4-Iodopropofol

4-Iodopropofol
Identifiers
	IUPAC name 2,6-diisopropyl-4-iodophenol;
CAS Number	169255-48-5 ;
PubChem CID	9882905;
ChemSpider	8058580 ;
ChEMBL	ChEMBL53267 ;
CompTox Dashboard (EPA)	DTXSID10432353 ;
ECHA InfoCard	100.220.512
Chemical and physical data
Formula	C12H17IO
Molar mass	304.167 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:JMJHJCFWTNRPEI-UHFFFAOYSA-N ;
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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 GABA_A 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

Trapani, G; Latrofa, A; Franco, M; Altomare, C; Sanna, E; Usala, M; Biggio, G; Liso, G (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.
Lingamaneni, R; Krasowski, MD; Jenkins, A; Truong, T; Giunta, AL; Blackbeer, J; MacIver, MB; Harrison, NL; Hemmings Jr, HC (2001). "Anesthetic properties of 4-iodopropofol: implications for mechanisms of anesthesia". Anesthesiology. 94 (6): 1050–7. doi:10.1097/00000542-200106000-00020. PMID 11465597.
Krasowski, MD; Hong, X; Hopfinger, AJ; Harrison, NL (2002). "4D-QSAR Analysis of a Set of Propofol Analogues: Mapping Binding Sites for an Anesthetic Phenol on the GABAA Receptor". Journal of Medicinal Chemistry. 45 (15): 3210–21. doi:10.1021/jm010461a. PMC 2864546. PMID 12109905.
Haeseler, G; Karst, M; Foadi, N; Gudehus, S; Roeder, A; Hecker, H; Dengler, R; Leuwer, M (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.
Sanna, E; Motzo, C; Usala, M; Serra, M; Dazzi, L; MacIocco, E; Trapani, G; Latrofa, A; Liso, G; Biggio, G (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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[1] Trapani, G; Latrofa, A; Franco, M; Altomare, C; Sanna, E; Usala, M; Biggio, G; Liso, G (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; MacIver, MB; Harrison, NL; Hemmings Jr, HC (2001). "Anesthetic properties of 4-iodopropofol: implications for mechanisms of anesthesia". Anesthesiology. 94 (6): 1050–7. doi:10.1097/00000542-200106000-00020. PMID 11465597.

[3] Krasowski, MD; Hong, X; Hopfinger, AJ; Harrison, NL (2002). "4D-QSAR Analysis of a Set of Propofol Analogues: Mapping Binding Sites for an Anesthetic Phenol on the GABAA 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; Dengler, R; Leuwer, M (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; Trapani, G; Latrofa, A; Liso, G; Biggio, G (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.

Anxiolytics (N05B)
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GABA_AR PAMs	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Chlormezanone^‡ Ethanol (alcohol) Etifoxine Imepitoin; Herbs: Kava Skullcap Valerian
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Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III