| 词条 | LR-5182 |
| 释义 |
| 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.[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] LR-5659 is planar and contains a Bicyclo-octene. This itself is fully active: DA 9nM, NE 27nM, SER 0.6 μM. References1. ^{{cite journal | url=http://www.sciencedirect.com/science/article/pii/0024320578906641 | title=An inhibitor of dopamine uptake, LR5182, CIS-3-(3,4-dichlorophenyl)-2-N, N-dimethylaminomethyl-bicyclo-[2,2,2]-octane, hydrochloride | author1=David T. Wong | author2=Frank P. Bymaster | journal=Life Sciences | date=September 1978 | volume=23 | issue=10 | pages=1041–1047 | doi=10.1016/0024-3205(78)90664-1 | pmid=713683}} {{Stimulants}}{{Antidepressants}}{{Monoamine reuptake inhibitors}}2. ^{{cite journal | url=http://www.sciencedirect.com/science/article/pii/0028390879900765 | 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 | author1=R.W. Fuller | author2=K.W. Perry | author3=H.D. Snoddy | journal=Neuropharmacology | date=May 1979 | volume=18 | issue=5 | pages=497–501 | doi=10.1016/0028-3908(79)90076-5 | pmid=460546}} 3. ^{{cite journal | title=Competitive Inhibition of Catecholamine Uptake in Synaptosomes of Rat Brain by Rigid Bicyclo-Octanes | author1=David T. Wong | author2=Frank P. Bymaster | author3=Leroy R. Reid | journal=Journal of Neurochemistry | date=June 1980 | volume=34 | issue=6 | pages=1453–1458 | doi=10.1111/j.1471-4159.1980.tb11225.x | pmid=7381469}} 4. ^{{cite journal | url=http://www.sciencedirect.com/science/article/pii/0006295278902071 | title=The inhibition of monoamine uptake into rat brain synaptosomes by selected bicyclo-octanes and an analogous bicyclo-octene | author1=Susan Wedley | author2=Joy L. Howard | author3=Bruce T. Large | author4=Ian A. Pullar | journal=Biochemical Pharmacology | date=1978 | volume=27 | issue=24 | pages=2907–2909 | doi=10.1016/0006-2952(78)90207-1 | pmid=736983}} 5. ^{{cite journal | url=http://www.sciencedirect.com/science/article/pii/S0960894X03006607 | title=Bicyclo[2.2.1]heptanes as novel triple re-uptake inhibitors for the treatment of depression | author1=Lorraine Axford | author2=John R. Boot | author3=Terrence M. Hotten | author4=Martine Keenan | author5=Fionna M. Martin | author6=Sandra Milutinovic | author7=Nick A. Moore | author8=Michael F. O'Neill | author9=Ian A. Pullar | author10=David E. Tupper | author11=Kristel R. Van Belle | author12=Vincent Vivien | journal=Bioorganic & Medicinal Chemistry Letters | date=October 2003 | volume=13 | issue=19 | pages=3277–3280 | doi=10.1016/S0960-894X(03)00660-7 | pmid=12951108}} 6. ^{{cite journal | 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 | author1=Howard M. Deutsch | author2=David M. Collard | author3=Liang Zhang | author4=Kikue S. Burnham | author5=Abhay K. Deshpande | author6=Stephan G. Holtzman | author7=Margaret M. Schweri | journal=Journal of Medicinal Chemistry | date=March 1999 | volume=42 | issue=5 | pages=882–895 | doi=10.1021/jm980566m | pmid=10072685}} 7. ^{{cite journal | title=Synthesis and Pharmacology of Site-Specific Cocaine Abuse Treatment Agents: 2-Substituted-6-amino-5-phenylbicyclo[2.2.2]octanes | author1=Sahar Javanmard | author2=Howard M. Deutsch | author3=David M. Collard | author4=Michael J. Kuhar | author5=Margaret M. Schweri | journal=Journal of Medicinal Chemistry | date=November 1999 | volume=42 | issue=23 | pages=4836–4843 | doi=10.1021/jm990306k | pmid=10579846}} 4 : Eli Lilly and Company|Norepinephrine-dopamine reuptake inhibitors|Stimulants|Chloroarenes |
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