# N-(3-Diethylamino-3-oxopropyl)-N-methyltryptamine

N-(3-Diethylamino-3-oxopropyl)-N-methyltryptamine (N-DEAOP-NMT) is a "partial" or "simplified" ergoline and a tryptamine derivative that is closely related to the extremely potent serotonergic psychedelic lysergic acid diethylamide (LSD). It is the analogue of LSD in which two of the carbon atoms, carbons 9 and 10, have been removed from the ergoline ring. This in turn renders the molecule flexible and makes it a non-rigid tryptamine rather than an ergoline. N-DEAOP-NMT is pharmacologically active, as are a number of analogues and derivatives of the compound, with activities of the compounds including serotonin 5-HT$_{2A}$ receptor agonism and LSD- or hallucinogenic-like effects.

## Pharmacology

N-DEAOP-NMT has been found to produce quantifiable oxytocic effects in animals. However, in contrast to other lysergamides such as lysergic acid and ergonovine, N-DEAOP-NMT was said to not possess significant oxytocic activity relative to clinically used oxytocic drugs, and hence to have little such activity. On the other hand, it was noted to possess 10-fold greater oxytocic activity than that of N-(3-diethylamino-3-oxopropyl)-N-methylphenethylamine (N-DEAOP-NMPEA), a phenethylamine-based simplified and non-rigid LSD analogue that was also evaluated in the study.

## Analogues and derivatives

The N-ethyl variant of N-DEAOP-NMT, as opposed to N-DEAOP-NMT itself (which is the N-methyl form), is N-(3-diethylamino-3-oxopropyl)-N-ethyl-5-tryptamine (N-DEAOP-NET). This compound is a simplified and non-rigid analogue of ETH-LAD rather than of LSD (which is also known as "METH-LAD"). In contrast to N-DEAOP-NMT, N-DEAOP-NET has been evaluated specifically for LSD- or hallucinogen-like effects in animals. LSD produced a typical behavioral and physiological syndrome at an effective-to-fatal dose range of 0.1–5.0 mg/kg in rats, whereas the range for N-DEAOP-NET was 1.0–10.0 mg/kg. The effects of N-DEAOP-NET were qualitatively similar to those of LSD, and included strong mydriasis, hyperreflexia, tremors, hypothermia, hyperactivity, skin hyperemia, stereotypy, fearful reactions, and disorientation, among others. Based on the preceding findings, it has been concluded that N-DEAOP-NET shows LSD-like effects and hence may produce psychedelic effects in humans but is about 10 times less potent than LSD at least in rodents.
The 5-methoxy analogue of N-DEAOP-NMT, N-(3-diethylamino-3-oxopropyl)-N-methyl-5-methoxytryptamine (5-MeO-N-DEAOP-NMT), also known as N-(2-eiethylcarbamoylethyl)-N-methyl-5-methoxytryptamine (5-MeO-N-DECE-NMT), has been described. Its affinities for serotonin receptors were 21 nM for the serotonin 5-HT$_{1A}$ receptor, 697 nM for the serotonin 5-HT$_{2A}$ receptor, and 1,184 nM for the serotonin 5-HT$_{2C}$ receptor. For comparison, the serotonergic psychedelic dimethyltryptamine (DMT) had affinities for these receptors of 38 nM, 1,093 nM, and 211 nM, respectively, while the psychedelic 5-MeO-DMT had affinities of 4.2 nM, 558 nM, and 187 nM, respectively. 5-MeO-N-DEAOP-NMT was a partial agonist of the serotonin 5-HT$_{2A}$ receptor, with an EC$_{50}$Tooltip half-maximal effective concentration of 2,338 nM and an E$_{max}$Tooltip maximal efficacy of 16–40%, whereas DMT was a partial agonist with an EC$_{50}$ of 2,239 nM and an E$_{max}$ of 16–41% while 5-MeO-DMT was a partial to full agonist with an EC$_{50}$ of 741 nM and an E$_{max}$ of 57–98%. Hence, 5-MeO-N-DEAOP-NMT showed fairly similar affinities for serotonin receptors and activational potencies and efficacies at the serotonin 5-HT$_{2A}$ receptor compared to the well-known DMT. N-DEAOP-NMT was also included in the study, but its values were not reported.
5-MeO-N-DEAOP-NET, or N-(3-diethylamino-3-oxopropyl)-N-ethyl-5-methoxytryptamine, the 5-methoxy analogue of N-DEAOP-NET, was also notably evaluated in the previously discussed animal study of LSD-like effects, but it was not as potent as N-DEAOP-NET and its dose range was not reported.
Other simplified non-rigid LSD analogues, like CT-5252 and NDTDI among others, have additionally been synthesized and assayed.