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]
The pyrethrins are a class of organic compounds normally derived from Chrysanthemum cinerariifolium that have potent insecticidal activity by targeting the nervous systems of insects. Pyrethrin naturally occurs in chrysanthemum flowers and is often considered an organic insecticide when it is not combined with piperonyl butoxide or other synthetic adjuvants. Their insecticidal and insect-repellent properties have been known and used for thousands of years.
Acetanilide 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.
Terthiophene is the organic compound with the formula [C4H3S]2C4H2S. It is an oligomer of the heterocycle thiophene, a shorter oligomer is dithienyl, and the parent polymer is polythiophene. In the most common isomer of terthiophene, two thienyl groups are connected via their 2 positions to a central thiophene, also at the carbon atoms flanking the sulfur.
Aminoethylpiperazine (AEP) is a derivative of piperazine. This ethyleneamine contains three nitrogen atoms; one primary, one secondary and one tertiary. It is a corrosive organic liquid and can cause second or third degree burns. Aminoethylpiperazine can also cause pulmonary edema as a result of inhalation. It is REACH and TSCA registered.
Acetarsol is an anti-infective drug.
Triaziquone is a drug used in chemotherapy.
1-Naphthol, or α-naphthol, is a 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.
Eugeroics, also known as wakefulness-promoting agents and wakefulness-promoting drugs, are a class of drugs that promote wakefulness and alertness. They are medically indicated for the treatment of certain sleep disorders including excessive daytime sleepiness (EDS) in narcolepsy or obstructive sleep apnea (OSA). Eugeroics are also often prescribed off-label for the treatment of EDS in idiopathic hypersomnia. In contrast to classical psychostimulants, such as methylphenidate and amphetamine, which are also used in the treatment of these disorders, eugeroics typically do not produce marked euphoria, and, consequently, have a lower addictive potential.
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.
Neoendorphins are a group of endogenous opioid peptides derived from the proteolytic cleavage of prodynorphin. They include α-neoendorphin and β-neoendorphin. The α-neoendorphin is present in greater amounts in the brain than β-neoendorphin. Both are products of the dynorphin gene, which also expresses dynorphin A, dynorphin A-(1-8), and dynorphin B. These opioid neurotransmitters are especially active in Central Nervous System receptors, whose primary function is pain sensation. These peptides all have the consensus amino acid sequence of Try-Gly-Gly-Phe-Met (met-enkephalin) or Tyr-Gly-Gly-Phe-Leu ( leu-enkephalin). Binding of neoendorphins to opioid receptors (OPR), in the dorsal root ganglion (DRG) neurons results in the reduction of time of calcium-dependent action potential. The α-neoendorphins bind OPRD1(delta), OPRK1(kappa), and OPRM1 (mu) and β-neoendorphin bind OPRK1.
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.
Triazofos is a chemical compound used in acaricides, insecticides, and nematicides.
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.
Pregnenolone acetate, also known as pregn-5-en-3β-ol-20-one 3β-acetate, is a synthetic pregnane steroid and an ester of pregnenolone which is described as a glucocorticoid and as a skin-conditioning and skin anti-aging agent. It has been reported to reduce wrinkles in elderly women when applied in the form of a 0.5% topical cream, effects which were suggested to be due to improved hydration of the skin. Pregnenolone acetate has been marketed in France in a topical cream containing 1% pregnenolone acetate and 10% "sex hormone" for the treatment of premature skin aging but was withdrawn from the market in 1992. Although the medication has been described by some sources as a glucocorticoid, other authors have stated that systemic pregnenolone acetate has no undesirable metabolic or toxic effects even at high doses.
Methionol is a methyl sulfide derived from propan-1-ol. It is found in nature, including as a metabolite of yeast and bacillus anthracis. It is a sulphurous aroma component of many foods, such as wine, cheese and roasted coffee. It is classed as an irritant. It has a very low olfactory threshold.
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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