N-DEAOP-NMT

N-(3-Diethylamino-3-oxopropyl)-N-methyltryptamine (N-DEAOP-NMT), also known as desvinyl-LSD or 9,10-dinor-LSD, is a tryptamine derivative and a "partial" or simplified lysergamide which is closely related to the highly potent serotonergic psychedelic lysergic acid diethylamide (LSD). It is the analogue of LSD in which two of LSD's carbon atoms in the ergoline ring, those at positions 9 and 10, have been removed. This in turn renders the N-DEAOP-NMT molecule flexible and makes it a non-rigid tryptamine rather than an ergoline. The compound is pharmacologically active, as are a number of its analogues and derivatives, with activities of the compounds including serotonin 5-HT2A receptor agonism and LSD- or hallucinogen-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 (ergometrine), 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 or PEA-NM-NDEPA), a phenethylamine-based simplified and non-rigid LSD analogue that was also evaluated in the study. The oxytocic effects of ergolines like ergonovine and methylergonovine (methylergometrine) are thought to most likely be mediated by agonism of serotonin 5-HT2 receptors in uterine smooth muscle tissue. Relatedly, activation of serotonin 5-HT2A receptors in the brain is also the mechanism of action underlying the hallucinogenic effects of LSD and other serotonergic psychedelics.

Chemistry

Analogues and derivatives

N-DEAOP-NET

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-ethyltryptamine (N-DEAOP-NET), and has been described.