Cannabidiol1 Cannabidiol Cannabidiol Systematic (IUPAC) name 2-[(1R,6R)-6-isopropenyl-3-methylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol Clinical data AHFS/Drugs.com International Drug Names [1] Pregnancy cat. Legal status ? Not Ranked (US) Schedule II (Can) (THC - Schedule/Level I; THC and CBD two main chemicals in cannabis) Identifiers CAS number ATC code PubChem ChemSpider UNII 13956-29-1 None CID 644019 24593618 [3] [5] Chemical data Formula Mol. mass C21H30O2 314.4636 [2] [4] 19GBJ60SN5 Physical data Melt. point Boiling point 66 °C (151 °F) 180 °C (356 °F) (range: 160–180 °C) (what is this?) (verify) [6] Cannabidiol (CBD) is one of at least 85 cannabinoids found in cannabis. It is a major constituent of the plant, second to THC, and represents up to 40% in its extracts. Compared with THC, cannabidiol is less psychoactive, and is considered to have a wider scope of medical applications than THC,[7] including to epilepsy, multiple sclerosis Cannabidiol spasms, anxiety disorders, bipolar disorder, schizophrenia, nausea, convulsion and inflammation, as well as inhibiting cancer cell growth. CBD may decrease the rate of THC clearance from the body, perhaps by interfering with the metabolism of THC in the liver. Cannabidiol has displayed sedative effects in animal tests. Other research indicates that CBD increases alertness. CBD has been shown to reduce growth of aggressive human breast cancer cells in vitro, and to reduce their invasiveness. 2 Clinical applications Cannabidiol's strong antioxidant properties have been shown to play a role in the compound's neuroprotective and anti-ischemic effects. Studies have shown cannabidiol decreases activity of the limbic system and decreases social isolation induced by THC. Cannabidiol has also been shown to reduce anxiety in social anxiety disorder. Cannabidiol has proven effective in treating an often drug-induced set of neurological movement disorders known as dystonia. In one study, five out of five participants showed noted improvement in their dystonic symptoms by 20-50%. In 1985, a single case study suggested that CBD may be effective in the management of levodopa-induced dyskinesia in a Parkinson's Disease patient. The bud of a Cannabis sativa flower coated with trichomes, which contain more CBD than any other part of the plant.[citation needed] CBD is shown to inhibit MRSA. CBD, along with the cannabis terpenoid pinene, are effective against MRSA, and may exhibit antiseptic effects against Propionibacterium acnes, the key pathogen in acne. CBD absorbed transcutaneously may also attenuate the increased sebum production at the root of acne. In 2010, a Modesto, California father reported that he had experienced success treating his son's case of Dravet syndrome with a CBD-rich tincture. Five year old Jayden David went from a daily dose of 22 pharmaceutical pills down to four, began eating solid food, and experiencing fewer and less intense seizures after beginning treatment with CBD. According to his father, before using the tincture, Jayden experienced Grand mal seizures "24 hours a day lasting an hour and a half" and had been taken away in an ambulance on at least 40 occasions. The first day Jayden used the CBD tincture was the first day he had gone seizure-free in his life.[8] Effects on the brain A 2010 study found that strains of cannabis containing higher concentrations of cannabidiol did not produce short-term memory impairment vs. strains with similar concentrations of THC, but lower concentrations of CBD. The researchers attributed this attenuation of memory effects to CBD's role as a CB1 antagonist. CBD also appears to protect against 'binge' alcohol induced neurodegeneration. Recent studies have shown cannabidiol to be as effective as atypical antipsychotics in treating schizophrenia. Studies have shown CBD may reduce schizophrenic symptoms due to its apparent ability to stabilize disrupted or disabled NMDA receptor pathways in the brain, which are shared and sometimes contested by norepinephrine and GABA. Leweke et al. performed a double blind, 4 week, explorative controlled clinical trial to compare the effects of purified cannabidiol and the atypical antipsychotic amisulpride on improving the symptoms of schizophrenia in 42 patients with acute paranoid schizophrenia. Both treatments were associated with a significant decrease of psychotic symptoms after 2 and 4 weeks as assessed by Brief Psychiatric Rating Scale and Positive and Negative Syndrome Scale. While there was no statistical difference between the two treatment groups, cannabidiol induced significantly fewer side effects (extrapyramidal symptoms, increase in prolactin, weight gain) when compared to amisulpride. Cannabidiol A 2008 study published in the British Journal of Psychiatry showed significant differences in the Oxford-Liverpool Inventory of Feelings and Experiences scores between three groups: the first consisted of non-cannabis users, the second consisted of users with THC detected, and the third consisted of users with both THC and CBD detected. The THC-only group scored significantly higher for unusual experiences than the THC-and-CBD group, whereas the THC-and-CBD group had significantly lower introvertive anhedonia scores than the THC-only group and the non-cannabis user group. This research indicates that CBD acts as an anti-psychotic and may counteract the potential psychotomimetic effects of THC on individuals with latent schizophrenia. 3 Cancer research In November 2007, researchers at the California Pacific Medical Center reported that CBD shows promise for controlling the spread of metastatic breast cancer. In vitro CBD down-regulates, or "turns off", the activity of ID1, the gene responsible for tumor metastasis in breast and other types of cancers, including the particularly aggressive triple negative breast cancer.[9] The researchers in September 2012 said they hope to start human trials soon.[10] Cannabidiol has been shown to inhibit cancer cell growth with low potency in non-cancer cells. Although the inhibitory mechanism is not yet fully understood, Ligresti et al. suggest that "cannabidiol exerts its effects on these cells through a combination of mechanisms that include either direct or indirect activation of CB2 and TRPV1 receptors, and induction of oxidative stress, all contributing to induce apoptosis." Non-psychoactive cannabinoids, including cannabidiol (CBD) and other more pronounced CB2 agonists such as cannabinol (CBN, an immunosuppressant), are now seen as promising targets for anti-tumor drugs since they experimentally reduce the size of in-vivo xenografts, for example gliomas. Combinations of submaximal THC doses and CBD have both been successfully applied to greatly increase in-vitro efficacy of temozolomide in glioblastoma multiforme cell lines. CBD likely exerts its effects through the induction of apoptosis by Reactive oxygen species. Non-psychoactive cannabinoids can be administered at much higher doses without the well-known side effects that are sometimes associated with the drop-out rate in trials involving psychoactive cannabinoids. A team of researchers from the University of California at Irvine proposed in February 2013 that CBD's anti-malignant effect by way of apoptosis may be due to its potential action on "mutant p53 proteins in cancer cells," due to cannabidiol's chemo-physical similarity to stictic acid, a promising anti-cancer compound found in some species of lichens that acts on the aforementioned proteins. The University biologists, chemists and computer scientists "identified an elusive pocket on the surface of the p53 protein that can be targeted by cancer-fighting drugs".[11] CBD-enhanced cannabis Decades ago, growers in the US bred CBD almost entirely out of cannabis plants because their customers preferred varietals that were more mind-altering due to a higher THC, lower CBD content.[] To meet the demands of medical cannabis patients, growers are developing more CBD-rich strains of the plant.[12] In November 2012, an Israeli medical cannabis facility announced a new strain of the plant which has only cannabidiol as an active ingredient, and virtually no THC, providing some of the medicinal benefits of cannabis without the euphoria. The researchers said the cannabis plant, enriched with CBD, "can be used for treating diseases like rheumatoid arthritis, colitis, liver inflammation, heart disease and diabetes". Research on CBD enhanced cannabis began in 2009, resulting in Avidekel, a cannabis strain that contains 15.8% CBD and less than 1% THC. Raphael Mechoulam, leading cannabinoid researcher, noted "It is possible that (Avidekel's) CBD to THC ratio is the highest among medical marijuana companies in the world, but the industry is not very organised, so one cannot keep exact track of what each company is doing". The 2013 CNN documentary Weed: Dr. Sanjay Gupta Reports noted that the strain R4, sold at a Denver, Colorado based medical marijuana dispensary, Greenwerkz, was reported to contain 0.76% THC and 17.61% CBD.[13] It also noted that the Stanley brothers of Colorado Springs, Colorado cultivated a cannabis strain with 0.5% THC and 17% Cannabidiol CBD, which they named Charlotte's Web after Charlotte Figi, a 5-year-old medical marijuana patient who uses the medicine to treat a rare form of epilepsy called Dravet syndrome, which is resistant to most anti-epileptic medications. 4 Pharmacology Cannabidiol has a very low affinity for CB1 and CB2 receptors but acts as an indirect antagonist of their agonists. While one would assume that this would cause cannabidiol to reduce the effects of THC, it may potentiate THC's effects by increasing CB1 receptor density or through another CB1-related mechanism. It is also an inverse agonist of CB2 receptors. Recently, it was found to be an antagonist at the putative new cannabinoid receptor, GPR55, a GPCR expressed in the caudate nucleus and putamen. Cannabidiol has also been shown to act as a 5-HT1A receptor agonist, an action which is involved in its antidepressant, anxiolytic, and neuroprotective effects. Cannabidiol is an allosteric modulator of μ and δ-opioid receptors. Cannabidiol's pharmacologial effects have also been attributed to PPAR-γ receptor agonism and intracellular calcium release. Pharmaceutical preparations A CBD extract made from industrial hemp was introduced to the US market in 2012. Because the FDA considers cannabinoids derived from hemp to be "food-based" products, no legal restrictions exist.[14] Nabiximols (USAN, trade name Sativex) is an aerosolized mist for oral administration containing a near 1:1 ratio of CBD and THC. The drug was approved by Canadian authorities in 2005 to alleviate pain associated with multiple sclerosis.[15][16] Isomerism Cannabidiol 5 7 double bond isomers and their 30 stereoisomers Formal numbering Short name Chiral centers 1 and 3 2-(6-isopropenyl-3-methyl-5-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol 1, 3 and 6 Δ -cannabidiol Δ -cannabidiol Δ2-cannabidiol 3,7 3 Terpenoid numbering Short name Chiral centers 1 and 3 4 1, 3 and 4 Δ -cannabidiol Δ -cannabidiol Δ1-cannabidiol 1,7 6 Number of Natural Convention Structure on Psychotropic Substances Schedule stereoisomers occurrence Full name Δ -cannabidiol Δ -cannabidiol 4 5 Δ -cannabidiol Δ -cannabidiol 5 4 No No unscheduled unscheduled 2-(6-isopropenyl-3-methyl-4-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol 8 1 and 6 2-(6-isopropenyl-3-methyl-3-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol 1 and 6 2-(6-isopropenyl-3-methylenecyclohex-1-yl)-5-pentyl-1,3-benzenediol 1 and 6 2-(6-isopropenyl-3-methyl-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol 3 and 4 4 3 and 4 4 3 and 4 4 ? No Yes unscheduled unscheduled unscheduled Δ1-cannabidiol Δ6-cannabidiol 3 and 6 2-(6-isopropenyl-3-methyl-1-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol 3 2-(6-isopropenyl-3-methyl-6-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol Δ2-cannabidiol Δ3-cannabidiol 1 and 4 4 1 2 No No unscheduled unscheduled Based on: Nagaraja, Kodihalli Nanjappa, Synthesis of delta-3-cannabidiol and the derived rigid analogs, Arizona University 1987 [17]. See also: Tetrahydrocannabinol#Isomerism, Abnormal cannabidiol. Chemistry Cannabidiol is insoluble in water but soluble in organic solvents, such as pentane. At room temperature it is a colorless crystalline solid. In strongly basic medium and the presence of air it is oxidized to a quinone. Under acidic conditions it cyclizes to THC. The synthesis of cannabidiol has been accomplished by several research groups. Biosynthesis Cannabis produces CBD-carboxylic acid through the same metabolic pathway as THC, until the last step, where CBDA synthase performs catalysis instead of THCA synthase. Natural occurrence Cannabis indica may have a CBD:THC ratio 3–5 times that of Cannabis sativa. Legal status Cannabidiol is not scheduled by the Convention on Psychotropic Substances. Cannabidiol is a Schedule II drug in Canada.[18] The legal status of cannabidiol in United States is unclear. In Schedule I[19][20] there is a broad category called "Tetrahydrocannabinols", although cannabidiol is not chemically a tetrahydrocannabinol. Cannabidiol has DEA statistical number 7372,[21] but it does not necessarily mean it is illegal. In October 2003, U.S. patent #6630507 entitled "Cannabinoids as antioxidants and neuroprotectants" was assigned to "The United States Of America As Represented By The Department Of Health And Human Services." The patent was filed in April 1999 and listed as the inventors: Aidan J. Hampson, Julius Axelrod, and Maurizio Grimaldi, who all held positions at the National Institute of Mental Health (NIMH) in Bethesda, MD, which is part of the National Cannabidiol Institutes of Health (NIH), an agency of the United States Department of Health and Human Services (HHS). The patent mentions cannabidiol's ability as an antiepileptic, to lower intraocular pressure in the treatment of glaucoma, lack of toxicity or serious side effects in large acute doses, its neuroprotectant properties, its ability to prevent neurotoxicity mediated by NMDA, AMPA, or kainate receptors; its ability to attenuate glutamate toxicity, its ability to protect against cellular damage, its ability to protect brains from ischemic damage, its anxiolytic effect, and its superior antioxidant activity which can be used in the prophylaxis and treatment of oxidation associated diseases. 6 “ "Oxidative associated diseases include, without limitation, free radical associated diseases, such as ischemia, ischemic reperfusion injury, inflammatory diseases, systemic lupus erythematosis, myocardial ischemia or infarction, cerebrovascular accidents (such as a thromboembolic or hemorrhagic stroke) that can lead to ischemia or an infarct in the brain, operative ischemia, traumatic hemorrhage (for example a hypovolemic stroke that can lead to CNS hypoxia or anoxia), spinal cord trauma, Down's syndrome, Crohn's disease, autoimmune diseases (e.g. rheumatoid arthritis or diabetes), cataract formation, uveitis, emphysema, gastric ulcers, oxygen toxicity, neoplasia, undesired cellular apoptosis, radiation sickness, and others. The present invention is believed to be particularly beneficial in the treatment of oxidative associated diseases of the CNS, because of the ability of the cannabinoids to cross the blood brain barrier and exert their antioxidant effects in the brain. In particular embodiments, the pharmaceutical composition of the present invention is used for preventing, arresting, or treating neurological damage in Parkinson's disease, Alzheimer's disease and HIV dementia; autoimmune neurodegeneration of the type that can occur in encephalitis, and hypoxic or anoxic neuronal damage that can result from apnea, respiratory arrest or cardiac arrest, and anoxia caused by drowning, brain surgery or trauma (such as concussion or spinal cord shock)." ” On November 17, 2011, the Federal Register published that the National Institutes of Health of the United States Department of Health and Human Services was "contemplating the grant of an exclusive patent license to practice the invention embodied in U.S. Patent 6,630,507" to the company KannaLife based in New York, for the development and sale of cannabinoid and cannabidiol based therapeutics for the treatment of hepatic encephalopathy in humans. References [1] [2] [3] [4] [5] [6] [7] http:/ / www. drugs. com/ international/ cannabidiol. html http:/ / www. nlm. nih. gov/ cgi/ mesh/ 2009/ MB_cgi?term=13956-29-1& rn=1 http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=644019 http:/ / www. chemspider. com/ Chemical-Structure. 24593618 http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=19GBJ60SN5 http:/ / en. wikipedia. org/ w/ index. php?title=Special:ComparePages& rev1=457636058& page2=Cannabidiol Ashton, C.H., Moore, P. B., Gallagher, P., Young, A. H. (2005). Cannabinoids in bipolar affective disorder: a review and discussion of their therapeutic potential. Journal of Psychopharmacology (U.K). [8] Modesto dad turns to medical marijuana to save son | News - KCRA Home (http:/ / www. kcra. com/ news/ modesto-dad-turns-to-medical-marijuana-to-save-son/ -/ 11797728/ 21394696/ -/ 8t8dypz/ -/ index. html) [9] Pot compound seen as tool against cancer (http:/ / www. sfgate. com/ health/ article/ Pot-compound-seen-as-tool-against-cancer-3875562. php#ixzz2GZmg5kGr). SFGate [10] Marijuana Compound Fights Cancer; Human Trials Next (http:/ / www. nbcbayarea. com/ news/ local/ Marijuana-Compound-Fights-Cancer-Human-Trials-Next-170406116. html). NBC Bay Area [11] UCI team finds new target for treating wide spectrum of cancers (http:/ / news. uci. edu/ press-releases/ uci-team-finds-new-target-for-treating-wide-spectrum-of-cancers/ ). UCIrvine News [12] Video: The rise of high CBD marijuana-Cannabis - Telegraph (http:/ / www. telegraph. co. uk/ health/ 8080247/ The-rise-of-high-CBD-marijuana-Cannabis. html) [13] http:/ / www. greenwerkz. com/ the-r4/ about-the-r4/ [14] Dixie Launches Cannabidiol-Based Dixie Products | Dixie Elixirs & Edibles (http:/ / dixieelixirs. com/ dixie-launches-cannabidol-based-dixie-products/ ) [15] United States Adopted Names Council: Statement on a nonproprietary name (http:/ / www. ama-assn. org/ ama1/ pub/ upload/ mm/ 365/ nabiximols. pdf) [16] GWPharma - Welcome (http:/ / www. gwpharm. com/ ) [17] http:/ / arizona. openrepository. com/ arizona/ handle/ 10150/ 184033 [18] Controlled Drugs and Substances Act - Schedule II (http:/ / laws-lois. justice. gc. ca/ eng/ acts/ c-38. 8/ page-25. html#h-29) [19] Resources - Controlled Substance Schedules (http:/ / www. deadiversion. usdoj. gov/ schedules/ index. html) [20] Section 1308.11 Schedule I (http:/ / www. deadiversion. usdoj. gov/ 21cfr/ cfr/ 1308/ 1308_11. htm#d27) Cannabidiol [21] DEA Form 225 - Application for Registration - Manufacturer, Distributor, Researcher, Analytical Laboratory, Importer, Exporter (http:/ / www. deadiversion. usdoj. gov/ drugreg/ reg_apps/ 225/ 225_instruct. htm) 7 External links • Erowid (http://www.erowid.org/plants/cannabis/cannabis_info2.shtml) Compounds found in Cannabis sativa • Project CBD (http://www.projectcbd.org/) Non-profit educational service dedicated to promoting and publicizing research into the medical utility of cannabidiol. Article Sources and Contributors 8 Article Sources and Contributors Cannabidiol Source: http://en.wikipedia.org/w/index.php?oldid=578470067 Contributors: 18hands, 2600:1004:B025:48DC:0:0:0:103, A scientist, A8UDI, ASmartKid, Acdx, Alex Ex, Alexrexpvt, Allethrin, Andrevan, Animated Cascade, Anypodetos, Ary29, Badgerbear, Badmusician, BakuninGoldmanKropotkin, Bayhemp, Beetstra, Benjah-bmm27, Benrr101, Bryan Derksen, C6541, Cacycle, Causa sui, Ceyockey, ChemNerd, Chemgirl131, Cheryladay, ChrisGualtieri, Ckatz, Codwiki, ComfyKem, CopperKettle, Custoo, DMacks, Danelo, David Hedlund, Dcirovic, DeLarge, DrM!KEY, Drphilharmonic, Dthomsen8, Dustin 3choes, Eagleye54321, Eeroth, Ehsan soltani, Elixir0219, Enix150, Eplebel, Eric Kvaalen, Exercisephys, Fireemblem555, FoCuSandLeArN, Frantik, Funandtrvl, Fuse809, Gamesguru2, Gobonobo, Gtziavelis, Götz, Harbinary, HartzR, Headbomb, Heah, Hermógenes Teixeira Pinto Filho, HeyItsAedan, Howrealisreal, Ioscius, Jtmorgan, Kefirmonger, Kwamikagami, Leodmacleod, LetTheSunshineIn, LilHelpa, Lofor, Louisajb, MadSurgeon, Meiskam, Meodipt, Merff, MrADHD, Mrt50, Nashmaximus, Nikos 1993, Nirmos, Noobeditor, NotWith, O0Alea0o, Ohnoitsjamie, Oldmaneinstein, Osterluzei, P-kun80, Panoramix303, Petrarchan47, Phil Boswell, Physchim62, Pigoutultra, Pmillerrhodes, Rachman321, Reach Out to the Truth, Redmitrow, Renice, Revaaron, Rich Farmbrough, Rjwilmsi, Royote, ScoutKnot, Selket, Sergivs-en, Shabadahabada, Shao, ShelfSkewed, Smartse, SouthernNights, St3vo, Steinsplitter, Subvertc, Sucrase, Supposed, Tankbank420, Tea with toast, Tentinator, Tgeller, TheBaur, Thoric, ThunderPeel2001, Tired canadian, UseTheCommandLine, Vanished user 1234567890, Viriditas, Vjiced, Webclient101, Wikieditor12, WriterHound, Yintan, Youtalkfunny, Zachorious, Zaslav, ﺣﺴﻦ ﻋﻠﻲ ﺍﻟﺒﻂ, 142 anonymous edits Image Sources, Licenses and Contributors file:Cannabidiol.svg Source: http://en.wikipedia.org/w/index.php?title=File:Cannabidiol.svg License: Public Domain Contributors: Harbin file:CBD-3D-balls.png Source: http://en.wikipedia.org/w/index.php?title=File:CBD-3D-balls.png License: Public Domain Contributors: Ben Mills File:Yes check.svg Source: http://en.wikipedia.org/w/index.php?title=File:Yes_check.svg License: Public Domain Contributors: Anomie Image:Kolkata-Kut.jpg Source: http://en.wikipedia.org/w/index.php?title=File:Kolkata-Kut.jpg License: Public Domain Contributors: Psychonaught (talk). Original uploader was Psychonaught at en.wikipedia File:Cannabidiol numbering.png Source: http://en.wikipedia.org/w/index.php?title=File:Cannabidiol_numbering.png License: Public Domain Contributors: Nikos 1993 File:2-(6-Isopropenyl-3-methyl-5-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png Source: http://en.wikipedia.org/w/index.php?title=File:2-(6-Isopropenyl-3-methyl-5-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png License: Creative Commons Zero Contributors: User:Nikos 1993 File:2-(6-Isopropenyl-3-methyl-4-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png Source: http://en.wikipedia.org/w/index.php?title=File:2-(6-Isopropenyl-3-methyl-4-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png License: Creative Commons Zero Contributors: User:Nikos 1993 File:2-(6-Isopropenyl-3-methyl-3-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png Source: http://en.wikipedia.org/w/index.php?title=File:2-(6-Isopropenyl-3-methyl-3-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png License: Creative Commons Zero Contributors: User:Nikos 1993 File:2-(6-Isopropenyl-3-methylenecyclohex-1-yl)-5-pentyl-1,3-benzenediol.png Source: http://en.wikipedia.org/w/index.php?title=File:2-(6-Isopropenyl-3-methylenecyclohex-1-yl)-5-pentyl-1,3-benzenediol.png License: Creative Commons Zero Contributors: User:Nikos 1993 File:2-(6-Isopropenyl-3-methyl-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png Source: http://en.wikipedia.org/w/index.php?title=File:2-(6-Isopropenyl-3-methyl-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png License: Creative Commons Zero Contributors: User:Nikos 1993 File:2-(6-Isopropenyl-3-methyl-1-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png Source: http://en.wikipedia.org/w/index.php?title=File:2-(6-Isopropenyl-3-methyl-1-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png License: Creative Commons Zero Contributors: User:Nikos 1993 File:2-(6-Isopropenyl-3-methyl-6-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png Source: http://en.wikipedia.org/w/index.php?title=File:2-(6-Isopropenyl-3-methyl-6-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol.png License: Creative Commons Zero Contributors: User:Nikos 1993 License Creative Commons Attribution-Share Alike 3.0 //creativecommons.org/licenses/by-sa/3.0/