DEMPDHPCA-2C-D

DEMPDHPCA-2C-D
Clinical data
Other names2C-D-DEMPDHPCA; "Compound 45"
Drug classPossible serotonergic psychedelic or hallucinogen
ATC code
  • None
Identifiers
  • N,N-diethyl-1-methyl-5-(2,5-dimethoxy-4-methylphenyl)-3,6-dihydro-2H-pyridine-3-carboxamide
Chemical and physical data
FormulaC20H30N2O3
Molar mass346.471 g·mol−1
3D model (JSmol)
  • CCN(CC)C(C1C=C(C2=CC(OC)=C(C)C=C2OC)CN(C)C1)=O
  • InChI=1S/C20H30N2O3/c1-7-22(8-2)20(23)16-10-15(12-21(4)13-16)17-11-18(24-5)14(3)9-19(17)25-6/h9-11,16H,7-8,12-13H2,1-6H3
  • Key:ZANDNBLJKNVGIE-UHFFFAOYSA-N

DEMPDHPCA-2C-D is a possible serotonergic psychedelic of the phenethylamine and 2C families. It is a cyclized phenethylamine and a partial or simplified lysergamide. More specifically, the compound is a derivative of 2C-D in which the β position has been cyclized with the amine to form a pyridine ring, an LSD-like N,N-diethylcarboxamide moiety has been added to the pyridine ring, and an N-methyl group has been added to the amine. Alternatively, it may be viewed as an analogue of LSD in which the atoms at positions 1 through 4 of the ergoline ring system have been removed and 4-methyl and 2,5-dimethoxy substitutions have been added to the phenyl ring (i.e., the A ring of LSD).

DEMPDHPCA-2C-D was synthesized and described by David E. Nichols in his thesis in 1973. Its pharmacology was not reported. However, several close analogues of DEMPDHPCA-2C-D, such as DEMPDHPCA and a few of its derivatives, have been reported to be potent serotonin 5-HT2A receptor agonists or to produce hallucinogen-like behavioral effects in animals. In addition, the established putative psychedelic LPH-5 is very similar to DEMPDHPCA-2C-D in chemical structure but most notably lacks the LSD-like N,N-diethylcarboxamide moiety.