5-I-R91150

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

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| verifiedrevid = 477224710

| IUPAC_name = 4-amino-N-[1-[3-(4-fluorophenoxy)propyl]-4-methyl-4-piperidinyl]-5-iodo-2-methoxybenzamide

| image = 5-I-R91150 Structure.svg

| width = 280

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 155928-24-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = T0W602CN0W

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| PubChem = 132997

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 117371

| C=23 | H=29 | F=1 | I=1 | N=3 | O=2

| smiles = Ic1cc(c(OC)cc1N)C(=O)NC3(CCN(CCCc2ccc(F)cc2)CC3)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C23H29FIN3O2/c1-23(27-22(29)18-14-19(25)20(26)15-21(18)30-2)9-12-28(13-10-23)11-3-4-16-5-7-17(24)8-6-16/h5-8,14-15H,3-4,9-13,26H2,1-2H3,(H,27,29)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = MIPHZURHMMOGLS-UHFFFAOYSA-N

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5-I-R91150 (or R93274) is a compound that acts as a potent and selective antagonist of 5-HT_2A receptors.{{cite journal | vauthors = Peremans K, Audenaert K, Coopman F, Jacobs F, Dumont F, Slegers G, Verschooten F, van Bree H, Mertens J, Dierckx R | display-authors = 6 | title = Regional binding index of the radiolabeled selective 5-HT2A antagonist 123I-5-I-R91150 in the normal canine brain imaged with single photon emission computed tomography | journal = Veterinary Radiology & Ultrasound | volume = 44 | issue = 3 | pages = 344–51 | year = 2003 | pmid = 12816380 | doi = 10.1111/j.1740-8261.2003.tb00467.x | doi-access = free }} Its main application is as its iodine-123 radiolabeled form, in which it can be used in SPECT scanning{{cite journal | vauthors = Busatto GF, Pilowsky LS, Costa DC, Mertens J, Terriere D, Ell PJ, Mulligan R, Travis MJ, Leysen JE, Lui D, Gacinovic S, Waddington W, Lingford-Hughes A, Kerwin RW | display-authors = 6 | title = Initial evaluation of 123I-5-I-R91150, a selective 5-HT2A ligand for single-photon emission tomography, in healthy human subjects | journal = European Journal of Nuclear Medicine | volume = 24 | issue = 2 | pages = 119–24 | date = February 1997 | pmid = 9021107 | doi = 10.1007/BF02439542 | s2cid = 33466680 }} in human neuroimaging studies, to examine the distribution of the 5-HT_2A receptor subtype in the brain, e.g. with respect to sex and age{{cite journal | vauthors = Baeken C, D'haenen H, Flamen P, Mertens J, Terriere D, Chavatte K, Boumon R, Bossuyt A | display-authors = 6 | title = 123I-5-I-R91150, a new single-photon emission tomography ligand for 5-HT2A receptors: influence of age and gender in healthy subjects | journal = European Journal of Nuclear Medicine | volume = 25 | issue = 12 | pages = 1617–22 | date = December 1998 | pmid = 9871092 | doi = 10.1007/s002590050339 | s2cid = 29644617 }} and in adults with Asperger syndrome{{cite journal | vauthors = Murphy DG, Daly E, Schmitz N, Toal F, Murphy K, Curran S, Erlandsson K, Eersels J, Kerwin R, Ell P, Travis M | display-authors = 6 | title = Cortical serotonin 5-HT2A receptor binding and social communication in adults with Asperger's syndrome: an in vivo SPECT study | journal = The American Journal of Psychiatry | volume = 163 | issue = 5 | pages = 934–6 | date = May 2006 | pmid = 16648340 | doi = 10.1176/appi.ajp.163.5.934 }} or Alzheimer's disease.{{cite journal | vauthors = Versijpt J, Van Laere KJ, Dumont F, Decoo D, Vandecapelle M, Santens P, Goethals I, Audenaert K, Slegers G, Dierckx RA, Korf J | display-authors = 6 | title = Imaging of the 5-HT2A system: age-, gender-, and Alzheimer's disease-related findings | journal = Neurobiology of Aging | volume = 24 | issue = 4 | pages = 553–61 | year = 2003 | pmid = 12714112 | doi = 10.1016/S0197-4580(02)00137-9 | s2cid = 44937787 }}

An alternative 5-HT_2A receptor ligand also used in neuroimaging is altanserin.