Lortalamine

Lortalamine
Clinical data
Routes of; administration	Oral
ATC code	None;
Pharmacokinetic data
Elimination half-life	5 hours
Excretion	Renal (98%)
Identifiers
	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;
CAS Number	70384-91-7;
PubChem CID	51047;
ChemSpider	16736803;
UNII	9GIR4SV22T;
KEGG	D04781;
CompTox Dashboard (EPA)	DTXSID00990578 ;
Chemical and physical data
Formula	C15H17ClN2O2
Molar mass	292.76 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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]

References

^ David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.
^ 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.
^ 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.
^ ^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.
^ 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.
^ 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.
^ 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.
^ 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.

[isbn0-412-46630-9-1] David J. Triggle (1997). Dictionary of pharmacological agents. London: Chapman & Hall. ISBN 0-412-46630-9.

[pmid6113932-2] 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.

[pmid4091869-3] 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.

[pmid15914010-4] 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.

[pmid4085522-5] 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.

[pmid2279460-6] 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.

[pmid15998285-7] 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.

[pmid17073682-8] 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.

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Lortalamine

See also

References

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