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N-DEAOP-NMT
Pharmaceutical compound From Wikipedia, the free encyclopedia
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N-(3-Diethylamino-3-oxopropyl)-N-methyltryptamine (N-DEAOP-NMT) is a tryptamine derivative and a "partial" or simplified ergoline which is closely related to the highly potent serotonergic psychedelic lysergic acid diethylamide (LSD).[1][2][3][4] 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.[1][2][3][4] This in turn renders the N-DEAOP-NMT molecule flexible and makes it a non-rigid tryptamine rather than an ergoline.[1][2][3][4] 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.[1][2][3][4]
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Pharmacology
N-DEAOP-NMT has been found to produce quantifiable oxytocic effects in animals.[1][4] 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.[1][4] 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.[4] 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.[5][6] 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.[7][8][9]
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Analogues and derivatives
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Perspective
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.[1][3] This compound is a simplified and non-rigid analogue of ETH-LAD rather than of LSD (which is also known as "METH-LAD").[1][3] In contrast to N-DEAOP-NMT, N-DEAOP-NET has been evaluated specifically for LSD- or hallucinogen-like effects in animals.[1][3] 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.[1][3] 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.[1][3] 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.[1][3] Various other analogues were also assessed and described.[3]
5-MeO-N-DEAOP-NMT
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-diethylcarbamoylethyl)-N-methyl-5-methoxytryptamine (5-MeO-N-DECE-NMT), has been described.[2] Its affinities (Ki) for serotonin receptors were 21 nM for the serotonin 5-HT1A receptor, 697 nM for the serotonin 5-HT2A receptor, and 1,184 nM for the serotonin 5-HT2C receptor.[2] 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.[2] 5-MeO-N-DEAOP-NMT was a partial agonist of the serotonin 5-HT2A receptor, with an EC50 of 2,338 nM and an Emax of 16–40%, whereas DMT was a partial agonist with an EC50 of 2,239 nM and an Emax of 16–41% while 5-MeO-DMT was a partial to full agonist with an EC50 of 741 nM and an Emax of 57–98%.[2] Hence, 5-MeO-N-DEAOP-NMT showed fairly similar affinities for serotonin receptors and activational potencies and efficacies at the serotonin 5-HT2A receptor compared to the well-known DMT.[2] N-DEAOP-NMT was also included in the study, but its values were not reported.[2]
5-MeO-N-DEAOP-NET
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 with N-DEAOP-NET and other analogues, but it was not as potent as N-DEAOP-NET and its dose range was not reported.[3]
N-DEAOP-NMPEA
N-(3-Diethylamino-3-oxopropyl)-N-methylphenethylamine (N-DEAOP-NMPEA or PEA-NM-NDEPA) is a phenethylamine-based simplified and non-rigid LSD analogue that is related to N-DEAOP-NMT.[4] It is the N-methylated analogue of the parent compound of the PEA-NDEPA series of compounds, such as DOB-NDEPA, DOI-NDEPA, and DOTFM-NDEPA.[10] The compound showed very weak oxytocic activity, 10-fold less potent than N-DEAOP-NMT, in a preclinical study.[4]
Others
Other simplified non-rigid LSD analogues, like CT-5252 and NDTDI among others, have additionally been synthesized and assayed.[1][2][3][4][11][12] NDTDI is a tricyclic analogue of LSD and N-DEAOP-NMT in which only the carbon atom at position 9 of the ergoline ring system has been removed, as opposed to removal of both carbons at positions 9 and 10 as in the case of N-DEAOP-NMT.[13] It has been encountered as an LSD-related designer drug and made illegal in parts of Europe.[14][15]
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History
N-DEAOP-NMT was first described in the scientific literature by 1952.[1][4] This followed the synthesis of LSD by chemist Albert Hofmann in 1938 and the discovery of LSD's psychedelic effects by Hofmann in 1943.[16] N-DEAOP-NMT and other simplified non-rigid LSD analogues were notably reviewed and discussed by psychedelic chemist David E. Nichols in his Ph.D. thesis on LSD analogues and other psychedelics in 1973.[1] N-DEAOP-NMT's derivatives N-DEAOP-NET and 5-MeO-N-DEAOP-NET, as well as LSD-like effects of these compounds, were first described in the literature by 1971,[1][3] while 5-MeO-N-DEAOP-NMT and its serotonin receptor interactions were first described by 2005.[2]
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