RTI-371

3β-(4-Methylphenyl)-2β-[3-(4-chlorophenyl)isoxazol-5-yl]tropane (RTI-4229-371) is a phenyltropane derived drug which acts as a potent and selective dopamine reuptake inhibitor in vitro, yet unusually for this class of compound, both RTI-371 and the closely related compound RTI-370 failed to produce locomotor stimulation in mice. In addition to this, in drug substitution tests RTI-370 weakly generalized to cocaine whereas RTI-371 did not generalize at all.

RTI-371

Identifiers
IUPAC name 3-(4-Chlorophenyl)-5-[(1R,2S,3S,5S)-8-methyl-3-(4-methylphenyl)-8-azabicyclo[3.2.1]octan-2-yl]-1,2-oxazole
CAS Number	652978-45-5^N
PubChem CID	11474847
Chemical and physical data
Formula	C24H25ClN2O
Molar mass	392.93 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC1=CC=C(C=C1)[C@H]2C[C@@H]3CC[C@H]([C@H]2C4=CC(=NO4)C5=CC=C(C=C5)Cl)N3C
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This phenomenon has also been observed for other dopamine reuptake inhibitors from other classes. It may be caused by lack of BBB penetration, or interactions at alternative receptor sites.[1][2]

See also

• List of cocaine analogues
• List of phenyltropanes

References

1. Navarro HA, Howard JL, Pollard GT, Carroll FI (April 2009). "Positive allosteric modulation of the human cannabinoid (CB) receptor by RTI-371, a selective inhibitor of the dopamine transporter". British Journal of Pharmacology. 156 (7): 1178–84. doi:10.1111/j.1476-5381.2009.00124.x. PMC 2697692. PMID 19226282.
2. Foster MD (2011). Computational study of RTI-371, a positive allosteric modulator of the cannabinoid CB1 receptor (PDF) (MSc thesis). The University of North Carolina at Greensboro.