4-Iodopropofol

4-Iodopropofol
Identifiers
IUPAC name
  • 2,6-diisopropyl-4-iodophenol
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.220.512
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Chemical and physical data
FormulaC12H17IO
Molar mass304.171 g·mol−1
3D model (JSmol)
SMILES
  • Oc1c(C(C)C)cc(I)cc1C(C)C
InChI
  • InChI=1S/C12H17IO/c1-7(2)10-5-9(13)6-11(8(3)4)12(10)14/h5-8,14H,1-4H3 checkY
  • Key:JMJHJCFWTNRPEI-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

4-Iodopropofol is a drug derived from the commonly used sedative anaesthetic agent, propofol. 4-Iodopropofol has similar effects to propofol on isolated receptors, acting primarily as a GABAA positive modulator and sodium channel blocker,[1][2][3][4] but when given to animals it has only anxiolytic and anticonvulsant effects, lacking the strong sedative-hypnotic profile of propofol.[5]

References

  1. ↑ Trapani G, Latrofa A, Franco M, Altomare C, Sanna E, Usala M, et al. (May 1998). "Propofol analogues. Synthesis, relationships between structure and affinity at GABAA receptor in rat brain, and differential electrophysiological profile at recombinant human GABAA receptors". Journal of Medicinal Chemistry. 41 (11): 1846–54. doi:10.1021/jm970681h. PMID 9599235.
  2. ↑ Lingamaneni R, Krasowski MD, Jenkins A, Truong T, Giunta AL, Blackbeer J, et al. (June 2001). "Anesthetic properties of 4-iodopropofol: implications for mechanisms of anesthesia". Anesthesiology. 94 (6): 1050–7. doi:10.1097/00000542-200106000-00020. PMID 11465597. S2CID 19229035.
  3. ↑ Krasowski MD, Hong X, Hopfinger AJ, Harrison NL (July 2002). "4D-QSAR analysis of a set of propofol analogues: mapping binding sites for an anesthetic phenol on the GABA(A) receptor". Journal of Medicinal Chemistry. 45 (15): 3210–21. doi:10.1021/jm010461a. PMC 2864546. PMID 12109905.
  4. ↑ Haeseler G, Karst M, Foadi N, Gudehus S, Roeder A, Hecker H, et al. (September 2008). "High-affinity blockade of voltage-operated skeletal muscle and neuronal sodium channels by halogenated propofol analogues". British Journal of Pharmacology. 155 (2): 265–75. doi:10.1038/bjp.2008.255. PMC 2538694. PMID 18574460.
  5. ↑ Sanna E, Motzo C, Usala M, Serra M, Dazzi L, Maciocco E, et al. (March 1999). "Characterization of the electrophysiological and pharmacological effects of 4-iodo-2,6-diisopropylphenol, a propofol analogue devoid of sedative-anaesthetic properties". British Journal of Pharmacology. 126 (6): 1444–54. doi:10.1038/sj.bjp.0702449. PMC 1565920. PMID 10217539.
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