25D-NM-NDEAOP

25D-NM-NDEAOP, or 25D-NM-NDEPA, is a chemical compound of the phenethylamine and 2C families.^[1][2][3] It is a simplified or partial lysergamide and is a derivative of 2C-D with a lysergic acid diethylamide (LSD)-like N-(3-diethylamino-3-oxopropyl)- substitution.^[1][2][3]

25D-NM-NDEAOP

Clinical data
Other names	25D-NM-NDECE; 25D-NM-NDEPA; N-Methyl-N-(3-diethylamino-3-oxopropyl)-2,5-dimethoxy-4-methylphenethylamine; N-Methyl-N-(3-diethylamino-3-oxopropyl)-2C-D; N-Methyl-N-(2-diethylcarbamoylethyl)-2,5-dimethoxy-4-methylphenethylamine; N-Methyl-N-(2-diethylcarbamoylethyl)-2C-D; NM-NDEAOP-2C-D; NM-NDECE-2C-D; "Compound 4"
Identifiers
IUPAC name 3-[2-(2,5-dimethoxy-4-methylphenyl)ethyl-methylamino]-N,N-diethylpropanamide
PubChem CID	90678176
ChemSpider	34249793
ChEMBL	ChEMBL3273532
Chemical and physical data
Formula	C19H32N2O3
Molar mass	336.476 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCN(CC)C(=O)CCN(C)CCC1=C(C=C(C(=C1)OC)C)OC
InChI InChI=1S/C19H32N2O3/c1-7-21(8-2)19(22)10-12-20(4)11-9-16-14-17(23-5)15(3)13-18(16)24-6/h13-14H,7-12H2,1-6H3 Key:GEVSOPBAZVTJIF-UHFFFAOYSA-N

The compound was assessed and found to inhibit prolactin secretion in rat pituitary glands in vitro at high concentrations, suggesting that it may possess weak dopamine receptor agonist activity.^[2][1] However, it was subsequently assessed in rats in vivo and, in contrast to LSD, was found to not significantly inhibit prolactin secretion.^[1] Other possible activities of 25D-NM-NDEAOP, such as serotonin receptor interactions and associated effects, were not evaluated or reported.^[1][2][3]

25D-NDEAOP was first described in the scientific literature in 1974.^[2][1]

The compound is a "PEA-NDEPA" and is similar in structure to other PEA-NDEPA compounds such as DOM-NDEPA and TMA-2-NDEPA, as well as DOB-NDEPA, DOI-NDEPA, and DOTFM-NDEPA.^[4] The latter three compounds have been predicted via QSAR modeling to be potent serotonin 5-HT_2A receptor agonists.^[4] A parent compound of 25D-NM-NEAOP is N-(3-diethylamino-3-oxopropyl)-N-methylphenethylamine (N-DEAOP-NMPEA or PEA-NM-NDEPA), which showed weak oxytocic activity in preclinical research.^[5]

Chemical structures of 25D-NM-NDEAOP (25D-NM-NDEPA), DOM-NDEPA, and LSD. LSD contains the structures of 25D-NM-NDEAOP and DOM-NDEPA except their 2,5-dimethoxy- and 4-methyl- phenyl ring substitutions.

See also

• Substituted methoxyphenethylamine
• Partial lysergamide
• List of miscellaneous 5-HT_2A receptor agonists
• DOB-NDEPA
• DOI-NDEPA
• DOTFM-NDEPA
• 25B-NAcPip
• N-DEAOP-NMT
• DEIMDHPCA
• DEMPDHPCA
• DEMPDHPCA-2C-D
• 25-NB
• 25D-NBOMe
• DOM-NBOMe