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| 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" |
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| Chemical and physical data | |
| Formula | C19H32N2O3 |
| Molar mass | 336.476 g·mol−1 |
| 3D model (JSmol) | |
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25D-NM-NDEAOP, or25D-NM-NDEPA, is achemical compound of thephenethylamine and2C families.[1][2][3] It is asimplified or partial lysergamide and is aderivative of2C-D with alysergic acid diethylamide (LSD)-likeN-(3-diethylamino-3-oxopropyl)-substitution.[1][2][3]
The compound was assessed and found to inhibitprolactinsecretion in ratpituitary glandsin vitro at high concentrations, suggesting that it may possess weakdopamine receptor agonist activity.[2][1] However, it was subsequently assessed in ratsin vivo and, in contrast to LSD, was found to not significantly inhibit prolactin secretion.[1] Other possible activities of 25D-NM-NDEAOP, such asserotonin receptor interactions and associated effects, were not evaluated or reported.[1][2][3]
25D-NDEAOP was first described in thescientific literature in 1974.[2][1]
The compound is aPEA-NDEPA derivative and is similar in structure to other PEA-NDEPA compounds such as DOM-NDEPA and TMA-2-NDEPA, as well asDOB-NDEPA,DOI-NDEPA, andDOTFM-NDEPA.[4] The latter three compounds have been predicted viaQSAR modeling to bepotentserotonin5-HT2A receptoragonists.[4] Aparent compound of 25D-NM-NEAOP isN-(3-diethylamino-3-oxopropyl)-N-methylphenethylamine (N-DEAOP-NMPEA or PEA-NM-NDEPA), which showed weakoxytocic activity inpreclinical research.[5]
%2c_DOM-NDEPA%2c_and_LSD_structures.png)
Table 3. New phenylalkylamine and tryptamine congeners. Cf. also Figure 5. [...] Figure 5. Molecular structures of the new 5-HT2A congeneric ligands. Cf. also Table 3. [...] Table 4. Predicted binding af®nities of new compounds, index by substance classes. [...]
Six esters and amides of derivatives of β-alanine which are related to lysergic acid have been prepared and tested for oxytocic activity. None of these products possess a significant oxytocic activity. [...] The purpose of this investigation was to synthesize amides and also esters of compounds (II–V) which represent fragments of the lysergic acid molecule in the hope that some of these products might possess oxytocic activity. Various modified fragments of the lysergic acid molecule have been synthesized previously; it was claimed that some of the compounds are active oxytocics (1—7). [...] Pharmacologic data indicated that none of the esters or amides of compounds II—V which were prepared possess a significant oxytocic action when compared to the clinically used oxytocics. However, the diethylamide of N-methyl-N-[β′-(3-indolyl)-ethyl]-β-alanine (IIIc) appeared to have an oxytocic activity approximately ten times stronger than that of the diethylamide of N-methyl-N-(β′-phenethyl)-β-alanine (IIc).