(-)-2β-(3-(4-Methylphenyl)isoxazol-5-yl)-3β-(4-chlorophenyl)tropane

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(-)-2β-(3-(4-Methylphenyl)isoxazol-5-yl)-3β-(4-chlorophenyl)tropane
RTI-336.png
Systematic (IUPAC) name
(1R,2S,3S,5S)-8-methyl-2-(3-(4-methylphenyl)isoxazol-5-yl)-3-(4-chlorophenyl)-8-azabicyclo[3.2.1]octane
Identifiers
PubChem CID: 9800708
Chemical data
Formula C24H25ClN2O
Molecular mass 392.920
  • CC1=CC=C(C=C1)C2=NOC(=C2)[C@@H]3[C@H]4CC[C@H](N4C)C[C@@H]3C5=CC=C(C=C5)Cl

RTI-336, (LS-193,309, (−)-2β-(3-(4-methylphenyl)isoxazol-5-yl)-3β-(4-chlorophenyl)tropane) is a phenyltropane derivative which acts as a potent and selective dopamine reuptake inhibitor and stimulant drug. It binds to the dopamine transporter with around 20x the affinity of cocaine,[1] however it produces relatively mild stimulant effects, with a slow onset and long duration of action.[2] These characteristics make it a potential candidate for treatment of cocaine addiction, as a possible substitute drug analogous to how methadone is used for treating heroin abuse.[3][4] RTI-336 fully substitutes for cocaine in addicted monkeys and supports self-administration,[5][6] and significantly reduces rates of cocaine use, especially when combined with SSRIs,[7] and research is ongoing to determine whether it could be a viable substitute drug in human cocaine addicts.

Update

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

Influence of chronic dopamine transporter inhibition by RTI-336 on motor behavior, sleep and hormone levels in rhesus monkeys.

Pharmacotherapy for Cocaine Abuse

Development of the Dopamine Transporter Selective RTI-336 as a Pharmacotherapy for Cocaine Abuse (FIC, et al. 2006).

LMAgraph.GIF
RTI336.png

HeteroCD.GIF

RTI X R [3H]CFT [3H]Nisoxetine [3H]Paroxetine N ÷ D S ÷ D
Coc — — 89.1 3298 (1986) 1045 (45) 37.01 11.79
177 Cl phenyl 1.28 504 (304) 2420 (220) 393.8 1891
176 Me phenyl 1.58 398 (239) 5110 (465) 251.9 3234
354 Me ethyl 1.62 299 (180) 6400 (582) 184.6 3951
336 Cl p-cresyl 4.09 1714 (1033) 5741 (522) 419.1 1404
386 Me p-anisyl 3.93 756 (450) 4027 (380) 192.4 1025

N.B. RTI-371[8]

See also

References

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  4. ↑ Sofuoglu M, Kosten TR. Emerging pharmacological strategies in the fight against cocaine addiction. Expert Opinion on Emerging Drugs. 2006 Mar;11(1):91-98. doi:10.1517/14728214.11.1.91
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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