Chemistry:LY-344864

LY-344864
Identifiers
	IUPAC name N-[(6R)-6-(dimethylamino)-6,7,8,9-tetrahydro-5H-carbazol-3-yl]-4-fluorobenzamide;
CAS Number	186544-26-3;
PubChem CID	5311097;
IUPHAR/BPS	21;
ChemSpider	4470627;
UNII	L4WN6HH63L;
ChEBI	CHEBI:93683;
ChEMBL	ChEMBL1628565;
Chemical and physical data
Formula	C21H22FN3O
Molar mass	351.425 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)[C@@H]1CCC2=C(C1)C3=C(N2)C=CC(=C3)NC(=O)C4=CC=C(C=C4)F;
	InChI InChI=1S/C21H22FN3O/c1-25(2)16-8-10-20-18(12-16)17-11-15(7-9-19(17)24-20)23-21(26)13-3-5-14(22)6-4-13/h3-7,9,11,16,24H,8,10,12H2,1-2H3,(H,23,26)/t16-/m1/s1; Key:GKWHICIUSVVNGX-MRXNPFEDSA-N;

LY-344,864 is an experimental drug of the triptan and tetrahydrocarbazolamine families with a tricyclic cyclized tryptamine structure which acts as an agonist for the 5-HT_1F serotonin receptor.^[1] It has antimigraine activity in animal models but was never developed for this indication as a medicine,^[2]^[3] however it continues to be used in scientific research and in recent years has been investigated as a potential agent for stimulating mitochondrial biogenesis, which can facilitate repair to damaged cells and tissues with a number of potential medical applications.^[4]^[5]^[6]^[7]^[8]

References

↑ "Characterization of LY344864 as a pharmacological tool to study 5-HT1F receptors: binding affinities, brain penetration and activity in the neurogenic dural inflammation model of migraine". Life Sciences 61 (21): 2117–2126. 1997. doi:10.1016/s0024-3205(97)00885-0. PMID 9395253.
↑ "Targeting to 5-HT1F receptor subtype for migraine treatment: lessons from the past, implications for the future". Central Nervous System Agents in Medicinal Chemistry 12 (4): 241–249. December 2012. doi:10.2174/187152412803760627. PMID 22934751.
↑ "The 5-HT_1F receptor as the target of ditans in migraine - from bench to bedside". Nature Reviews. Neurology 19 (8): 489–505. August 2023. doi:10.1038/s41582-023-00842-x. PMID 37438431.
↑ "Agonism of the 5-hydroxytryptamine 1F receptor promotes mitochondrial biogenesis and recovery from acute kidney injury". The Journal of Pharmacology and Experimental Therapeutics 350 (2): 257–264. August 2014. doi:10.1124/jpet.114.214700. PMID 24849926.
↑ "5-HT_1F receptor-mediated mitochondrial biogenesis for the treatment of Parkinson's disease". British Journal of Pharmacology 175 (2): 348–358. January 2018. doi:10.1111/bph.14076. PMID 29057453.
↑ "Intracerebroventricular microinjection of the 5-HT_1F receptor agonist LY 344864 inhibits methamphetamine conditioned place preference reinstatement in rats". Pharmacology, Biochemistry, and Behavior 173: 27–35. October 2018. doi:10.1016/j.pbb.2018.08.001. PMID 30077744.
↑ "The 5-hydroxytryptamine receptor 1F stimulates mitochondrial biogenesis and angiogenesis in endothelial cells". Biochemical Pharmacology 169. November 2019. doi:10.1016/j.bcp.2019.113644. PMID 31542386.
↑ "5-hydroxytryptamine 1F Receptor Agonist Induces Mitochondrial Biogenesis and Promotes Recovery from Spinal Cord Injury". The Journal of Pharmacology and Experimental Therapeutics 372 (2): 216–223. February 2020. doi:10.1124/jpet.119.262410. PMID 31776207.

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Original source: https://en.wikipedia.org/wiki/LY-344864. Read more

[1] "Characterization of LY344864 as a pharmacological tool to study 5-HT1F receptors: binding affinities, brain penetration and activity in the neurogenic dural inflammation model of migraine". Life Sciences 61 (21): 2117–2126. 1997. doi:10.1016/s0024-3205(97)00885-0. PMID 9395253.

[2] "Targeting to 5-HT1F receptor subtype for migraine treatment: lessons from the past, implications for the future". Central Nervous System Agents in Medicinal Chemistry 12 (4): 241–249. December 2012. doi:10.2174/187152412803760627. PMID 22934751.

[3] "The 5-HT_1F receptor as the target of ditans in migraine - from bench to bedside". Nature Reviews. Neurology 19 (8): 489–505. August 2023. doi:10.1038/s41582-023-00842-x. PMID 37438431.

[4] "Agonism of the 5-hydroxytryptamine 1F receptor promotes mitochondrial biogenesis and recovery from acute kidney injury". The Journal of Pharmacology and Experimental Therapeutics 350 (2): 257–264. August 2014. doi:10.1124/jpet.114.214700. PMID 24849926.

[5] "5-HT_1F receptor-mediated mitochondrial biogenesis for the treatment of Parkinson's disease". British Journal of Pharmacology 175 (2): 348–358. January 2018. doi:10.1111/bph.14076. PMID 29057453.

[6] "Intracerebroventricular microinjection of the 5-HT_1F receptor agonist LY 344864 inhibits methamphetamine conditioned place preference reinstatement in rats". Pharmacology, Biochemistry, and Behavior 173: 27–35. October 2018. doi:10.1016/j.pbb.2018.08.001. PMID 30077744.

[7] "The 5-hydroxytryptamine receptor 1F stimulates mitochondrial biogenesis and angiogenesis in endothelial cells". Biochemical Pharmacology 169. November 2019. doi:10.1016/j.bcp.2019.113644. PMID 31542386.

[8] "5-hydroxytryptamine 1F Receptor Agonist Induces Mitochondrial Biogenesis and Promotes Recovery from Spinal Cord Injury". The Journal of Pharmacology and Experimental Therapeutics 372 (2): 216–223. February 2020. doi:10.1124/jpet.119.262410. PMID 31776207.

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IUPAC name N-[(6R)-6-(dimethylamino)-6,7,8,9-tetrahydro-5H-carbazol-3-yl]-4-fluorobenzamide
CAS Number	186544-26-3
PubChem CID	5311097
IUPHAR/BPS	21
ChemSpider	4470627
UNII	L4WN6HH63L
ChEBI	CHEBI:93683
ChEMBL	ChEMBL1628565
Chemical and physical data
Formula	C₂₁H₂₂FN₃O
Molar mass	351.425 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN(C)[C@@H]1CCC2=C(C1)C3=C(N2)C=CC(=C3)NC(=O)C4=CC=C(C=C4)F
InChI InChI=1S/C21H22FN3O/c1-25(2)16-8-10-20-18(12-16)17-11-15(7-9-19(17)24-20)23-21(26)13-3-5-14(22)6-4-13/h3-7,9,11,16,24H,8,10,12H2,1-2H3,(H,23,26)/t16-/m1/s1 Key:GKWHICIUSVVNGX-MRXNPFEDSA-N

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