| Record Information |
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| Version | 1.0 |
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| Created at | 2020-03-19 00:29:40 UTC |
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| Updated at | 2020-12-07 19:07:20 UTC |
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| CannabisDB ID | CDB000300 |
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| Secondary Accession Numbers | Not Available |
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| Cannabis Compound Identification |
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| Common Name | α-pinene |
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| Description | Alpha-Pinene, also known as 2-pinene or acintene A, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-pinene is considered to be an isoprenoid lipid molecule. There are two isomers of alpha-Pinene: (−)-α-pinene and (+)-α-pinene. The (−)-α-pinene isomer is more common in European pines, whereas the (+)-α-isomer is more common in North America. alpha-Pinene is a neutral, hydrophobic molecule, practically insoluble in water. It exists as a clear, colorless oil. Alpha-pinene has a woody, camphoreous, piney or turpentine-like odor and a spicy, woody or herbal taste. It is widely used as a flavor and a fragrance additive and has one of the lowest boiling points of all monoterpenes. Industrially, α-pinene is largely used as starting material for the synthesis of terpineol, camphor, borneol and terpene resin, synthetic perfumes and resins, medicines and other synthetic organic chemicals. Alpha-pinene is found naturally in the essential oils and resins of many coniferous tree species, notably the pine (where it gets its name) as well as in non-coniferous plants such as camphorweed (Heterotheca) and big sagebrush (Artemisia tridentata). It is also found in the essential oil of rosemary, eucalyptus oil and orange peel oil. α-Pinene is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645 ) and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita. α-Pinene, in particular, contributes significantly to many of the varied, distinct, and unique odor profiles of different cannabis strains, varieties and cultivars. Monoterpenes, of which α-pinene is one of the principal species, are emitted in substantial amounts by vegetation. In the atmosphere α-pinene undergoes reactions with ozone, hydroxyl radicals and NO3 radicals to produce several compounds including: pinonaldehyde, norpinonaldehyde, pinic acid, pinonic acid and pinalic acid (PMID: 20017184 ). α-Pinene exhibits a wide range of physiological or drug like effects. There are well-substantiated claims that has anticoagulant, antitumor, antimicrobial, antimalarial, antioxidant, anti-inflammatory, anti-Leishmania, analgesic, gastroprotective, anxiolytic, cytoprotective, anticonvulsant, and neuroprotective effects (PMID: 31739596 ). α-Pinene exhibits activity as an acetylcholinesterase inhibitor, which may aid in memory retention. α-Pinene, in particular, is thought to reduce the memory deficits commonly reported as a side-effect of THC consumption (PMID: 31739596 ). α-Pinene is a positive modulator of GABAA receptors and binds to the benzodiazepine binding site of the GABAA receptor (PMID: 31739596 ). (+)-α-Pinene also binds to Cytochrome P450 2B6 and is a potent inhibitor of this enzyme (PMID: 23786449 ). | Read more...
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| Structure | |
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| Synonyms | | Value | Source |
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| (+)-3,6,6-TRIMETHYLBICYCLO[3.1.1]hept-2-ene | ChEBI | | (1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene | ChEBI | | (1R,5R)-alpha-Pinene | ChEBI | | alpha-Pinene(dextro) | ChEBI | | (1R,5R)-a-Pinene | Generator | | (1R,5R)-Α-pinene | Generator | | a-Pinene(dextro) | Generator | | Α-pinene(dextro) | Generator | | (+)-a-Pinene | Generator | | (+)-Α-pinene | Generator | | (+)-(1R)-alpha-Pinene | HMDB | | (+)-(1R)-α-Pinene | HMDB | | (+)-(1R,5R)-alpha-Pinene | HMDB | | (+)-(1R,5R)-α-Pinene | HMDB | | (+)-2-Pinene | HMDB | | (+)-alpha-Pinene | HMDB | | (1R)-(+)-alpha-Pinene | HMDB | | (1R)-(+)-α-Pinene | HMDB | | (1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene | HMDB | | (1R)-alpha-Pinene | HMDB | | (1R)-α-Pinene | HMDB | | (1R,5R)-(+)-alpha-Pinene | HMDB | | (1R,5R)-(+)-α-Pinene | HMDB | | (R)-(+)-alpha-Pinene | HMDB | | (R)-(+)-α-Pinene | HMDB | | (±)-2-Pinene | HMDB | | (±)-alpha-Pinene | HMDB | | (±)-α-Pinene | HMDB | | 2,6,6-Trimethylbicyclo[3.1.1]hept-2-ene | HMDB | | 2-Pinene | HMDB | | alpha-Pinene | HMDB | | α-Pinene | HMDB | | (1R,5R)-(+)-2-Pinene | PhytoBank | | d-alpha-Pinene | PhytoBank | | d-α-Pinene | PhytoBank |
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| Chemical Formula | C10H16 |
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| Average Molecular Weight | 136.23 |
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| Monoisotopic Molecular Weight | 136.1252 |
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| IUPAC Name | (1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene |
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| Traditional Name | (+)-α-pinene |
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| CAS Registry Number | 7785-70-8 |
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| SMILES | CC1=CC[C@@H]2C[C@H]1C2(C)C |
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| InChI Identifier | InChI=1S/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h4,8-9H,5-6H2,1-3H3/t8-,9-/m1/s1 |
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| InChI Key | GRWFGVWFFZKLTI-RKDXNWHRSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Monoterpenoids |
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| Direct Parent | Bicyclic monoterpenoids |
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| Alternative Parents | |
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| Substituents | - Pinane monoterpenoid
- Bicyclic monoterpenoid
- Branched unsaturated hydrocarbon
- Polycyclic hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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| Role | Industrial application: Biological role: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -62 °C | Not Available | | Boiling Point | 155 to 156 °C | Wikipedia | | Water Solubility | Not Available | Not Available | | logP | 4.44 | GRIFFIN,S ET AL. (1999) |
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| Predicted Properties | [] |
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| Spectra |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| GC-MS | α-pinene, non-derivatized, GC-MS Spectrum | splash10-0006-9100000000-efa1a7d8bd0221192f0d | Spectrum | | GC-MS | α-pinene, non-derivatized, GC-MS Spectrum | splash10-0006-9100000000-efa1a7d8bd0221192f0d | Spectrum | | Predicted GC-MS | α-pinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0079-1900000000-7a79889acc60a4543bcf | Spectrum | | Predicted GC-MS | α-pinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-89e84f859d8f1f97d5c2 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-fb8d56b761aae12a505c | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dr-0900000000-bfe7e4ba927cd83956b4 | 2016-06-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-5e150dd4370565464dad | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-5e150dd4370565464dad | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kr-0900000000-b5dcbaea24fd03f1cbf9 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-a013b4ae27f975ab5621 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-a013b4ae27f975ab5621 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-0900000000-1a368fcdf84da3da6f72 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-32bfa268614bcd6c4f81 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-32bfa268614bcd6c4f81 | 2021-09-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-0900000000-eb6403ceb156dbbc7ce8 | 2021-09-25 | View Spectrum |
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| NMR | Not Available |
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| Pathways |
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| Pathways | Not Available |
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| Protein Targets |
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| Enzymes | |
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| Transporters | |
| Gamma-aminobutyric acid receptor subunit alpha-1 | GABRA1 | 5q34-q35 | P14867 | details |
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| Metal Bindings | |
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| Receptors | |
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| Transcriptional Factors | Not Available |
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| Concentrations Data |
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| 8-Ball Kush | Detected and Quantified | 0.621 mg/g dry wt | | details | | 9 Lb Hammer | Detected and Quantified | 3.323 mg/g dry wt | | details | | 97 Sage | Detected and Quantified | 3.686 mg/g dry wt | | details | | Adonis | Detected and Quantified | 0.387 mg/g dry wt | | details | | Alien Dawg (Indica dominant) | Detected and Quantified | 0.23 +/- 0.04 mg/g dry wt | | details | | Alien Sour Apple | Detected and Quantified | 1.471 mg/g dry wt | | details | | Black Boss | Detected and Quantified | 0.973 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 0.639 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 0.679 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 4.343 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 5.196 mg/g dry wt | | details | | Blue Dream | Detected and Quantified | 4.2 +/- 1.3 mg/g dry wt | | details | | Bob Marley | Detected and Quantified | 1.149 mg/g dry wt | | details | | Chemdawg | Detected and Quantified | 0.266 mg/g dry wt | | details | | Chemdawg #4 | Detected and Quantified | 0.286 mg/g dry wt | | details | | Chemdawg #4 | Detected and Quantified | 0.422 mg/g dry wt | | details | | Cookies and Cream | Detected and Quantified | 0.37 mg/g dry wt | | details | | Cosmic Lotus | Detected and Quantified | 2.686 mg/g dry wt | | details | | Crown Og | Detected and Quantified | 0.3 +/- 0.3 mg/g dry wt | | details | | Dairy Queen | Detected and Quantified | 0.432 mg/g dry wt | | details | | Dark Shadow Haze | Detected and Quantified | 0.56 mg/g dry wt | | details | | FLO | Detected and Quantified | 0.201 mg/g dry wt | | details | | Gas | Detected and Quantified | 0.5 +/- 0.3 mg/g dry wt | | details | | Gelato | Detected and Quantified | 1 +/- 0.1 mg/g dry wt | | details | | Godfather | Detected and Quantified | 2.9 +/- 1 mg/g dry wt | | details | | Goji OG | Detected and Quantified | 0.45 mg/g dry wt | | details | | Golden Cobra | Detected and Quantified | 1.314 mg/g dry wt | | details | | Golden Sage | Detected and Quantified | 0.632 mg/g dry wt | | details | | Gorilla Glue | Detected and Quantified | 0.282 mg/g dry wt | | details | | Gorilla Glue #4 | Detected and Quantified | 0.276 mg/g dry wt | | details | | Grape Ape | Detected and Quantified | 2 +/- 1 mg/g dry wt | | details | | Grape Stomper | Detected and Quantified | 1.033 mg/g dry wt | | details | | Grape Stomper | Detected and Quantified | 1.178 mg/g dry wt | | details | | Grizzly Kush | Detected and Quantified | 0.468 mg/g dry wt | | details | | Hash Plant | Detected and Quantified | 0.133 mg/g dry wt | | details | | Hash Plant | Detected and Quantified | 0.411 mg/g dry wt | | details | | Hemlock | Detected and Quantified | 0.68 mg/g dry wt | | details | | Jabberwocky | Detected and Quantified | 0.403 mg/g dry wt | | details | | Jabberwocky | Detected and Quantified | 0.493 mg/g dry wt | | details | | Jack Herer | Detected and Quantified | 0.213 mg/g dry wt | | details | | Kandy Kush | Detected and Quantified | 0.124 mg/g dry wt | | details | | Kush Puppy | Detected and Quantified | 2.228 mg/g dry wt | | details | | La Choco | Detected and Quantified | 0.356 mg/g dry wt | | details | | Lemon Balm | Detected and Quantified | 0.28 mg/g dry wt | | details | | Lemon Goji | Detected and Quantified | 0.149 mg/g dry wt | | details | | Lemon OG | Detected and Quantified | 2.668 mg/g dry wt | | details | | Lemon Sherbet | Detected and Quantified | 0.323 mg/g dry wt | | details | | Lemon Skunk | Detected and Quantified | 0.493 mg/g dry wt | | details | | Lemon Skunk | Detected and Quantified | 0.659 mg/g dry wt | | details | | Liberty Haze | Detected and Quantified | 4.06 mg/g dry wt | | details | | Lohan | Detected and Quantified | 0.421 mg/g dry wt | | details | | Lucky Charms | Detected and Quantified | 0.55 mg/g dry wt | | details | | Maui Haze | Detected and Quantified | 0.343 mg/g dry wt | | details | | Miami White Kush | Detected and Quantified | 0.8 +/- 0.4 mg/g dry wt | | details | | Moby Dick | Detected and Quantified | 0.305 mg/g dry wt | | details | | Moonshine Ghost Trane Haze | Detected and Quantified | 0.272 mg/g dry wt | | details | | Nightmare Cookie | Detected and Quantified | 0.23 mg/g dry wt | | details | | Og Kush | Detected and Quantified | 0.4 +/- 0.4 mg/g dry wt | | details | | Orange Skunk | Detected and Quantified | 0.111 mg/g dry wt | | details | | Pineapple Skunk | Detected and Quantified | 2.425 mg/g dry wt | | details | | Pipe Dream | Detected and Quantified | 5.241 mg/g dry wt | | details | | Platinum Delight | Detected and Quantified | 0.303 mg/g dry wt | | details | | Purple Cream | Detected and Quantified | 2.1 +/- 0.4 mg/g dry wt | | details | | Purple Eclipse | Detected and Quantified | 0.31 mg/g dry wt | | details | | Purple Princess | Detected and Quantified | 2.7 +/- 0.6 mg/g dry wt | | details | | Purple Urkle | Detected and Quantified | 3.2 +/- 0.6 mg/g dry wt | | details | | Rocket Fuel | Detected and Quantified | 0.386 mg/g dry wt | | details | | Rollex OG | Detected and Quantified | 0.693 mg/g dry wt | | details | | Rosetta Stone | Detected and Quantified | 0.344 mg/g dry wt | | details | | Satori | Detected and Quantified | 2.034 mg/g dry wt | | details | | Sensi Star (Pure Indica) | Detected and Quantified | 0.25 +/- 0.03 mg/g dry wt | | details | | Sherbert | Detected and Quantified | 0.6 +/- 0.3 mg/g dry wt | | details | | Skunk Haze | Detected and Quantified | 3.578 mg/g dry wt | | details | | Skywalker OG | Detected and Quantified | 1.1 mg/g dry wt | | details | | Skywalker Og Kush | Detected and Quantified | 0.4 +/- 0.3 mg/g dry wt | | details | | Spectrum | Detected and Quantified | 0.081 mg/g dry wt | | details | | Star Bud | Detected and Quantified | 0.244 mg/g dry wt | | details | | Star Killer | Detected and Quantified | 0.169 mg/g dry wt | | details | | Strawberry Fields | Detected and Quantified | 0.32 mg/g dry wt | | details | | Strawberry Fields | Detected and Quantified | 0.363 mg/g dry wt | | details | | Strawberry Haze | Detected and Quantified | 1.1 +/- 0.1 mg/g dry wt | | details | | Sunset Sherbet | Detected and Quantified | 0.238 mg/g dry wt | | details | | Sunset Sherbet | Detected and Quantified | 0.241 mg/g dry wt | | details | | Superman Og Kush | Detected and Quantified | 0.5 +/- 0.3 mg/g dry wt | | details | | Tahoe Og Kush | Detected and Quantified | 0.5 +/- 0.3 mg/g dry wt | | details | | Tangerine Dream | Detected and Quantified | 3 mg/g dry wt | | details | | Tangerine Dream (Sativa dominant) | Detected and Quantified | 0.50 +/- 0.07 mg/g dry wt | | details | | The Sauce | Detected and Quantified | 0.304 mg/g dry wt | | details | | Trainwreck | Detected and Quantified | 0.9 +/- 0.2 mg/g dry wt | | details | | Triple O | Detected and Quantified | 0.5 +/- 0.2 mg/g dry wt | | details | | Venom OG | Detected and Quantified | 0.597 mg/g dry wt | | details | | White Widow | Detected and Quantified | 0.325 mg/g dry wt | | details | | Wonder Woman | Detected and Quantified | 0.222 mg/g dry wt | | details |
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| External Links |
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| HMDB ID | HMDB0006525 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | FDB013765 |
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| KNApSAcK ID | C00034999 |
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| Chemspider ID | 74205 |
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| KEGG Compound ID | C06306 |
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| BioCyc ID | CPD-8754 |
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| BiGG ID | Not Available |
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| Wikipedia Link | Alpha-Pinene |
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| METLIN ID | Not Available |
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| PubChem Compound | 82227 |
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| PDB ID | Not Available |
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| ChEBI ID | 28261 |
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| References |
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| General References | - Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
- McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
- Neuenschwander U, Guignard F, Hermans I: Mechanism of the aerobic oxidation of alpha-pinene. ChemSusChem. 2010;3(1):75-84. doi: 10.1002/cssc.200900228. [PubMed:20017184 ]
- Salehi B, Upadhyay S, Erdogan Orhan I, Kumar Jugran A, L D Jayaweera S, A Dias D, Sharopov F, Taheri Y, Martins N, Baghalpour N, Cho WC, Sharifi-Rad J: Therapeutic Potential of alpha- and beta-Pinene: A Miracle Gift of Nature. Biomolecules. 2019 Nov 14;9(11). pii: biom9110738. doi: 10.3390/biom9110738. [PubMed:31739596 ]
- Wilderman PR, Shah MB, Jang HH, Stout CD, Halpert JR: Structural and thermodynamic basis of (+)-alpha-pinene binding to human cytochrome P450 2B6. J Am Chem Soc. 2013 Jul 17;135(28):10433-40. doi: 10.1021/ja403042k. Epub 2013 Jul 3. [PubMed:23786449 ]
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