N-DEAOP-NMT

Overview

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.[1–4] WP

Pharmacology

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.[1][4–9] WP

History

History

N-DEAOP-NMT was first described in the scientific literature by 1952. This followed the synthesis of LSD by chemist Albert Hofmann in 1938 and the discovery of LSD's psychedelic effects by Hofmann in 1943. 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. 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, while 5-MeO-N-DEAOP-NMT and its serotonin receptor interactions were first described by 2005.[1–4][10] WP

Chemistry

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

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Sources

1. Other Nichols DE. Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid. May 1973
2. Journal / agency Jensen N. Tryptamines as Ligands and Modulators of the Serotonin 5‑HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens. 2005. doi:10.53846/goediss-2111
3. Journal / agency Sklar S, Nieforth KA, Malone M. Synthesis and preliminary screening of N-ethyltryptamine derivatives related to reserpine and lysergic acid. J Pharm Sci. February 1971. doi:10.1002/jps.2600600235 · PMID 5572462
4. Journal / agency Norris PE, Blicke FF. Potential ergot substitutes: esters and amides of beta-amino acids. J Am Pharm Assoc. December 1952. doi:10.1002/jps.3030411204 · PMID 13022416
5. Journal / agency Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. October 2006. doi:10.5688/aj700598 · PMID 17149427 · PMC1637017
6. Journal / agency Vallera C, Choi LO, Cha CM, Hong RW. Uterotonic Medications: Oxytocin, Methylergonovine, Carboprost, Misoprostol. Anesthesiol Clin. June 2017. doi:10.1016/j.anclin.2017.01.007 · PMID 28526143
7. Journal / agency Nichols DE. Dark Classics in Chemical Neuroscience: Lysergic Acid Diethylamide (LSD). ACS Chem Neurosci. October 2018. doi:10.1021/acschemneuro.8b00043 · PMID 29461039
8. Journal / agency Halberstadt AL. Recent advances in the neuropsychopharmacology of serotonergic hallucinogens. Behav Brain Res. January 2015. doi:10.1016/j.bbr.2014.07.016 · PMID 25036425 · PMC4642895
9. Journal / agency Kwan AC, Olson DE, Preller KH, Roth BL. The neural basis of psychedelic action. Nat Neurosci. November 2022. doi:10.1038/s41593-022-01177-4 · PMID 36280799 · PMC9641582
10. Other A. Hofmann. 50 Years of LSD: Current Status and Perspectives of Hallucinogens. A Symposium of the Swiss Academy of Medical Sciences, Lugano-Agno (Switzerland), October 21 and 22, 1993. 15 August 1994

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