Fluorenol

Fluorenol

Fluorenol[1]
Identifiers
CAS number  YesY
PubChem
ChemSpider  N
EC number
ChEBI  N
Jmol-3D images Image 1
Properties
Molecular formula 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)
Solubility in water Practically insoluble [2]
Hazards
NFPA 704
0
0
0
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/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. It does not have known toxicity or carcinogenicity in humans.[3]

Fluorenol was patented as an insecticide in 1939, [4] and is an algaecide against the green algae Dunaliella bioculata.[3]

Eugeroic

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. It is a weak dopamine reuptake inhibitor with an IC50 of 9 μM, notably 59% weaker than modafinil despite being a stronger wakefulness-promoting agent, potentially making it even less liable for addiction.[5] It also showed no affinity for cytochrome P450 2C19, unlike modafinil.[6] No human trials have yet been published as of 2014.

According to the paper,[6] modafinil has dopamine transporter IC50 (μM) 3.70, whereas fluorenol is 9.

References

  1. ^ 9-Hydroxyfluorene, chemicalland21.com
  2. ^ 9H-Fluoren-9-olRecord of in the GESTIS Substance Database from the IFA, accessed on 5 November 2008
  3. ^ a b MSDS
  4. ^ US patent 2197249: Insecticide
  5. ^ Wise, R. A. (1996). "Neurobiology of addiction". Current opinion in neurobiology 6 (2): 243–51.  
  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.