DEMPDHPCA-2C-D

{{Infobox drug

| drug_name =

| image = DEMPDHPCA-2C-D.svg

| width = 175px

| caption =

| pronounce =

| tradename =

| Drugs.com =

| MedlinePlus =

| licence_CA =

| licence_EU =

| DailyMedID =

| licence_US =

| pregnancy_AU =

| pregnancy_category =

| dependency_liability =

| addiction_liability =

| routes_of_administration =

| class = Possible serotonergic psychedelic or hallucinogen

| ATC_prefix = None

| ATC_suffix =

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

| metabolites =

| onset =

| elimination_half-life =

| duration_of_action =

| excretion =

| CAS_number =

| CAS_supplemental =

| PubChem =

| PubChemSubstance =

| IUPHAR_ligand =

| DrugBank =

| ChemSpiderID =

| UNII =

| KEGG =

| ChEBI =

| ChEMBL =

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = 2C-D-DEMPDHPCA; "Compound 45"

| IUPAC_name = N,N-diethyl-1-methyl-5-(2,5-dimethoxy-4-methylphenyl)-3,6-dihydro-2H-pyridine-3-carboxamide

| C=20 | H=30 | N=2 | O=3

| SMILES = CCN(CC)C(C1C=C(C2=CC(OC)=C(C)C=C2OC)CN(C)C1)=O

| StdInChI = 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

| StdInChIKey = ZANDNBLJKNVGIE-UHFFFAOYSA-N

}}

DEMPDHPCA-2C-D is a possible serotonergic psychedelic of the phenethylamine and 2C families.{{cite thesis | vauthors = Nichols DE | title = Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid | pages = 23 | date = May 1973 | publisher = University of Iowa | oclc = 1194694085 | url = https://bitnest.netfirms.com/external/Theses/Nichols1973#page=65 | quote = Part III. Proposed Synthesis of an LSD AD-Ring Congener To study the importance of the D ring of LSD it was proposed to prepare 45. This system presumably would possess a high HOMO as conferred on the system by the 2,5- dimethoxy-4-methyl substitution and is a close analog of LSD. [...] }} 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-HT_2A receptor agonists{{cite patent | title = Ergoline-like compounds for promoting neural plasticity | number = 2021076572 | country = WO | inventor = Olson DE, Dunlap L, Wagner F, Chytil M, Powell NA | pubdate = 22 April 2021 | fdate = 14 October 2020 | pridate = 14 October 2020 | assign1 = Delix Therapeutics, Inc. | assign2 = The Regents of the University of California | url = https://patents.google.com/patent/WO2021076572/ | quote = Example 1: Preparation of N,N-diethyl-1-methyl-5-phenyl-1,2,3,6-tetrahydropyridine-3-carboxamide (I-5) [...] Example 2: Compounds 1 and 2 via Chiral resolution of I-5 [...] Table 1. In vitro 5-HT2A and 5-HT2C Radioligand Binding and Cellular IPOne Agonism Activity [...] }} or to produce hallucinogen-like behavioral effects in animals.{{cite thesis | vauthors = Mangner TJ | title = Potential Psychotomimetic Antagonists. N,N -Diethyl-1-methyl-3-aryl-1,2,5,6-tetrahydropyridine-5-carboxamides. | date = 1978 | doi = 10.7302/11268 | degree = Ph.D. | publisher = University of Michigan | url = https://www.proquest.com/openview/f845a6810749d00f70305960adfde737/ | archive-url = https://web.archive.org/web/20250330031605/https://media.proquest.com/media/hms/ORIG/2/9yQxJ?cit%3Aauth=MANGNER%2C+THOMAS+JOSEPH&cit%3Atitle=POTENTIAL+PSYCHOTOMIMETIC+ANTAGONISTS.+N%2CN+...&cit%3Apub=ProQuest+Dissertations+and+Theses&cit%3Avol=&cit%3Aiss=&cit%3Apg=&cit%3Adate=1978&ic=true&cit%3Aprod=ProQuest+Dissertations+%26+Theses+Global&_a=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&_s=QP3F3liRMGFAbHtX3wDWE8eO1gs%3D | archive-date = 30 March 2025 | quote = The gross behavior of the test animals under the influence of 160a-d was observed during the course of the dose-response study depicted by Figure 7. The gross behavioral signs displayed by rats under the influence of the phenyl (160a) and trimethoxyphenyl (160c) homologs were indistinguishable from those exhibited with LSD, DMT or mescaline, and were characterized by general inactivity, muscle twitching and the occurrence of a Straub tail reaction (a somewhat specific indication of the influence of a psychotomimetic drug in which the tail is held in an upright 191 position ). The naphthyl homolog (160d) produced similar behavioral signs but the rats were more active than with 160a and 160c. The gross behavioral pattern of rats under the influence of the methoxy homolog (160b), in contrast, was not at all similar to that caused by LSD, 160a or 160c. It more closely resembled the pattern exhibited with amphetamine, characterized by very marked hyperactivity. [...] Initial indications, based on the gross behavioral comparisons mentioned previously, are that 160a,c,d possess psychotomimetic activity similar to LSD, while 160b possesses amphetamine-like stimulatory activity. [...] On the other hand, 160a, whose structure more closely resembles that of LSD, seems to have LSD-like activity of greater potency than either 160b or 160c. Since the structure of 160a is very closely related to the structure of LSD and contains no aryl methoxy groups necessary for psychotomimetic activity in the methoxyamphetamine series, it could be inferred that 160a acts via an LSD-like mechanism. [...] SUMMARY [...] }} 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.{{cite journal | vauthors = Gumpper RH, Nichols DE | title = Chemistry/structural biology of psychedelic drugs and their receptor(s) | journal = British Journal of Pharmacology | date = October 2024 | pmid = 39354889 | doi = 10.1111/bph.17361 }}{{cite journal | vauthors = M Ro Rsted E, Jensen AA, Smits G, Frydenvang K, Kristensen JL | title = Discovery and Structure-Activity Relationships of 2,5-Dimethoxyphenylpiperidines as Selective Serotonin 5-HT2A Receptor Agonists | journal = Journal of Medicinal Chemistry | volume = 67 | issue = 9 | pages = 7224–7244 | date = May 2024 | pmid = 38648420 | pmc = 11089506 | doi = 10.1021/acs.jmedchem.4c00082 }}