View source for Chemistry:1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 455011578
| IUPAC_name = 1-(2-Dimethylaminoethyl)-8,9-dihydropyrano[3,2-''e'']indole
| drug_name = 4,5-DHP-DMT
| image = 4,5-DHP-DMT.svg
| width = 

<!--Clinical data-->
| tradename =  
| pregnancy_AU =  
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| legal_AU =  
| legal_CA =  
| legal_UK =  
| legal_US =  
| legal_status =  
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability =  
| protein_bound =  
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<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 135360-97-3 
| ATC_prefix =  
| ATC_suffix =  
| PubChem = 15011385
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UW9YPK64EU
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID      = 19425248
| ChEMBL = 412876

<!--Chemical data-->
| C=15 | H=20 | N=2 | O=1 
| smiles = CN(C)CCc1c[nH]c3ccc2OCCCc2c13
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI          = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey       = RMMYVKPVLLBYDW-UHFFFAOYSA-N
| melting_point =  
| melting_high =  
}}

'''1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole''' ('''4,5-DHP-DMT''') is a [[Chemistry:Tricyclic|tricyclic]] [[Chemistry:Tryptamine|tryptamine]] derivative which acts as a potent and reasonably selective [[Chemistry:Partial agonist|partial agonist]] for the [[Chemistry:Serotonin|serotonin]] [[Biology:Receptor (biochemistry)|receptor]] [[Biology:5-HT2A receptor|5-HT{{sub|2A}}]], with a [[Chemistry:Dissociation constant#Protein-ligand binding|Ki]] of 17.0 nM, and moderate selectivity over related serotonin receptors. It has lower 5-HT{{sub|2}} affinity and efficacy than the related compound [[Chemistry:AL-37350A|AL-37350A]], but higher [[Chemistry:Lipophilicity|lipophilicity]].<ref name="pmid1433172">{{cite journal |vauthors=Macor JE, Fox CB, Johnson C, Koe BK, Lebel LA, Zorn SH |title=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=Journal of Medicinal Chemistry |volume=35 |issue=20 |pages=3625–32 |date=October 1992|pmid=1433172 |doi= 10.1021/jm00098a005}}</ref><ref name="pmid12954071">{{cite journal |vauthors=May JA, Chen HH, Rusinko A, Lynch VM, Sharif NA, McLaughlin MA |title=A novel and selective 5-HT2 receptor agonist with ocular hypotensive activity: (S)-(+)-1-(2-aminopropyl)-8,9-dihydropyrano[3,2-e]indole |journal=Journal of Medicinal Chemistry |volume=46 |issue=19 |pages=4188–95 |pmid=12954071 |doi=10.1021/jm030205t |date=September 2003|citeseerx=10.1.1.688.6169 }}</ref>

==See also==
* [[Chemistry:4,5-MDO-DMT|4,5-MDO-DMT]]
* [[Chemistry:4,5-MDO-DiPT|4,5-MDO-DiPT]]
* [[Chemistry:5-MeO-DMT|5-MeO-DMT]]
* [[Chemistry:CP-132,484|CP-132,484]]
* [[Chemistry:RU-28306|RU-28306]]

== References ==
{{reflist}}

{{Serotonergics}}
{{Tryptamines}}

{{DEFAULTSORT:Dimethylaminoethyl)dihydropyrano(3, 2-e)indole, 1-(2-}}
[[Category:Serotonin receptor agonists]]
[[Category:Tryptamines]]
[[Category:Dihydropyrans]]
[[Category:Heterocyclic compounds with 3 rings]]
[[Category:Dimethylamino compounds]]



{{Sourceattribution|1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole|1}}