DEMPDHPCA-2C-D

DEMPDHPCA-2C-D
Clinical data
Other names	2C-D-DEMPDHPCA; "Compound 45"
Drug class	Possible serotonergic psychedelic or hallucinogen
ATC code	None;
Identifiers
	IUPAC name N,N-diethyl-1-methyl-5-(2,5-dimethoxy-4-methylphenyl)-3,6-dihydro-2H-pyridine-3-carboxamide;
Chemical and physical data
Formula	C20H30N2O3
Molar mass	346.471 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)C(C1C=C(C2=CC(OC)=C(C)C=C2OC)CN(C)C1)=O;
	InChI 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.^[1] It is a cyclized phenethylamine and a partial or simplified lysergamide.^[1] 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.^[1] 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).^[1]

Quick Facts Clinical data, Other names ...

DEMPDHPCA-2C-D was synthesized and described by David E. Nichols in his thesis in 1973.^[1] Its pharmacology was not reported.^[1] 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-HT_2A receptor agonists^[2] or to produce hallucinogen-like behavioral effects in animals.^[3] 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.^[4]^[5]

Chemical structures of DEMPDHPCA-2C-D and related compounds

See also