(-)-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
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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
Molar mass 392.920[[Script error: No such module "String".]]
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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.

See also

References

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  1. Carroll, F.; Pawlush, N.; Kuhar, M.; Pollard, G.; Howard, J. (2004). "Synthesis, monoamine transporter binding properties, and behavioral pharmacology of a series of 3beta-(substituted phenyl)-2beta-(3'-substituted isoxazol-5-yl)tropanes". Journal of Medicinal Chemistry. 47 (2): 296–302. doi:10.1021/jm030453p. PMID 14711303.  edit
  2. Carroll, F.; Fox, B.; Kuhar, M.; Howard, J.; Pollard, G.; Schenk, S. (2006). "Effects of dopamine transporter selective 3-phenyltropane analogs on locomotor activity, drug discrimination, and cocaine self-administration after oral administration". European journal of pharmacology. 553 (1-3): 149–156. doi:10.1016/j.ejphar.2006.09.024. PMID 17067572.  More than one of |author2= and |last2= specified (help); More than one of |author3= and |last3= specified (help); More than one of |author4= and |last4= specified (help); More than one of |author5= and |last5= specified (help); More than one of |author6= and |last6= specified (help) edit
  3. Carroll, F.; Howard, J.; Howell, L.; Fox, B.; Kuhar, M. (2006). "Development of the dopamine transporter selective RTI-336 as a pharmacotherapy for cocaine abuse". The AAPS journal. 8 (1): E196–E203. doi:10.1208/aapsj080124. PMC 2751440Freely accessible. PMID 16584128.  edit
  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. Kimmel, H.; O'Connor, J.; Carroll, F.; Howell, L. (2007). "Faster onset and dopamine transporter selectivity predict stimulant and reinforcing effects of cocaine analogs in squirrel monkeys". Pharmacology, biochemistry, and behavior. 86 (1): 45–54. doi:10.1016/j.pbb.2006.12.006. PMC 1850383Freely accessible. PMID 17258302.  edit
  6. Kimmel, H.; Negus, S.; Wilcox, K.; Ewing, S.; Stehouwer, J.; Goodman, M.; Votaw, J.; Mello, N.; Carroll, F. (2008). "Relationship between rate of drug uptake in brain and behavioral pharmacology of monoamine transporter inhibitors in rhesus monkeys". Pharmacology, biochemistry, and behavior. 90 (3): 453–462. doi:10.1016/j.pbb.2008.03.032. PMC 2453312Freely accessible. PMID 18468667.  edit
  7. Howell, L.; Carroll, F.; Votaw, J.; Goodman, M.; Kimmel, H. (2007). "Effects of combined dopamine and serotonin transporter inhibitors on cocaine self-administration in rhesus monkeys". The Journal of pharmacology and experimental therapeutics. 320 (2): 757–765. doi:10.1124/jpet.106.108324. PMID 17105829.  edit