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TerpeneMonoterpene

Linalool

C₁₀H₁₈O154.25 g/mol

A monoterpene of lavender, coriander and hemp: a terpene, not a cannabinoid, whose action at CB1 remains disputed.

UnscheduledUpdated on
2D structure, after PubChem.

In plain terms

Linalool is one of the main constituents of lavender essential oil, of which it makes up nearly a third, and of coriander oil. Hemp makes it too. It is a terpene, not a cannabinoid: laboratory studies disagree on its action at THC's receptors, one finding none, the other a weak effect at very high concentration. On contact with air, it oxidises into compounds that can cause a skin allergy.

Receptors and activity

  • CB1No measured activity

    No hyperpolarisation of its own and no change in the response to CP55,940 (1 µM) or to Δ9-THC (Santiago 2019)

    Santiago et al. 2019, Cannabis Cannabinoid Res (new tab) · membrane potential (FLIPR), AtT20 cells expressing human CB1; racemic linalool from 1 nM to 100 µM

  • CB2No measured activity

    No hyperpolarisation of its own and no change in the response to CP55,940 (1 µM) or to Δ9-THC (Santiago 2019)

    Santiago et al. 2019, Cannabis Cannabinoid Res (new tab) · membrane potential (FLIPR), AtT20 cells expressing human CB2; racemic linalool from 1 nM to 100 µM

  • CB1Agonist

    Low-potency activation, at high micromolar concentrations (500 µM in the rimonabant assay), with no fittable curve; no measurable [3H]CP55,940 displacement and no β-arrestin 2 recruitment (LaVigne 2021)

    LaVigne et al. 2021, Sci Rep (new tab) · ERK phosphorylation blocked by rimonabant and partial inhibition of forskolin-stimulated cAMP, CHO cells expressing human CB1

  • CB2Not established

    ERK phosphorylation reported in a supplementary figure, with no antagonist test and no pharmacological characterisation (LaVigne 2021)

    LaVigne et al. 2021, Sci Rep (new tab) · ERK phosphorylation, CHO cells expressing human CB2

  • GABA-APositive allosteric modulator

    Current raised to 160 ± 14% of control by 2 mM linalool (Milanos 2017)

    Milanos et al. 2017, Front Chem (new tab) · chloride current induced by 10 µM GABA, α1β2γ2 receptor expressed in HEK293 cells (whole-cell)

  • GABA-ANo measured activity

    No effect on [3H]muscimol binding (Brum 2001)

    Brum, Elisabetsky & Souza 2001, Phytother Res (new tab) · [3H]muscimol binding (GABA site), cortical membranes

  • NMDABinding (function not established)

    IC50 = 2970 µM · mouse

    Brum, Elisabetsky & Souza 2001, Phytother Res (new tab) · non-competitive inhibition of [3H]MK801 binding, cortical membranes

Measured effects

Not characterised. No placebo-controlled human trial has measured the effects of Linalol, so no level is shown.

Levels computed from placebo-controlled human trials: difference from placebo on 100, at the dose and route stated. Read the method

Boiling point

  • α-Pinene156 °C
  • Myrcene167 °C
  • Limonene178 °C
  • Linalool198 °C
  • β-Caryophyllene256 °C

At atmospheric pressure, among the profile’s terpenes.

Sources: Myrcene, PubChem (HSDB), Limonene, NIST Chemistry WebBook, β-Caryophyllene, PubChem (JECFA), Linalool, PubChem (CRC Handbook), α-Pinene, PubChem (HSDB).

Pharmacology

Linalool is a terpene, not a cannabinoid: an acyclic ten-carbon monoterpene alcohol, it has neither the skeleton of phytocannabinoids nor an established affinity for their receptors. It exists as two enantiomers, (R)-(−)-linalool, isolated from lavender oil, and (S)-(+)-linalool, isolated from coriander oil (Sugawara 2000); in 20 authentic lavender oils, the (R) form made up 93.8 % of the linalool (Capetti 2021). Its action at cannabinoid receptors remains disputed. In cells expressing human CB1 or CB2, it produced no effect up to 100 µM, alone or combined with Δ9-THC (Santiago 2019); the study by Finlay et al. (2020), often cited alongside it, did not test linalool. LaVigne et al. (2021), by contrast, described rimonabant-sensitive CB1 activation, at concentrations above 10 µM and up to 500 µM depending on the terpene, with no measurable binding at the orthosteric site; in mice, 200 mg/kg given intraperitoneally produced hypothermia, catalepsy and hypolocomotion, as well as weak antinociception blocked by rimonabant. Other targets appear only at millimolar concentrations: potentiation of GABA-A receptors (Milanos 2017), non-competitive inhibition of binding to the NMDA receptor (Brum 2001). In mice, linalool odour produced an anxiolytic-like effect without motor impairment, absent in animals made anosmic and abolished by flumazenil (Harada 2018); inhaled for one hour at 1 or 3 %, it prolonged pentobarbital-induced sleep without impairing motor coordination (Linck 2009). In humans, pharmacokinetic data are limited to a few measurements, including a peak plasma level of 121 ng/ml 19 minutes after a massage with lavender oil in one volunteer (EMA 2012). In air, linalool oxidises into allergenic hydroperoxides: tested at 6.0 % in 2 900 patients from six countries, oxidised linalool gave 6.9 % positive reactions (Bråred Christensson 2012). In the United States, it is listed among synthetic flavouring substances generally recognised as safe (21 CFR 182.60).

Going further

A monoterpene alcohol found in the essential oils of many aromatic plants. It made up 23.8 to 33.0 % of true lavender essential oil (Lavandula angustifolia) in 20 authentic batches, against a range of 20.0 to 45.0 % set by the European Pharmacopoeia (Capetti 2021), and about 70 % of coriander fruit essential oil (Burdock 2009). It is among the most common terpenoids of cannabis (Santiago 2019), without being one of the three most abundant on average in US commercial samples, which are myrcene, β-caryophyllene and limonene (Smith 2022). Hemp makes it itself through terpene synthases in its trichomes (Zager 2019).

Like other monoterpenes, linalool derives from geranyl pyrophosphate, the ten-carbon precursor that terpene synthases convert into monoterpenes and that is also used in cannabinoid biosynthesis (Booth 2017). In the glandular trichomes of cannabis, two functionally characterised enzymes, CsTPS18VF and CsTPS19BL, are nerolidol/linalool synthases (Zager 2019). Content depends on the variety: the hemp « Finola » contains few monoterpene alcohols such as linalool, although they are common in other varieties (Booth 2017).

References

  1. Santiago et al. 2019, Cannabis Cannabinoid Res: absence of entourage, terpenoids commonly found in Cannabis sativa do not modulate Δ9-THC at human CB1 and CB2 receptors (linalool included) (new tab)PMID 31559333
  2. LaVigne et al. 2021, Sci Rep: cannabimimetic cannabis terpenes, CB1 activation at high concentrations (new tab)PMID 33859287
  3. Finlay et al. 2020, Front Pharmacol: terpenoids from cannabis do not mediate an entourage effect by acting at cannabinoid receptors (linalool not tested) (new tab)PMID 32269529
  4. Zager et al. 2019, Plant Physiol: gene networks underlying cannabinoid and terpenoid accumulation in cannabis, nerolidol and linalool synthases (new tab)PMID 31138625
  5. Booth et al. 2017, PLoS One: terpene synthases of Cannabis sativa (new tab)PMID 28355238
  6. Harada et al. 2018, Front Behav Neurosci: linalool odor-induced anxiolytic effects in mice (new tab)PMID 30405369
  7. Linck et al. 2009, Phytomedicine: inhaled linalool-induced sedation in mice (new tab)PMID 18824339
  8. Milanos et al. 2017, Front Chem: metabolic products of linalool and modulation of GABAA receptors (new tab)PMID 28680877
  9. Brum, Elisabetsky & Souza 2001, Phytother Res: effects of linalool on [3H]MK801 and [3H]muscimol binding in mouse cortical membranes (new tab)PMID 11507735
  10. Leal-Cardoso et al. 2010, Eur J Pharmacol: linalool blocks excitability in peripheral nerves and voltage-dependent Na+ current (new tab)PMID 20655301
  11. Sugawara et al. 2000, Chem Senses: odor distinctiveness between enantiomers of linalool (new tab)PMID 10667997
  12. Capetti et al. 2021, Molecules: adulteration of essential oils, lavender case study (linalool and enantiomeric composition) (new tab)PMID 34577081
  13. Burdock & Carabin 2009, Food Chem Toxicol: safety assessment of coriander essential oil (linalool, about 70%) (new tab)PMID 19032971
  14. Smith et al. 2022, PLoS One: the phytochemical diversity of commercial cannabis in the United States (new tab)PMID 35588111
  15. Chadha & Madyastha 1984, Xenobiotica: metabolism of geraniol and linalool in the rat (new tab)PMID 6475100
  16. Meesters, Duisken & Hollender 2007, Xenobiotica: cytochrome P450-mediated oxidative metabolism of linalool (new tab)PMID 17614007
  17. Debong et al. 2024, Mol Nutr Food Res: linalool, 1,8-cineole and eugenol transfer from a curry dish into human urine (new tab)PMID 37953385
  18. Doroshyenko et al. 2013, Drug Metab Dispos: Silexan (oral lavender oil) and cytochromes P450 in healthy volunteers (new tab)PMID 23401474
  19. Heuberger, Redhammer & Buchbauer 2004, Neuropsychopharmacology: transdermal absorption of (-)-linalool in humans (new tab)PMID 15238993
  20. Sköld et al. 2004, Chem Res Toxicol: contact allergens formed on air exposure of linalool (new tab)PMID 15606147
  21. Christensson et al. 2010, Contact Dermatitis: linalool, a significant contact sensitizer after air exposure (new tab)PMID 20136877
  22. Bråred Christensson et al. 2012, Contact Dermatitis: air-oxidized linalool, a frequent cause of fragrance contact allergy (new tab)PMID 22906042
  23. Fischedick et al. 2010, Phytochemistry: metabolic fingerprinting of Cannabis sativa, cannabinoids and terpenoids (validated GC-FID) (new tab)PMID 21040939
  24. EMA/HMPC/143183/2010, assessment report on Lavandula angustifolia (27 March 2012): pharmacokinetics and toxicology of linalool (new tab)
  25. Implementing Regulation (EU) No 872/2012: Union list of flavouring substances, FL 02.013 linalool (new tab)
  26. Regulation (EC) No 1223/2009 on cosmetic products, Annex III, entry 84 (linalool) (new tab)
  27. Regulation (EU) 2017/776: harmonised CLP classification of linalool, Skin Sens. 1B (index 603-235-00-2) (new tab)
  28. 21 CFR 182.60: synthetic flavoring substances and adjuvants (linalool) (new tab)
  29. INCB, Green List, 36th ed. 2025 (1971 Convention) (new tab)
  30. PubChem CID 6549, linalool (new tab)

Identifiers

Names

Common name
Linalool
IUPAC name
3,7-diméthylocta-1,6-dién-3-ol
Other names
β-linalol · β-linalool · alcool linalylique · 3,7-diméthylocta-1,6-dién-3-ol

Identifiers

Formula
C₁₀H₁₈O
CAS
78-70-6
PubChem CID
6549(new tab)
InChIKey
CDOSHBSSFJOMGT-UHFFFAOYSA-N
SMILES
CC(=CCCC(C)(C=C)O)C

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.

In the Journal

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