RTI-120

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 449586048

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

| image = RTI-120_structure.png

| tradename =

| CAS_number = 146145-20-2

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

| UNII = 532Y5K4NMA

| ATC_prefix =

| ATC_suffix =

| PubChem = 10109793

| ChemSpiderID = 34948082

| C=22 | H=25 | N=1 | O=2

| smiles = CN1[C@@H]2C[C@H](C3=CC=C(C)C=C3)[C@H](C(OC4=CC=CC=C4)=O)[C@H]1CC2

| StdInChI = 1S/C22H25NO2/c1-15-8-10-16(11-9-15)19-14-17-12-13-20(23(17)2)21(19)22(24)25-18-6-4-3-5-7-18/h3-11,17,19-21H,12-14H2,1-2H3/t17-,19+,20+,21-/m0/s1

| StdInChIKey = HIQHQNWJRSNELD-KCLUMXDGSA-N

}}

(–)-2β-Carbophenoxy-3β-(p-tolyl)tropane (RTI-4229-120) is a phenyltropane derivative which acts as a reasonably selective dopamine reuptake inhibitor, along with weaker inhibition of noradrenaline and serotonin reuptake.{{cite journal |vauthors=Silverthorn ML, Dersch CM, Baumann MH, Cadet JL, Partilla JS, Rice KC, Carroll FI, Becketts KM, Brockington A, Rothman RB |title=Studies of the biogenic amine transporters. V. Demonstration of two binding sites for the cocaine analog [125I]RTI-55 associated with the 5-HT transporter in rat brain membranes |journal=The Journal of Pharmacology and Experimental Therapeutics |volume=273 |issue=1 |pages=213–22 |date=April 1995 |pmid=7714769 }} It has a reasonably fast rate of occupancy of dopamine transporters in the brain, though slower than that of cocaine itself.{{cite journal |vauthors=Stathis M, Scheffel U, Lever SZ, Boja JW, Carroll FI, Kuhar MJ |title=Rate of binding of various inhibitors at the dopamine transporter in vivo |journal=Psychopharmacology |volume=119 |issue=4 |pages=376–84 |date=June 1995 |pmid=7480516 |doi= 10.1007/BF02245852|url=https://zenodo.org/record/1232524}} RTI-120 has a short duration of action, along with other p-methyl substituted phenyltropanes such as RTI-150, RTI-171 and RTI-199, giving it a more similar pharmacological profile to cocaine compared to longer acting analogues like RTI-121 and RTI-177.{{cite journal |vauthors=Kimmel HL, Carroll FI, Kuhar MJ |title=Locomotor stimulant effects of novel phenyltropanes in the mouse |journal=Drug and Alcohol Dependence |volume=65 |issue=1 |pages=25–36 |date=December 2001 |pmid=11714587 |doi= 10.1016/S0376-8716(01)00144-2}}