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

4,5-DHP-DMT
Identifiers
	IUPAC name 1-(2-Dimethylaminoethyl)-8,9-dihydropyranoindole;
CAS Number	135360-97-3 ;
PubChem CID	15011385;
ChemSpider	19425248 ;
UNII	UW9YPK64EU;
ChEMBL	ChEMBL412876;
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)CCc1cc3ccc2OCCCc2c13;
	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 ; Key:RMMYVKPVLLBYDW-UHFFFAOYSA-N ;
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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 K_i 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]

References

^ Macor JE, Fox CB, Johnson C, Koe BK, Lebel LA, Zorn SH (October 1992). "1-(2-Aminoethyl)-3-methyl-8,9-dihydropyranoindole: 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.
^ 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-dihydropyranoindole". Journal of Medicinal Chemistry. 46 (19): 4188–95. CiteSeerX 10.1.1.688.6169. doi:10.1021/jm030205t. PMID 12954071.

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[pmid1433172-1] Macor JE, Fox CB, Johnson C, Koe BK, Lebel LA, Zorn SH (October 1992). "1-(2-Aminoethyl)-3-methyl-8,9-dihydropyranoindole: 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.

[pmid12954071-2] 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-dihydropyranoindole". Journal of Medicinal Chemistry. 46 (19): 4188–95. CiteSeerX 10.1.1.688.6169. doi:10.1021/jm030205t. PMID 12954071.

[1]

[2]

Identifiers

IUPAC name 1-(2-Dimethylaminoethyl)-8,9-dihydropyranoindole
CAS Number	135360-97-3^Y
PubChem CID	15011385
ChemSpider	19425248^Y
UNII	UW9YPK64EU
ChEMBL	ChEMBL412876
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)CCc1cc3ccc2OCCCc2c13
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

References