5-I-R91150

5-I-R91150

Identifiers
IUPAC name 4-amino-N-[1-[3-(4-fluorophenoxy)propyl]-4-methyl-4-piperidinyl]-5-iodo-2-methoxybenzamide
CAS Number	155928-24-8  N
PubChem CID	132997
ChemSpider	117371  Y
UNII	T0W602CN0W
CompTox Dashboard (EPA)	DTXSID90165995
Chemical and physical data
Formula	C23H29FIN3O2
Molar mass	525.407 g·mol−1
3D model (JSmol)	Interactive image
SMILES Ic1cc(c(OC)cc1N)C(=O)NC3(CCN(CCCc2ccc(F)cc2)CC3)C
InChI InChI=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) Y Key:MIPHZURHMMOGLS-UHFFFAOYSA-N Y
NY  (what is this?)    (verify)

5-I-R91150 (or R93274) is a compound that acts as a potent and selective antagonist of 5-HT_2A receptors. ^[1] Its main application is as its iodine-123 radiolabeled form, in which it can be used in SPECT scanning ^[2] 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 ^[3] and in adults with Asperger syndrome ^[4] or Alzheimer's disease. ^[5]

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

References

1. Peremans K, Audenaert K, Coopman F, Jacobs F, Dumont F, Slegers G, et al. (2003). "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". Veterinary Radiology & Ultrasound. 44 (3): 344–51. doi: 10.1111/j.1740-8261.2003.tb00467.x . PMID   12816380.
2. Busatto GF, Pilowsky LS, Costa DC, Mertens J, Terriere D, Ell PJ, et al. (February 1997). "Initial evaluation of 123I-5-I-R91150, a selective 5-HT2A ligand for single-photon emission tomography, in healthy human subjects". European Journal of Nuclear Medicine. 24 (2): 119–24. doi:10.1007/BF02439542. PMID   9021107. S2CID   33466680.
3. Baeken C, D'haenen H, Flamen P, Mertens J, Terriere D, Chavatte K, et al. (December 1998). "123I-5-I-R91150, a new single-photon emission tomography ligand for 5-HT2A receptors: influence of age and gender in healthy subjects". European Journal of Nuclear Medicine. 25 (12): 1617–22. doi:10.1007/s002590050339. PMID   9871092. S2CID   29644617.
4. Murphy DG, Daly E, Schmitz N, Toal F, Murphy K, Curran S, et al. (May 2006). "Cortical serotonin 5-HT2A receptor binding and social communication in adults with Asperger's syndrome: an in vivo SPECT study". The American Journal of Psychiatry. 163 (5): 934–6. doi:10.1176/appi.ajp.163.5.934. PMID   16648340.
5. Versijpt J, Van Laere KJ, Dumont F, Decoo D, Vandecapelle M, Santens P, et al. (2003). "Imaging of the 5-HT2A system: age-, gender-, and Alzheimer's disease-related findings". Neurobiology of Aging. 24 (4): 553–61. doi:10.1016/S0197-4580(02)00137-9. PMID   12714112. S2CID   44937787.

Further reading

• Catafau AM, Danus M, Bullich S, Llop J, Perich J, Cunningham VJ, et al. (June 2006). "Characterization of the SPECT 5-HT2A receptor ligand 123I-R91150 in healthy volunteers: Part 1--pseudoequilibrium interval and quantification methods". Journal of Nuclear Medicine. 47 (6): 919–28. PMID   16741300.
• Catafau AM, Danus M, Bullich S, Nucci G, Llop J, Abanades S, et al. (June 2006). "Characterization of the SPECT 5-HT2A receptor ligand 123I-R91150 in healthy volunteers: part 2--ketanserin displacement". Journal of Nuclear Medicine. 47 (6): 929–37. PMID   16741301.