beta-Caryophyllene
PubChem records this structure as (-)-Caryophyllene.
Also known as(-)-Caryophyllene · Caryophyllene · (-)-trans-Caryophyllene · L-Caryophyllene · trans-beta-caryophyllene · beta-Caryophyllen · (-)-E-Caryophyllene · trans-Caryophyllene
(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
- PubChem CID
- 5281515
- ChEMBL
- CHEMBL445740
- Measurements
- 1
- InChIKey
- NPNUFJAVOOONJE-GFUGXAQUSA-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
Beta-caryophyllene is a pale yellow oily liquid with an odor midway between odor of cloves and turpentine. (NTP, 1992)
CAMEO ChemicalsNational Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
(-)-beta-caryophyllene is a beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. It has a role as an insect attractant, a metabolite, a non-steroidal anti-inflammatory drug and a fragrance. It is an enantiomer of a (+)-beta-caryophyllene.
caryophyllene has been reported in Camellia sinensis, Trichogonia grazielae, and other organisms with data available.
Cannabinoid is any compound capable of activating the cannabinoid receptor CB1 and/or CB2. Cannabinoids include phytocannabinoids, endocannabinoids and (semi-)synthetic cannabinoids. They exert a wide variety of biological activities including anti-inflammatory, anti-emetic, anticonvulsant, antiglaucoma, analgesic and neuroprotective effects; while some exert psychoactive effects, including euphoria.
Recognized use
Found in many essential oils, especially clove oil; Used in perfumes; [Merck Index] Used as flavoring agent or adjuvant and coloring agent for foods; [FDA] Also used to suppress intestinal bacteria; [NTP]
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.
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
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 beta-Caryophyllene 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 beta-Caryophyllene 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 — nothing published for beta-Caryophyllene. An absent record is an absence of study, not evidence of safety.
- Legal — listed by the DEA among its drugs of concern, with no schedule stated in the record held here.
- 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 beta-Caryophyllene 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
- C15H24R
- Molecular weight
- 204.36g/molR
- Exact mass
- 204.1878DaR
- cLogP
- 4.73R
- TPSA
- 0.0ŲR
- H-bond donors
- 0R
- H-bond acceptors
- 0R
- Rotatable bonds
- 0R
- Aromatic rings
- 0R
- Heavy atoms
- 15R
- Fraction sp³
- 0.733R
- Formal charge
- 0R
Computed with RDKit 2025.09.2 from the SMILES returned by PubChem. Audit run 26/09/2026.
Bemis–Murcko scaffold
C=C1CC/C=C/CC[C@H]2CC[C@H]12
No other compound in this archive shares it. 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
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.
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.
None of the 0 records this archive holds for this compound uses a term from any of the clinical domains. That is a statement about the literature recorded here, not about the compound.
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 16.6, midbrain 5.0, spinal cord 3.8, pituitary gland 2.4.
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.
retina
16.6 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX16.6
basal ganglia
5.2 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX5.2
midbrain
5.0 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX5.0
amygdala
4.9 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX4.9
cerebral cortex
4.6 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX4.6
spinal cord
3.8 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX3.8
hippocampal formation
3.7 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX3.7
hypothalamus
3.3 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX3.3
pituitary gland
2.4 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX2.4
cerebellum
1.9 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX1.9
Peripheral & autonomic
Tissues outside the CNS expressing the same targets — where a compound's bodily effects become possible.
liver
30.8 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX30.8
heart muscle
26.2 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX26.2
skeletal muscle
24.0 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX24.0
kidney
20.8 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX20.8
small intestine
18.1 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX18.1
duodenum
17.6 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX17.6
colon
10.7 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX10.7
pancreas
7.1 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX7.1
salivary gland
7.1 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX7.1
thyroid gland
6.9 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX6.9
adrenal gland
6.2 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX6.2
stomach 1
5.5 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX5.5
urinary bladder
4.7 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX4.7
smooth muscle
4.3 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX4.3
spleen
4.2 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX4.2
lung
4.1 nTPM- Peroxisome proliferator-activated receptor alphaPPARA5.0 pX4.1
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.
No hERG, cytochrome, cytotoxicity or transport measurement exists for beta-Caryophyllene in this archive.
Published toxicology
— None. The toxicology databases this site reads — HSDB, RTECS and LiverTox, by way of PubChem — hold no record for beta-Caryophyllene. They index compounds that have been studied for decades, so most of this archive has no entry. An absent record is an absence of study, not evidence of safety.
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 |
|---|---|---|---|---|---|---|
| Peroxisome proliferator-activated receptor alpha | Nuclear receptors | EC50 | 9,580 | 5.02 | Homo sapiens | CHEMBL5241794 |
- 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.
3T
Registered studies
1T
Open or ongoing
3T
With a phase recorded
By phase
A study may carry two phase codes at once, so these count studies bearing each phase and do not sum to the total.
- Phase 13
- Phase 21
By status
The registry’s own status for each record. Withdrawn and terminated studies are counted here rather than hidden — a stopped trial is part of what is known.
- Completed1
- Active, not recruiting1
- Withdrawn1
Every matched study
Newest first by start date. Each identifier opens the registry record it came from; the title is the sponsor’s own, quoted.
- NCT06218407Completed · Phase 1
Development and Evaluation of Computerized Chemosensory Based Orbitofrontal Networks Training for Treatment of Pain
- Enrollment
- 86Tactual
- Started
- 2023-04-27
- Sponsor
- Evon Medics LLC
Conditions Chronic Pain · Low Back Pain
Matched “beta-Caryophyllene” in the study’s intervention “Computerized Chemosensory-Based Orbitofrontal Cortex Training plus beta caryophyllene (CBOT-Plus)”
- NCT04451863Active, not recruiting · Phase 1
Analgesic and Subjective Effects of Terpenes
- Enrollment
- 45Testimated
- Started
- 2021-12-15
- Sponsor
- University of California, Los Angeles
Conditions Pain · Abuse, Drug
Matched “beta-Caryophyllene” in the study’s intervention “Low Beta-Caryophyllene”
- NCT04794205Withdrawn · Phase 1 / Phase 2
Acute Changes In Thermal Pain Response Following Single Oral Dose of Beta-Cary
- Enrollment
- 0Tactual
- Started
- 2021-09
- Sponsor
- Hartford Hospital
Conditions Beta-Caryophyllene
Matched “beta-Caryophyllene” in the study’s intervention “Low Dose Beta-Caryophyllene”
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 beta-Caryophyllene · (-)-Caryophyllene · Caryophyllene. Run this search at the registry — it returns the unfiltered result, including studies this page rejected as belonging to a different molecule.
A registered trial is a protocol somebody filed with the registry. It is not a result, and nothing on this plate says whether beta-Caryophyllene worked.
X · Legal
Controlled-substance status
United States federal scheduling, read from the DEA records this archive holds and shown with the passage each was read from. Not legal advice, and not necessarily current.
- DEA class
- Other Substances
- Added
- March 2022
As the DEA states it
Quoted whole. The badge above is a reading of these passages and adds nothing to them.
beta-Caryophyllene (Class: Other Substances, Added Date: 03-2022)
Other regulatory records
Registers outside the DEA that hold an entry for beta-Caryophyllene — chemical-safety and national inventories, each naming itself. They are not scheduling decisions.
Chemical: Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 19-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/20872
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-: Does not have an individual approval but may be used under an appropriate group standard
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.
No reference is recorded against any value for this compound. Its measurements come from ChEMBL assay records that carry an assay identifier but no publication, so there is no paper to cite here — an absence in the upstream record, not a judgment about the evidence. The assay identifiers in Every measurement resolve to the records the values were read from.