LR-5182

{{Short description|Stimulant drug}}

{{Drugbox

| verifiedrevid = 415309432

| IUPAC_name = 1-[(2R,3S)-3-(3,4-dichlorophenyl)-2-bicyclo[2.2.2]octanyl]-N,N-dimethylmethanamine

| image = LR-5182.svg

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| index2_label = HCl

| CAS_number =

| CAS_number2 = 62373-97-1

| ATC_prefix =

| ATC_suffix =

| PubChem = 44024

| PubChem2 = 44023

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID = 40076

| ChemSpiderID2 = 40075

| ChEMBL = 322067

| synonyms = (cis)-LR-5182, (cis)-LR-5182 hydrochloride

| C=17 | H=23 | Cl=2 | N=1

| molecular_weight =

| smiles = CN(C)C[C@@H]1C2CCC(CC2)[C@@H]1c3ccc(Cl)c(Cl)c3

| smiles2 = [Cl-].C[NH+](C)C[C@@H]1C2CCC(CC2)[C@@H]1c3ccc(Cl)c(Cl)c3

| StdInChI = 1S/C17H23Cl2N/c1-20(2)10-14-11-3-5-12(6-4-11)17(14)13-7-8-15(18)16(19)9-13/h7-9,11-12,14,17H,3-6,10H2,1-2H3/t11?,12?,14-,17-/m1/s1

| StdInChI2 =1S/C17H23Cl2N.ClH/c1-20(2)10-14-11-3-5-12(6-4-11)17(14)13-7-8-15(18)16(19)9-13;/h7-9,11-12,14,17H,3-6,10H2,1-2H3;1H/t11?,12?,14-,17-;/m1./s1

| StdInChIKey = JOQQHMGSIKNGAF-HLFYOVGASA-N

| StdInChIKey2 = CWRRQXXGIKGNJA-PQTJMFGHSA-N

}}

LR-5182 is a stimulant drug which acts as a norepinephrine–dopamine reuptake inhibitor, structurally related to the better known drug fencamfamine.{{cite journal | vauthors = Wong DT, Bymaster FP | title = An inhibitor of dopamine uptake, LR5182, cis-3-(3,4-dichlorophenyl)-2-n,n-dimethylaminomethyl-bicyclo-[2,2,2]-octane, hydrochloride | journal = Life Sciences | volume = 23 | issue = 10 | pages = 1041–7 | date = September 1978 | pmid = 713683 | doi = 10.1016/0024-3205(78)90664-1 }}{{cite journal | vauthors = Fuller RW, Perry KW, Snoddy HD | title = 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 | journal = Neuropharmacology | volume = 18 | issue = 5 | pages = 497–501 | date = May 1979 | pmid = 460546 | doi = 10.1016/0028-3908(79)90076-5 | s2cid = 38863316 }}{{cite journal | vauthors = Wong DT, Bymaster FP, Reid LR | title = Competitive inhibition of catecholamine uptake in synaptosomes of rat brain by rigid bicyclo-octanes | journal = Journal of Neurochemistry | volume = 34 | issue = 6 | pages = 1453–8 | date = June 1980 | pmid = 7381469 | doi = 10.1111/j.1471-4159.1980.tb11225.x | s2cid = 20372228 }} 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.{{cite journal | vauthors = Wedley S, Howard JL, Large BT, Pullar IA | title = The inhibition of monoamine uptake into rat brain synaptosomess by selected bicyclo-octanes and an analogous bicyclo-octene | journal = Biochemical Pharmacology | volume = 27 | issue = 24 | pages = 2907–9 | date = 1978 | pmid = 736983 | doi = 10.1016/0006-2952(78)90207-1 }}

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,{{cite journal | vauthors = 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 | display-authors = 6 | title = Bicyclo[2.2.1]heptanes as novel triple re-uptake inhibitors for the treatment of depression | journal = Bioorganic & Medicinal Chemistry Letters | volume = 13 | issue = 19 | pages = 3277–80 | date = October 2003 | pmid = 12951108 | doi = 10.1016/S0960-894X(03)00660-7 }} or as substitute drugs for the treatment of cocaine abuse.{{cite journal | vauthors = Deutsch HM, Collard DM, Zhang L, Burnham KS, Deshpande AK, Holtzman SG, Schweri MM | title = 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 = Journal of Medicinal Chemistry | volume = 42 | issue = 5 | pages = 882–95 | date = March 1999 | pmid = 10072685 | doi = 10.1021/jm980566m }}{{cite journal | vauthors = Javanmard S, Deutsch HM, Collard DM, Kuhar MJ, Schweri MM | title = Synthesis and pharmacology of site-specific cocaine abuse treatment agents: 2-substituted-6-amino-5-phenylbicyclo[2.2.2]octanes | journal = Journal of Medicinal Chemistry | volume = 42 | issue = 23 | pages = 4836–43 | date = November 1999 | pmid = 10579846 | doi = 10.1021/jm990306k }}