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.
List 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
Related compounds
Structure Name Chemical name CAS # Chanoclavine (chanoclavine-I) [9(9a)E]-9-methyl-9,9a-didehydro-7,8-seco-9a-homoergolin-8-ol 2390-99-0 Chanoclavine II (2E)-2-methyl-3-[(4R,5S)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol 1466-08-6 Paliclavine (9R)-6,8-dimethyl-7,8-didehydro-6,7-secoergolin-9-ol 52052-66-1 DLX-0002700 (see DLX-2270) 6-fluoro-N,5-dimethyl-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7-tetraen-10-amine ? Compound 21 Sabnis RW. Novel Mixed Serotonin Receptor Binder Compounds as 5‑HT2C Agonists for Treating Psychotic Disorders. ACS Med Chem Lett. 2025 Jul 29;16(8):1505-1506. (10S)-3-bromo-N,N-dimethyl-1-azatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-10-amine 3091662-68-6 2C-B-5-hemiFLY-α6 (BNAP) 8-bromo-6-methoxy-2a,3,4,5-tetrahydro-2H-naphtho[1,8-bc]furan-4-amine ? Mefloquine (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl]-[(2R)-piperidin-2-yl]methanol 51742-87-1 DOB-5-hemiFLY (bromo-semi-fly; B-SF; 5-MeO-7-Br-4-APDB) 1-(7-bromo-5-methoxy-2,3-dihydro-1-benzofuran-4-yl)propan-2-amine 178557-10-3 2C-B-morpholine 2-(4-bromo-2,5-dimethoxyphenyl)morpholine 807631-07-8 Naxagolide (4aR,10bR)-4-propyl-2,3,4a,5,6,10b-hexahydrobenzo[h][1,4]benzoxazin-9-ol 88058-88-2 S32504 (4aR,10bR)-4-propyl-2,3,4a,5,6,10b-hexahydrobenzo[h][1,4]benzoxazine-9-carboxamide ? Pardoprunox 7-(4-methylpiperazin-1-yl)-3H-1,3-benzoxazol-2-one 269718-84-5 Bifeprunox 7-[4-(biphenyl-3-ylmethyl)piperazin-1-yl]-1,3-benzoxazol-2(3H)-one 350992-10-8 Quinpirole (4aR,8aR)-5-propyl-1,4,4a,6,7,8,8a,9-octahydropyrazolo[5,4-g]quinoline 80373-22-4 Quinelorane (5aR,9aR)-6-propyl-5a,7,8,9,9a,10-hexahydro-5H-pyrido[2,3-g]quinazolin-2-amine 97466-90-5 Quinagolide N,N-diethyl-N-[(3S,4aS,10aR)-6-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-3-yl]sulfamide 87056-78-8 25B-NAcPip N-(piperidin-1-ylcarbonylmethyl)-4-bromo-2,5-dimethoxyphenethylamine 25B-NBOMe N-(2-methoxybenzyl)-4-bromo-2,5-dimethoxyphenethylamine 1026511-90-9 "Compound 37"Marini-Bettolo, G. B., Chiavarelli, S., & Bovet, D. (1951). Synthetic Sympatholytic Substances of the Ergotamine Series. I. Nitrogen-Substituted Derivatives of the dl-1, 2, 3, 4-Tetrahydro-2-Naphthylamine-Containing Amino and Amido Functional Groups. Gazz. Chim. Ital, 80, 281–298. https://scholar.google.com/scholar?cluster=2759784031777399013 N-(2-diethylamino-2-oxoethyl)-N-methyl-2-amino-1,2,3,4,4a,8a-hexahydronaphthalene Tochergamine N,N-diethyl-2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)acetamide
See also Nor-LSD (disambiguation) Seco-LSD Secoergoline Des-LSD Substituted lysergamide Substituted tryptamine Substituted phenethylamine
References
External links Hallucinogens You Probably Haven't Heard of: Tricyclic Tryptamines - Nervewing - Blogspot Hallucinogens You Probably Haven't Heard of: PEA-NDEPA's - Blogspot