Fluorenol

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Fluorenol[1]
Fluorenol.png
9-fluorenol.png
Names
IUPAC name
9H-Fluoren-9-ol
Other names
9-Hydroxyfluorene
Identifiers
1689-64-1 YesY
ChEBI CHEBI:16904 N
ChemSpider 66916 N
EC number 216-879-0
Jmol-3D images Image
PubChem 74318
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
Flammability code 0: Will not burn. E.g., water Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what is: YesY/N?)
Infobox references

Fluorenol 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.

Toxicity[edit]

Fluorenol is toxic to aquatic organisms including algae, bacteria, and crustaceans.[3] Fluorenol was patented as an insecticide in 1939,[4] and is an algaecide against the green algae Dunaliella bioculata.[5]

Its toxicity and carcinogenicity in humans are unknown.[5]

Eugeroic[edit]

A study published by chemists working for the biopharmaceutical company Cephalon to develop a successor to the wakefulness-promoting agent (or eugeroic) modafinil reported that fluorenol was 39% more effective than modafinil at keeping mice awake over a 4-hour period.[6] It is a weak dopamine reuptake inhibitor with an IC50 of 9 μM, notably 59% weaker than modafinil (IC50 = 3.70 μM) despite being a stronger wakefulness-promoting agent, potentially making it even less liable for addiction.[7] It also showed no affinity for cytochrome P450 2C19, unlike modafinil.[6] No human trials have yet been published as of 2015. This information is not found online. There is not way to check without having the physical journal or access to these journals.

References[edit]

  1. ^ 9-Hydroxyfluorene, chemicalland21.com
  2. ^ Record of 9H-Fluoren-9-ol in the GESTIS Substance Database of the IFA, accessed on 5 November 2008
  3. ^ Šepič, Ester; Bricelj, Mihael; Leskovšek, Hermina (2003). "Toxicity of fluoranthene and its biodegradation metabolites to aquatic organisms". Chemosphere 52 (7): 1125. doi:10.1016/S0045-6535(03)00321-7. PMID 12820993. 
  4. ^ US patent 2197249: Insecticide
  5. ^ a b MSDS
  6. ^ a b Dunn, D.; Hostetler, G.; Iqbal, M.; Marcy, V. R.; Lin, Y. G.; Jones, B.; Aimone, L. D.; Gruner, J.; Ator, M. A.; Bacon, E. R.; Chatterjee, S. (2012). "Wake promoting agents: Search for next generation modafinil, lessons learned: Part III". Bioorganic & Medicinal Chemistry Letters 22 (11): 3751–3753. doi:10.1016/j.bmcl.2012.04.031. PMID 22546675. 
  7. ^ Wise, R. A. (1996). "Neurobiology of addiction". Current opinion in neurobiology 6 (2): 243–51. doi:10.1016/S0959-4388(96)80079-1. PMID 8725967.