4,5-MDO-DMT

4,5-MDO-DMT, or 4,5-methylenedioxy-N,N-dimethyltryptamine, is a lesser-known psychedelic drug. It is the 4,5-methylenedioxy analog of DMT. 4,5-MDO-DMT was first synthesized by Alexander Shulgin, though in his book TiHKAL it was not tested to determine its psychoactive effects. 4,5-MDO-DMT has been the subject of limited subsequent testing; with behavioral disruption studies performed in male rats indicating that its hallucinogenic potency is less than that of 4,5-MDO-DiPT but greater than that of 5,6-MDO-DiPT.[1]

4,5-MDO-DMT
Names
Preferred IUPAC name
2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-dimethylethan-1-amine
Other names
4,5-Methylenedioxy-N,N-dimethyltryptamine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C13H16N2O2/c1-15(2)6-5-9-7-14-10-3-4-11-13(12(9)10)17-8-16-11/h3-4,7,14H,5-6,8H2,1-2H3
    Key: ZMKRWFZFMOKVCP-UHFFFAOYSA-N
SMILES
  • CN(C)CCC1=CNC2=C1C(OCO3)=C3C=C2
Properties
Chemical formula
 C14H16N2O2
Molar mass 232.28
Melting point 93–95 °C (199–203 °F; 366–368 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Kline, Toni B.; Benington, Frederick; Morin, Richard D.; Beaton, John M. (August 1982). "Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety". Journal of Medicinal Chemistry. 25 (8): 908–913. doi:10.1021/jm00350a005. PMID 7120280.


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