Lysergamides
Class of chemical compounds
From Wikipedia, the free encyclopedia
Lysergamides, also known as ergoamides[1][2][3] or as lysergic acid amides, are amides of lysergic acid (LA). They are ergolines, with some lysergamides being found naturally in ergot as well as other fungi. Lysergamides are notable in containing embedded phenethylamine and tryptamine moieties within their ergoline ring system.[4]

The simplest lysergamides are ergine (lysergic acid amide; LSA) and isoergine (iso-lysergic acid amide; iso-LSA). In terms of pharmacology, the lysergamides include numerous serotonin and dopamine receptor agonists, most notably the psychedelic drug lysergic acid diethylamide (LSD) but also a number of pharmaceutical drugs like ergometrine, methylergometrine, methysergide, and cabergoline.[5][6][7][8][9][10][11][12][13][14][15][16][17] Various analogues of LSD, such as the psychedelics ALD-52 (1A-LSD), ETH-LAD, LSZ, and 1P-LSD and the non-hallucinogenic 2-bromo-LSD (BOL-148), have also been developed. Ergopeptines like ergotamine, dihydroergotamine, and bromocriptine are also lysergamides, but with addition of a small peptide moiety at the amide. Close analogues of lysergamides that are not technically lysergamides themselves include lisuride, terguride, bromerguride, and JRT.
Lysergamides were first discovered and described in the 1930s.[18][19][20]
Simplified or partial ergolines and lysergamides, such as NDTDI (8,10-seco-LSD), DEMPDHPCA, and N-DEAOP-NMT, are also known.[21][22][23]
Use and effects
The doses, potencies, durations, and effects of lysergamides have been reviewed by Alexander Shulgin.[24][25][26][27][28] They have also been reviewed by Albert Hofmann,[29] David E. Nichols,[30] and other researchers.[31][32][33][34][35][36][37][38][39]
| Common name | Code | Dose | Potency (×LSD) | Duration |
|---|---|---|---|---|
| Lysergic acid amide (LSA; ergine) | LA-111 | 500–6,000 μg | ≤10% | ~4–10 hours |
| Isolysergic acid amide (iso-LSA; isoergine) | Iso-LA-819 | 2,000–5,000 μg | <10% | ~4–10 hours |
| Lysergic acid methylamide | LAM | ~500 μg | ≤20% | Unknown |
| Lysergic acid dimethylamide | DAM-57 | 500–1,200 μg | 10% | Unknown |
| Lysergic acid ethylamide (LAE) | LAE-32 | 500–1,600 μg | ≤10% | Unknown |
| 1-Acetyl-LAE | ALA-10, 1A-LAE | ~1,200 μg | ≤10% | Unknown |
| 1-Methyl-LAE | MLA-74 | ~2,000 μg | 5% | Unknown |
| Lysergic acid methylethylamide | LME-54 | Unknown | ~33% | Unknown |
| Lysergic acid diethylamide (LSD) | LSD-25, METH-LAD | 50–200 μg | 100% | 8–12 hours |
| Isolysergic acid diethylamide | Iso-LSD | >4,000 μg | <2% | Unknown |
| l-Lysergic acid diethylamide | l-LSD | >10,000 μg | <1% | Unknown |
| l-Isolysergic acid diethylamide | l-Iso-LSD | >500 μg | <5% | Unknown |
| 2,3-Dihydro-LSD | 2,3-DH-LSD | ~150–400 μg | ~15% | ~8–12 hours |
| 9,10-Dihydro-LSD | 9,10-DH-LSD | >2,500 μg | <2% | Unknown |
| 10-Hydroxy-9,10-dihydro-LSD | Lumi-LSD | Unknown | <1% | Unknown |
| 2-Bromo-LSD | BOL-148 | >1,000 μg (≥6,000 μg) | <10% (≤2%) | Unknown |
| 2-Iodo-LSD | IOL | Unknown | Unknown | Unknown |
| 2-Oxo-LSD (2-oxy-LSD) | – | >300 μg | Unknown | Unknown |
| 1-Acetyl-LSD | ALD-52, 1A-LSD | 100–200 μg | 100% | ~8–12 hours[40] |
| 1-Methyl-LSD | MLD-41 | 200–300 μg | 30% | Unknown |
| 1-Hydroxymethyl-LSD | OML-632 | Unknown | ~70% | Unknown |
| 1-Propionyl-LSD | 1P-LSD | 100–200 μg | 100% | ~8–12 hours[41][40] |
| 1-Methyl-2-bromo-LSD | MBL-61, MOB-61 | >10,000 μg | <1% | Unknown |
| 1-Methyl-2-iodo-LSD | MIL | Unknown | Unknown | Unknown |
| Lysergic acid propylamide | LAP | >500 μg | <20% | Unknown |
| Lysergic acid methylpropylamide | LMP-55; LAMPA; MPLA | >100 μg | <100% | Unknown |
| Lysergic acid ethylpropylamide | LEP-57; EPLA | Unknown | ~33% | Unknown |
| Lysergic acid methylisopropylamide | MiPLA | 180–300 μg | ~33–50% | Unknown |
| Lysergic acid dipropylamide | DPL | >1,000 μg | <10% | Unknown |
| Lysergic acid dibutylamide | LBB-66 | Unknown | 0% | Unknown |
| Lysergic acid diallylamide | DAL | >1,000 μg | <10% | Unknown |
| Ergonovine (ergometrine)a | – | 5,000–10,000 μg | ≤1% | Unknown |
| Methylergonovine (methylergometrine)b | – | 2,000 μg | 5% | Unknown |
| Propisergidec | PML-946 | >3,000 μg | Unknown | Unknown |
| Methysergided | UML-491 | 4,000–8,000 μg | 2% | Unknown |
| Lysergic acid piperidide | LA-Pip | Unknown | Unknown | Unknown |
| Lysergic acid pyrrolidide (LPD) | LPD-824 | ~800 μg | 5–10% | Unknown |
| Lysergic acid pyrrolinide | LPN | Unknown | Unknown | Unknown |
| 1-Methyl-LPD | MPD-75 | >1,600 μg | ≤10% | Unknown |
| Lysergic acid morpholide | LSM-775, SLM | 300–600 μg | 10–30% | Unknown |
| Lysergic acid 2,4-dimethylazetidide | LA-SS-Az, LSZ | 100–300 μg | 50% | ~4–10 hours[41] |
| Nor-LSD (6-nor-LSD) | H-LAD | >500 μg | <20% | Unknown |
| 6-Ethyl-nor-LSD | ETH-LAD | 40–150 μg | 200% | 8–12 hours |
| 6-Propyl-nor-LSD | PRO-LAD | 80–200 μg | 100% | 6–8 hours |
| 6-Allyl-nor-LSD | AL-LAD, ALLY-LAD | 50–160 μg | 100% | 6–8 hours |
| 6-n-Butyl-nor-LSD | BU-LAD | ≥400–500 μg | <30% | Unknown |
| 6-Propynyl-nor-LSD | PARGY-LAD | 160–500 μg | 20–60% | Unknown |
| 6-(β-Phenethyl)-nor-LSD | PHENETH-LAD | >350–500 μg | <30% | Unknown |
| Footnotes: a = Ergonovine is lysergic acid hydroxyisopropylamide. b = Methylergonovine is lysergic acid hydroxy-sec-butylamide. c = Propisergide is 1-methylergonovine. d = Methysergide is 1-methylmethylergonovine. Refs: Main: [24][25][26][27][28][42][43][44][38][39][18][32][33][36][35][45][41] Additional: [17][40][46][47][48][49] | ||||
The properties of various additional lysergamides, for instance in terms of serotonin antagonism, have also been described.[50]
Interactions
Pharmacology
Pharmacodynamics
| Compound | 5-HT1A | 5-HT1B | 5-HT1D | 5-HT1E | 5-HT2A | 5-HT2B | 5-HT2C | 5-HT3 | 5-HT5A | 5-HT6 | 5-HT7 | D1 | D2 | D3 | D4 | D5 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| LSD | 5.9 | 21 | 3.5 | 135 | 8.5 | 5.5 | 17 | – | 1.8 | 16 | 8.5 | 288 | 204 | 37 | 112 | 955 |
| DAM-57 | 14 | 18 | 17 | 56 | 12 | 16 | 87 | – | 42 | 19 | 23 | 676 | – | 309 | 955 | 2,000 |
| DiPLA | 58 | 89 | 25 | 457 | 15 | 17 | 234 | – | 17 | 49 | 26 | 135 | 234 | 25 | 219 | 316 |
| LAMPA | 13 | 27 | 6.6 | – | 11 | 4.9 | 58 | – | 19 | 35 | 6.5 | 339 | 204 | 35 | 32 | 794 |
| LSZ | 2.3 | 63 | 18 | 224 | 16 | 3.5 | 15 | – | 32 | 18 | 35 | 468 | 115 | 9.1 | 129 | 1,150 |
| NorLSD | 7.8 | 141 | 37 | 407 | 15 | 54 | 525 | – | 100 | 14 | 51 | – | – | 76 | 275 | – |
| ETH-LAD | 3.5 | 32 | 15 | 85 | 9.3 | 18 | 56 | – | 21 | 21 | 11 | 417 | 158 | 81 | 240 | 891 |
| AL-LAD | 6.0 | 275 | 78 | 479 | 17 | 14 | 68 | – | 11 | 50 | 42 | – | 269 | 27 | 155 | – |
| MAL-LAD | 174 | – | 295 | – | 28 | 54 | 479 | – | 89 | 1,050 | 200 | – | – | 363 | 3,240 | – |
| BU-LAD | 21 | 2,190 | 129 | 1,350 | 21 | 16 | 25 | – | 91 | 26 | 123 | 417 | 813 | 91 | 661 | 3,630 |
| Lisuride | 4.1 | 63 | 13 | 93 | 25 | 16 | 50 | – | 5.6 | 18 | 9.5 | 174 | 10 | 5.6 | 10 | 1,050 |
| Compound | 5-HT1A | 5-HT1B | 5-HT1D | 5-HT1E | 5-HT2A | 5-HT2B | 5-HT2C | 5-HT3 | 5-HT5A | 5-HT6 | 5-HT7 | D1 | D2 | D3 | D4 | D5 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| LSD | 7.3 | 3.9 | 7.8 | 93 | 11 | 30 | 31 | >10,000 | 9 | 6.9 | 6.6 | 177 | 110 | 27 | 158 | 344 |
| LSZ | 0.4 | 2.4 | ? | 276 | 19 | 27 | 37 | >10,000 | 27 | 15 | 14 | 292 | 74 | 6 | 96 | 402 |
| Lisuride | 0.3 | 16 | >10,000 | 44 | 5.4 | 2.9 | >10,000 | >10,000 | 3.1 | 7.3 | 6.8 | >10,000 | 6.7 | 136 | 3.8 | 77 |
History

Lysergamides, such as ergine, isoergine, and ergometrine, were discovered by the early 1930s,[18][19][20] and LSD was discovered by 1938 and its hallucinogenic effects in 1943 by Albert Hofmann.[53][54] Many synthetic lysergamide analogues of LSD, modified at the amide and/or 1 or 2 positions, were first described by Hofmann and colleagues in the mid-to-late 1950s.[29][34][42][55] N(6)-Substituted lysergamides were first reported in 1970 and thereafter in the 1970s and 1980s by multiple groups, including Hofmann and colleagues, Yuji Nakahara and Tetsukichi Niwaguchi and colleagues, and David E. Nichols and colleagues.[56][57][58][6] The psychedelic effects of N(6)-substituted lysergamides were reported by Alexander Shulgin in 1986 and thereafter.[59][37][25][28] Additional novel lysergamides modified at the amide, like LA-3Cl-SB and LA-Aziridine, were described by Nichols and Robert Oberlender and colleagues in the late 1980s,[60][37][56] while LSZ (LA-Azetidine) was described by the same group in 2002.[9] Numerous 1-substituted LSD prodrugs such as 1P-LSD and 1V-LSD and other psychedelic lysergamides were developed by Lizard Labs in the 2010s and 2020s.[61][62][63]
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 | |
| LAM (lysergic acid methylamide) | 50485-06-8 | H | CH3 | CH3 | H | - | |
| 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; PML-946) | 5793-04-4 | CH3 | CH3 | CH(CH3)CH2OH | H | - | |
| Methylergometrine (methylergonovine; lysergic acid butanolamide) | 113-42-8 | H | CH3 | CH(CH2CH3)CH2OH | H | - | |
| Methysergide (1-methyl-lysergic acid butanolamide; UML-491) | 361-37-5 | CH3 | CH3 | CH(CH2CH3)CH2OH | H | - | |
| Amesergide (LY-237733; 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 | - | |
| LAP (lysergic acid propylamide) | ? | H | CH3 | CH2CH2CH3 | H | - | |
| iPLA (lysergic acid isopropylamide; LAiP) | 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 | - | ||
| DiPLA (lysergic acid diisopropylamide) | H | CH3 | CH(CH3)2 | CH(CH3)2 | - | ||
| LBB-66 (lysergic acid dibutylamide) | H | CH3 | CH2CH2CH2CH3 | CH2CH2CH2CH3 | - | ||
| 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 | - | ||
| LEO (lysergic acid ethyl-2-hydroxyethylamide) | 65527-58-4 | H | CH3 | CH2CH2OH | CH2CH3 | - | |
| LA-MeO (lysergic acid ethyl-2-methoxyethylamide) | H | CH3 | CH2CH2OCH3 | CH2CH3 | - | ||
| ETFELA (lysergic acid N-ethyl-N-(2,2,2-trifluoroethyl)amide) | H | CH3 | CH2CF3 | CH2CH3 | - | ||
| EFELA (TRALA-04; WO 2022/008627 Compound 4)[64] | H | CH3 | CH2CH2F | CH2CH3 | - | ||
| DFELA (TRALA-08; WO 2022/226408 Example 29)[65] | H | CH3 | CH2CH2F | CH2CH2F | - | ||
| LA-3Cl-SB (lysergic acid N-(3-chloro-sec-butyl)amide) | H | CH3 | CH(CH3)CClHCH3 | H | - | ||
| LME-54 (lysergic acid methylethylamide) | H | CH3 | CH2CH3 | CH3 | - | ||
| LAMPA (LMP-55; 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 | - | |
| Iso-LSD | 2126-78-5 | H | CH3 | CH2CH3 | CH2CH3 | 8-epi | |
| l-LSD | 3184-49-4 | H | CH3 | CH2CH3 | CH2CH3 | 5,8-epi | |
| l-Iso-LSD | H | CH3 | CH2CH3 | CH2CH3 | 5-epi | ||
| Nor-LSD (6-nor-LSD) | 35779-43-2 | H | H | CH2CH3 | CH2CH3 | - | |
| ETH-LAD (6-ethyl-6-nor-LSD) | 65527-62-0 | H | CH2CH3 | CH2CH3 | CH2CH3 | - | |
| PARGY-LAD (6-propynyl-6-nor-LSD) | 2767597-51-1 | 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 | - | ||
| MAL-LAD (METAL-LAD; 6-methallyl-6-nor-LSD) | H | CH2=C(CH3)CH2 | CH2CH3 | CH2CH3 | - | ||
| CYP-LAD (TRALA-22; 6-cyclopropyl-6-nor-LSD) | H | C3H5 | CH2CH3 | CH2CH3 | - | ||
| CPM-LAD (6-cyclopropylmethyl-6-nor-LSD) | H | CH2C3H5 | CH2CH3 | CH2CH3 | - | ||
| BU-LAD (6-butyl-6-nor-LSD) | 96930-87-9 | H | CH2CH2CH2CH3 | CH2CH3 | CH2CH3 | - | |
| PHENETH-LAD (6-(phenethyl)-6-nor-LSD) | H | CH2CH2C6H5 | CH2CH3 | CH2CH3 | - | ||
| NBOMe-LAD (6-(2-methoxybenzyl)-LAD) | H | CH2C6H4-o-OCH3 | CH2CH3 | CH2CH3 | - | ||
| FLUORETH-LAD (FE-LAD; TRALA-15; 6-(2-fluoroethyl)-6-nor-LSD) | H | CH2CH2F | CH2CH3 | CH2CH3 | - | ||
| FP-LAD (WO 2022/226408 Example 2; TRALA-16; 6-(3-fluoropropyl)-6-nor-LSD) | H | CH2CH2CH2F | CH2CH3 | CH2CH3 | - | ||
| CE-LAD (CHLORETH-LAD; 6-(2-chloroethyl)-6-nor-LSD) | H | CH2CH2Cl | CH2CH3 | CH2CH3 | - | ||
| 1-Formyl-LSD (1F-LSD) | CH=O | CH3 | CH2CH3 | CH2CH3 | - | ||
| ALD-52 (1-acetyl-LSD; 1A-LSD) | 3270-02-8 | COCH3 | CH3 | CH2CH3 | CH2CH3 | - | |
| ALA-10 (1-acetyl-LAE; 1A-LAE) | 50485-03-5 | COCH3 | CH3 | CH2CH3 | H | - | |
| 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 | - | ||
| 1F-LSD (1-(furan-2-carbonyl)-LSD; 1-(2-furoyl)-LSD; SYN-L-005) | COC4H3O | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1T-LSD (1-(thiophene-2-carbonyl)-LSD) | COC4H3S | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1Bz-LSD (1-benzoyl-LSD; SYN-L-018) | COC6H5 | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1N-LSD (1-(pyridin-3-ylcarbonyl)-LSD) | COC5H4N | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1C-LSD (1-(cypionyl)-LSD) | CO(CH2)2C5H8 | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1PP-LSD (1-(phenylpropionyl)-LSD) | CO(CH2)2C6H5 | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1MS-LSD (1-(methylsuccinyl)-LSD) | CO(CH2)2COOCH3 | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1OX-LSD (1-(oxetan-3-yl)-LSD) | COCH(CH2)2O | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1E-LSD (1-(enacarbil)-LSD) | COOCH(CH3)OCOCH(CH3)2 | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1S-LSD (1-(3-(trimethylsilyl)propionyl)-LSD) | CO(CH2)2Si(CH3)3 | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1SB-LSD (1BS-LSD; 1-(4-(trimethylsilyl)benzoyl)-LSD) | CO(C6H4)-p-Si(CH3)3 | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1DP-LSD (1-(3-(dimethylphosphoryl)propionyl)-LSD) | CO(CH2)2PO(CH3)2 | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1BP-LSD (1-(3-(tetramethyldioxaborolane)propionyl)-LSD) | CO(CH2)2BO2(C(CH3)2)2 | CH3 | CH2CH3 | CH2CH3 | - | ||
| 1Fe-LSD (1-(ferrocenecarbonyl)-LSD) | 3029080-72-3 | CO(C5H4)FeC5H5 | 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 | - | ||
| 1D-AL-LAD (1-(1,2-dimethylcyclobutane-1-carbonyl)-AL-LAD) | COC4H5(CH3)2 | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - | ||
| 1T-AL-LAD (1-(2-thienoyl)-6-allyl-6-nor-LSD)[66] | 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 | - | ||
| 1cP-MiPLA (1-cyclopropionyl-lysergic acid methylisopropylamide) | 3028950-74-2 | COC3H5 | CH3 | CH(CH3)2 | CH3 | - | |
| MLD-41 (1-methyl-LSD) | 4238-85-1 | CH3 | CH3 | CH2CH3 | CH2CH3 | - | |
| MLA-74 (1-methyl-LAE) | 7240-57-5 | CH3 | CH3 | CH2CH3 | H | - | |
| OML-632 (1-hydroxymethyl-LSD) | 114004-70-5 | CH2OH | CH3 | CH2CH3 | CH2CH3 | - | |
| 1-Dimethylaminomethyl-LSD | ? | CH2NCH2CH2 | 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 | - | ||
| MPD-75 (1-methyllysergic acid pyrrolidide) | 7221-79-6 | CH3 | CH3 | (CH2)4 | - | ||
| Lysergic acid pyrrolinide | ? | H | CH3 | CH2-CH=CH-CH2 | - | ||
| LA-Cispyr | ? | H | CH3 | cis-CH(CH3)-CH2CH2-CH(CH3) | - | ||
| LA-Pip (lysergic acid piperidide) | 50485-23-9 | H | CH3 | (CH2)5 | - | ||
| LA-Azepane (lysergic acid azepane)[67] | H | CH3 | (CH2)6 | - | |||
| Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ, LA-Azetidine) | 470666-31-0 | H | CH3 | CH2(CHCH3)2CH2 | - | ||
| 2-Oxa-6-azaspiro[3.3]heptyl-lysergamide (WO 2022/008627 compound)[68] | H | CH3 | (CH2)2C(CH2)2O | - | |||
| Lysergic acid-(2,3-dimethylaziridinyl)amide (LA-Aziridine) | ? | H | CH3 | ? | - | ||
| 2-Bromo-LSD (BOL-148; bromolysergide) | 478-84-2 | H | CH3 | CH2CH3 | CH2CH3 | 2-Br | |
| 2-Iodo-LSD (IOL) | 3712-25-2 | H | CH3 | CH2CH3 | CH2CH3 | 2-I | |
| 2-Oxo-LSD (2-oxy-LSD) | ? | H | CH3 | CH2CH3 | CH2CH3 | 2-Oxo | |
| 2-Oxo-3-hydroxy-LSD | ? | H | CH3 | CH2CH3 | CH2CH3 | 2-Oxo, 3-OH | |
| MBL-61 (MOB-61; 1-methyl-2-bromo-LSD) | 50484-98-5 | CH3 | CH3 | CH2CH3 | CH2CH3 | 2-Br | |
| MIL (1-methyl-2-iodo-LSD) | 97165-34-9 | CH3 | CH3 | CH2CH3 | CH2CH3 | 2-I | |
| 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[69] | H | CH3 | CH2CH3 | CH2CH3 | 13-F | ||
| 13-Hydroxy-LSD | H | CH3 | CH2CH3 | CH2CH3 | 13-OH | ||
| 13-Methoxy-LSD | H | CH3 | CH2CH3 | CH2CH3 | 13-OMe | ||
| 14-Hydroxy-LSD | H | CH3 | CH2CH3 | CH2CH3 | 14-OH | ||
| 14-Methoxy-LSD | H | CH3 | CH2CH3 | CH2CH3 | 14-OMe | ||
Related compounds
| Structure | Name | Chemical name | CAS # |
|---|---|---|---|
| 2,3-Dihydro-LSD (2,3-DH-LSD) | N,N-diethyl-6-methyl-9,10-didehydro-2,3-dihydroergoline-8β-carboxamide | ? | |
| 9,10-Dihydro-LSD (9,10-DH-LSD) | (10ξ)-N,N-diethyl-6-methylergoline-8β-carboxamide | 3031-47-8 | |
| AWD 52-39 | N,N-diacetoxyethyl-9,10-dihydrolysergamide | 109002-91-7 | |
| Bromerguride (2-bromolisuride) | 1,1-diethyl-3-(2-bromo-9,10-didehydro-6-methyl-8α-ergolinyl)urea | 83455-48-5 | |
| Bromocriptine | (5′α)-2-bromo-12′-hydroxy-5′-(2-methylpropyl)-3′,6′,18-trioxo-2′-(propan-2-yl)ergotaman | 25614-03-3 | |
| D13H (2-cyclopropyl-9,10-dihydromethysergide; possibly XC101-D13H) | (6aR,9R,10aR)-5-cyclopropyl-N-((S)-1-hydroxybutan-2-yl)-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide | ||
| Descarboxylysergic acid (DCLA) | 6-methyl-9,10-didehydroergoline | 51867-17-5 | |
| Dihydroergotamine (DHE-45) | (5'α)-9,10-dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)-ergotaman-3',6',18-trione | 511-12-6 | |
| Disulergine | N,N-dimethyl-N'-(6-methylergoline-8α-yl)sulfamide | 59032-40-5 | |
| Dosergoside | N-((1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl)-6-methylergoline-8β-carboxamide | 87178-42-5 | |
| Ergoline | (6aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline | 478-88-6 | |
| Ergotamine | 5′α-benzyl-12′-hydroxy-2′-methyl-3′,6′,18-trioxoergotaman | 113-15-5 | |
| Etisulergine | N,N-diethyl-N'-(6-methylergolin-8α-yl)sulfamide | 64795-23-9 | |
| GYKI-32887 (RGH-7825) | 8-((N-2-azidoethyl-N-methylsulfonylamino)methyl)-6-methylergol-8-ene | 78463-86-2 | |
| JRT (isoindole-LSD) | (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 | ? | |
| Lumi-LSD (10-hydroxy-9,10-dihydro-LSD) | N,N-diethyl-10-hydroxy-6-methylergoline-8β-carboxamide | ||
| Lysergine | 9,10-didehydro-6,8β-dimethylergoline | 519-10-8 | |
| Lysergol | (6-methyl-9,10-didehydroergolin-8β-yl)methanol | 1413-67-8 | |
| Lysergic acid (LA) | 6-methyl-9,10-didehydroergoline-8β-carboxylic acid | 82-58-6 | |
| Lergotrile | 2-chloro-6-methylergoline-8β-acetonitrile | 36945-03-6 | |
| Lisuride | 1,1-diethyl-3-(6-methyl-9,10-didehydroergolin-8α-yl)urea | 18016-80-3 | |
| 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 | ? | |
| Proterguride (6-propyl-9,10-dihydrolisuride) | 1,1-diethyl-3-(6-n-propyl-8α-ergolinyl)urea | 77650-95-4 | |
| Terguride (9,10-dihydrolisuride) | N,N-diethyl-N'-[(8α)-6-methylergolin-8-yl]urea | 37686-84-3 | |