Lortalamine

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Lortalamine
Lortalamine.svg
Systematic (IUPAC) name
8-chloro-1,2,3,4,10,10a-hexahydro-2-methyl-4a,10-(iminoethano)-4aH-[1]-benzopyrano[3,2-c]-pyridin-12-one
Clinical data
Oral
Pharmacokinetic data
Half-life 5 hours
Excretion Renal (98%)
Identifiers
70384-91-7
None
PubChem CID 51047
ChemSpider 16736803
UNII 9GIR4SV22T YesY
KEGG D04781
Chemical data
Formula C15H17ClN2O2
292.76 g/mol

Lortalamine (LM-1404) is an antidepressant which was synthesized in the early 1980s.[1][2] It acts as a potent and highly selective norepinephrine reuptake inhibitor.[3][4] Lortalamine was under development for clinical use but was shelved, likely due to the finding that it produced ocular toxicity in animals.[5][6] It has been used to label the norepinephrine transporter in positron emission tomography studies.[4][7][8]

See also[edit]

References[edit]

  1. ^ David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9. 
  2. ^ Belleville M, Grand M, Briet P (1981). "Plasma levels, elimination and metabolic fate of 4a-amino-8-chloro-2-methyl-1,2,3,4,4a,10a-hexahydro-10H-benzopyrano[3,2-c]pyridin-10-ylacetic acid lactam, a new antidepressive agent, in rats and dogs". Drug Metabolism and Disposition: the Biological Fate of Chemicals 9 (3): 233–9. PMID 6113932. 
  3. ^ Depin JC, Betbeder-Matibet A, Bonhomme Y, Muller AJ, Berthelon JJ (1985). "Pharmacology of lortalamine, a new potent non-tricyclic antidepressant". Arzneimittel-Forschung 35 (11): 1655–62. PMID 4091869. 
  4. ^ a b Lin KS, Ding YS (August 2005). "Synthesis and C-11 labeling of three potent norepinephrine transporter selective ligands ((R)-nisoxetine, lortalamine, and oxaprotiline) for comparative PET studies in baboons". Bioorganic & Medicinal Chemistry 13 (15): 4658–66. doi:10.1016/j.bmc.2005.04.062. PMID 15914010. 
  5. ^ Elsom LF, Biggs SR, Chasseaud LF, Hawkins DR, Pulsford J, Darragh A (1985). "Metabolism of the anti-depressant lortalamine". European Journal of Drug Metabolism and Pharmacokinetics 10 (3): 209–15. doi:10.1007/bf03189744. PMID 4085522. 
  6. ^ Mally C, Thiebault JJ (1990). "Ocular toxicity in beagle dogs with lortalamine, a non tricyclic antidepressant compound". Drug and Chemical Toxicology 13 (4): 309–23. doi:10.3109/01480549009032289. PMID 2279460. 
  7. ^ Ding YS, Lin KS, Logan J, Benveniste H, Carter P (July 2005). "Comparative evaluation of positron emission tomography radiotracers for imaging the norepinephrine transporter: (S,S) and (R,R) enantiomers of reboxetine analogs ([11C]methylreboxetine, 3-Cl-[11C]methylreboxetine and [18F]fluororeboxetine), (R)-[11C]nisoxetine, [11C]oxaprotiline and [11C]lortalamine". Journal of Neurochemistry 94 (2): 337–51. doi:10.1111/j.1471-4159.2005.03202.x. PMID 15998285. 
  8. ^ Ding YS, Lin KS, Logan J (2006). "PET imaging of norepinephrine transporters". Current Pharmaceutical Design 12 (30): 3831–45. doi:10.2174/138161206778559687. PMID 17073682.