiyama K: Hepatoprotective effect of myristicin from nutmeg (Myristica fragrans) on lipopolysaccharide/d-galactosamine-induced liver injury. J Agric Food Chem. 2003 Mar 12;51(6):1560-5.
3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.