Partial lysergamide
Class of chemical compounds
Partial or simplified ergolines and lysergamides, also known as deconstructed LSD analogues, are analogues of ergolines and lysergamides like the psychedelic drug LSD in which one or more atoms or bonds, for instance within the ergoline ring system, have been removed. Additional substitutions may also be added, for instance on the A ring of the ergoline nucleus. It is notable that the ergoline ring system contains embedded tryptamine and phenethylamine moieties within its structure, and so some partial ergolines are simple tryptamines, cyclized tryptamines, simple phenethylamines, and/or cyclized phenethylamines.
In terms of pharmacology, partial lysergamides include serotonin and dopamine receptor agonists. Some, like NDTDI (9-nor-LSD), UCD0120 (dides-B,C-LSD), UCD0179 (4-nor-LSD), and LPH-5 ((S)-2C-TFM-3PIP), are serotonin 5-HT2A receptor agonists and have psychedelic-like and/or psychoplastogenic effects. Some, like 8-OH-DPAT, LY-178210 (LY-228729; 4,α-methylene-5-carboxamido-DPT), Bay R 1531 (LY-197206; 4,α-methylene-5-MeO-DPT), and LY-293284 (4,α-methylene-5-acetyl-DPT), are selective serotonin 5-HT1A receptor agonists. Others, like ropinirole, rotigotine, nolomirole, and RU-28251 (4,α-methylene-DPT), are dopamine D2-like receptor agonists. Though limitedly studied, partial ergolines have generally shown markedly reduced potency in terms of hallucinogen-like effects compared to LSD.
Examples of partial lysergamides that are simple tryptamines include N-DEAOP-NMT (9,10-dinor-LSD) and 5-MeO-N-DEAOP-NMT and examples that are simple phenethylamines include N-DEAOP-NMPEA and 25D-NM-NDEAOP. An example of a cyclized tryptamine-like compound is UCD0179, while examples of cyclized phenethylamines include UCD0120, UCD0120-2C-D, and LPH-5. Some, like 8-OH-DPAT and rotigotine, are 2-aminotetralins. Others, like NDTDI and LY-178210, are tricyclic compounds that contain both tryptamine and phenethylamine components. Tochergamine is a simplified analogue of ergometrine that was studied as an oxytocic agent but was abandoned.
Structures within the ergoline ring system01List of simplified or partial lysergamides
| Structure | Name | Chemical name | CAS # |
|---|---|---|---|
| Descarboxylysergic acid (DCLA; 9,10-didehydro-6-methylergoline) | (6aR)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline | 51867-17-5 | |
| NDTDI (9-desmethine-LSD; 9-nor-LSD; 8,10-seco-LSD) | N,N-diethyl-3-(methyl(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)amino)propanamide | ? | |
| RU-28251 (4,α-methylene-DPT) | N,N-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine | ? | |
| Bay R 1531 (LY-197206; 4,α-methylene-5-MeO-DPT) | 1,3,4,5-tetrahydro-6-methoxy-N,N-dipropyl-benz[cd]indol-4-amine | 98770-54-8 | |
| LY-293284 (4,α-methylene-5-acetyl-DPT) | (4R)-6-acetyl-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[c,d]indole | 141318-62-9 | |
| LY-178210 (LY-228729; 4,α-methylene-5-carboxamido-DPT) | 4-(dipropylamino)-1,3,4,5-tetrahydrobenzo[cd]indole-6-carboxamide | 114943-19-0 | |
| LY-301317 ((R)-4,α-methylene-5-(1,3-oxazol-5-yl)-DPT) | (4R)-6-(1,3-oxazol-5-yl)-N,N-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine | ? | |
| RU-28306 (UCD0094; 4,α-methylene-DMT) | N,N-dimethyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine | 73625-11-3 | |
| 6-MeO-RU-28306 (4,α-methylene-5-MeO-DMT) | 6-methoxy-N,N-dimethyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine | ? | |
| RU-27849 (4,α-methylene-T) | 1,3,4,5-tetrahydrobenzo[cd]indol-4-amine | 77963-70-3 | |
| FHATHBIN (4,α-methylene-5-HT; 6-HO-RU-27849) | 6-hydroxy-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine | ? | |
| 6-MeO-RU-27849 (4,α-methylene-5-MT) | 6-methoxy-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine | ? | |
| N-DEAOP-NMT (desvinyl-LSD; 9,10-dinor-LSD) | N-(3-diethylamino-3-oxopropyl)-N-methyltryptamine | ||
| N-DEAOP-NET (desvinyl-ETH-LAD; 9,10-dinor-ETH-LAD) | N-(3-diethylamino-3-oxopropyl)-N-ethyl-5-tryptamine | ||
| N-DEAOP-5-MeO-NMT | N-(3-diethylamino-3-oxopropyl)-N-methyl-5-methoxytryptamine | ||
| N-DEAOP-5-MeO-NET | N-(3-diethylamino-3-oxopropyl)-N-ethyl-5-methoxytryptamine | ||
| 10,11-Seco-LSD (UCD0121) | 9,10-didehydro-N,N-diethyl-6-methyl-10,11-secoergoline-8β-carboxamide | 2640392-96-5 | |
| CT-5252 | methyl-12-bromo-8,9-didehydro-2,3β-dihydro-6-methyl-10,11-secoergoline-8-carboxylate | ||
| 10,11-Secoergoline (α,N-tetramethylene-T) | 3-(piperidin-2-ylmethyl)-1H-indole | 5275-05-8 | |
| FAEFHI | 4-(2-aminoethyl)-1H-indol-5-ol | ||
| 4-API | 4-(2-aminopropyl)indole | 21005-59-4 | |
| DMAI (UCD0076; 4-DMAEI; BD-214) | 4-(N,N-dimethylaminoethyl)indole | 84401-01-4 | |
| DEAI (4-DEAEI; BD-271) | 4-(N,N-diethylaminoethyl)indole | ? | |
| DPAI (4-DPAEI; 2-desoxo-2-ene-ropinirole; BD-179) | 4-(N,N-dipropylaminoethyl)indole | 76149-15-0 | |
| Ropinirole (SK&F-101468) | 4-[2-(dipropylamino)ethyl]-1,3-dihydro-2H-indol-2-one | 91374-21-9 | |
| 7-Hydroxyropinirole (SK&F-89124) | 4-[2-(dipropylamino)ethyl]-7-hydroxy-1,3-dihydroindol-2-one | 81654-62-8 | |
| UCD0179 (4-desmethylene-LSD; 4-nor-LSD; 3,5-seco-LSD) | (3R)-N,N-diethyl-5-(1H-indol-4-yl)-1-methyl-3,6-dihydro-2H-pyridine-3-carboxamide | 2640392-28-3 | |
| RU-27251 (3,5-secoergoline) | 4-piperidin-3-yl-1H-indole | 16176-75-3 | |
| WXVL_BT0793LQ2118 | 6-fluoro-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole | ? | |
| Diaza-2C-DFLY | 8-(aminoethyl)-1,5-dihydropyrrolo[2,3-f]indole | ||
| UCD0120 (dides-B,C-LSD; 1-deaza-2,3,4-trinor-LSD) | N,N-diethyl-1-methyl-5-phenyl-3,6-dihydro-2H-pyridine-3-carboxamide | ||
| UCD0120-PMA | N,N-diethyl-1-methyl-3-(4-methoxyphenyl)-1,2,5,6-tetrahydropyridine-5-carboxamide | ||
| UCD0120-M (UCD0120-mescaline) | N,N-diethyl-1-methyl-3-(3,4,5-trimethoxyphenyl)-1,2,5,6-tetrahydropyridine-5-carboxamide | ||
| UCD0120-NAP | N,N-diethyl-1-methyl-3-(1-naphthyl)-1,2,5,6-tetrahydropyridine-5-carboxamide | ||
| UCD0120-2C-D | 1-methyl-3-(1-oxo-1-diethylaminomethyl)-5-(2,5-dimethoxy-4-methylphenyl)-3,6-dihydro-2H-pyridine | ||
| "Compound XXIII" | ? | ? | |
| 2C-B-3PIP | 3-(4-bromo-2,5-dimethoxyphenyl)piperidine | ? | |
| LPH-5 ((S)-2C-TFM-3PIP) | (S)-3-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)piperidine | 2641630-97-7 | |
| UCD0068 (des-B-LSD) | N,N-diethyl-4-methyl-2,3,4,4a,5,6-hexahydrobenzo(f)quinoline-2-carboxamide | ||
| Des-A-LSD | ? | ? | |
| Debenzergoline (propyldebenzergoline) | trans-(±)-2,3,4,4a,5,7,9,9a-octahydro-1-propyl-1H-pyrrolo[3,4-g]quinoline | ||
| UCD0829 | N,N-dimethyl-4,5,6,7-tetrahydro-2H-isoindol-5-amine | ||
| N-DEAOP-PEA (PEA-NDEPA) | N-diethylaminocarbonylethylphenethylamine | ||
| N-DEAOP-NMPEA (PEA-NM-NDEPA; 1-deaza-2,3,4,9-tetranor-LSD) | N-diethylaminocarbonylethyl-N-methylphenethylamine | ||
| 3,4-DMPEA-NDEPA | N-diethylaminocarbonylethyl-3,4-dimethoxyphenethylamine | ||
| M-NDEPA (mescaline-NDEPA) | N-diethylaminocarbonylethyl-3,4,5-trimethoxyamphetamine | ? | |
| DOM-NDEPA | N-diethylaminocarbonylethyl-2,5-dimethoxy-4-methylamphetamine | ? | |
| DOB-NDEPA | N-diethylaminocarbonylethyl-2,5-dimethoxy-4-bromoamphetamine | 260810-30-8 | |
| DOI-NDEPA | N-diethylaminocarbonylethyl-2,5-dimethoxy-4-iodoamphetamine | 260810-31-9 | |
| DOTFM-NDEPA | N-diethylaminocarbonylethyl-2,5-dimethoxy-4-trifluoromethylamphetamine | 260810-29-5 | |
| TMA-2-NDEPA | N-diethylaminocarbonylethyl-2,4,5-trimethoxyphenethylamine | ||
| 25D-NM-NDEAOP (25D-NM-NDEPA) | N-methyl-N-(3-diethylamino-3-oxopropyl)-2,5-dimethoxy-4-methylphenethylamine | ||
| 2-Aminotetralin (2-AT) | 1,2,3,4-tetrahydronaphthalen-2-amine | 2954-50-9 | |
| UCD0830 | N,N-dimethyl-2-aminotetralin | 6945-44-4 | |
| CHF-1024 | 5,6-dihydroxy-N-methyl-2-aminotetralin | 39478-89-2 | |
| Nolomirole (CHF-1035) | 5,6-diisobutyryloxy-N-methyl-2-aminotetralin | 90060-42-7 | |
| 5-OH-DPAT | 5-hydroxy-N,N-dipropyl-2-aminotetralin | 68593-96-4 | |
| 7-OH-DPAT | 7-hydroxy-N,N-dipropyl-2-aminotetralin | 74938-11-7 | |
| 8-OH-DPAT | 8-hydroxy-N,N-dipropyl-2-aminotetralin | 78950-78-4 | |
| UH-301 | (S)-5-fluoro-8-hydroxy-N,N-dipropyl-2-aminotetralin | 127126-22-1 | |
| UH-232 | (1S,2R)-5-methoxy-1-methyl-N,N-propyl-2-aminotetralin | 95999-12-5 | |
| U-92016A | (8R)-8-(dipropylamino)-6,7,8,9-tetrahydro-3H-benzo[e]indole-2-carbonitrile | 136924-88-4 | |
| Rotigotine | 6-[propyl(2-thiophen-2-ylethyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol | 99755-59-6 | |
| Dides-A,B-LSD | ? | ? | |
| THPC (UCD0162) | N,N-diethyl-1-methyl-3,6-dihydro-2H-pyridine-5-carboxamide | 26070-52-0 | |
| Nikethamide | N,N-diethyl-3-pyridinecarboxamide | 59-26-7 |
Structural comparisons
Sources and credits
This article is adapted from the Wikipedia article “Partial lysergamide”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Ergolin num ABCD.svg by NEUROtiker, Public domain
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