Contents

RTI-177

Chemical compound

RTI-177

Identifiers
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
CAS Number	171236-00-3 HCl: 170939-95-4
PubChem CID	9821147
ChemSpider	7996896
ChEMBL	ChEMBL298580 Y
Chemical and physical data
Formula	C23H23ClN2O
Molar mass	378.90 g·mol−1
3D model (JSmol)	Interactive image
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
InChI InChI=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 Key:ZGCYMNJHHKQEGA-KPYOPSEVSA-N

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.^[1] 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.^[2]

"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)."^[3]

Update[edit]

Lower reinforcing strength of the phenyltropane cocaine analogs RTI-336 and RTI-177 compared to cocaine in nonhuman primates.

Comparison of six MAT inhibitors[edit]

In the Lindsey paper, RTI-177 was wrongly considered to be a dual inhibitor of the NET, although this was later found out to be incorrect.^{[citation needed]}

"In acute toxicity studies in male rats, 3β-(4-chlorophenyl)-2β-[3-(4’-methylphenyl)isoxazol-5-yl]tropane (RTI-336) possessed an LD50 of 180 mg/kg after oral administration, compared with 49 mg/kg for RTI-177 (unpublished results, Howell 2005; Table 9). These results suggested that RTI-336 was a better candidate than RTI-177 for further preclinical development."^[2]

Also the potency of the heterocyclic compounds is not as great as would be predicted based on in vitro test results.

References[edit]