Ergoamides
Class of chemical compounds From Wikipedia, the free encyclopedia
Ergoamides[1][2] (syn. lysergamides) are amides of lysergic acid (LA). The ergoamides include numerous serotonin and dopamine receptor agonists, most notably lysergic acid diethylamide (LSD); lysergic acid amide is the simplest ergoamide. Ergoamides have an embedded tryptamine structure, so some of them induce psychedelic effects similar to psychedelic tryptamines.[3][4][5][6][7][8][9][10][11][12][13][14][15][excessive citations] Ergoamides also have a phenethylamine (e.g., mescaline) pharmacophore.[16]
 | A request that this article title be changed to Lysergamides is under discussion. Please do not move this article until the discussion is closed. |
Use and effects
Summarize
Perspective
The dosages, potencies, durations, and effects of ergoamides have been reviewed by Alexander Shulgin.[17][18][19][20][21] They have also been reviewed by Albert Hofmann,[22] David E. Nichols,[23] and other researchers.[24][25][26][27][28][29][30][31][32]
| Common name | Code | Dose (mg) | Potency (×LSD) | Duration (h) |
|---|---|---|---|---|
| Lysergic acid amide (LSA; ergine) | LA-111 | 0.5–6 | <0.1 | ~4–10 |
| Isolysergic acid amide (iso-LSA; isoergine) | Iso-LA-819 | 2–5 | <0.1 | ~4–10 |
| Lysergic acid methylamide | LAM | ~0.5 | ≤0.2 | ? |
| Lysergic acid dimethylamide | DAM-57 | 0.5–1.2 | 0.1 | ? |
| Lysergic acid ethylamide | LAE-32 | 0.5–1.6 | ≤0.1 | ? |
| 1-Acetyllysergic acid ethylamide | ALA-10 | ~1.2 | ≤0.1 | ? |
| 1-Methyllysergic acid ethylamide | MLA-74 | ~2 | 0.05 | ? |
| Lysergic acid isopropylamide | LAiP | ? | ? | ? |
| Lysergic acid methylethylamide | LME-54 | ? | ~0.33 | ? |
| Lysergic acid diethylamide | LSD-25, METH-LAD | 0.05–0.2 | 1 | 8–12 |
| Isolysergic acid diethylamide | Iso-LSD | >0.5 | <0.05 | ? |
| 2,3-Dihydro-LSD[33] | DH-LSD | ~0.15–0.4 | ~0.15 | ~8–12 |
| 9,10-Dihydro-LSD | – | >2.5 | <0.02 | ? |
| 2-Bromo-LSD | BOL-148 | >1 (≥6–20) | <0.1 (≤0.005–0.02) | ? |
| 2-Iodo-LSD | IOL | ? | ? | ? |
| 2-Keto-LSD (2-oxy-LSD) | ? | >0.3 | ? | ? |
| 1-Acetyl-LSD | ALD-52 | 0.1–0.2 | 1 | ? |
| 1-Methyl-LSD | MLD-41 | 0.2–0.3 | 0.3 | ? |
| 1-Hydroxymethyl-LSD | OML-632 | ? | ~0.7 | ? |
| 1-Methyl-2-bromo-LSD | MBL-61 | >10 | <0.01 | ? |
| 1-Methyl-2-iodo-LSD | MIL | ? | ? | ? |
| Lysergic acid propylamide | LAP | >0.5 | <0.2 | ? |
| Lysergic acid methylpropylamide | LMP | >0.1 | <1 | ? |
| Lysergic acid ethylpropylamide | LEP-57 | ? | ~0.33 | ? |
| Lysergic acid dipropylamide | DPL | >1 | <0.1 | ? |
| Lysergic acid dibutylamide | LBB-66 | ? | 0 | ? |
| Lysergic acid diallylamide | DAL | >1 | <0.1 | ? |
| Lysergic acid 2,4-dimethylazetidide | LA-SS-Az, LSZ | 0.1–0.3 | 0.5 | ? |
| Ergonovine (ergometrine)a | – | 5–10 | ≤0.01 | ? |
| Methylergonovine (methylergometrine)b | – | 2 | 0.05 | ? |
| Methysergidec | UML-491 | 4–8 | 0.02 | ? |
| Lysergic acid piperidide | LSD-Pip | ? | ? | ? |
| Lysergic acid pyrrolide | LPD-824 | ~0.8 | 0.05–0.1 | ? |
| 1-Methyllysergic acid pyrrolide | MPD-75 | >1.6 | ≤0.1 | ? |
| Lysergic acid pyrrolinide | – | ? | 0.1 | ? |
| Lysergic acid morpholide | LSM-775 | 0.3–0.6 | 0.1–0.3 | ? |
| Nor-LSD (6-nor-LSD) | – | >0.5 | <0.2 | ? |
| 6-Ethyl-nor-LSD | ETH-LAD | 0.04–0.15 | 2 | 8–12 |
| 6-Propyl-nor-LSD | PRO-LAD | 0.08–0.2 | 1 | 6–8 |
| 6-Allyl-nor-LSD | AL-LAD, ALLY-LAD | 0.05–0.16 | 1 | 6–8 |
| 6-n-Butyl-nor-LSD | BU-LAD | ≥0.4–0.5 | <0.3 | ? |
| 6-Propynyl-nor-LSD | PARGY-LAD | 0.16–0.5 | 0.2–0.6 | ? |
| 6-(β-Phenethyl)-nor-LSD | PHENETHY-LAD | >0.35–0.5 | <0.3 | ? |
| Footnotes: a = Ergonovine is lysergic acid hydroxyisopropylamide. b = Methylergonovine is lysergic acid hydroxy-sec-butylamide. c = Methysergide is 1-methylmethylergonovine (1-methyllysergic acid hydroxy-sec-butylamide). Refs: [17][18][19][20][21][34][35][36][31][32][37][25][26][38][39][40] | ||||
List of lysergamides
| Structure | Name (synonyms) | CAS # | R1 | R6 | R2 | R3 | Other |
|---|---|---|---|---|---|---|---|
 | Ergine (lysergic acid amide, lysergamide) | 478-94-4 | H | CH3 | H | H | - |
 | Isoergine (isolysergic acid amide, isolysergamide) | 2889-26-1 | H | CH3 | H | H | 8-epi |
 | DAM-57 (lysergic acid dimethylamide) | 4238-84-0 | H | CH3 | CH3 | CH3 | - |
 | Ergometrine (ergonovine; lysergic acid propanolamide) | 60-79-7 | H | CH3 | CH(CH3)CH2OH | H | - |
 | Propisergide (1-methylergonovine) | 5793-04-4 | CH3 | CH3 | CH(CH3)CH2OH | H | - |
 | Ergotamine (an ergopeptine) | 113-15-5 | H | CH3 | -- | C17H18N2O4 | - |
 | Methylergometrine (methylergonovine; lysergic acid butanolamide) | 113-42-8 | H | CH3 | CH(CH2CH3)CH2OH | H | - |
 | Methysergide (1-methyl-lysergic acid butanolamide) | 361-37-5 | CH3 | CH3 | CH(CH2CH3)CH2OH | H | - |
 | Amesergide (9,10-dihydro-11-isopropyllysergic acid cyclohexylamide) | 121588-75-8 | CH(CH3)2 | CH3 | C6H11 | H | - |
 | LY-215840 (1-isopropyl-9,10-dihydro-N-(2-hydroxycyclopent-anyl)lysergamide) | 137328-52-0 | CH(CH3)2 | CH3 | C5H8OH | H | - |
 | Cabergoline (N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-(prop-2-en-1-yl)-9,10-dihydrolysergamide) | 81409-90-7 | H | H2C=CH-CH2 | CONHCH2CH3 | CH2CH2CH2N(CH3)2 | - |
 | LAE-32 (lysergic acid ethylamide) | 478-99-9 | H | CH3 | CH2CH3 | H | - |
 | LAiP (lysergic acid isopropylamide) | H | CH3 | CH(CH3)2 | H | - | |
 | LAtB (lysergic acid tert-butylamide) | H | CH3 | C(CH3)3 | H | - | |
 | LAcB (lysergic acid cyclobutylamide) | H | CH3 | (CH2)4 | H | - | |
 | Cepentil (lysergic acid cyclopentylamide) | H | CH3 | (CH2)5 | H | - | |
 | LSB (lysergic acid 2-butylamide) | 137765-82-3 | H | CH3 | CH(CH3)CH2CH3 | H | - |
 | LSP (lysergic acid 3-pentylamide) | H | CH3 | CH(CH2CH3)CH2CH3 | H | - | |
 | DPL (lysergic acid dipropylamide) | H | CH3 | CH2CH2CH3 | CH2CH2CH3 | - | |
 | DAL (lysergic acid diallylamide) | H | CH3 | H2C=CH-CH2 | H2C=CH-CH2 | - | |
 | MIPLA (lysergic acid methylisopropylamide) | 100768-08-9 | H | CH3 | CH(CH3)2 | CH3 | - |
 | EIPLA (lysergic acid ethylisopropylamide) | H | CH3 | CH(CH3)2 | CH2CH3 | - | |
 | ECPLA (lysergic acid ethylcyclopropylamide) | H | CH3 | C3H5 | CH2CH3 | - | |
 | ETFELA (lysergic acid N-ethyl-N-(2,2,2-trifluoroethyl)amide) | H | CH3 | CH2CF3 | CH2CH3 | - | |
 | LAMPA (lysergic acid methylpropylamide) | 40158-98-3 | H | CH3 | CH2CH2CH3 | CH3 | - |
 | EPLA (lysergic acid ethylpropylamide; LEP-57) | H | CH2CH3 | CH2CH2CH3 | CH3 | - | |
 | LSD (lysergic acid diethylamide; LAD) | 50-37-3 | H | CH3 | CH2CH3 | CH2CH3 | - |
 | ETH-LAD (6-ethyl-6-nor-LSD) | 65527-62-0 | H | CH2CH3 | CH2CH3 | CH2CH3 | - |
 | PARGY-LAD (6-propynyl-6-nor-LSD) | H | HC≡C−CH2 | CH2CH3 | CH2CH3 | - | |
 | AL-LAD (6-allyl-6-nor-LSD) | 65527-61-9 | H | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - |
 | PRO-LAD (6-propyl-6-nor-LSD) | 65527-63-1 | H | CH2CH2CH3 | CH2CH3 | CH2CH3 | - |
 | IP-LAD (6-isopropyl-6-nor-LSD) | H | CH(CH3)2 | CH2CH3 | CH2CH3 | - | |
 | CYP-LAD (6-cyclopropyl-6-nor-LSD) | H | C3H5 | CH2CH3 | CH2CH3 | - | |
 | BU-LAD (6-butyl-6-nor-LSD) | 96930-87-9 | H | CH2CH2CH2CH3 | CH2CH3 | CH2CH3 | - |
 | FLUORETH-LAD (FE-LAD; 6-(2-fluoroethyl)-6-nor-LSD) | H | CH2CH2F | CH2CH3 | CH2CH3 | - | |
 | CE-LAD (CHLORETH-LAD; 6-(2-chloroethyl)-6-nor-LSD) | H | CH2CH2Cl | CH2CH3 | CH2CH3 | - | |
 | ALD-52 (1-acetyl-LSD) | 3270-02-8 | COCH3 | CH3 | CH2CH3 | CH2CH3 | - |
 | 1P-LSD (1-propionyl-LSD) | 2349358-81-0 | COCH2CH3 | CH3 | CH2CH3 | CH2CH3 | - |
 | 1B-LSD (1-butanoyl-LSD) | 2349376-12-9 | COCH2CH2CH3 | CH3 | CH2CH3 | CH2CH3 | - |
 | 1V-LSD (1-valeryl-LSD) | CO(CH2)3CH3 | CH3 | CH2CH3 | CH2CH3 | - | |
 | 1H-LSD (1-hexanoyl-LSD) | CO(CH2)4CH3 | CH3 | CH2CH3 | CH2CH3 | - | |
 | 1DD-LSD (1-dodecanoyl-LSD) | CO(CH2)10CH3 | CH3 | CH2CH3 | CH2CH3 | - | |
 | 1cP-LSD (1-cyclopropylmethanoyl-LSD) | COC3H5 | CH3 | CH2CH3 | CH2CH3 | - | |
 | 1D-LSD (1-(1,2-dimethylcyclobutane-1-carbonyl)-LSD) | COC4H5(CH3)2 | CH3 | CH2CH3 | CH2CH3 | - | |
 | 1T-LSD (1-(thiophene-2-carbonyl)-LSD) | COC4H3S | CH3 | CH2CH3 | CH2CH3 | - | |
 | 1S-LSD (1-(3-(trimethylsilyl)propionyl)-LSD) | CO(CH2)2Si(CH3)3 | CH3 | CH2CH3 | CH2CH3 | - | |
 | 1P-AL-LAD (1-propionyl-6-allyl-6-nor-LSD) | COCH2CH3 | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - | |
 | 1cP-AL-LAD (1-cyclopropylmethanoyl-6-allyl-6-nor-LSD) | COC3H5 | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - | |
 | 1T-AL-LAD (1-(2-thienoyl)-6-allyl-6-nor-LSD)[41] | COC4H3S | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - | |
 | 1P-ETH-LAD (1-propionyl-6-ethyl-6-nor-LSD) | COCH2CH3 | CH2CH3 | CH2CH3 | CH2CH3 | - | |
 | 1P-MIPLA (1-propionyl-lysergic acid methylisopropylamide) | COCH2CH3 | CH3 | CH(CH3)2 | CH3 | - | |
 | MLD-41 (1-methyl-LSD) | 4238-85-1 | CH3 | CH3 | CH2CH3 | CH2CH3 | - |
 | OML-632 (1-hydroxymethyl-LSD) | 114004-70-5 | CH2OH | CH3 | CH2CH3 | CH2CH3 | - |
 | LSM-775 (lysergic acid morpholide) | 4314-63-0 | H | CH3 | CH2CH2-O-CH2CH2 | - | |
 | LPD-824 (lysergic acid pyrrolidide) | 2385-87-7 | H | CH3 | (CH2)4 | - | |
 | LSD-Pip (lysergic acid piperidide) | 50485-23-9 | H | CH3 | (CH2)5 | - | |
 | LSD-Azepane (lysergic acid azepane)[42][43][44] | H | CH3 | (CH2)6 | - | ||
 | Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) | 470666-31-0 | H | CH3 | CH2(CHCH3)2CH2 | - | |
 | 2-Bromo-LSD (BOL-148; bromolysergide) | 478-84-2 | H | CH3 | CH2CH3 | CH2CH3 | 2-Br |
 | 1P-BOL-148 (1-propionyl-2-bromo-LSD) | COCH2CH3 | CH3 | CH2CH3 | CH2CH3 | 2-Br | |
 | 12-Hydroxy-LSD (12-OH-LSD) | 60573-89-9 | H | CH3 | CH2CH3 | CH2CH3 | 12-OH |
 | 12-Methoxy-LSD (12-MeO-LSD) | 50484-99-6 | H | CH3 | CH2CH3 | CH2CH3 | 12-OMe |
 | 13-Fluoro-LSD[45] | H | CH3 | CH2CH3 | CH2CH3 | 13-F | |
 | 14-Hydroxy-LSD[46] | H | CH3 | CH2CH3 | CH2CH3 | 14-OH | |
Related compounds
Summarize
Perspective
| Structure | Name | Chemical name | CAS # |
|---|---|---|---|
 | Ergoline | (6aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline | 478-88-6 |
 | Descarboxylysergic acid | 6-methyl-9,10-didehydroergoline | 51867-17-5 |
 | Lysergine | 9,10-didehydro-6,8β-dimethylergoline | 519-10-8 |
 | Lysergol | (6-methyl-9,10-didehydroergolin-8β-yl)methanol | 1413-67-8 |
 | Lysergic acid | 6-methyl-9,10-didehydroergoline-8β-carboxylic acid | 82-58-6 |
| Dosergoside[47] | N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-6-methylergoline-8-carboxamide | 87178-42-5 | |
 | Lisuride | 1,1-diethyl-3-(6-methyl-9,10-didehydroergolin-8α-yl)urea | 18016-80-3 |
 | Bromerguride | 1,1-diethyl-3-(2-bromo-9,10-didehydro-6-methyl-8α-ergolinyl)urea | 83455-48-5 |
 | Terguride | N,N-diethyl-N'-[(8α)-6-methylergolin-8-yl]urea | 37686-84-3 |
| Proteguride[48][49] | 1,1-diethyl-3-(6-n-propyl-8α-ergolinyl)urea | ? | |
| Etisulergine[50] | N,N-diethyl-N'-(6-methylergolin-8α-yl)sulfamide | 64795-23-9 | |
 | JRT | (7S)-N,N-diethyl-6-methyl-6,9-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,10,12(16),13-pentaene-4-carboxamide | ? |
Simplified or partial lysergamides
Simplified or "partial" ergolines and lysergamides in which one or more carbon atoms or bonds in the ergoline ring system have been removed are known.[51][52][53]
| Structure | Name | Chemical name | CAS # |
|---|---|---|---|
 | NDTDI | N,N-diethyl-3-(methyl(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)amino)propanamide | |
 | RU-28251[54][55] | N,N-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine | |
 | Bay R 1531 (LY-197206) | 1,3,4,5-tetrahydro-6-methoxy-N,N-dipropyl-benz[cd]indol-4-amine | 98770-54-8 |
 | LY-293284 | (4R)-6-acetyl-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[c,d]indole | 141318-62-9 |
 | LY-178210 | 4-(dipropylamino)-1,3,4,5-tetrahydrobenzo[cd]indole-6-carboxamide | 114943-19-0 |
 | RU-28306 | N,N-dimethyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine | 73625-11-3 |
 | RU-27849 | 1,3,4,5-tetrahydrobenzo[c,d]indol-4-amine | 77963-70-3 |
 | N-DEAOP-NMT | N-(3-diethylamino-3-oxopropyl)-N-methyltryptamine | |
 | N-DEAOP-NET | 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 ("[0124]")[45] | 9,10-didehydro-N,N-diethyl-6-methyl-10,11-secoergoline-8β-carboxamide | |
 | CT-5252 | methyl-12-bromo-8,9-didehydro-2,3β-dihydro-6-methyl-10,11-secoergoline-8-carboxylate | |
 | 10,11-Secoergoline | 3-(piperidin-2-ylmethyl)-1H-indole | 5275-05-8 |
 | RU-27251[56] | 4-piperidin-3-yl-1H-indole | 16176-75-3 |
 | DEIMDHPCA | (3R)-N,N-diethyl-5-(1H-indol-4-yl)-1-methyl-3,6-dihydro-2H-pyridine-3-carboxamide | 2640392-28-3 |
 | WXVL_BT0793LQ2118 | 6-fluoro-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole | |
 | DEMPDHPCA ("compound 160a")[25][45] | N,N-diethyl-1-methyl-5-phenyl-3,6-dihydro-2H-pyridine-3-carboxamide | |
 | DEMMPDHPCA ("compound 160b")[25] | N,N-diethyl-1-methyl-3-(4-methoxyphenyl)-1,2,5,6-tetrahydropyridine-5-carboxamide | |
 | DEMTMPDHPCA ("compound 160c")[25] | N,N-diethyl-1-methyl-3-(3,4,5-trimethoxyphenyl)-1,2,5,6-tetrahydropyridine-5-carboxamide | |
 | DEMNDHPCA ("compound 160d")[25] | N,N-diethyl-1-methyl-3-(1-naphthyl)-1,2,5,6-tetrahydropyridine-5-carboxamide | |
_structure.png) | "Compound 45"[52] | 1-methyl-3-(1-oxo-1-diethylaminomethyl)-5-(2,5-dimethoxy-4-methylphenyl)-3,6-dihydro-2H-pyridine | |
.png) | "Compound 163" or "VIII"[25][57][58] | N,N-diethyl-4-methyl-2,3,4,4a,5,6-hexahydrobenzo(f)quinoline-2-carboxamide | |
 | N-DEAOP-NMPEA (PEA-NM-NDEPA)[59] | N-diethylaminocarbonylethyl-N-methylphenethylamine | |
 | 3,4-DMPEA-NDEPA | N-diethylaminocarbonylethyl-3,4-dimethoxyphenethylamine | |
 | DOM-NDEPA[60] | N-diethylaminocarbonylethyl-2,5-dimethoxy-4-methylamphetamine | |
 | DOB-NDEPA[61] | N-diethylaminocarbonylethyl-2,5-dimethoxy-4-bromoamphetamine | |
 | DOI-NDEPA[61] | N-diethylaminocarbonylethyl-2,5-dimethoxy-4-iodoamphetamine | |
 | DOTFM-NDEPA[61] | N-diethylaminocarbonylethyl-2,5-dimethoxy-4-trifluoromethylamphetamine | |
 | TMA-2-NDEPA[62] | N-diethylaminocarbonylethyl-2,4,5-trimethoxyphenethylamine | |
 | M-NDEPA (mescaline-NDEPA)[63] | N-diethylaminocarbonylethyl-3,4,5-trimethoxyamphetamine | |
 | 25D-NM-NDEAOP (25D-NM-NDEPA) | N-methyl-N-(3-diethylamino-3-oxopropyl)-2,5-dimethoxy-4-methylphenethylamine | |
 | 25B-NAcPip | N-(piperidin-1-ylcarbonylmethyl)-4-bromo-2,5-dimethoxyphenethylamine | |
_structure.png) | "Compound 37"[64][52][65] | N-(2-diethylamino-2-oxoethyl)-N-methyl-2-amino-1,2,3,4,4a,8a-hexahydronaphthalene | |
 | 2-Aminotetralin | 1,2,3,4-tetrahydronaphthalen-2-amine | 2954-50-9 |
 | 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 |
 | Rotigotine | 6-[propyl(2-thiophen-2-ylethyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol | 99755-59-6 |
See also
References
External links
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