Myristicin
Also known as6-Allyl-4-methoxy-1,3-benzodioxole · Myristicine · 5-Allyl-2,3-(methylendioxy)anisole · Myristicin (6CI) · Myristicin_major · Myristicin (Standard) · MYRISTICIN [MI] · Myristicin, analytical standard
4-methoxy-6-prop-2-enyl-1,3-benzodioxole
- PubChem CID
- 4276
- ChEMBL
- CHEMBL481044
- Measurements
- 1
- InChIKey
- BNWJOHGLIBDBOB-UHFFFAOYSA-N
I · Summary
What is known
Published passages, each quoted whole and attributed to the database that published it. Two blocks are written here rather than quoted, and both say so where they stand: the synthesized summary at the top, which may draw only on the passages beneath it, and the history note, which cites the works it came from. Every claim in either carries a marker to its source.
What it is
Myristicin is an organic molecular entity. It has a role as a metabolite.
myristicin has been reported in Perilla frutescens, Asarum hypogynum, and other organisms with data available.
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 hepatoprotecti…
asaricin is an isomer; structure; a methylene dioxy version of elemicin;
Recognized use
An aromatic ether found in nutmeg, parsley, and carrots; [Merck Index] Thought to be the main active ingredient in nutmeg; [Goldfrank, p. 626]
Haz-Map, Information on Hazardous Chemicals and Occupational DiseasesMerck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
Myristicin [5-allyl-1-methoxy-2,3-(methylenedioxy)benzene] is a flavoring plant constituent and has been known to produce significant psychopharmacological responses as well as insecticidal activity.
Hazardous Substances Data Bank (HSDB)PMID 9521577Lee HS et al; J Chromatogr B: Biomed Sci Appl 705 (2): 367-72 (1998)
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. (L1271)
How it acts
To evaluate the hepatoprotective activity of spices, 21 different spices were fed to rats with liver damage caused by lipopolysaccharide (LPS) plus d-galactosamine (D-GalN). As assessed by plasma aminotranferase activities, nutmeg showed the most potent hepatoprotective activity. Bioassay-guided isolation of the active compound from nutmeg was carried out in mice by a single oral administration of the respective fractions. Myristicin, one of the major essential oils of nutmeg, was found to possess extraordinarily potent hepatoprotective activity. Myristicin markedly suppressed LPS/D-GalN-induced enhancement of serum TNF-alpha concentrations and hepatic DNA fragmentation in mice. These findin…
Hazardous Substances Data Bank (HSDB)PMID 12617584Morita T et al; J Agric Food Chem 51 (6): 1560-5 (2003)
Mouse hepatoma Hepa-1c1c7 (Hepa-1) cells were treated with myristicin to assess the role of myristicin in the process of Cyp1a-1 induction. Treatment of Hepa-1 cells with myristicin increased Cyp1a-1 transcription in a dose-dependent manner as shown by analysis of 7-ethoxyresorufin O-deethylase activity, Cyp1a-1 protein level, and Cyp1a-1 mRNA. Myristicin, however, did not competitively displace [3H]2,3,7,8-tetrachlorodibenzo-p-dioxin from the Hepa-1 cytosolic aryl hydrocarbon (Ah) receptor in a competitive Ah receptor binding analysis using sucrose density gradient sedimentation and did not affect formation of DNA-protein complexes between the Ah receptor and its DRE target in a gel mobilit…
Hazardous Substances Data Bank (HSDB)PMID 9168900Jeong HG et al; Biochem Biophys Res Commun 233 (3): 619-22 (1997)
Behavior carries the pharmacological classes and the acute-effect durations, with plasma half-life kept separate from duration of effect.
In the body
In mice, the major metabolic pathway for ... myristicin includes cleavage of the methylenedioxyphenol residue and exhalation of the methylene carbon atom as carbon dioxide.
Hazardous Substances Data Bank (HSDB)The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 304
Myristicin yields 3-methoxycatechol probably in mouse, housefly; yields 1-(3-methoxy-4,5-methylenedioxyphenyl)-3-piperidyl-1-propanone in rat, guinea pig; yields 1-(3-methoxy-4,5-methylenedioxyphenyl)-3-pyrrolidinyl-1-propanone in rat, guinea pig. /From table/
Hazardous Substances Data Bank (HSDB)Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. M-48
Myristicin was converted into 3-methoxy-4,5-methylenedioxyamphetamine during perfusion of isolated rat liver or incubation with rat liver homogenates.
Hazardous Substances Data Bank (HSDB)PMID 4737998BRAUN U, KALBHEN DA; PHARMACOLOGY 9 (5): 312 (1973)
2 N-containing metabolites of myristicin were excreted in the urine of rats and guinea pigs following oral or ip admin. In the rats the metabolite was 3-piperidyl-1,3-methoxy-4,5-mehtylenedioxyphenyl)-1-propanone while the major metabolite in the guinea pig was 3-pyrrolidinyl-1(3-methoxy-4,5-methylenedioxy-phenyl)-1-propanone.
Hazardous Substances Data Bank (HSDB)PMID 5125615OSWALD ED ET AL; BIOCHIM BIOPHYS ACTA 244 (2): 322 (1971)
History, discovery and cultural use
— Not in this archive. PubChem, ChEMBL and the Human Protein Atlas publish pharmacology, regulation and toxicology, and none of them publishes a heading for when Myristicin was first made, by whom, or how it has been used. That is a gap in the databases this site reads and not a gap in the literature — the history of these compounds is written, at length and under peer review, in the works below. This site does not summarize them; it says where they are. Where a published passage above happens to touch origin or traditional use, it appears inside the entry that carries it.
Histories of this field
Scholarship on psychedelics generally, not on Myristicin specifically. Whether any of these treats this compound is a question for the book, not for this page.
Mescaline: A Global History of the First Psychedelic
Traces mescaline and the peyote and San Pedro cacti from pre-Columbian ritual use through nineteenth-century chemistry to twentieth-century psychiatry and the counterculture.
Jay M. Mescaline: A Global History of the First Psychedelic. Yale University Press, New Haven and London; 2019. ISBN 9780300231076.
Expanding Mindscapes: A Global History of Psychedelicsopen access
Essays on the international and cross-cultural history of psychedelic science, deliberately decentring the standard North American and European account.
Dyck E, Elcock C, editors. Expanding Mindscapes: A Global History of Psychedelics. The MIT Press, Cambridge MA; 2023. ISBN 9780262546935 (paper), 9780262376891 (open access). doi:10.7551/mitpress/14417.001.0001.
Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers
Botany, ethnography and chemistry of the principal hallucinogenic plants, by the founder of modern ethnobotany and the chemist who first synthesized LSD.
Schultes RE, Hofmann A, Rätsch C. Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers. 2nd ed. Healing Arts Press, Rochester VT; 2001. ISBN 9780892819799.
Psychonauts: Drugs and the Making of the Modern Mind
The tradition of scientific self-experimentation with psychoactive drugs, and its part in the emergence of psychology and of modernism.
Jay M. Psychonauts: Drugs and the Making of the Modern Mind. Yale University Press, New Haven; 2023. ISBN 9780300257946.
Ancient Psychoactive Substances
Archaeological and bioarchaeological evidence for psychoactive plant use across the ancient world.
Fitzpatrick SM, editor. Ancient Psychoactive Substances. University Press of Florida, Gainesville; 2018. ISBN 9780813056708.
A chapter tracing psychedelic and entactogen research from earlier ritual use through the mid-century research period to current clinical trials.
Stroud C, Posey Norris SM, Matney C, editors. History and Current Status of Psychedelics and Entactogens for the Treatment of Psychiatric Disorders. In: Exploring Psychedelics and Entactogens as Treatments for Psychiatric Disorders: Proceedings of a Workshop. National Academies Press, Washington DC; 2022. NBK587225.
Workshop proceedings record what participants said; they are not a consensus statement of the National Academies.
Peer-reviewed review covering the isolation, synthesis, pharmacology and ritual use of peyote and mescaline.
Dinis-Oliveira RJ, Pereira CL, da Silva DD. Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions. Current Molecular Pharmacology 12(3):184–194; 2019. doi:10.2174/1874467211666181010154139.
Institutional archives
- Heffter Research Institute Funds and coordinates clinical research on psilocybin, and keeps records of the studies it has supported since 1993. Sponsors the research it archives.
- Multidisciplinary Association for Psychedelic Studies (MAPS) Sponsors clinical research, chiefly on MDMA-assisted therapy, and publishes an archive of historical and contemporary documents. A sponsor and an advocacy organization, not a disinterested archive; its clinical programme has a commercial arm.
The rest of this dossier
- Affinity — 1 measurement in this archive, equilibrium constants kept apart from functional readouts.
- Toxicology — 6 published passages, plus any assay in this archive bearing on toxicity.
- Legal — no DEA record is held here — which is not a finding that this compound is uncontrolled.
- Systems — where this compound’s targets are transcribed, by brain region and tissue.
Passages via PubChem descriptive sections, aggregating DrugBank, LiverTox, FDA, DEA, HSDB, EPA. Each is quoted whole and attributed to the database that published it. The only prose written here about Myristicin is the history note, which says so on its face and carries a reference for every claim in it.
II · Identity
Structure and descriptors
Descriptors are computed here with RDKit from the structure PubChem returns — not from the archive's stored copy, so an edited local structure cannot reach this table.
- Formula
- C11H12O3R
- Molecular weight
- 192.21g/molR
- Exact mass
- 192.0786DaR
- cLogP
- 2.15R
- TPSA
- 27.7ŲR
- H-bond donors
- 0R
- H-bond acceptors
- 3R
- Rotatable bonds
- 3R
- Aromatic rings
- 1R
- Heavy atoms
- 14R
- Fraction sp³
- 0.273R
- Formal charge
- 0R
Computed with RDKit 2025.09.2 from the SMILES returned by PubChem. Audit run 26/09/2026.
Bemis–Murcko scaffold
c1ccc2c(c1)OCO2
Shared with 1,3-Benzodioxolyl-N-ethylbutanamine, 1,3-Benzodioxolyl-N-ethylpentanamine, 1,3-Benzodioxolyl-N-methylpentanamine, 1,3-Benzodioxolylbutanamine, 2-Bromo-4,5-methylenedioxyamphetamine, 2,3-Dimethoxy-4,5-methylenedioxyamphetamine and 31 more. All families
III · Behavior
Behavioral summary
Class, mechanism, and the duration of acute effects — each quoted from the record or trial that publishes it. Duration of effects and plasma half-life are shown separately, because they are different quantities and diverge by a factor of three or four.
Classification
MeSH indexes no pharmacological class for this compound.
Duration of acute subjective effects
—
No controlled human trial reporting a duration for this compound is cited here. The archive holds no other record of one either. A duration is not inferred from a chemical relative.
Plasma elimination half-life
How fast the body clears the drug — not how long the effects last. The two diverge sharply: LSD is cleared with a half-life of about 2.6 h while its subjective effects run 8–12 h.
No half-life is published for this compound in the sources this site reads.
Primary pharmacological drivers
ChEMBL holds no curated mechanism-of-action record for this compound. The measured affinities below are the evidence this archive has for what it binds.
Mechanism, as published
Quoted verbatim from the database named after each passage, never summarized.
To evaluate the hepatoprotective activity of spices, 21 different spices were fed to rats with liver damage caused by lipopolysaccharide (LPS) plus d-galactosamine (D-GalN). As assessed by plasma aminotranferase activities, nutmeg showed the most potent hepatoprotective activity. Bioassay-guided isolation of the active compound from nutme…
Hazardous Substances Data Bank (HSDB)PMID 12617584Morita T et al; J Agric Food Chem 51 (6): 1560-5 (2003) Mouse hepatoma Hepa-1c1c7 (Hepa-1) cells were treated with myristicin to assess the role of myristicin in the process of Cyp1a-1 induction. Treatment of Hepa-1 cells with myristicin increased Cyp1a-1 transcription in a dose-dependent manner as shown by analysis of 7-ethoxyresorufin O-deethylase activity, Cyp1a-1 protein level, and Cyp1a-1…
Hazardous Substances Data Bank (HSDB)PMID 9168900Jeong HG et al; Biochem Biophys Res Commun 233 (3): 619-22 (1997)
IV · Clinical
Clinical description
Where this compound's substance class sits in ICD-11 and DSM-5-TR, and how much of the recorded literature speaks to each domain of a mental status examination.
No diagnostic chapter is shown for this compound. Either PubChem records no MeSH pharmacological class for it, or the class it records is not one of the substance classes ICD-11 gives a chapter to. Inferring a chapter from the compound’s name or its binding profile would be a diagnosis this archive is in no position to make.
How much has been written about each domain
The clinical domains, and how many of the records this archive holds for this compound say something under each. What the terms mean, and the word list behind every spoke, are set out in the method.
- Perception 1
- matched on “hallucinat” · in Toxicology: Hazardous Substances Data Bank (HSDB)
- Cognition 1
- matched on “concentrat” · in PMID 12617584
V · Systems
Systems physiology
Where the targets this compound binds are transcribed — brain regions on the left, peripheral and autonomic tissues on the right. A join of two measurements, not a claim about what the compound does to either.
Brain
basal ganglia: drawn as the caudate nucleus, putamen and globus pallidus.
Measured but not drawn — this anatomogram has no outline for them: retina 0.3, pituitary gland 0.2.
Body
Square-root ramp · shared scale across both plates
Shading is transcript level — not affinity, and not affinity combined with expression. Outlined but unshaded organs hold none of this compound’s resolved targets above the atlas’s detection threshold. Anatomy from EMBL-EBI Anatomogram (Apache License 2.0); regions identified by Uberon (uberon.org), CC BY 3.0.
Brain regions
Regions where this compound's measured targets are transcribed. Linked from the plate above.
Peripheral & autonomic
Tissues outside the CNS expressing the same targets — where a compound's bodily effects become possible.
liver
3367.1 nTPM- Cytochrome P450 3A4CYP3A45.0 pX3367.1
small intestine
754.5 nTPM- Cytochrome P450 3A4CYP3A45.0 pX754.5
duodenum
713.0 nTPM- Cytochrome P450 3A4CYP3A45.0 pX713.0
pancreas
25.3 nTPM- Cytochrome P450 3A4CYP3A45.0 pX25.3
kidney
4.2 nTPM- Cytochrome P450 3A4CYP3A45.0 pX4.2
adrenal gland
3.4 nTPM- Cytochrome P450 3A4CYP3A45.0 pX3.4
colon
2.9 nTPM- Cytochrome P450 3A4CYP3A45.0 pX2.9
skeletal muscle
1.5 nTPM- Cytochrome P450 3A4CYP3A45.0 pX1.5
stomach 1
1.1 nTPM- Cytochrome P450 3A4CYP3A45.0 pX1.1
salivary gland
0.2 nTPM- Cytochrome P450 3A4CYP3A45.0 pX0.2
heart muscle
0.1 nTPM- Cytochrome P450 3A4CYP3A45.0 pX0.1
spleen
0.1 nTPM- Cytochrome P450 3A4CYP3A45.0 pX0.1
Each row joins two published measurements and nothing else: the affinity this archive holds for the compound at that target, and the transcript level the Human Protein Atlas reports for that target’s gene in that region. Bars scale with expression only. Expression is not activation — a receptor transcribed in a region is a receptor available to be bound there, which is a weaker and more defensible claim than saying the region is affected.
Expression data from Human Protein Atlas (CC BY-SA 3.0), RNA expression, nTPM (normalized transcripts per million), consensus tissue dataset. Uhlén M, et al. Tissue-based map of the human proteome. Science. 2015;347(6220):1260419.
VI · Profile
Affinity rosette
The strongest measurement at each of 1 molecular targets. Cell-line and whole-organism screens are excluded here — they carry no affinity — and appear in the table below.
VII · Toxicology
Toxicological profile
What has been measured, and what has been published — kept apart, and neither scored. There is no risk rating on this page; the archive once carried one, identical for every compound, produced by a stub.
Measured in this archive
Assays that bear on toxicity, drawn from the same ChEMBL records as everything else on this page. They are measurements of what a compound binds or does to cells — not verdicts about what it does to a person.
Cytochrome P450 inhibition 1
Inhibition of a drug-metabolising enzyme, which is how interactions arise — the harmala alkaloids' MAO inhibition is the same kind of fact, and appears with the measurements above.
- Cytochrome P450 3A4Potency10,000nMCHEMBL1613886
As published
Quoted verbatim from the database named after each passage, never summarized — a summary of a toxicology statement is a new claim.
Toxicity Summary
Myristicin exerts possible neurotoxic effects on dopaminergic neurons and is a weak inhibitor of monoamine oxidase. (L1271)
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Ingestion of five or more grams of nutmeg causes acute nutmeg poisoning, which includes giddiness, hallucinations, and feelings of depersonalization. Symptoms usually appear three to six hours after ingestion of 1-3 whole nutmegs or 5-15 gm of the grated spice. Recovery usually occurs within 24 hours. Nevertheless, duration of action may extend beyond several days and even include death. /Nutmeg/
Hazardous Substances Data Bank (HSDB)Green RC, Jr; JAMA 171 (10): 1342-4 (1959); Painter JC et al; Clin Toxicol 4 (1): 1-4 (1971)
/SIGNS AND SYMPTOMS/ Chronic poisoning by oral administration has caused temporary (up to six months) psychosis in prison inmates. /Myristica fragrans/
Hazardous Substances Data Bank (HSDB)International Programme on Chemical Safety (IPCS); Poisons Information Monograph: Myristica Fragrans Houtt (PIM 355) (1991) Available from, as of June 14, 2007: https://www.inchem.org/pages/pims.html
/SIGNS AND SYMPTOMS/ Myristicin, or methoxysafrole, is the principal aromatic constituent of the volatile oil of nutmeg, the dried ripe seed of Myristica fragrans. Myristicin is also found in several members of the carrot family (Umbelliferae). Several intoxications have been reported after an ingestion of approximately 5 g of nutmeg, corresponding to 1-2 mg myristicin/kg body weight (b.w.). Although these intoxicati…
Hazardous Substances Data Bank (HSDB)PMID 9496377Hallstrom H, Thuvander A; Nat Toxins 5 (5): 186-92 (1997)
/SIGNS AND SYMPTOMS/ The effects by inhalation are generally similar to those experienced via oral administration with the exception that onset is faster by 15 minutes. /Myristica fragrans/
Hazardous Substances Data Bank (HSDB)International Programme on Chemical Safety (IPCS); Poisons Information Monograph: Myristica Fragrans Houtt (PIM 355) (1991) Available from, as of June 14, 2007: https://www.inchem.org/pages/pims.html
For more Human Toxicity Excerpts (Complete) data for MYRISTICIN (11 total), please visit the HSDB record page.
Published passages via PubChem toxicology sections, aggregating Hazardous Substances Data Bank (HSDB), RTECS, LiverTox. No figure on this page is scored, ranked or combined into a risk level.
VIII · Evidence
Every measurement
One row per published value. The identifier in the last column resolves to the ChEMBL assay record it was read from.
Functional readouts 1
IC₅₀, EC₅₀, AC₅₀ and potency. Assay-dependent, and not interchangeable with a binding constant.
| Target | Class | Type | Value (nM) | pX | Organism | Assay |
|---|---|---|---|---|---|---|
| Cytochrome P450 3A4 | Enzymes | Potency | 10,000 | 5.00 | Homo sapiens | CHEMBL1613886 |
- P
- PubChem
- C
- ChEMBL
- R
- Computed here with RDKit
- D
- Derived here from the stored measurement
IX · Trials
Registered clinical trials
Studies filed with ClinicalTrials.gov that name this compound as an intervention. A registered trial is a protocol, not a result — status and enrollment are printed beside every row, and withdrawn studies are counted rather than hidden.
— No registered study names Myristicin as an intervention. That is an absence of registered research, not evidence about the compound. Most of this archive has never been the subject of a registered trial.
Records from ClinicalTrials.gov (U.S. National Library of Medicine, NIH), API v2. A study is listed against a compound only when a verified name for that compound appears as a whole word in one of the study's own intervention names. A short code must appear as written, and a name the registry uses for something else (Aleph, a vaccine maker) is not matched. Title matches are not accepted. The matched name and the intervention text it matched are shown with every row.
Searched as Myristicin · 6-Allyl-4-methoxy-1,3-benzodioxole · Myristicine. Run this search at the registry.
A registered trial is a protocol somebody filed with the registry. It is not a result, and nothing on this plate says whether Myristicin worked.
X · Legal
Controlled-substance status
United States federal scheduling, read from the DEA records this archive holds. Not legal advice, and an absent record is not a finding that a compound is uncontrolled.
An absent DEA record is not a finding that Myristicin is legal. It means this archive holds no DEA passage for it. The Controlled Substances Analogue Enforcement Act reaches substances that appear on no schedule by name, and many compounds here are ring-substituted analogues of scheduled drugs. Nothing on this plate should be read as saying a compound may lawfully be made, held or supplied.
United States federal status only. State law differs, and so does the law of every other country — none of it is represented here. Scheduling changes, and this reflects the DEA records held by PubChem descriptive sections when the monograph was last harvested, not necessarily today. This is a record of what a database publishes, not legal advice.
XI · Literature
Sources behind this dossier
The papers this compound's values were read from, ranked by what each contributed. Not a review of the field.
Every paper below is one some value on this page came from — a binding constant, a passage of pharmacology or toxicology, or a measured duration. Each entry says what this archive took from it. Nothing else is claimed about any of them: the title is the study’s own account of itself, and a summary written here would be an assertion with no source behind it.
- 01
Morita T, Jinno K, Kawagishi H et al. · Journal of agricultural and food chemistry 2003
- · Mechanism of Action
- 02
Murine Cyp1a-1 induction in mouse hepatoma Hepa-1C1C7 cells by myristicin
Jeong HG, Lee SS, Kim HK et al. · Biochemical and biophysical research communications 1997
- · Mechanism of Action
- 03
Toxicological evaluation of myristicin
Hallström H, Thuvander A · Natural toxins 1997
- · Human Toxicity Excerpts