Fluorenol[1]
Fluorenol.png
9-fluorenol.png
Names
IUPAC name
9H-Fluoren-9-ol
Other names
9-Hydroxyfluorene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.015.345 Edit this at Wikidata
EC Number
  • 216-879-0
UNII
  • InChI=1S/C13H10O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8,13-14H ☒N
    Key: AFMVESZOYKHDBJ-UHFFFAOYSA-N ☒N
  • InChI=1/C13H10O/c14-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)13/h1-8,13-14H
    Key: AFMVESZOYKHDBJ-UHFFFAOYAM
  • C1=CC=C2C(=C1)C(C3=CC=CC=C32)O
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)
0
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

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

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.[6] 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.[6] Fluorenol is a weak dopamine reuptake inhibitor with an IC50 of 9 μM, notably 59% weaker than modafinil (IC50 = 3.70 μM),[6] potentially making it even less liable for addiction.[7] It also showed no affinity for cytochrome P450 2C19, unlike modafinil.[6]

See also

References

  1. ^ 9-Hydroxyfluorene, chemicalland21.com
  2. ^ Record of 9H-Fluoren-9-ol in the GESTIS Substance Database of the Institute for Occupational Safety and Health, 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): 1125–33. doi:10.1016/S0045-6535(03)00321-7. PMID 12820993.
  4. ^ US patent 2197249: Insecticide
  5. ^ a b MSDS Archived 2016-03-04 at the Wayback Machine
  6. ^ a b c d 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.
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