Chemistry:LR-5182
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| Other names | (cis)-LR-5182, (cis)-LR-5182 hydrochloride |
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| Formula | C17H23Cl2N |
| Molar mass | 312.28 g·mol−1 |
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LR-5182 is a stimulant drug which acts as a norepinephrine–dopamine reuptake inhibitor, structurally related to the better known drug fencamfamine.[1][2][3] It was developed by the pharmaceutical company Eli Lilly in the 1970s, and researched for potential use as an antidepressant, although never marketed. LR-5182 has two stereoisomers, both of which are active, although one isomer blocks reuptake of only dopamine and noradrenaline, while the other blocks reuptake of serotonin as well.[4]
While LR-5182 itself never proceeded beyond initial animal studies, discovery of monoamine reuptake inhibition activity and stimulant effects in drugs of this type has subsequently led to the development of many other stimulant drugs of related chemical structure, primarily developed as potential antidepressants,[5] or as substitute drugs for the treatment of cocaine abuse.[6][7]
References
- ↑ "An inhibitor of dopamine uptake, LR5182, cis-3-(3,4-dichlorophenyl)-2-n,n-dimethylaminomethyl-bicyclo-[2,2,2]-octane, hydrochloride". Life Sciences 23 (10): 1041–7. September 1978. doi:10.1016/0024-3205(78)90664-1. PMID 713683.
- ↑ "In vivo effects of LR5182, cis-3-(3,4-dichlorophenyl)-2-n,n-dimethylaminomethyl- bicyclo-[2,2,2]-octane hydrochloride, an inhibitor of uptake into dopamine and norepinephrine neurons". Neuropharmacology 18 (5): 497–501. May 1979. doi:10.1016/0028-3908(79)90076-5. PMID 460546.
- ↑ "Competitive inhibition of catecholamine uptake in synaptosomes of rat brain by rigid bicyclo-octanes". Journal of Neurochemistry 34 (6): 1453–8. June 1980. doi:10.1111/j.1471-4159.1980.tb11225.x. PMID 7381469.
- ↑ "The inhibition of monoamine uptake into rat brain synaptosomess by selected bicyclo-octanes and an analogous bicyclo-octene". Biochemical Pharmacology 27 (24): 2907–9. 1978. doi:10.1016/0006-2952(78)90207-1. PMID 736983.
- ↑ "Bicyclo[2.2.1]heptanes as novel triple re-uptake inhibitors for the treatment of depression". Bioorganic & Medicinal Chemistry Letters 13 (19): 3277–80. October 2003. doi:10.1016/S0960-894X(03)00660-7. PMID 12951108.
- ↑ "Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-(aminomethyl)-3-phenylbicyclo[2.2.2]- and -[2.2.1]alkane dopamine uptake inhibitors". Journal of Medicinal Chemistry 42 (5): 882–95. March 1999. doi:10.1021/jm980566m. PMID 10072685.
- ↑ "Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-substituted-6-amino-5-phenylbicyclo[2.2.2]octanes". Journal of Medicinal Chemistry 42 (23): 4836–43. November 1999. doi:10.1021/jm990306k. PMID 10579846.
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