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LR-5182
Systematic (IUPAC) name
N,N-dimethyl-1-((1S,2 S,3R,4R)-3-phenylbicyclo[2.2.2]octan-2-yl)methanamine
Identifiers
CAS number 62373-97-1
ATC code  ?
PubChem 6328354
Chemical data
Formula C 17H23Cl2N 
Mol. mass 312.276 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Legal
Routes  ?

LR-5182 is a stimulant drug which acts as a norepinephrine and 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 only blocks reuptake of 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

  1. ^ Wong DT, Bymaster FP. An inhibitor of dopamine uptake, LR5182, cis-3-(3,4-dichlorophenyl)-2-N,N-dimethylaminomethyl-bicyclo-[2,2,2]-octane hydrochloride. Life Sciences. 1978, 23(10):1041-1047.
  2. ^ Fuller RW, Perry KW, Snoddy HD. 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. 1979, 18(5):497-501.
  3. ^ Wong DT, Bymaster FP, Reid LR. Competitive inhibition of catecholamine uptake in synaptosomes of rat brain by rigid bicyclo-octanes. Journal of Neurochemistry. 1980 Jun;34(6):1453-8. PMID 7381469
  4. ^ Wedney S, Howard JL, Large BT, Pullar IA. The inhibition of monoamine uptake into rat brain synaptosomes by selected bicyclo-octanes and an analogous bicyclo-octene. Biochemical Pharmacology. 1978, 27(24):2907-2909.
  5. ^ Axford L, Boot JR, Hotten TM, Keenan M, Martin FM, Milutinovic S, Moore NA, O'Neill MF, Pullar IA, Tupper DE, Van Belle KR, Vivien V. Bicyclo[2.2.1]heptanes as novel triple re-uptake inhibitors for the treatment of depression. Bioorganic and Medicinal Chemistry Letters. 2003 Oct 6;13(19):3277-80. PMID 12951108
  6. ^ Deutsch HM, Collard DM, Zhang L, Burnham KS, Deshpande AK, Holtzman SG, Schweri MM. 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. 1999 Mar 11;42(5):882-95. PMID 10072685
  7. ^ Javanmard S, Deutsch HM, Collard DM, Kuhar MJ, Schweri MM. Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-substituted-6-amino-5-phenylbicyclo[2.2.2]octanes. Journal of Medicinal Chemistry. 1999 Nov 18;42(23):4836-43. PMID 10579846
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