Lortalamine

Chemical compound
  • None
Pharmacokinetic dataElimination half-life5 hoursExcretionRenal (98%)Identifiers
  • 8-chloro-1,2,3,4,10,10a-hexahydro-2-methyl-4a,10-(iminoethano)-4aH-[1]-benzopyrano[3,2-c]-pyridin-12-one
CAS Number
  • 70384-91-7
PubChem CID
  • 51047
ChemSpider
  • 16736803
UNII
  • 9GIR4SV22T
KEGG
  • D04781
CompTox Dashboard (EPA)
  • DTXSID00990578 Edit this at Wikidata
Chemical and physical dataFormulaC15H17ClN2O2Molar mass292.76 g·mol−13D model (JSmol)
  • Interactive image
  • Clc1ccc2O[C@]34NC(=O)C[C@@H](c2c1)[C@H]4CN(C)CC3

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

References

  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. 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. S2CID 2196891.
  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. S2CID 25110597.
  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.
  • v
  • t
  • e
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Miscellaneous
  • v
  • t
  • e
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip Vesicular monoamine transporters
Others
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins