1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole

1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole (4,5-DHP-DMT) is a tricyclic tryptamine derivative which acts as a potent and reasonably selective partial agonist for the serotonin receptor 5-HT2A, with a Ki of 17.0 nM, and moderate selectivity over related serotonin receptors. It has lower 5-HT2 affinity and efficacy than the related compound AL-37350A, but higher lipophilicity.[1][2]

4,5-DHP-DMT
Identifiers
  • 1-(2-Dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H20N2O
Molar mass244.338 g·mol−1
3D model (JSmol)
  • CN(C)CCc1c[nH]c3ccc2OCCCc2c13
  • InChI=1S/C15H20N2O/c1-17(2)8-7-11-10-16-13-5-6-14-12(15(11)13)4-3-9-18-14/h5-6,10,16H,3-4,7-9H2,1-2H3 ☒N
  • Key:RMMYVKPVLLBYDW-UHFFFAOYSA-N ☒N
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See also

References
  1. Macor JE, Fox CB, Johnson C, Koe BK, Lebel LA, Zorn SH (October 1992). "1-(2-Aminoethyl)-3-methyl-8,9-dihydropyrano[3,2-e]indole: a rotationally restricted phenolic analog of the neurotransmitter serotonin and agonist selective for serotonin (5-HT2-type) receptors". Journal of Medicinal Chemistry. 35 (20): 3625–32. doi:10.1021/jm00098a005. PMID 1433172.
  2. May JA, Chen HH, Rusinko A, Lynch VM, Sharif NA, McLaughlin MA (September 2003). "A novel and selective 5-HT2 receptor agonist with ocular hypotensive activity: (S)-(+)-1-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole". Journal of Medicinal Chemistry. 46 (19): 4188–95. CiteSeerX 10.1.1.688.6169. doi:10.1021/jm030205t. PMID 12954071.


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