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TerpeneMonoterpene

α-Pinene

C₁₀H₁₆136.23 g/mol

A monoterpene of pine, turpentine and hemp, with no measurable activity at CB1 or CB2 (Santiago 2019, Finlay 2020).

UnscheduledUpdated on
2D structure, after PubChem.

In plain terms

Alpha-pinene is a pine-scented terpene, the main constituent of turpentine; it is also found in rosemary and in hemp itself. It is not a cannabinoid: tested in the laboratory, it acts on neither the CB1 nor the CB2 receptor. It is authorised as a food flavouring in the European Union; breathed at high concentration, it irritated the eyes, nose and throat of volunteers, and in rats and mice exposed by inhalation for two years it increased the frequency of several tumours.

Receptors and activity

  • CB1No measured activity

    No change in membrane potential, nor in the response to CP55,940 (1 µM) or to Δ9-THC

    Santiago et al. 2019, Cannabis Cannabinoid Res (new tab) · membrane potential (potassium channels), AtT20 cells expressing human CB1; (+)-α-pinene from 1 nM to 100 µM

  • CB2No measured activity

    No change in membrane potential, nor in the response to CP55,940 (1 µM) or to Δ9-THC

    Santiago et al. 2019, Cannabis Cannabinoid Res (new tab) · membrane potential (potassium channels), AtT20 cells expressing human CB2; (+)-α-pinene from 1 nM to 100 µM

  • CB1No measured activity

    Radioligand binding unchanged and cAMP not modified, alone or with Δ9-THC, cannabidiol or 2-AG

    Finlay et al. 2020, Front Pharmacol (new tab) · [3H]CP55,940 displacement, membranes of HEK cells expressing human CB1, and cAMP signalling (CAMYEL BRET biosensor); α-pinene at 10 µM

  • CB2No measured activity

    Radioligand binding unchanged and cAMP not modified, alone or with Δ9-THC, cannabidiol or 2-AG

    Finlay et al. 2020, Front Pharmacol (new tab) · [3H]CP55,940 displacement, membranes of HEK cells expressing human CB2, and cAMP signalling (CAMYEL BRET biosensor); α-pinene at 10 µM

  • TRPA1No measured activity

    No change in intracellular calcium, nor in activation by cinnamaldehyde, Δ9-THC or 2-AG

    Heblinski et al. 2020, Cannabis Cannabinoid Res (new tab) · intracellular calcium, HEK Flp-In T-Rex cells expressing human TRPA1; (+)-α-pinene at 10 µM

  • TRPV1No measured activity

    No change in intracellular calcium, nor in activation by capsaicin or anandamide

    Heblinski et al. 2020, Cannabis Cannabinoid Res (new tab) · intracellular calcium, HEK Flp-In T-Rex cells expressing human TRPV1; (+)-α-pinene at 10 µM

  • AChEInhibitor

    IC50 = 630 µM · human

    Perry et al. 2000, J Pharm Pharmacol (new tab) · human erythrocyte acetylcholinesterase, Ellman method; uncompetitive and reversible inhibition

  • AChEInhibitor

    (+)- and (−)-α-pinene among the potent inhibitors of the 17 bicyclic monoterpenoids tested (colorimetric method); uncompetitive inhibition

    Miyazawa & Yamafuji 2005, J Agric Food Chem (new tab)

  • Site des benzodiazépines (récepteur GABA-A)Modulator

    Lengthens the decay constant of spontaneous inhibitory postsynaptic currents; effect abolished by flumazenil; binding to the α1 and γ2 subunits proposed by molecular docking

    Yang et al. 2016, Mol Pharmacol (new tab) · electrophysiology in hippocampal slices, CA1 pyramidal neurons; (−)-α-pinene

Measured effects

Not characterised. No placebo-controlled human trial has measured the effects of alpha-Pinene, 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

α-Pinene is a bicyclic monoterpene, a terpene and not a cannabinoid: it does not carry the cannabinoid skeleton and does not act on cannabinoid receptors. In cells expressing the human receptors, it altered the activity of neither CB1 nor CB2, alone or combined with Δ9-THC, up to 100 µM (Santiago 2019), and neither displaced a radioligand nor altered cAMP signalling through these receptors at 10 µM (Finlay 2020): these two studies do not support an 'entourage effect' acting through the cannabinoid receptors. The 2021 study that calls some cannabis terpenes 'cannabimimetic' did not test α-pinene but β-pinene (LaVigne 2021). Other targets have been described at high concentration or in animals: inhibition of human acetylcholinesterase in vitro (IC50 = 0.63 mM, Perry 2000) and, in mice, a modulation of GABA-A receptors abolished by flumazenil, orally given (−)-α-pinene having lengthened non-rapid eye movement sleep and shortened sleep latency (Yang 2016). The main constituent of turpentine, present in pine trees, rosemary and cannabis (NTP 2026), it is formed in hemp trichomes by a (+)-α-pinene synthase (Booth 2017). In volunteers exposed by inhalation, pulmonary uptake was about 60% at the higher exposures (Falk 1990). In 2026 the National Toxicology Program concluded that there was clear evidence of carcinogenic activity in female rats and in mice of both sexes exposed for two years by inhalation, and some evidence in male rats (NTP 2026). In the United States, 21 CFR 172.515 lists it among the synthetic flavouring substances permitted in food.

Going further

A monoterpene widespread in the plant kingdom, produced notably by pine trees, rosemary and other aromatic herbs, and by cannabis; it is the main constituent of turpentine, which contains 44 to 94% of it (NTP 2026). Hemp makes it itself: in the female flowers of the 'Finola' variety, (+)-α-pinene accounts on average for 23 ± 17% of the monoterpenes (22 plants), and the transcript of the (+)-α-pinene synthase CsTPS2 was the most abundant of the six terpene synthase transcripts measured (Booth 2017). It is a terpene, not a cannabinoid.

A bicyclic monoterpene formed by monoterpene synthases from geranyl pyrophosphate (GPP), the ten-carbon precursor of monoterpenes, itself usually derived from the methylerythritol phosphate pathway. In the trichomes of 'Finola' hemp, the enzyme CsTPS2FN produces mostly (+)-α-pinene, with small amounts of (+)-β-pinene, myrcene and (−)-limonene; the enzyme CsTPS5FN forms mainly myrcene and, among four other monoterpenes, (−)-α-pinene (23% of its products) (Booth 2017). GPP is also used in the biosynthesis of hemp's cannabinoids, but α-pinene, a ten-carbon hydrocarbon without an aromatic ring, does not belong to that pathway.

References

  1. Santiago et al. 2019, Cannabis Cannabinoid Res: « Absence of Entourage », terpenoids and Δ9-THC activity at human CB1 and CB2 receptors (new tab)PMID 31559333
  2. Finlay et al. 2020, Front Pharmacol: terpenoids from cannabis, no entourage effect via cannabinoid receptors (new tab)PMID 32269529
  3. Heblinski et al. 2020, Cannabis Cannabinoid Res: terpenoids, phytocannabinoids and TRPA1 and TRPV1 channels (new tab)PMID 33376801
  4. LaVigne et al. 2021, Sci Rep: Cannabis sativa terpenes « cannabimimetic » (β-pinene tested, not α-pinene) (new tab)PMID 33859287
  5. Booth et al. 2017, PLoS One: terpene synthases from Cannabis sativa (new tab)PMID 28355238
  6. Yang et al. 2016, Mol Pharmacol: α-pinene, NREM sleep and GABAA-benzodiazepine receptors in mice (new tab)PMID 27573669
  7. Perry et al. 2000, J Pharm Pharmacol: in vitro inhibition of human erythrocyte acetylcholinesterase by Salvia lavandulaefolia oil and its terpenes (new tab)PMID 10933142
  8. Miyazawa & Yamafuji 2005, J Agric Food Chem: inhibition of acetylcholinesterase by bicyclic monoterpenoids (new tab)PMID 15740071
  9. Falk et al. 1990, Scand J Work Environ Health: uptake, distribution and elimination of alpha-pinene in humans after inhalation (new tab)PMID 2255878
  10. Levin et al. 1992, Int Arch Occup Environ Health: renal elimination of verbenols after alpha-pinene inhalation (new tab)PMID 1587632
  11. Eriksson & Levin 1990, Int Arch Occup Environ Health: identification of cis- and trans-verbenol in urine after occupational exposure to terpenes (new tab)PMID 2228258
  12. Schmidt & Göen 2017, Arch Toxicol: human metabolism of α-pinene and metabolite kinetics after oral administration (new tab)PMID 26679931
  13. Schmidt, Belov & Göen 2013, Anal Chim Acta: monitoring of monoterpene metabolites in human urine by GC-PCI-MS/MS (new tab)PMID 23953203
  14. Waidyanatha et al. 2021, Toxicol Appl Pharmacol: toxicokinetic evaluation of α-pinene and α-pinene oxide after inhalation in rodents (new tab)PMID 33744279
  15. Silinski et al. 2020, J Anal Toxicol: quantitation of alpha-pinene in rodent blood and mammary gland by headspace GC-MS (new tab)PMID 33336684
  16. National Toxicology Program 2026, Technical Report 606: toxicology and carcinogenesis of α-pinene by inhalation in rats and mice (new tab)PMID 42531438
  17. Gomes-Carneiro et al. 2005, Food Chem Toxicol: beta-myrcene, alpha-terpinene and (+)- and (-)-alpha-pinene in the Salmonella/microsome test (new tab)PMID 15621337
  18. Karlberg & Lepoittevin 2021, Contact Dermatitis: one hundred years of allergic contact dermatitis due to oxidized terpenes, turpentine allergy (new tab)PMID 34453446
  19. Implementing Regulation (EU) No 872/2012: Union list of flavouring substances (FL 01.004, pin-2(3)-ene) (new tab)
  20. Regulation (EC) No 1272/2008 (CLP), consolidated version of 1 July 2026, Annex VI (new tab)
  21. ANSM, consolidated list of substances classified as narcotics, updated 26/06/2026 (new tab)
  22. INCB, Yellow List of narcotic drugs under international control, 65th edition, July 2026 (new tab)
  23. INCB, Green List of psychotropic substances under international control, 36th edition, 2025 (new tab)
  24. eCFR, 21 CFR 172.515: synthetic flavoring substances and adjuvants (α-pinene; 2-pinene) (new tab)
  25. PubChem, α-pinene, CID 6654 (identifiers and properties) (new tab)
  26. ChEBI, α-pinene, CHEBI:36740 (new tab)

Identifiers

Names

Common name
α-Pinene
IUPAC name
2,6,6-triméthylbicyclo[3.1.1]hept-2-ène
Other names
alpha-pinène · alpha-pinene · pin-2(3)-ène · 2-pinène · 2,6,6-triméthylbicyclo[3.1.1]hept-2-ène

Identifiers

Formula
C₁₀H₁₆
CAS
80-56-8
PubChem CID
6654(new tab)
InChIKey
GRWFGVWFFZKLTI-UHFFFAOYSA-N
SMILES
CC1=CCC2CC1C2(C)C

Machine-readable entry (JSON)

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

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