ContaminantDB: Myristicin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-07-23 18:26:23 UTC

Update Date

2026-04-03 04:19:38 UTC

Accession Number

CHEM002443

Identification

Common Name

Myristicin

Class

Small 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
Pesticide
Plant Toxin

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
5-Allyl-1-methoxy-2,3-(methylenedioxy)benzene	MeSH
Asaricin	MeSH
1,3-Benzodioxole, 4-methoxy-6-(2-propenyl)- (9ci)	HMDB
1-Allyl-3-methoxy-4,5-methylenedioxybenzene	HMDB
1-Methoxy-2,3-methylenedioxy-5-(2-propenyl)benzene	HMDB
4-Methoxy-6-(2-propenyl)-1,3-benzodioxole	HMDB
4-Methoxy-6-(2-propenyl)-1,3-benzodioxole, 9ci	HMDB
4-Methoxy-6-[2-propenyl]-1,3-benzodioxole	HMDB
5-Allyl-1-methoxy-2,3-(methylenedioxy)-benzene	HMDB
5-Allyl-2,3-(methylendioxy)anisole	HMDB
6-Allyl-4-methoxy-1,3-benzodioxole	HMDB
Myristicin (6ci)	HMDB
Myristicin from parsley leaf oil	HMDB
Myristicine	HMDB

Chemical Formula

C₁₁H₁₂O₃

Average Molecular Mass

192.211 g/mol

Monoisotopic Mass

192.079 g/mol

CAS Registry Number

607-91-0

IUPAC Name

4-methoxy-6-(prop-2-en-1-yl)-2H-1,3-benzodioxole

Traditional Name

myristicin

SMILES

COC1=C2OCOC2=CC(CC=C)=C1

InChI Identifier

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

InChI Key

BNWJOHGLIBDBOB-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic molecular entity (CHEBI:68234 )
Monolignols (C10480 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	< -20°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.83 g/L	ALOGPS
logP	2.47	ALOGPS
logP	2.54	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	52.58 m³·mol⁻¹	ChemAxon
Polarizability	20.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03fr-1900000000-f2a18c6e6e42ac39f661	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0api-2900000000-351fe6c26efba614a881	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-ac75cb6f6c3586da7aea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-1900000000-b85689ec228e938e0ecc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00lu-5900000000-b81250e22454ed5d59d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-3477a22f9a26a9c1d389	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-d7d0d133097da9fb4ec3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-005i-4900000000-223806e9de1823c5a6e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-f50d22f4768250e3bdf7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-eccd8c2af56eaae25cc6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03fu-9300000000-7be3c7d384d05c36876b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-3b8fc77e2c5dffca7765	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-bdb133e54a9aea38147a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01p9-7900000000-cea14d0b0dcb3a57c352	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-5900000000-371b2263b19500bf8f81	Spectrum

Toxicity Profile

Route of Exposure

Oral (ingestion) (5) ; dermal (5)

Mechanism of Toxicity

Myristicin exerts possible neurotoxic effects on dopaminergic neurons and is a weak inhibitor of monoamine oxidase. (3)

Metabolism

Not Available

Toxicity Values

LD50: 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 Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Myristicin 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 Level

Not Available

Health Effects

Myristicin has neurotoxic effects and hallucinogenic properties. (3)

Symptoms

Myristicin 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)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0035873

FooDB ID

FDB014654

Phenol Explorer ID