RTI-177

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (1R,2S,3S,5S)-3-(4-chlorophenyl)-8-methyl-2-(3-phenyl-1,2-oxazol-5-yl)-8-azabicyclo[3.2.1]octane

| image = RTI-177 Structure.svg

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| CAS_number = 171236-00-3

| CAS_number2 = 170939-95-4

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| index2_label = HCl

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| PubChem = 9821147

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 298580

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

| UNII = 8VL7AW8T35

| ChemSpiderID = 7996896

| C=23 | H=23 | Cl=1 | N=2 | O=1

| smiles = CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)C3=CC=C(C=C3)Cl)C4=CC(=NO4)C5=CC=CC=C5

| StdInChI = 1S/C23H23ClN2O/c1-26-18-11-12-21(26)23(19(13-18)15-7-9-17(24)10-8-15)22-14-20(25-27-22)16-5-3-2-4-6-16/h2-10,14,18-19,21,23H,11-13H2,1H3/t18-,19+,21+,23-/m0/s1

| StdInChIKey = ZGCYMNJHHKQEGA-KPYOPSEVSA-N

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RTI(-4229)-177 (2β-(3-phenylisoxazol-5-yl)-3β-(4-chlorophenyl)tropane, β-CPPIT) is a synthetic stimulant drug from the phenyltropane family, which acts as a DRI with micromolar affinity for the SERT.{{cite journal | vauthors = Lindsey KP, Wilcox KM, Votaw JR, Goodman MM, Plisson C, Carroll FI, Rice KC, Howell LL | display-authors = 6 | title = Effects of dopamine transporter inhibitors on cocaine self-administration in rhesus monkeys: relationship to transporter occupancy determined by positron emission tomography neuroimaging | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 309 | issue = 3 | pages = 959–69 | date = June 2004 | pmid = 14982963 | doi = 10.1124/jpet.103.060293 | s2cid = 39794215 | url = http://research.yerkes.emory.edu/Howell/JPET309.pdf | url-status = dead | archive-url = https://web.archive.org/web/20100611202853/http://research.yerkes.emory.edu/Howell/JPET309.pdf | archive-date = 2010-06-11 }} RTI-177 has an unusually long duration of action of 20 hours or more, substantially longer than the related compound RTI-336 from which it differs in molecular structure only by the absence of a p-methyl group.{{cite journal | vauthors = Carroll FI, Howard JL, Howell LL, Fox BS, Kuhar MJ | title = Development of the dopamine transporter selective RTI-336 as a pharmacotherapy for cocaine abuse | journal = The AAPS Journal | volume = 8 | issue = 1 | pages = E196-203 | date = March 2006 | pmid = 16584128 | pmc = 2751440 | doi = 10.1208/aapsj080124 | url = http://www.aapsj.org/view.asp?art=aapsj080124 }}

"the nonselective monoamine transporter inhibitor RTI-126 and the DAT-selective inhibitors RTI-150 and RTI-336 both had a faster rate of onset (30 min) and a short duration of action (4h). In contrast, the nonselective monoamine transporter inhibitor RTI-112 had a slower rate of onset (30–60 min) and a longer duration of action (10h). The DAT-selective inhibitors RTI-171 and RTI-177 also had slower rates of onset (30–120 min), but RTI-171 had a short duration of action (2.5 h) while RTI-177 had a very long duration of action (20 h)."{{cite journal | vauthors = Kimmel HL, O'Connor JA, Carroll FI, Howell LL | title = Faster onset and dopamine transporter selectivity predict stimulant and reinforcing effects of cocaine analogs in squirrel monkeys | journal = Pharmacology, Biochemistry, and Behavior | volume = 86 | issue = 1 | pages = 45–54 | date = January 2007 | pmid = 17258302 | pmc = 1850383 | doi = 10.1016/j.pbb.2006.12.006 }}