Classification Term: 226
2,2-dimethyl-1-benzopyrans (ontology term: CHEMONTID:0003522)
Organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position." []
found 51 associated metabolites at category metabolite taxonomy ontology rank level.
Ancestor: 1-benzopyrans
Child Taxonomies: Precocenes
Tetrahydrocannabinol
Tetrahydrocannabinol, abbreviated THC, is a cannabinoid identified in cannabis and is its principal psychoactive constituent. First isolated in 1964, in its pure form, it is a glassy solid when cold, and becomes viscous and sticky if warmed. Synthetically prepared THC, officially referred to by its INN, dronabinol, is available by prescription in the U.S. and Canada under the brand name Marinol. The mechanism of action of THC is not completely understood. It is thought that cannabinoid receptors in neural tissues may mediate the effects of cannabinoids. Animal studies suggest that Marinols antiemetic effects may be due to inhibition of the vomiting control mechanism in the medulla oblongata. A literature review on the subject concluded that "Cannabis use appears to be neither a sufficient nor a necessary cause for psychosis. It is a component cause, part of a complex constellation of factors leading to psychosis." Likewise, a French review from 2009 came to a conclusion that cannabis use, particularly that before age 15, was a factor in the development of schizophrenic disorders. An aromatic terpenoid, THC has a very low solubility in water, but good solubility in most organic solvents, specifically lipids and alcohols. The presence of these specialized cannabinoid receptors in the brain led researchers to the discovery of endocannabinoids, such as anandamide and 2-arachidonoyl glyceride (2-AG). THC targets receptors in a manner far less selective than endocannabinoid molecules released during retrograde signalling, as the drug has a relatively low cannabinoid receptor efficacy and affinity. In populations of low cannabinoid receptor density, THC may act to antagonize endogenous agonists that possess greater receptor efficacy. THC is a lipophilic molecule and may bind non-specifically to a variety of receptors in the brain and body, such as adipose tissue. Dronabinol is only found in individuals that have used or taken this drug. It is extracted from the resin of Cannabis sativa (marijuana, hashish). The isomer delta-9-tetrahydrocannabinol is considered the most active form, producing the characteristic mood and perceptual changes associated with this compound. In the United States, Marinol has been rescheduled from Schedule II to Schedule III of the Controlled Substances Act in 1999, reflecting a finding that THC had a potential for abuse less than that of cocaine and heroin. As a Schedule III drug, it is available by prescription and is considered to be non-narcotic and to have a low risk of physical or mental dependence. Marinol has been approved by the U.S. Food and Drug Administration (FDA) in the treatment of anorexia in AIDS patients, as well as for refractory nausea and vomiting of patients undergoing chemotherapy, which has raised much controversy as to why natural THC is still a Schedule I drug. Efforts to get cannabis rescheduled as analogous to Marinol have not succeeded thus far. In April 2005, Canadian authorities approved the marketing of Sativex, a mouth spray for multiple sclerosis patients, who can use it to alleviate neuropathic pain and spasticity. Sativex contains tetrahydrocannabinol together with cannabidiol and is a preparation of whole cannabis rather than individual cannabinoids. It is marketed in Canada by GW Pharmaceuticals, being the first cannabis-based prescription drug in the world (in modern times). In addition, Sativex received European regulatory approval in 2010. An analog of dronabinol, nabilone, is available commercially in Canada under the trade name Cesamet, manufactured by Valeant Pharmaceuticals. Cesamet has also received FDA approval and began marketing in the U.S. in 2006. It is a Schedule II drug. Δ9tetrahydrocannabinol, also known as delta(9)-thc or marinol, is a member of the class of compounds known as 2,2-dimethyl-1-benzopyrans. 2,2-dimethyl-1-benzopyrans are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. Δ9tetrahydrocannabinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Δ9tetrahydrocannabinol can be found in a number of food items such as wakame, cloves, burbot, and black cabbage, which makes Δ9tetrahydrocannabinol a potential biomarker for the consumption of these food products. Δ9tetrahydrocannabinol can be found primarily in blood and urine. Δ9tetrahydrocannabinol is a non-carcinogenic (not listed by IARC) potentially toxic compound. Δ9tetrahydrocannabinol is a drug which is used for the treatment of anorexia associated with weight loss in patients with aids, and nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetic treatment. The mechanism of action of marinol is not completely understood. It is thought that cannabinoid receptors in neural tissues may mediate the effects of dronabinol and other cannabinoids. Animal studies with other cannabinoids suggest that marinols antiemetic effects may be due to inhibition of the vomiting control mechanism in the medulla oblongata (DrugBank). A potentially serious oral ingestion, if recent, should be managed with gut decontamination. In unconscious patients with a secure airway, instill activated charcoal (30 to 100 g in adults, 1 to 2 g/kg in infants) via a nasogastric tube. A saline cathartic or sorbitol may be added to the first dose of activated charcoal. Patients experiencing depressive, hallucinatory or psychotic reactions should be placed in a quiet area and offered reassurance. Benzodiazepines (5 to 10 mg diazepam po) may be used for treatment of extreme agitation. Hypotension usually responds to Trendelenburg position and IV fluids. Pressors are rarely required (L1712) (T3DB). D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D063385 - Cannabinoid Receptor Modulators D018377 - Neurotransmitter Agents > D063385 - Cannabinoid Receptor Modulators > D063386 - Cannabinoid Receptor Agonists A - Alimentary tract and metabolism > A04 - Antiemetics and antinauseants > A04A - Antiemetics and antinauseants D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents C78272 - Agent Affecting Nervous System > C267 - Antiemetic Agent D002491 - Central Nervous System Agents > D000700 - Analgesics
Precocene II
D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals Precocene II is the insect antijuvenile hormone[1].
N-(6-Cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl)-N-methylethanesulfonamide
D002317 - Cardiovascular Agents > D026902 - Potassium Channel Blockers D049990 - Membrane Transport Modulators
Cromakalim
D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents
6-Acetyl-2,2-dimethyl-2H-1-benzopyran
6-Acetyl-2,2-dimethyl-2H-1-benzopyran is a 1-benzopyran. 1-(2,2-Dimethylchromen-6-yl)ethanone is a natural product found in Ageratina altissima, Viguiera pazensis, and other organisms with data available. 6-Acetyl-2,2-dimethyl-2H-1-benzopyran is found in fats and oils. 6-Acetyl-2,2-dimethyl-2H-1-benzopyran is a constituent of Helianthus annuus (sunflower) Constituent of Helianthus annuus (sunflower). 6-Acetyl-2,2-dimethyl-2H-1-benzopyran is found in sunflower and fats and oils. Demethoxyencecalin is a chromene isolated from Helianthus annuus, has antifungal activities[1].
11-Hydroxy-delta-9-THC
11-Hydroxy-delta-9-THC is a metabolite of dronabinol. Dronabinol is the for a pure isomer of THC, (–)-trans-delta9-tetrahydrocannabinol, which is the main isomer found in cannabis.
Mollicellin B
Mollicellin B is produced by Chaetomium species and mutagenic mycotoxin. Production by Chaetomium subspecies and mutagenic mycotoxin.
11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol
11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol, also known as delta(1)-Tetrahydrocannabinol-7-Oic acid or delta-9-11-Carboxytetrahydrocannabinol, is classified as a member of the 2,2-dimethyl-1-benzopyrans. 2,2-dimethyl-1-benzopyrans are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol is considered to be practically insoluble (in water) and acidic
Anofinic acid
Anofinic acid is found in mushrooms. Anofinic acid is a metabolite of Lactarius deliciosus. Metabolite of Lactarius deliciosus. Anofinic acid is found in mushrooms.
6-(1-Hydroxyethyl)-2,2-dimethyl-2H-1-benzopyran
6-(1-Hydroxyethyl)-2,2-dimethyl-2H-1-benzopyran is found in fats and oils. 6-(1-Hydroxyethyl)-2,2-dimethyl-2H-1-benzopyran is a constituent of Helianthus annuus (sunflower)
Diosgenin 3-[glucosyl-(1->4)-rhamnosyl-(1->4)-glucoside]
Diosgenin 3-[glucosyl-(1->4)-rhamnosyl-(1->4)-glucoside] is found in onion-family vegetables. Diosgenin 3-[glucosyl-(1->4)-rhamnosyl-(1->4)-glucoside] is a constituent of Allium vineale (wild garlic).
Fusarochromanone
Fusarochromanone is found in animal foods. Fusarochromanone is a mycotoxin produced by Fusarium roseum and the cereal fungus Fusarium equiseti (Fusarium graminearum). Affects growth and development of poultry. Mycotoxin production by Fusarium roseum and the cereal fungus Fusarium equiseti (Fusarium graminearum). Affects growth and development of poultry. Fusarochromanone is found in animal foods.
Coriandrone B
Constituent of Coriandrum sativum (coriander). Coriandrone B is found in coriander and herbs and spices. Coriandrone B is found in coriander. Coriandrone B is a constituent of Coriandrum sativum (coriander).
2,3-Dihydro-6-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one
2,3-Dihydro-6-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one is found in mushrooms. 2,3-Dihydro-6-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one is isolated from the mushroom Lentinus crinitus (palatability not certain). Isolated from the mushroom Lentinus crinitus (palatability not certain). 2,3-Dihydro-6-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one is found in mushrooms.
Salfredin B11
Salfredin B11 is found in herbs and spices. Salfredin B11 is a constituent of the seeds of Nigella sativa (black cumin). Constituent of the seeds of Nigella sativa (black cumin). Salfredin B11 is found in herbs and spices.
3,4-Dihydro-6-methoxy-2,2-dimethyl-2H-1-benzopyran-4-ol
3,4-Dihydro-6-methoxy-2,2-dimethyl-2H-1-benzopyran-4-ol is found in mushrooms. 3,4-Dihydro-6-methoxy-2,2-dimethyl-2H-1-benzopyran-4-ol is isolated from mushroom Lentinus crinitus. Isolated from mushroom Lentinus crinitus. 3,4-Dihydro-6-methoxy-2,2-dimethyl-2H-1-benzopyran-4-ol is found in mushrooms.
5-Amino-2,3-dihydro-6-(3-hydroxy-4-methoxy-1-oxobutyl)-2,2-dimethyl-4H-1-benzopyran-4-one
5-Amino-2,3-dihydro-6-(3-hydroxy-4-methoxy-1-oxobutyl)-2,2-dimethyl-4H-1-benzopyran-4-one is isolated from rice cultures of Fusarium equiseti. Isolated from rice cultures of Fusarium equiseti
8-Hydroxy-delta-9-THC
8-Hydroxy-delta-9-THC is a metabolite of dronabinol. Dronabinol is the for a pure isomer of THC, (–)-trans-Δ9-tetrahydrocannabinol, which is the main isomer found in cannabis. (Wikipedia)
9-alpha,10-alpha-epoxyhexahydrocannabinol
9-alpha,10-alpha-epoxyhexahydrocannabinol is a metabolite of dronabinol. Dronabinol is the for a pure isomer of THC, (–)-trans-delta9-tetrahydrocannabinol, which is the main isomer found in cannabis. (Wikipedia)
Diacetylfusarochromanone
Diacetylfusarochromanone is produced by Fusarium equiseti. Production by Fusarium equiseti
Formylfusarochromanone
Formylfusarochromanone is produced by Fusarium equiseti. Production by Fusarium equiseti
7-Hydroxy-6-(methoxyacetyl)-2,2-dimethyl-2H-1-benzopyran
7-Hydroxy-6-(methoxyacetyl)-2,2-dimethyl-2H-1-benzopyran is found in fats and oils. 7-Hydroxy-6-(methoxyacetyl)-2,2-dimethyl-2H-1-benzopyran is a constituent of Madia sativa (Chile tarweed)
3'-N'-Acetylfusarochromanone
3-N-Acetylfusarochromanone is a mycotoxin produced by Fusarium equiseti. Mycotoxin production by Fusarium equiseti
3'-N-Acetyl-4'-O-(14-methylpentadecanoyl)fusarochromanone
3-N-Acetyl-4-O-(14-methylpentadecanoyl)fusarochromanone is produced by Fusarium equiseti. Production by Fusarium equiseti
3'-N-Acetyl-4'-O-(14-methylheptadecanoyl)fusarochromanone
3-N-Acetyl-4-O-(14-methylheptadecanoyl)fusarochromanone is produced by Fusarium equiseti. Production by Fusarium equiseti
3'-N-Acetyl-4'-O-(9-octadecenoyl)fusarochromanone
3-N-Acetyl-4-O-(9-octadecenoyl)fusarochromanone is produced by Fusarium equiseti. Production by Fusarium equiseti
3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol
3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol is found in fats and oils. 3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol is an antioxidant for edible oils and fats. Antioxidant for edible oils and fats. 3,4-Dihydro-2,2,5,7,8-pentamethyl-2H-1-benzopyran-6-ol is found in fats and oils. C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C146993 - Androgen Receptor Inhibitor C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist > C242 - Anti-Androgen D020011 - Protective Agents > D000975 - Antioxidants
3'-Deaminofusarochromanone
3-Deaminofusarochromanone is produced by Fusarium equiseti. Production by Fusarium equiseti
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone
5-Amino-6-(4-hydroxy-2-butenoyl)-2,2-dimethyl-4-chromanone is produced by Fusarium equiseti. Production by Fusarium equiseti
2,3-Dihydro-3-hydroxy-6-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one
2,3-Dihydro-3-hydroxy-6-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one is found in mushrooms. 2,3-Dihydro-3-hydroxy-6-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one is isolated from the mushroom Lentinus crinitus (palatability uncertain). Isolated from the mushroom Lentinus crinitus (palatability uncertain). 2,3-Dihydro-3-hydroxy-6-methoxy-2,2-dimethyl-4H-1-benzopyran-4-one is found in mushrooms.
7-beta-Hydroxy-delta-9-THC
7-beta-Hydroxy-delta-9-THC is a metabolite of dronabinol. Dronabinol is the for a pure isomer of THC, (–)-trans-delta9-tetrahydrocannabinol, which is the main isomer found in cannabis. (Wikipedia)
8-beta-Hydroxy-delta-9-THC
8-beta-Hydroxy-delta-9-THC is a metabolite of dronabinol. Dronabinol is the for a pure isomer of THC, (–)-trans-delta9-tetrahydrocannabinol, which is the main isomer found in cannabis. (Wikipedia)
11-hydroxy-Delta(9)-tetrahydrocannabinol
11-hydroxy-Delta(9)-tetrahydrocannabinol, also known as (-)-11-Hydroxy-Delta(9)-THC or 11-OH-THC, is classified as a member of the 2,2-dimethyl-1-benzopyrans. 2,2-dimethyl-1-benzopyrans are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 11-hydroxy-Delta(9)-tetrahydrocannabinol is considered to be practically insoluble (in water) and acidic
(6Ar,10ar)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6h-benzo[c]chromene-9-carboxylic acid
11-Hydroxy-delta(8)-thc
9-Carboxy-thc
Ajulemic acid
Butyrolactone derivative
Guanidine, N-(4-chlorophenyl)-N'-cyano-N'-(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)-, trans-
delta9-Tetrahydrocannabinol hemisuccinate
Dexanabinol
(6AR,10AR)-3-(1,1-Dimethylbutyl)-6A,7,10,10A-tetrahydro-6,6,9-trimethyl-6H-dibenzo[B,D]pyran
Rilmakalim
(6Ar,10aR)-1-hydroxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,9,10,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid
1-(3-Hydroxy-2,2,6-trimethyl-3,4-dihydrochromen-4-yl)pyrrolidin-2-one
delta-9-tetrahydrocannabinolate
delta9-tetrahydrocannabinolate is also known as thca or δ9-tetrahydrocannabinolic acid. delta9-tetrahydrocannabinolate is practically insoluble (in water) and a moderately acidic compound (based on its pKa). delta9-tetrahydrocannabinolate can be found in a number of food items such as devilfish, arrowhead, potato, and cereals and cereal products, which makes delta9-tetrahydrocannabinolate a potential biomarker for the consumption of these food products.
