Structure via PubChem · Public domain (PubChem)
LR-5182
Sign in to saveLR-5182 is a stimulant drug which acts as a norepinephrine–dopamine reuptake inhibitor, structurally related to the better known drug fencamfamine. 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.
In the Vinony graph
Vinony's link graph records 803 inbound references to LR-5182, and connects out to histamine antagonist, indopan and tetracyclic antidepressant.
It sits within the topics Chemical articles with multiple CAS registry numbers, Chemical articles with multiple PubChem CIDs and Chemical articles without CAS registry number.
Vinony links it to 4 Wikipedia language editions.
Chemical data
- Formula
- C17H23Cl2N
- Molecular weight
- 312.3 g/mol
- IUPAC name
- 1-[(2S,3R)-3-(3,4-dichlorophenyl)-2-bicyclo[2.2.2]octanyl]-N,N-dimethylmethanamine
- SMILES
- CN(C)C[C@@H]1[C@@H](C2CCC1CC2)C3=CC(=C(C=C3)Cl)Cl
- InChIKey
- JOQQHMGSIKNGAF-NXDIHJKXSA-N
- XLogP
- 5.8
- Polar surface area
- 3.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 311.120755
Show 3 more facts
- chemical formula
- C₁₇H₂₃Cl₂N
- canonical SMILES
- CN(C)CC1C2CCC(C1C3=CC(=C(C=C3)Cl)Cl)CC2
- isomeric SMILES
- CN(C)C[C@@H]1[C@@H](C2CCC1CC2)C3=CC(=C(C=C3)Cl)Cl
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
LR-5182 is a stimulant drug which acts as a norepinephrine–dopamine reuptake inhibitor, structurally related to the better known drug fencamfamine. 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.
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, or as substitute drugs for the treatment of cocaine abuse.
Excerpted from Wikipedia’s “LR-5182” article, available under the CC BY-SA 4.0 licence.