Record Information
Version1.0
Created at2020-03-19 00:29:40 UTC
Updated at2020-12-07 19:07:20 UTC
CannabisDB IDCDB000300
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nameα-pinene
DescriptionAlpha-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 ).
Structure
Thumb
Synonyms
ValueSource
(+)-3,6,6-TRIMETHYLBICYCLO[3.1.1]hept-2-eneChEBI
(1R,5R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-eneChEBI
(1R,5R)-alpha-PineneChEBI
alpha-Pinene(dextro)ChEBI
(1R,5R)-a-PineneGenerator
(1R,5R)-Α-pineneGenerator
a-Pinene(dextro)Generator
Α-pinene(dextro)Generator
(+)-a-PineneGenerator
(+)-Α-pineneGenerator
(+)-(1R)-alpha-PineneHMDB
(+)-(1R)-Α-pineneHMDB
(+)-(1R,5R)-alpha-PineneHMDB
(+)-(1R,5R)-Α-pineneHMDB
(+)-2-PineneHMDB
(1R)-(+)-alpha-PineneHMDB
(1R)-(+)-Α-pineneHMDB
(1R)-2,6,6-Trimethylbicyclo[3.1.1]hept-2-eneHMDB
(1R)-alpha-PineneHMDB
(1R)-Α-pineneHMDB
(1R,5R)-(+)-alpha-PineneHMDB
(1R,5R)-(+)-Α-pineneHMDB
(R)-(+)-alpha-PineneHMDB
(R)-(+)-Α-pineneHMDB
(±)-2-pineneHMDB
(±)-alpha-pineneHMDB
(±)-α-pineneHMDB
2,6,6-Trimethylbicyclo[3.1.1]hept-2-eneHMDB
2-PineneHMDB
alpha-PineneHMDB
Α-pineneHMDB
(+)-alpha-PineneHMDB
(1R,5R)-(+)-2-PinenePhytoBank
d-alpha-PinenePhytoBank
d-α-PinenePhytoBank
Chemical FormulaC10H16
Average Molecular Weight136.23
Monoisotopic Molecular Weight136.1252
IUPAC Name(1R,5R)-2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
Traditional Name(+)-α-pinene
CAS Registry Number7785-70-8
SMILES
CC1=CC[C@@H]2C[C@H]1C2(C)C
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
InChI KeyGRWFGVWFFZKLTI-RKDXNWHRSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Pinane monoterpenoid
  • Bicyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-62 °CNot Available
Boiling Point155 to 156 °CWikipedia
Water SolubilityNot AvailableNot Available
logP4.44GRIFFIN,S ET AL. (1999)
Predicted Properties
PropertyValueSource
logP3.66ALOGPS
logP2.8ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.72 m³·mol⁻¹ChemAxon
Polarizability17.22 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSα-pinene, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-efa1a7d8bd0221192f0dSpectrum
GC-MSα-pinene, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-efa1a7d8bd0221192f0dSpectrum
Predicted GC-MSα-pinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-1900000000-7a79889acc60a4543bcfSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-89e84f859d8f1f97d5c2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-fb8d56b761aae12a505cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-0900000000-bfe7e4ba927cd83956b4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-5e150dd4370565464dadSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-5e150dd4370565464dadSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-0900000000-b5dcbaea24fd03f1cbf9Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
AcetylcholinesteraseACHE7q22P22303 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Gamma-aminobutyric acid receptor subunit alpha-1GABRA15q34-q35P14867 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Cytochrome P450 2B6CYP2B619q13.2P20813 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
AcetylcholinesteraseACHE7q22P22303 details
Gamma-aminobutyric acid receptor subunit alpha-1GABRA15q34-q35P14867 details
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
8-Ball KushDetected and Quantified0.621 mg/g dry wt details
9 Lb HammerDetected and Quantified3.323 mg/g dry wt details
97 SageDetected and Quantified3.686 mg/g dry wt details
AdonisDetected and Quantified0.387 mg/g dry wt details
Alien Dawg (Indica dominant)Detected and Quantified0.23 +/- 0.04 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Alien Sour AppleDetected and Quantified1.471 mg/g dry wt details
Black BossDetected and Quantified0.973 mg/g dry wt details
Blue DreamDetected and Quantified0.639 mg/g dry wt details
Blue DreamDetected and Quantified0.679 mg/g dry wt details
Blue DreamDetected and Quantified4.343 mg/g dry wt details
Blue DreamDetected and Quantified5.196 mg/g dry wt details
Blue DreamDetected and Quantified4.2 +/- 1.3 mg/g dry wt details
Bob MarleyDetected and Quantified1.149 mg/g dry wt details
ChemdawgDetected and Quantified0.266 mg/g dry wt details
Chemdawg #4Detected and Quantified0.286 mg/g dry wt details
Chemdawg #4Detected and Quantified0.422 mg/g dry wt details
Cookies and CreamDetected and Quantified0.37 mg/g dry wt details
Cosmic LotusDetected and Quantified2.686 mg/g dry wt details
Crown OgDetected and Quantified0.3 +/- 0.3 mg/g dry wt details
Dairy QueenDetected and Quantified0.432 mg/g dry wt details
Dark Shadow HazeDetected and Quantified0.56 mg/g dry wt details
FLODetected and Quantified0.201 mg/g dry wt details
GasDetected and Quantified0.5 +/- 0.3 mg/g dry wt details
GelatoDetected and Quantified1 +/- 0.1 mg/g dry wt details
GodfatherDetected and Quantified2.9 +/- 1 mg/g dry wt details
Goji OGDetected and Quantified0.45 mg/g dry wt details
Golden CobraDetected and Quantified1.314 mg/g dry wt details
Golden SageDetected and Quantified0.632 mg/g dry wt details
Gorilla GlueDetected and Quantified0.282 mg/g dry wt details
Gorilla Glue #4Detected and Quantified0.276 mg/g dry wt details
Grape ApeDetected and Quantified2 +/- 1 mg/g dry wt details
Grape StomperDetected and Quantified1.033 mg/g dry wt details
Grape StomperDetected and Quantified1.178 mg/g dry wt details
Grizzly KushDetected and Quantified0.468 mg/g dry wt details
Hash PlantDetected and Quantified0.133 mg/g dry wt details
Hash PlantDetected and Quantified0.411 mg/g dry wt details
HemlockDetected and Quantified0.68 mg/g dry wt details
JabberwockyDetected and Quantified0.403 mg/g dry wt details
JabberwockyDetected and Quantified0.493 mg/g dry wt details
Jack HererDetected and Quantified0.213 mg/g dry wt details
Kandy KushDetected and Quantified0.124 mg/g dry wt details
Kush PuppyDetected and Quantified2.228 mg/g dry wt details
La ChocoDetected and Quantified0.356 mg/g dry wt details
Lemon BalmDetected and Quantified0.28 mg/g dry wt details
Lemon GojiDetected and Quantified0.149 mg/g dry wt details
Lemon OGDetected and Quantified2.668 mg/g dry wt details
Lemon SherbetDetected and Quantified0.323 mg/g dry wt details
Lemon SkunkDetected and Quantified0.493 mg/g dry wt details
Lemon SkunkDetected and Quantified0.659 mg/g dry wt details
Liberty HazeDetected and Quantified4.06 mg/g dry wt details
LohanDetected and Quantified0.421 mg/g dry wt details
Lucky CharmsDetected and Quantified0.55 mg/g dry wt details
Maui HazeDetected and Quantified0.343 mg/g dry wt details
Miami White KushDetected and Quantified0.8 +/- 0.4 mg/g dry wt details
Moby DickDetected and Quantified0.305 mg/g dry wt details
Moonshine Ghost Trane HazeDetected and Quantified0.272 mg/g dry wt details
Nightmare CookieDetected and Quantified0.23 mg/g dry wt details
Og KushDetected and Quantified0.4 +/- 0.4 mg/g dry wt details
Orange SkunkDetected and Quantified0.111 mg/g dry wt details
Pineapple SkunkDetected and Quantified2.425 mg/g dry wt details
Pipe DreamDetected and Quantified5.241 mg/g dry wt details
Platinum DelightDetected and Quantified0.303 mg/g dry wt details
Purple CreamDetected and Quantified2.1 +/- 0.4 mg/g dry wt details
Purple EclipseDetected and Quantified0.31 mg/g dry wt details
Purple PrincessDetected and Quantified2.7 +/- 0.6 mg/g dry wt details
Purple UrkleDetected and Quantified3.2 +/- 0.6 mg/g dry wt details
Rocket FuelDetected and Quantified0.386 mg/g dry wt details
Rollex OGDetected and Quantified0.693 mg/g dry wt details
Rosetta StoneDetected and Quantified0.344 mg/g dry wt details
SatoriDetected and Quantified2.034 mg/g dry wt details
Sensi Star (Pure Indica)Detected and Quantified0.25 +/- 0.03 mg/g dry wt
    • Jiamin Zheng, Yil...
details
SherbertDetected and Quantified0.6 +/- 0.3 mg/g dry wt details
Skunk HazeDetected and Quantified3.578 mg/g dry wt details
Skywalker OGDetected and Quantified1.1 mg/g dry wt details
Skywalker Og KushDetected and Quantified0.4 +/- 0.3 mg/g dry wt details
SpectrumDetected and Quantified0.081 mg/g dry wt details
Star BudDetected and Quantified0.244 mg/g dry wt details
Star KillerDetected and Quantified0.169 mg/g dry wt details
Strawberry FieldsDetected and Quantified0.32 mg/g dry wt details
Strawberry FieldsDetected and Quantified0.363 mg/g dry wt details
Strawberry HazeDetected and Quantified1.1 +/- 0.1 mg/g dry wt details
Sunset SherbetDetected and Quantified0.238 mg/g dry wt details
Sunset SherbetDetected and Quantified0.241 mg/g dry wt details
Superman Og KushDetected and Quantified0.5 +/- 0.3 mg/g dry wt details
Tahoe Og KushDetected and Quantified0.5 +/- 0.3 mg/g dry wt details
Tangerine DreamDetected and Quantified3 mg/g dry wt details
Tangerine Dream (Sativa dominant)Detected and Quantified0.50 +/- 0.07 mg/g dry wt
    • Jiamin Zheng, Yil...
details
The SauceDetected and Quantified0.304 mg/g dry wt details
TrainwreckDetected and Quantified0.9 +/- 0.2 mg/g dry wt details
Triple ODetected and Quantified0.5 +/- 0.2 mg/g dry wt details
Venom OGDetected and Quantified0.597 mg/g dry wt details
White WidowDetected and Quantified0.325 mg/g dry wt details
Wonder WomanDetected and Quantified0.222 mg/g dry wt details
HMDB IDHMDB0006525
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013765
KNApSAcK IDC00034999
Chemspider ID74205
KEGG Compound IDC06306
BioCyc IDCPD-8754
BiGG IDNot Available
Wikipedia LinkAlpha-Pinene
METLIN IDNot Available
PubChem Compound82227
PDB IDNot Available
ChEBI ID28261
References
General References
  1. 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 ]
  2. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525

Transporters

General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4