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-HT_2A, 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]

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

Identifiers
IUPAC name 1-(2-Dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole
CAS Number	135360-97-3^N
PubChem CID	15011385
ChemSpider	19425248^N
CompTox Dashboard (EPA)	DTXSID10566920
Chemical and physical data
Formula	C15H20N2O
Molar mass	244.338 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CN(C)CCc1c[nH]c3ccc2OCCCc2c13
InChI 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
^NY (what is this?)  (verify)

See also

• 4,5-MDO-DMT
• 4,5-MDO-DiPT
• 5-MeO-DMT
• CP-132,484
• RU-28306

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.