Names | |
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IUPAC name 9H-Fluoren-9-ol | |
Other names 9-Hydroxyfluorene | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.015.345 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C13H10O | |
Molar mass | 182.22 g/mol |
Appearance | Off-white crystalline powder |
Density | 1.151 g/mL |
Melting point | 152 to 155 °C (306 to 311 °F; 425 to 428 K) |
Practically insoluble [2] | |
Hazards | |
NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Fluorenol, also known as hydrafinil, [3] is an alcohol derivative of fluorene. In the most significant isomer, fluoren-9-ol or 9-hydroxyfluorene, the hydroxy group is located on the bridging carbon between the two benzene rings. Hydroxyfluorene can be converted to fluorenone by oxidation. It is a white-cream colored solid at room temperature.
Fluorenol is toxic to aquatic organisms including algae, bacteria, and crustaceans. [4] Fluorenol was patented as an insecticide in 1939, [5] and is an algaecide against the green algae Dunaliella bioculata . [6]
Its toxicity and carcinogenicity in humans are unknown. [6]
The mechanism of action of fluorenol is unknown. [7]
The lipophilicity of fluorenol (LogP 2.4) is higher than that of drugs like modafinil (LogP 1.7) and amphetamine (LogP 1.8), suggesting that it may penetrate the blood brain barrier more readily. [8] [9] [10]
A study published by Cephalon describing research to develop a successor to the eugeroic modafinil reported that the corresponding fluorenol derivative was 39% more effective than modafinil at keeping mice awake over a 4-hour period. [11] However, after further investigation it was determined that the eugeroic activity of the fluorenol analog was likely due to an active metabolite, which they identify as fluorenol itself. [11] Fluorenol is a weak dopamine reuptake inhibitor with an IC50 of 9 μM, notably 59% weaker than modafinil (IC50 = 3.70 μM), [11] potentially making it even less liable for addiction. [12] It also showed no affinity for cytochrome P450 2C19, unlike modafinil. [11]
There is no evidence (binding assays, occupancy, predicted structure) to suggest that fluorenol acts as a 5-HT6 antagonist, contrary to some popular claims.[ medical citation needed ]
The unscheduled nature of fluorenol has caused it to fall into a legal grey area in most countries. Despite being associated with modafinil, [13] fluorenol is not a substituted derivative of it, making its scheduling unimplied by analogue acts.
Fluorenol is a relatively obscure compound in the research chemical market. According to an online survey with over 3000 respondents, only 2% of modafinil users have reported using fluorenol. [14]
Acetanilide is the organic compound with the formula C6H5NHC(O)CH3. It is the N-acetylated derivative of aniline. It is an odourless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin.
Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of a carboxylate ester, it is a colorless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other compounds of commercial interest.
Aminorex, sold under the brand names Menocil and Apiquel among others, is a weight loss (anorectic) stimulant drug. It was withdrawn from the market after it was found to cause pulmonary hypertension (PPH). In the United States, aminorex is a Schedule I controlled substance.
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Triaziquone is a drug used in chemotherapy.
Arsthinol (INN) is an antiprotozoal agent. It was synthesized for the first time in 1949 by Ernst A.H. Friedheim by complexation of acetarsol with 2,3-dimercaptopropanol and has been demonstrated to be effective against amoebiasis and yaws. It was marketed a few years later by Endo Products.
1-Naphthol, or α-naphthol, is an organic compound with the formula C10H7OH. It is a fluorescent white solid. 1-Naphthol differs from its isomer 2-naphthol by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol. Both isomers are soluble in simple organic solvents. They are precursors to a variety of useful compounds.
A eugeroic, or eugregoric, is a type of drug that increases wakefulness. The term has been used inconsistently and in multiple ways in the scientific literature, either to refer specifically to modafinil-type wakefulness-promoting agents or to refer to wakefulness-promoting agents generally. It was first introduced in the French literature in 1987 as a descriptor for modafinil-like wakefulness-promoting drugs and for purposes of distinguishing such drugs from psychostimulants. However, the term "eugeroic" has not been widely adopted in the literature, and instead the term "wakefulness-promoting agent" has been more widely used, both for modafinil-type drugs and other agents.
Demeton, sold as an amber oily liquid with a sulphur like odour under the name Systox, is an organophosphate derivative causing irritability and shortness of breath to individuals repeatedly exposed. It was used as a phosphorothioate insecticide and acaricide and has the chemical formula C8H19O3PS2. Although it was previously used as an insecticide, it is now largely obsolete due to its relatively high toxicity to humans. Demeton consists of two components, demeton-S and demeton-O in a ratio of approximately 2:1 respectively. The chemical structure of demeton is closely related to military nerve agents such as VX and a derivative with one of the ethoxy groups replaced by methyl was investigated by both the US and Soviet chemical-weapons programs under the names V-sub x and GD-7.
The benzodioxans are a group of isomeric chemical compounds with the molecular formula C8H8O2. There are three isomers of benzodioxan, as the second atom of oxygen of the dioxane can be in a second, third or fourth position: 1,2-dioxane, 1,3-dioxane and 1,4-dioxane, which respectively give 1,2-benzodioxan, 1,3-benzodioxan and 1,4-benzodioxan.
1-Phenylpiperazine is a simple chemical compound and drug featuring a phenyl group bound to a piperazine ring. The suffix ‘-piprazole’ is sometimes used in the names of drugs to indicate they belong to this class.
Methoxyethylmercuric acetate is a chemical compound formerly used as a pesticide for seeds of cotton and small grains. It is highly toxic, and can pose a threat to the brain and central nervous system.
Dioscorine is an alkaloid toxin isolated from the tubers of tropical yam on several continents. It has been used as a monkey poison in some African countries, and as an arrow poison to aid in hunting in several parts of Asia. It was first isolated from Dioscorea hirsute by Boorsma in 1894 and obtained in a crystalline form by Schutte in 1897, and has since been found in other Dioscorea species. Dioscorine is a neurotoxin that acts by blocking the nicotinic acetylcholine receptor. Dioscorine is generally isolated in tandem with other alkaloids such as dioscin but is usually the most potent toxin in the mixture. It is a convulsant, producing symptoms similar to picrotoxin, with which it shares a similar mechanism of action.
Flmodafinil, also known as bisfluoromodafinil and lauflumide, is a wakefulness-promoting agent related to modafinil which has been developed for treatment of a variety of different medical conditions. These include chronic fatigue syndrome, idiopathic hypersomnia, narcolepsy, attention deficit hyperactivity disorder (ADHD), and Alzheimer's disease. Aside its development as a potential pharmaceutical drug, flmodafinil is sold online and used non-medically as a nootropic.
Peripherally acting μ-opioid receptor antagonists (PAMORAs) are a class of chemical compounds that are used to reverse adverse effects caused by opioids interacting with receptors outside the central nervous system (CNS), mainly those located in the gastrointestinal tract. PAMORAs are designed to specifically inhibit certain opioid receptors in the gastrointestinal tract and with limited ability to cross the blood–brain barrier. Therefore, PAMORAs do not affect the analgesic effects of opioids within the central nervous system.
Diglycidyl aniline is an aromatic organic chemical in the glycidyl compound family. It is used to reduce the viscosity of epoxy resin systems. It has the empirical formula C12H15NO2 and the IUPAC name is N,N-bis(oxiran-2-ylmethyl)aniline. The CAS number is 2095-06-9. It is REACH registered in Europe with the EC number 218-259-5. A key use is in the viscosity reduction of epoxy resin systems functioning as a reactive diluent.
Laccaic acids or laccainic acids are a group of five anthraquinone derivatives, designated A through E, which are components of the red shellac obtained from the insect Kerria lacca, similar to carminic acid and kermesic acid. This article focuses primarily on laccaic acid A (LCA).
Coriamyrtin is a toxic γ-lactone naturally present in a multitude of plants.
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