Lysergamides

thumb|right|150px|class=skin-invert-image|The lysergamide core, with common substitution positions denoted.

Lysergamides, also known as ergoamides 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.

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.

Use and effects

The doses, potencies, durations, and effects of lysergamides have been reviewed by Alexander Shulgin. They have also been reviewed by Albert Hofmann, David E. Nichols, and other researchers.

|-

| 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

|-

| Propisergide^c || PML-946 || >3,000 μg || Unknown || Unknown

|-

| Methysergide^d || 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 Additional:

|}

The properties of various additional lysergamides, for instance in terms of serotonin antagonism, have also been described.

Interactions

Pharmacology

Pharmacodynamics

{| class="wikitable sticky-header"

|+

|-

! Compound !! 5-HT_1A !! 5-HT_1B !! 5-HT_1D !! 5-HT_1E !! 5-HT_2A !! 5-HT_2B !! 5-HT_2C !! 5-HT₃ !! 5-HT_5A !! 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

|}

{| class="wikitable sticky-header"

|+

|-

! Compound !! 5-HT_1A !! 5-HT_1B !! 5-HT_1D !! 5-HT_1E !! 5-HT_2A !! 5-HT_2B !! 5-HT_2C !! 5-HT₃ !! 5-HT_5A !! 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

thumb|right|350px|class=skin-invert-image|Major types of [[structural modifications of LSD.]]

Lysergamides, such as ergine, isoergine, and ergometrine, were discovered by the early 1930s, and LSD was discovered by 1938 and its hallucinogenic effects in 1943 by Albert Hofmann. 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. 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.

List of lysergamides

{| class="wikitable sticky-header"

|+ Lysergamides, tabulated by structure

|-

! Structure !! Name (synonyms) !! CAS # !! R1 !! R6 !! R2 !! R3 !! Other

|-

| 125px|class=skin-invert-image || Ergine (lysergic acid amide; LSA; LA-111; lysergamide) || 478-94-4 || H || CH₃ || H || H || -

|-

| 125px|class=skin-invert-image || Isoergine (isolysergic acid amide; iso-LSA; iso-LA-819; isolysergamide) || 2889-26-1 || H || CH₃ || H || H || 8-epi

|-

| 125px|class=skin-invert-image || LAM (lysergic acid methylamide) || 50485-06-8 || H || CH₃ || CH₃ || H || -

|-

| 125px|class=skin-invert-image || DAM-57 (lysergic acid dimethylamide) || 4238-84-0 || H || CH₃ || CH₃ || CH₃ || -

|-

| 125px|class=skin-invert-image || LSH (LAH; lysergic acid hydroxyethylamide) || 3343-15-5 || H || CH₃ || CH₃CHOH || H || -

|-

| 125px|class=skin-invert-image || Ergometrine (ergonovine; lysergic acid propanolamide) || 60-79-7 || H || CH₃ || CH(CH₃)CH₂OH || H || -

|-

| 125px|class=skin-invert-image || Propisergide (1-methylergonovine; PML-946) || 5793-04-4 || CH₃ || CH₃ || CH(CH₃)CH₂OH || H || -

|-

| 125px|class=skin-invert-image || Methylergometrine (methylergonovine; lysergic acid butanolamide) || 113-42-8 || H || CH₃ || CH(CH₂CH₃)CH₂OH || H || -

|-

| 125px|class=skin-invert-image || Methysergide (1-methyl-lysergic acid butanolamide; UML-491) || 361-37-5 || CH₃ || CH₃ || CH(CH₂CH₃)CH₂OH || H || -

|-

| 125px|class=skin-invert-image || Amesergide (LY-237733; 9,10-dihydro-11-isopropyllysergic acid cyclohexylamide) || 121588-75-8 || CH(CH₃)₂ || CH₃ || C₆H₁₁ || H || -

|-

| 125px|class=skin-invert-image || LY-215840 (1-isopropyl-9,10-dihydro-N-(2-hydroxycyclopent-anyl)lysergamide) || 137328-52-0 || CH(CH₃)₂ || CH₃ || C₅H₈OH || H || -

|-

| 125px|class=skin-invert-image || 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 || -

|-

| 125px|class=skin-invert-image || LAE-32 (lysergic acid ethylamide) || 478-99-9 || H || CH₃ || CH₂CH₃ || H || -

|-

| 125px|class=skin-invert-image || LAP (lysergic acid propylamide) || ? || H || CH₃ || CH₂CH₂CH₃ || H || -

|-

| 125px|class=skin-invert-image || iPLA (lysergic acid isopropylamide; LAiP) || || H || CH₃ || CH(CH₃)₂ || H || -

|-

| 125px|class=skin-invert-image || LAtB (lysergic acid tert-butylamide) || || H || CH₃ || C(CH₃)₃ || H || -

|-

| 125px|class=skin-invert-image || Lysergic acid butylamide || 50583-88-5 || H || CH₃ || CH₂CH₂CH₂CH₃ || H || -

|-

| 125px|class=skin-invert-image || Lysergic acid amylamide (lysergic acid pentylamide) || ? || H || CH₃ || CH₂CH₂CH₂CH₂CH₃ || H || -

|-

| 125px|class=skin-invert-image || LEK-8804 (N-(2-propynyl)lysergamide) || 153415-44-2 || H || CH₃ || CH₂C≡CH || H || -

|-

| 125px|class=skin-invert-image || LEK-8842 (N-methyl-N-(2-propynyl)lysergamide; TRALA-01) || || H || CH₃ || CH₂C≡CH || CH₃ || -

|-

| 125px|class=skin-invert-image || LAcB (lysergic acid cyclobutylamide) || || H || CH₃ || (CH₂)₄ || H || -

|-

| 125px|class=skin-invert-image || Cepentil (lysergic acid cyclopentylamide) || || H || CH₃ || (CH₂)₅ || H || -

|-

| 125px|class=skin-invert-image || LSB (lysergic acid 2-butylamide) || 137765-82-3 || H || CH₃ || CH(CH₃)CH₂CH₃ || H || -

|-

| 125px|class=skin-invert-image || LSP (3-LSP; lysergic acid 3-pentylamide) || 162105-96-6 || H || CH₃ || CH(CH₂CH₃)CH₂CH₃ || H || -

|-

| 125px|class=skin-invert-image || 2-LSP (lysergic acid 2-pentylamide) || ? || H || CH₃ || CH(CH₃)C₃H₇ || H || -

|-

| 125px|class=skin-invert-image || Lysergic acid 2-hexylamide (N2He-LA, 2-LSHe) || ? || H || CH₃ || CH(CH₃)C₄H₉ || H || -

|-

| 125px|class=skin-invert-image || Lysergic acid 2-heptylamide (N2Hp-LA, 2-LSHp) || ? || H || CH₃ || CH(CH₃)C₅H₁₁ || H || -

|-

| 125px|class=skin-invert-image || Lysergic acid α-methylbenzylamide (N-(α-methylbenzyl)lysergamide) || ? || H || CH₃ || CH(CH₃)C₆H₅ || H || -

|-

| 125px|class=skin-invert-image || Lysergic acid methyl-2-butylamide || ? || H || CH₃ || CH(CH₃)CH₂CH₃ || CH₃ || -

|-

| 125px|class=skin-invert-image || Lysergic acid ethyl-2-butylamide || ? || H || CH₃ || CH(CH₃)CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || DPL (lysergic acid dipropylamide) || || H || CH₃ || CH₂CH₂CH₃ || CH₂CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || DiPLA (lysergic acid diisopropylamide) || || H || CH₃ || CH(CH₃)₂ || CH(CH₃)₂ || -

|-

| 125px|class=skin-invert-image || LBB-66 (lysergic acid dibutylamide) || || H || CH₃ || CH₂CH₂CH₂CH₃ || CH₂CH₂CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || DAL (lysergic acid diallylamide) || 73032-97-0 || H || CH₃ || H₂C=CH-CH₂ || Allyl|H₂C=CH-CH₂ || -

|-

| 125px|class=skin-invert-image || MiPLA (lysergic acid methylisopropylamide) || 100768-08-9 || H || CH₃ || CH(CH₃)₂ || CH₃ || -

|-

| 125px|class=skin-invert-image || EiPLA (lysergic acid ethylisopropylamide) || 154504-04-8 || H || CH₃ || CH(CH₃)₂ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || EcPLA (lysergic acid ethylcyclopropylamide) || 2349367-50-4 || H || CH₃ || C₃H₅ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || LEO (lysergic acid ethyl-2-hydroxyethylamide) || 65527-58-4 || H || CH₃ || CH₂CH₂OH || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || LA-MeO (lysergic acid ethyl-2-methoxyethylamide) || || H || CH₃ || CH₂CH₂OCH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || ETFELA (TRALA-06; lysergic acid N-ethyl-N-(2,2,2-trifluoroethyl)amide) || 3024529-99-2 || H || CH₃ || CH₂CF₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || EFELA (TRALA-04; WO 2022/008627 Compound 4) || || H || CH₃ || CH₂CH₂F || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || DFELA (TRALA-08; WO 2022/226408 Example 29) || || H || CH₃ || CH₂CH₂F || CH₂CH₂F || -

|-

| 125px|class=skin-invert-image || LA-3Cl-SB (lysergic acid N-(3-chloro-sec-butyl)amide) || || H || CH₃ || CH(CH₃)CClHCH₃ || H || -

|-

| 125px|class=skin-invert-image || LME-54 (lysergic acid methylethylamide) || || H || CH₃ || CH₂CH₃ || CH₃ || -

|-

| 125px|class=skin-invert-image || LAMPA (LMP-55; lysergic acid methylpropylamide) || 40158-98-3 || H || CH₃ || CH₂CH₂CH₃ || CH₃ || -

|-

| 125px|class=skin-invert-image || TRALA-12 (lysergic acid vinylethylamide; likely didehydro-LSD or DDH-LSD) || 65527-59-5 || H || CH₃ || CHCH₂ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || EPLA (lysergic acid ethylpropylamide; LEP-57) || || H || CH₂CH₃ || CH₂CH₂CH₃ || CH₃ || -

|-

| 125px|class=skin-invert-image || LSD (lysergic acid diethylamide; LAD) || 50-37-3 || H || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || Iso-LSD || 2126-78-5 || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 8-epi

|-

| 125px|class=skin-invert-image || l-LSD || 3184-49-4 || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 5,8-epi

|-

| 125px|class=skin-invert-image || l-Iso-LSD || || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 5-epi

|-

| 125px|class=skin-invert-image || Nor-LSD (6-nor-LSD) || 35779-43-2 || H || H || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || ETH-LAD (6-ethyl-6-nor-LSD) || 65527-62-0 || H || CH₂CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || PARGY-LAD (6-propynyl-6-nor-LSD) || 2767597-51-1 || H || HC≡C−CH₂ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || AL-LAD (6-allyl-6-nor-LSD) || 65527-61-9 || H || H₂C=CH-CH₂ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || PRO-LAD (6-propyl-6-nor-LSD) || 65527-63-1 || H || CH₂CH₂CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || IP-LAD (6-isopropyl-6-nor-LSD) || 96930-86-8 || H || CH(CH₃)₂ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || MAL-LAD (METAL-LAD; 6-methallyl-6-nor-LSD) || || H || CH₂=C(CH₃)CH₂ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || CYP-LAD (TRALA-22; 6-cyclopropyl-6-nor-LSD) || 3024530-20-6 || H || C₃H₅ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || CPM-LAD (6-cyclopropylmethyl-6-nor-LSD) || || H || CH₂C₃H₅ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || BU-LAD (6-butyl-6-nor-LSD) || 96930-87-9 || H || CH₂CH₂CH₂CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 150px|class=skin-invert-image || PHENETH-LAD (6-(phenethyl)-6-nor-LSD) || || H || CH₂CH₂C₆H₅ || CH₂CH₃ || CH₂CH₃ || -

|-

| 150px|class=skin-invert-image || NIBR2130 (6-(phenylcarbamoyl)-6-nor-LSD) || || H || ? || CH₂CH₃ || CH₂CH₃ || -

|-

| 150px|class=skin-invert-image || NBOMe-LAD (6-(2-methoxybenzyl)-LAD) || || H || CH₂C₆H₄-o-OCH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || FLUORETH-LAD (FE-LAD; TRALA-15; 6-(2-fluoroethyl)-6-nor-LSD) || 2757566-18-8 || H || CH₂CH₂F || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || FP-LAD (PROF-LAD; TRALA-16; WO 2022/226408 Example 2; 6-(3-fluoropropyl)-6-nor-LSD) || || H || CH₂CH₂CH₂F || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || CE-LAD (CHLORETH-LAD; 6-(2-chloroethyl)-6-nor-LSD) || || H || CH₂CH₂Cl || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || LEK-8827 (6-methyl-LEK-8842; 6-methyl-N-methyl-N-(2-propynyl)lysergamide) || || H || (CH₃)₂ || CH₂C≡CH || CH₃ || -

|-

| 125px|class=skin-invert-image || 1-Formyl-LSD (1F-LSD) || || CH=O || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || ALD-52 (1-acetyl-LSD; 1A-LSD) || 3270-02-8 || COCH₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || ALA-10 (1-acetyl-LAE; 1A-LAE) || 50485-03-5 || COCH₃ || CH₃ || CH₂CH₃ || H || -

|-

| 125px|class=skin-invert-image || 1P-LSD (1-propionyl-LSD) || 2349358-81-0 || COCH₂CH₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1B-LSD (1-butanoyl-LSD) || 2349376-12-9 || COCH₂CH₂CH₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1V-LSD (1-valeryl-LSD) || 3028950-70-8 || CO(CH₂)₃CH₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1H-LSD (1-hexanoyl-LSD) || 3028949-65-4 || CO(CH₂)₄CH₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 150px|class=skin-invert-image || 1DD-LSD (1-dodecanoyl-LSD) || 3028949-80-3 || CO(CH₂)₁₀CH₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1cP-LSD (1-cyclopropylmethanoyl-LSD) || 2767597-50-0 || COC₃H₅ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1D-LSD (1-(1,2-dimethylcyclobutane-1-carbonyl)-LSD) || || COC₄H₅(CH₃)₂ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1F-LSD (1-(furan-2-carbonyl)-LSD; 1-(2-furoyl)-LSD; SYN-L-005) || || COC₄H₃O || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1T-LSD (1-(thiophene-2-carbonyl)-LSD) || 3028949-85-8 || COC₄H₃S || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1Bz-LSD (1-benzoyl-LSD; SYN-L-018) || || COC₆H₅ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1N-LSD (1-(pyridin-3-ylcarbonyl)-LSD) || || COC₅H₄N || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1C-LSD (1-(cypionyl)-LSD) || || CO(CH₂)₂C₅H₈ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1PP-LSD (1-(phenylpropionyl)-LSD) || || CO(CH₂)₂C₆H₅ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1MS-LSD (1-(methylsuccinyl)-LSD) || || CO(CH₂)₂COOCH₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1OX-LSD (1-(oxetan-3-yl)-LSD) || || COCH(CH₂)₂O || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1E-LSD (1-(enacarbil)-LSD) || || COOCH(CH₃)<br />OCOCH(CH₃)₂ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 135px|class=skin-invert-image || 1S-LSD (1-(3-(trimethylsilyl)propionyl)-LSD) || || CO(CH₂)₂Si(CH₃)₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 145px|class=skin-invert-image || 1SB-LSD (1BS-LSD; 1-(4-(trimethylsilyl)benzoyl)-LSD) || || CO(C₆H₄)-p-Si(CH₃)₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 135px|class=skin-invert-image || 1DP-LSD (1-(3-(dimethylphosphoryl)propionyl)-LSD) || || CO(CH₂)₂PO(CH₃)₂ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 135px|class=skin-invert-image || 1BP-LSD (1-(3-(tetramethyldioxaborolane)propionyl)-LSD) || || CO(CH₂)₂BO₂<br />(C(CH₃)₂)₂ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1Fe-LSD (1-(ferrocenecarbonyl)-LSD) || 3029080-72-3 || CO(C₅H₄)FeC₅H₅ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1P-AL-LAD (1-propionyl-6-allyl-6-nor-LSD) || 3028950-71-9 || COCH₂CH₃ || H₂C=CH-CH₂ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1cP-AL-LAD (1-cyclopropylmethanoyl-6-allyl-6-nor-LSD) || || COC₃H₅ || H₂C=CH-CH₂ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1D-AL-LAD (1-(1,2-dimethylcyclobutane-1-carbonyl)-AL-LAD) || || COC₄H₅(CH₃)₂ || H₂C=CH-CH₂ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1T-AL-LAD (1-(2-thienoyl)-6-allyl-6-nor-LSD) || || COC₄H₃S || H₂C=CH-CH₂ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1P-ETH-LAD (1-propionyl-6-ethyl-6-nor-LSD) || 2230715-45-2 || COCH₂CH₃ || CH₂CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1P-MiPLA (1-propionyl-lysergic acid methylisopropylamide) || || COCH₂CH₃ || CH₃ || CH(CH₃)₂ || CH₃ || -

|-

| 125px|class=skin-invert-image || 1cP-MiPLA (1-cyclopropionyl-lysergic acid methylisopropylamide) || 3028950-74-2 || COC₃H₅ || CH₃ || CH(CH₃)₂ || CH₃ || -

|-

| 125px|class=skin-invert-image || MLD-41 (1-methyl-LSD) || 4238-85-1 || CH₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || MLA-74 (1-methyl-LAE) || 7240-57-5 || CH₃ || CH₃ || CH₂CH₃ || H || -

|-

| 125px|class=skin-invert-image || OML-632 (1-hydroxymethyl-LSD) || 114004-70-5 || CH₂OH || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || 1-Dimethylaminomethyl-LSD || ? || CH₂NCH₂CH₂ || CH₃ || CH₂CH₃ || CH₂CH₃ || -

|-

| 125px|class=skin-invert-image || Lysergic acid-(2,3-dimethylaziridinyl)amide (LA-Aziridine) || ? || H || CH₃ || colspan=2| ? || -

|-

| 125px|class=skin-invert-image || Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ, LA-Azetidine) || 470666-31-0 || H || CH₃ || colspan=2|CH₂(CHCH₃)₂CH₂ || -

|-

| 125px|class=skin-invert-image || LPD-824 (lysergic acid pyrrolidide) || 2385-87-7 || H || CH₃ || colspan=2|(CH₂)₄ || -

|-

| 125px|class=skin-invert-image || MPD-75 (1-methyllysergic acid pyrrolidide) || 7221-79-6 || CH₃ || CH₃ || colspan=2|(CH₂)₄ || -

|-

| 125px|class=skin-invert-image || Lysergic acid pyrrolinide || ? || H || CH₃ || colspan=2|CH₂-CH=CH-CH₂ || -

|-

| 125px|class=skin-invert-image || LA-Cispyr (LA-cis-2,5-DiMePyr) || ? || H || CH₃ || colspan=2|cis-CH(CH₃)-CH₂CH₂-CH(CH₃) || -

|-

| 125px|class=skin-invert-image || LA-Pip (lysergic acid piperidide) || 50485-23-9 || H || CH₃ || colspan=2|(CH₂)₅ || -

|-

| 125px|class=skin-invert-image || LA-cis-2,6-DiMePip (lysergic acid cis-2,6-dimethylpiperidide) || ? || H || CH₃ || colspan=2 | ? || -

|-

| 125px|class=skin-invert-image || LSM-775 (lysergic acid morpholide) || 4314-63-0 || H || CH₃ || colspan=2|CH₂CH₂-O-CH₂CH₂ || -

|-

| 125px|class=skin-invert-image || LA-Azepane (lysergic acid azepane) || || H || CH₃ || colspan=2| (CH₂)₆ || -

|-

| 125px|class=skin-invert-image || 2-Oxa-6-azaspiro[3.3]heptyl-lysergamide (WO 2022/008627 compound) || || H || CH₃ || colspan=2| (CH₂)₂C(CH₂)₂O || -

|-

| 125px|class=skin-invert-image || 2-Bromo-LSD (BOL-148; bromolysergide) || 478-84-2 || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 2-Br

|-

| 125px|class=skin-invert-image || 2-Iodo-LSD (IOL) || 3712-25-2 || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 2-I

|-

| 125px|class=skin-invert-image || 2-Oxo-LSD (2-oxy-LSD) || ? || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 2-Oxo

|-

| 125px|class=skin-invert-image || 2-Oxo-3-hydroxy-LSD || 111295-09-1 || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 2-Oxo, 3-OH

|-

| 125px|class=skin-invert-image || MBL-61 (MOB-61; 1-methyl-2-bromo-LSD) || 50484-98-5 || CH₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || 2-Br

|-

| 125px|class=skin-invert-image || MIL (1-methyl-2-iodo-LSD) || 97165-34-9 || CH₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || 2-I

|-

| 125px|class=skin-invert-image || LEK-8841 (2-bromo-LEK-8842; 2-bromo-N-methyl-N-(2-propynyl)lysergamide) || || H || CH₃ || CH₂C≡CH || CH₃ || 2-Br

|-

| 125px|class=skin-invert-image || 1P-BOL-148 (1-propionyl-2-bromo-LSD) || || COCH₂CH₃ || CH₃ || CH₂CH₃ || CH₂CH₃ || 2-Br

|-

| 125px|class=skin-invert-image || 12-Hydroxy-LSD (12-OH-LSD) || 60573-89-9 || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 12-OH

|-

| 125px|class=skin-invert-image || 12-Methoxy-LSD (12-MeO-LSD) || 50484-99-6 || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 12-OMe

|-

| 125px|class=skin-invert-image || 13-Fluoro-LSD || || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 13-F

|-

| 125px|class=skin-invert-image || 13-Hydroxy-LSD || || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 13-OH

|-

| 125px|class=skin-invert-image || 13-Methoxy-LSD || || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 13-OMe

|-

| 125px|class=skin-invert-image || 14-Hydroxy-LSD || || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 14-OH

|-

| 125px|class=skin-invert-image || 14-Methoxy-LSD || || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 14-OMe

|-

| 125px|class=skin-invert-image || 14-Methyl-LSD || 3069948-26-8 || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 14-Me

|-

| 125px|class=skin-invert-image || 2-Br-14-Me-LSD || || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 2-Br, 14-Me

|}

Related compounds

{| class="wikitable sticky-header"

|-

! Structure !! Name !! Chemical name !! CAS #

|-

| 125px|class=skin-invert-image || 2,3-Dihydro-LSD (2,3-DH-LSD) || N,N-diethyl-6-methyl-9,10-didehydro-2,3-dihydroergoline-8β-carboxamide || None

|-

| 125px|class=skin-invert-image || 9,10-Dihydro-LSD (9,10-DH-LSD) || (10ξ)-N,N-diethyl-6-methylergoline-8β-carboxamide || 3031-47-8

|-

| 125px|class=skin-invert-image || AWD 52-39 || N,N-diacetoxyethyl-9,10-dihydrolysergamide || 109002-91-7

|-

| 150px|class=skin-invert-image || Bromerguride (2-bromolisuride) || 1,1-diethyl-3-(2-bromo-9,10-didehydro-6-methyl-8α-ergolinyl)urea || 83455-48-5

|-

| 150px|class=skin-invert-image || Bromocriptine || (5′α)-2-bromo-12′-hydroxy-5′-(2-methylpropyl)-3′,6′,18-trioxo-2′-(propan-2-yl)ergotaman || 25614-03-3

|-

| 150px|class=skin-invert-image || 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 || ?

|-

| 85px|class=skin-invert-image || Descarboxylysergic acid (DCLA) || 6-methyl-9,10-didehydroergoline || 51867-17-5

|-

| 150px|class=skin-invert-image || Dihydroergotamine (DHE-45) || (5'α)-9,10-dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)-ergotaman-3',6',18-trione || 511-12-6

|-

| 125px|class=skin-invert-image || Disulergine || N,N-dimethyl-N<nowiki>'</nowiki>-(6-methylergoline-8α-yl)sulfamide || 59032-40-5

|-

| 150px|class=skin-invert-image || Dosergoside || N-((1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl)-6-methylergoline-8β-carboxamide || 87178-42-5

|-

| 85px|class=skin-invert-image || Ergoline || (6aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline || 478-88-6

|-

| 150px|class=skin-invert-image || Ergotamine || 5′α-benzyl-12′-hydroxy-2′-methyl-3′,6′,18-trioxoergotaman || 113-15-5

|-

| 125px|class=skin-invert-image || Etisulergine || N,N-diethyl-N<nowiki>'</nowiki>-(6-methylergolin-8α-yl)sulfamide || 64795-23-9

|-

| 150px|class=skin-invert-image || GYKI-32887 (RGH-7825) || 8-((N-2-azidoethyl-N-methylsulfonylamino)methyl)-6-methylergol-8-ene || 78463-86-2

|-

| 125px|class=skin-invert-image || JRT (isotryptamine-LSD) || (7S)-N,N-diethyl-6-methyl-6,9-diazatetracyclo[7.6.1.0^2,7.0^12,16]hexadeca-1(15),2,10,12(16),13-pentaene-4-carboxamide || ?

|-

| 125px|class=skin-invert-image || Compound 3A || [(4R,7S)-6-methyl-6,9-diazatetracyclo[7.6.1.0^2,7.0^12,16]hexadeca-1(15),2,10,12(16),13-pentaen-4-yl]methanol || 3081797-69-2

|-

| 125px|class=skin-invert-image || LEK-8822 (9,10-dihydro-LEK-8842) || N-methyl-N-(2-propynyl)-6-methylergoline-8β-carboxamide || ?

|-

| 125px|class=skin-invert-image || LEK-8829 (desoxy-LEK-8842) || 9,10-didehydro-N-methyl-N-(2-propynyl)-6-methyl-8β-(aminomethyl)ergoline || 145204-78-0

|-

| 125px|class=skin-invert-image || Lumi-LSD (10-hydroxy-9,10-dihydro-LSD) || N,N-diethyl-10-hydroxy-6-methylergoline-8β-carboxamide || ?

|-

| 125px|class=skin-invert-image || Lysergine || 9,10-didehydro-6,8β-dimethylergoline || 519-10-8

|-

| 125px|class=skin-invert-image || Lysergol || (6-methyl-9,10-didehydroergolin-8β-yl)methanol || 1413-67-8

|-

| 125px|class=skin-invert-image || Lysergic acid (LA) || 6-methyl-9,10-didehydroergoline-8β-carboxylic acid || 82-58-6

|-

| 125px|class=skin-invert-image || Lergotrile || 2-chloro-6-methylergoline-8β-acetonitrile || 36945-03-6

|-

| 125px|class=skin-invert-image || Lisuride || 1,1-diethyl-3-(6-methyl-9,10-didehydroergolin-8α-yl)urea || 18016-80-3

|-

| 125px|class=skin-invert-image || 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 || ?

|-

| 125px|class=skin-invert-image || Proterguride (6-propyl-9,10-dihydrolisuride) || 1,1-diethyl-3-(6-propyl-8α-ergolinyl)urea || 77650-95-4

|-

| 100px|class=skin-invert-image || Romergoline (FCE-23884) || 4-(9,10-didehydro-6-methylergolin-8β-yl)methylpiperazine-2,6-dione || 107052-56-2

|-

| 100px|class=skin-invert-image || RU-29717 (N-propyl-9-oxaergoline) || N-propyl-9-oxaergoline || 85351-27-5

|-

| 125px|class=skin-invert-image || Terguride (9,10-dihydrolisuride) || N,N-diethyl-N<nowiki>'</nowiki>-(6-methylergolin-8α-yl)urea || 37686-84-3

|-

|}

See also

• Substituted ergoline
• Partial lysergamide
• Substituted tryptamine
• Substituted phenethylamine
• Lizard Labs

References

External links

• Lysergamide Psychedelics - Tripsitter
• Designer Drug Exposé: Lysergamides - Tripsitter
• Lysergamides - Wikipedia Massviews Analysis (Wikipedia Page Views of Individual Lysergamides)