Fluorenol - alcohol , hydroxy derivative of fluorene . Its most significant isomer, fluoren-9-ol or 9-hydroxyfluorene, whose hydroxyl group is located on a linking carbon atom between two benzene rings. At room temperature, it is a white-cream solid.
| Fluorenol | |
|---|---|
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| Are common | |
| Systematic name | 9H-fluoren-9-ol |
| Chem. formula | C 13 H 10 O |
| Physical properties | |
| Molar mass | 182.22 g / mol |
| Density | 1,151 g / cm³ |
| Thermal properties | |
| T. melt. | 152-155 ° C |
| Chemical properties | |
| Water solubility | practically insoluble [1] |
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Content
Toxicity
Fluorenol is toxic to aquatic organisms, including algae, bacteria, and crustaceans [2] . It was patented as an insecticide in 1939 [3] , and is used as an algicide against the green alga Dunaliella bioculata [4] .
There are no data on its toxicity or carcinogenicity to humans [4] .
Fluorenol Derivatives
A study published by chemists working for the biopharmaceutical company Cephalon who developed an alternative to the drug against drowsiness, modafinil, reported that a modafinil analogue based on flurenol was 39% more effective in maintaining wakefulness in mice for a 4-hour period [5] . The fluorenol derivative is a weak dopamine reuptake inhibitor with an IC 50 of 9 μm, 59% weaker than modafinil (IC 50 = 3.70 μm), despite its stronger stimulating effect, which potentially reduces the likelihood of a possible dependence [6] . This compound also showed no affinity for cytochrome P450 2C19, in contrast to modafinil [5]
See also
- Modafinil
Notes
- ↑ Record of 9H-Fluoren-9-ol in the GESTIS Substance Database of the IFA , accessed on 5 November 2008
- Š Šepič Ester, Bricelj Mihael, Leskovšek Hermina. Toxicity of fluoranthene and its biodegradation metabolites to aquatic organisms (Eng.) // Chemosphere: journal. - 2003. - Vol. 52 , no. 7 - P. 1125-1133 . - DOI : 10.1016 / S0045-6535 (03) 00321-7 . - PMID 12820993 .
- US patent 2197249: Insecticide
- ↑ 1 2 MSDS Archived March 4, 2016.
- ↑ 1 2 Dunn, D .; Hostetler, G .; Iqbal, M .; Marcy, VR; Lin, YG; Jones, B .; Aimone, LD; Gruner, J .; Ator, MA; Bacon, ER; Chatterjee, S. Wake-up, modafinil, lessons learned: Part III (Eng.) // Bioorganic & Medicinal Chemistry Letters : journal. - 2012. - Vol. 22 , no. 11 - P. 3751-3753 . - DOI : 10.1016 / j.bmcl.2012.04.031 . - PMID 22546675 .
- ↑ Wise RA Neurobiology of addiction (eng.) // Current Opinion in Neurobiology. - Elsevier , 1996. - Vol. 6 , no. 2 - P. 243-251 . - DOI : 10.1016 / S0959-4388 (96) 80079-1 . - PMID 8725967 .