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Class of chemical compounds
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The lysergamide core, with common substitution positions denoted.

Lysergamides, also known as ergoamides[1][2][3][4] 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.[5]

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.[6][7][8][9][10][11][12][13][14][15][16][17][18] 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.[19][20][21]

Simplified or partial ergolines and lysergamides, such as NDTDI (8,10-seco-LSD), DEMPDHPCA, and N-DEAOP-NMT, are also known.[22][23][24]

Use and effects

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The doses, potencies, durations, and effects of lysergamides have been reviewed by Alexander Shulgin.[25][26][27][28][29] They have also been reviewed by Albert Hofmann,[30] David E. Nichols,[31] and other researchers.[32][33][34][35][36][37][38][39][40]

Doses, potencies, and durations of LSD and its analogues
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[41]
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[42][41]
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[42]
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: [25][26][27][28][29][43][44][45][39][40][19][33][34][37][36][46][42] Additional: [18][41][47][48][49][50]

The properties of various additional lysergamides, for instance in terms of serotonin antagonism, have also been described.[51]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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Serotonin and dopamine receptor affinities (Ki, nM) of selected lysergamides and related compounds (Jain et al., 2025)[52]
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
Serotonin and dopamine receptor affinities (Ki, nM) of selected lysergamides and related compounds (Ray, 2010)[53]
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

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Major types of structural modifications of LSD.

Lysergamides, such as ergine, isoergine, and ergometrine, were discovered by the early 1930s,[19][20][21] and LSD was discovered by 1938 and its hallucinogenic effects in 1943 by Albert Hofmann.[54][55] 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.[30][35][43][56] 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.[57][58][59][7] The psychedelic effects of N(6)-substituted lysergamides were reported by Alexander Shulgin in 1986 and thereafter.[60][38][26][29] 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,[61][38][57] while LSZ (LA-Azetidine) was described by the same group in 2002.[10] 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.[62][63][64]

List of lysergamides

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Lysergamides, tabulated by structure
Structure Name (synonyms) CAS # R1 R6 R2 R3 Other
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 Ergine (lysergic acid amide; LSA; LA-111; lysergamide) 478-94-4 H CH3 H H -
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 Isoergine (isolysergic acid amide; iso-LSA; iso-LA-819; isolysergamide) 2889-26-1 H CH3 H H 8-epi
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 LAM (lysergic acid methylamide) 50485-06-8 H CH3 CH3 H -
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 DAM-57 (lysergic acid dimethylamide) 4238-84-0 H CH3 CH3 CH3 -
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 LSH (LAH; lysergic acid hydroxyethylamide) 3343-15-5 H CH3 CH3CHOH H -
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 Ergometrine (ergonovine; lysergic acid propanolamide) 60-79-7 H CH3 CH(CH3)CH2OH H -
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 Propisergide (1-methylergonovine; PML-946) 5793-04-4 CH3 CH3 CH(CH3)CH2OH H -
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 Methylergometrine (methylergonovine; lysergic acid butanolamide) 113-42-8 H CH3 CH(CH2CH3)CH2OH H -
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 Methysergide (1-methyl-lysergic acid butanolamide; UML-491) 361-37-5 CH3 CH3 CH(CH2CH3)CH2OH H -
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 Amesergide (LY-237733; 9,10-dihydro-11-isopropyllysergic acid cyclohexylamide) 121588-75-8 CH(CH3)2 CH3 C6H11 H -
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 LY-215840 (1-isopropyl-9,10-dihydro-N-(2-hydroxycyclopent-anyl)lysergamide) 137328-52-0 CH(CH3)2 CH3 C5H8OH H -
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 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 -
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 LAE-32 (lysergic acid ethylamide) 478-99-9 H CH3 CH2CH3 H -
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 LAP (lysergic acid propylamide) ? H CH3 CH2CH2CH3 H -
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 iPLA (lysergic acid isopropylamide; LAiP) H CH3 CH(CH3)2 H -
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 LAtB (lysergic acid tert-butylamide) H CH3 C(CH3)3 H -
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 Lysergic acid butylamide 50583-88-5 H CH3 CH2CH2CH2CH3 H -
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 Lysergic acid amylamide (lysergic acid pentylamide) ? H CH3 CH2CH2CH2CH2CH3 H -
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 LEK-8804 (N-(2-propynyl)lysergamide) 153415-44-2 H CH3 CH2C≡CH H -
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 LEK-8842 (N-methyl-N-(2-propynyl)lysergamide; TRALA-01) H CH3 CH2C≡CH CH3 -
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 LAcB (lysergic acid cyclobutylamide) H CH3 (CH2)4 H -
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 Cepentil (lysergic acid cyclopentylamide) H CH3 (CH2)5 H -
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 LSB (lysergic acid 2-butylamide) 137765-82-3 H CH3 CH(CH3)CH2CH3 H -
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 LSP (3-LSP; lysergic acid 3-pentylamide) 162105-96-6 H CH3 CH(CH2CH3)CH2CH3 H -
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 2-LSP (lysergic acid 2-pentylamide) ? H CH3 CH(CH3)C3H7 H -
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 Lysergic acid 2-hexylamide (N2He-LA, 2-LSHe)[65] ? H CH3 CH(CH3)C4H9 H -
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 Lysergic acid 2-heptylamide (N2Hp-LA, 2-LSHp)[66] ? H CH3 CH(CH3)C5H11 H -
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 Lysergic acid α-methylbenzylamide (N-(α-methylbenzyl)­lysergamide)[67][68] ? H CH3 CH(CH3)C6H5 H -
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 Lysergic acid methyl-2-butylamide[69] ? H CH3 CH(CH3)CH2CH3 CH3 -
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 Lysergic acid ethyl-2-butylamide[70] ? H CH3 CH(CH3)CH2CH3 CH2CH3 -
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 DPL (lysergic acid dipropylamide) H CH3 CH2CH2CH3 CH2CH2CH3 -
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 DiPLA (lysergic acid diisopropylamide) H CH3 CH(CH3)2 CH(CH3)2 -
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 LBB-66 (lysergic acid dibutylamide) H CH3 CH2CH2CH2CH3 CH2CH2CH2CH3 -
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 DAL (lysergic acid diallylamide) 73032-97-0 H CH3 H2C=CH-CH2 H2C=CH-CH2 -
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 MiPLA (lysergic acid methylisopropylamide) 100768-08-9 H CH3 CH(CH3)2 CH3 -
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 EiPLA (lysergic acid ethylisopropylamide) 154504-04-8 H CH3 CH(CH3)2 CH2CH3 -
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 EcPLA (lysergic acid ethylcyclopropylamide) 2349367-50-4 H CH3 C3H5 CH2CH3 -
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 LEO (lysergic acid ethyl-2-hydroxyethylamide) 65527-58-4 H CH3 CH2CH2OH CH2CH3 -
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 LA-MeO (lysergic acid ethyl-2-methoxyethylamide) H CH3 CH2CH2OCH3 CH2CH3 -
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 ETFELA (TRALA-06; lysergic acid N-ethyl-N-(2,2,2-trifluoroethyl)amide) 3024529-99-2 H CH3 CH2CF3 CH2CH3 -
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 EFELA (TRALA-04; WO 2022/008627 Compound 4)[71] H CH3 CH2CH2F CH2CH3 -
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 DFELA (TRALA-08; WO 2022/226408 Example 29)[72] H CH3 CH2CH2F CH2CH2F -
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 LA-3Cl-SB (lysergic acid N-(3-chloro-sec-butyl)amide) H CH3 CH(CH3)CClHCH3 H -
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 LME-54 (lysergic acid methylethylamide) H CH3 CH2CH3 CH3 -
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 LAMPA (LMP-55; lysergic acid methylpropylamide) 40158-98-3 H CH3 CH2CH2CH3 CH3 -
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 TRALA-12 (lysergic acid vinylethylamide; likely didehydro-LSD or DDH-LSD) 65527-59-5 H CH3 CHCH2 CH2CH3 -
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 EPLA (lysergic acid ethylpropylamide; LEP-57) H CH2CH3 CH2CH2CH3 CH3 -
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 LSD (lysergic acid diethylamide; LAD) 50-37-3 H CH3 CH2CH3 CH2CH3 -
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 Iso-LSD 2126-78-5 H CH3 CH2CH3 CH2CH3 8-epi
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 l-LSD 3184-49-4 H CH3 CH2CH3 CH2CH3 5,8-epi
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 l-Iso-LSD H CH3 CH2CH3 CH2CH3 5-epi
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 Nor-LSD (6-nor-LSD) 35779-43-2 H H CH2CH3 CH2CH3 -
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 ETH-LAD (6-ethyl-6-nor-LSD) 65527-62-0 H CH2CH3 CH2CH3 CH2CH3 -
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 PARGY-LAD (6-propynyl-6-nor-LSD) 2767597-51-1 H HC≡C−CH2 CH2CH3 CH2CH3 -
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 AL-LAD (6-allyl-6-nor-LSD) 65527-61-9 H H2C=CH-CH2 CH2CH3 CH2CH3 -
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 PRO-LAD (6-propyl-6-nor-LSD) 65527-63-1 H CH2CH2CH3 CH2CH3 CH2CH3 -
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 IP-LAD (6-isopropyl-6-nor-LSD) 96930-86-8 H CH(CH3)2 CH2CH3 CH2CH3 -
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 MAL-LAD (METAL-LAD; 6-methallyl-6-nor-LSD) H CH2=C(CH3)CH2 CH2CH3 CH2CH3 -
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 CYP-LAD (TRALA-22; 6-cyclopropyl-6-nor-LSD) 3024530-20-6 H C3H5 CH2CH3 CH2CH3 -
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 CPM-LAD (6-cyclopropylmethyl-6-nor-LSD) H CH2C3H5 CH2CH3 CH2CH3 -
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 BU-LAD (6-butyl-6-nor-LSD) 96930-87-9 H CH2CH2CH2CH3 CH2CH3 CH2CH3 -
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 PHENETH-LAD (6-(phenethyl)-6-nor-LSD) H CH2CH2C6H5 CH2CH3 CH2CH3 -
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 NIBR2130 (6-(phenylcarbamoyl)-6-nor-LSD) H ? CH2CH3 CH2CH3 -
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 NBOMe-LAD (6-(2-methoxybenzyl)-LAD) H CH2C6H4-o-OCH3 CH2CH3 CH2CH3 -
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 FLUORETH-LAD (FE-LAD; TRALA-15; 6-(2-fluoroethyl)-6-nor-LSD) 2757566-18-8 H CH2CH2F CH2CH3 CH2CH3 -
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 FP-LAD (PROF-LAD; TRALA-16; WO 2022/226408 Example 2; 6-(3-fluoropropyl)-6-nor-LSD) H CH2CH2CH2F CH2CH3 CH2CH3 -
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 CE-LAD (CHLORETH-LAD; 6-(2-chloroethyl)-6-nor-LSD) H CH2CH2Cl CH2CH3 CH2CH3 -
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 LEK-8827 (6-methyl-LEK-8842; 6-methyl-N-methyl-N-(2-propynyl)lysergamide) H (CH3)2 CH2C≡CH CH3 -
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 1-Formyl-LSD (1F-LSD) CH=O CH3 CH2CH3 CH2CH3 -
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 ALD-52 (1-acetyl-LSD; 1A-LSD) 3270-02-8 COCH3 CH3 CH2CH3 CH2CH3 -
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 ALA-10 (1-acetyl-LAE; 1A-LAE) 50485-03-5 COCH3 CH3 CH2CH3 H -
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 1P-LSD (1-propionyl-LSD) 2349358-81-0 COCH2CH3 CH3 CH2CH3 CH2CH3 -
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 1B-LSD (1-butanoyl-LSD) 2349376-12-9 COCH2CH2CH3 CH3 CH2CH3 CH2CH3 -
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 1V-LSD (1-valeryl-LSD) 3028950-70-8 CO(CH2)3CH3 CH3 CH2CH3 CH2CH3 -
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 1H-LSD (1-hexanoyl-LSD) 3028949-65-4 CO(CH2)4CH3 CH3 CH2CH3 CH2CH3 -
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 1DD-LSD (1-dodecanoyl-LSD) 3028949-80-3 CO(CH2)10CH3 CH3 CH2CH3 CH2CH3 -
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 1cP-LSD (1-cyclopropylmethanoyl-LSD) 2767597-50-0 COC3H5 CH3 CH2CH3 CH2CH3 -
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 1D-LSD (1-(1,2-dimethylcyclobutane-1-carbonyl)-LSD) COC4H5(CH3)2 CH3 CH2CH3 CH2CH3 -
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 1F-LSD (1-(furan-2-carbonyl)-LSD; 1-(2-furoyl)-LSD; SYN-L-005) COC4H3O CH3 CH2CH3 CH2CH3 -
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 1T-LSD (1-(thiophene-2-carbonyl)-LSD) 3028949-85-8 COC4H3S CH3 CH2CH3 CH2CH3 -
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 1Bz-LSD (1-benzoyl-LSD; SYN-L-018) COC6H5 CH3 CH2CH3 CH2CH3 -
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 1N-LSD (1-(pyridin-3-ylcarbonyl)-LSD) COC5H4N CH3 CH2CH3 CH2CH3 -
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 1C-LSD (1CPP-LSD; 1-(cypionyl)-LSD) CO(CH2)2C5H8 CH3 CH2CH3 CH2CH3 -
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 1PP-LSD (1-(phenylpropionyl)-LSD) CO(CH2)2C6H5 CH3 CH2CH3 CH2CH3 -
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 1MS-LSD (1-(methylsuccinyl)-LSD) CO(CH2)2COOCH3 CH3 CH2CH3 CH2CH3 -
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 1OX-LSD (1-(oxetan-3-yl)-LSD) COCH(CH2)2O CH3 CH2CH3 CH2CH3 -
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 1E-LSD (1-(enacarbil)-LSD) COOCH(CH3)
OCOCH(CH3)2		 CH3 CH2CH3 CH2CH3 -
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 1S-LSD (1-(3-(trimethylsilyl)propionyl)-LSD) CO(CH2)2Si(CH3)3 CH3 CH2CH3 CH2CH3 -
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 1SB-LSD (1BS-LSD; 1-(4-(trimethylsilyl)benzoyl)-LSD) CO(C6H4)-p-Si(CH3)3 CH3 CH2CH3 CH2CH3 -
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 1DP-LSD (1-(3-(dimethylphosphoryl)­propionyl)-LSD) CO(CH2)2PO(CH3)2 CH3 CH2CH3 CH2CH3 -
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 1BP-LSD (1-(3-(tetramethyldioxa­borolane)propionyl)-LSD) CO(CH2)2BO2
(C(CH3)2)2		 CH3 CH2CH3 CH2CH3 -
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 1Fe-LSD (1-(ferrocenecarbonyl)-LSD) 3029080-72-3 CO(C5H4)FeC5H5 CH3 CH2CH3 CH2CH3 -
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 1P-AL-LAD (1-propionyl-6-allyl-6-nor-LSD) 3028950-71-9 COCH2CH3 H2C=CH-CH2 CH2CH3 CH2CH3 -
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 1cP-AL-LAD (1-cyclopropylmethanoyl-6-allyl-6-nor-LSD) COC3H5 H2C=CH-CH2 CH2CH3 CH2CH3 -
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 1D-AL-LAD (1-(1,2-dimethylcyclobutane-1-carbonyl)-AL-LAD) COC4H5(CH3)2 H2C=CH-CH2 CH2CH3 CH2CH3 -
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 1T-AL-LAD (1-(2-thienoyl)-6-allyl-6-nor-LSD)[73] COC4H3S H2C=CH-CH2 CH2CH3 CH2CH3 -
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 1P-ETH-LAD (1-propionyl-6-ethyl-6-nor-LSD) 2230715-45-2 COCH2CH3 CH2CH3 CH2CH3 CH2CH3 -
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 1P-MiPLA (1-propionyl-lysergic acid methylisopropylamide) COCH2CH3 CH3 CH(CH3)2 CH3 -
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 1cP-MiPLA (1-cyclopropionyl-lysergic acid methylisopropylamide) 3028950-74-2 COC3H5 CH3 CH(CH3)2 CH3 -
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 MLD-41 (1-methyl-LSD) 4238-85-1 CH3 CH3 CH2CH3 CH2CH3 -
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 MLA-74 (1-methyl-LAE) 7240-57-5 CH3 CH3 CH2CH3 H -
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 OML-632 (1-hydroxymethyl-LSD) 114004-70-5 CH2OH CH3 CH2CH3 CH2CH3 -
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 1-Dimethylaminomethyl-LSD ? CH2NCH2CH2 CH3 CH2CH3 CH2CH3 -
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 Lysergic acid-(2,3-dimethylaziridinyl)amide (LA-Aziridine) ? H CH3 ? -
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 Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ, LA-Azetidine) 470666-31-0 H CH3 CH2(CHCH3)2CH2 -
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 LPD-824 (lysergic acid pyrrolidide) 2385-87-7 H CH3 (CH2)4 -
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 MPD-75 (1-methyllysergic acid pyrrolidide) 7221-79-6 CH3 CH3 (CH2)4 -
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 Lysergic acid pyrrolinide ? H CH3 CH2-CH=CH-CH2 -
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 LA-Cispyr (LA-cis-2,5-DiMePyr)[74] ? H CH3 cis-CH(CH3)-CH2CH2-CH(CH3) -
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 LA-Pip (lysergic acid piperidide) 50485-23-9 H CH3 (CH2)5 -
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 LA-cis-2,6-DiMePip (lysergic acid cis-2,6-dimethylpiperidide)[75] ? H CH3 ? -
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 LSM-775 (lysergic acid morpholide) 4314-63-0 H CH3 CH2CH2-O-CH2CH2 -
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 LA-Azepane (lysergic acid azepane)[76] H CH3 (CH2)6 -
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 2-Oxa-6-azaspiro[3.3]heptyl-lysergamide (WO 2022/008627 compound)[77] H CH3 (CH2)2C(CH2)2O -
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 2-Bromo-LSD (BOL-148; bromolysergide) 478-84-2 H CH3 CH2CH3 CH2CH3 2-Br
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 2-Iodo-LSD (IOL) 3712-25-2 H CH3 CH2CH3 CH2CH3 2-I
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 2-Oxo-LSD (2-oxy-LSD) ? H CH3 CH2CH3 CH2CH3 2-Oxo
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 2-Oxo-3-hydroxy-LSD 111295-09-1 H CH3 CH2CH3 CH2CH3 2-Oxo, 3-OH
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 MBL-61 (MOB-61; 1-methyl-2-bromo-LSD) 50484-98-5 CH3 CH3 CH2CH3 CH2CH3 2-Br
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 MIL (1-methyl-2-iodo-LSD) 97165-34-9 CH3 CH3 CH2CH3 CH2CH3 2-I
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 LEK-8841 (2-bromo-LEK-8842; 2-bromo-N-methyl-N-(2-propynyl)lysergamide) H CH3 CH2C≡CH CH3 2-Br
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 1P-BOL-148 (1-propionyl-2-bromo-LSD) COCH2CH3 CH3 CH2CH3 CH2CH3 2-Br
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 12-Hydroxy-LSD (12-OH-LSD) 60573-89-9 H CH3 CH2CH3 CH2CH3 12-OH
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 12-Methoxy-LSD (12-MeO-LSD) 50484-99-6 H CH3 CH2CH3 CH2CH3 12-OMe
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 13-Fluoro-LSD[78] H CH3 CH2CH3 CH2CH3 13-F
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 13-Hydroxy-LSD H CH3 CH2CH3 CH2CH3 13-OH
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 13-Methoxy-LSD H CH3 CH2CH3 CH2CH3 13-OMe
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 14-Hydroxy-LSD H CH3 CH2CH3 CH2CH3 14-OH
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 14-Methoxy-LSD H CH3 CH2CH3 CH2CH3 14-OMe
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 14-Methyl-LSD 3069948-26-8 H CH3 CH2CH3 CH2CH3 14-Me
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 2-Br-14-Me-LSD[79] H CH3 CH2CH3 CH2CH3 2-Br, 14-Me

Related compounds

[edit]
See also: Substituted ergoline, Partial lysergamide, and List of miscellaneous 5-HT2A receptor agonists
Structure Name Chemical name CAS #
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 2,3-Dihydro-LSD (2,3-DH-LSD) N,N-diethyl-6-methyl-9,10-didehydro-2,3-dihydroergoline-8β-carboxamide None
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 9,10-Dihydro-LSD (9,10-DH-LSD) (10ξ)-N,N-diethyl-6-methylergoline-8β-carboxamide 3031-47-8
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 AWD 52-39 N,N-diacetoxyethyl-9,10-dihydrolysergamide 109002-91-7
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 Bromerguride (2-bromolisuride) 1,1-diethyl-3-(2-bromo-9,10-didehydro-6-methyl-8α-ergolinyl)urea 83455-48-5
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 Bromocriptine (5′α)-2-bromo-12′-hydroxy-5′-(2-methylpropyl)-3′,6′,18-trioxo-2′-(propan-2-yl)ergotaman 25614-03-3
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 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 ?
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 Descarboxylysergic acid (DCLA) 6-methyl-9,10-didehydroergoline 51867-17-5
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 Dihydroergotamine (DHE-45) (5'α)-9,10-dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)-ergotaman-3',6',18-trione 511-12-6
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 Disulergine N,N-dimethyl-N'-(6-methylergoline-8α-yl)sulfamide 59032-40-5
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 Dosergoside N-((1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl)-6-methylergoline-8β-carboxamide 87178-42-5
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 Ergoline (6aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline 478-88-6
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 Ergotamine 5′α-benzyl-12′-hydroxy-2′-methyl-3′,6′,18-trioxoergotaman 113-15-5
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 Etisulergine N,N-diethyl-N'-(6-methylergolin-8α-yl)sulfamide 64795-23-9
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 GYKI-32887 (RGH-7825) 8-((N-2-azidoethyl-N-methylsulfonylamino)methyl)-6-methylergol-8-ene 78463-86-2
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 JRT (isotryptamine-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 ?
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 Compound 3A [80][81][82] [(4R,7S)-6-methyl-6,9-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,10,12(16),13-pentaen-4-yl]methanol 3081797-69-2
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 LEK-8822 (9,10-dihydro-LEK-8842) N-methyl-N-(2-propynyl)-6-methylergoline-8β-carboxamide ?
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 LEK-8829 (desoxy-LEK-8842) 9,10-didehydro-N-methyl-N-(2-propynyl)-6-methyl-8β-(aminomethyl)ergoline 145204-78-0
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 Lumi-LSD (10-hydroxy-9,10-dihydro-LSD) N,N-diethyl-10-hydroxy-6-methylergoline-8β-carboxamide ?
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 Lysergine 9,10-didehydro-6,8β-dimethylergoline 519-10-8
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 Lysergol (6-methyl-9,10-didehydroergolin-8β-yl)methanol 1413-67-8
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 Lysergic acid (LA) 6-methyl-9,10-didehydroergoline-8β-carboxylic acid 82-58-6
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 Lergotrile 2-chloro-6-methylergoline-8β-acetonitrile 36945-03-6
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 Lisuride 1,1-diethyl-3-(6-methyl-9,10-didehydroergolin-8α-yl)urea 18016-80-3
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 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 ?
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 Proterguride (6-propyl-9,10-dihydrolisuride) 1,1-diethyl-3-(6-propyl-8α-ergolinyl)urea 77650-95-4
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 Romergoline (FCE-23884) 4-(9,10-didehydro-6-methylergolin-8β-yl)methylpiperazine-2,6-dione 107052-56-2
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 RU-29717 (N-propyl-9-oxaergoline) N-propyl-9-oxaergoline 85351-27-5
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 Terguride (9,10-dihydrolisuride) N,N-diethyl-N'-(6-methylergolin-8α-yl)urea 37686-84-3

See also

[edit]

References

[edit]
  1. ^ Jamieson CS, Misa J, Tang Y, Billingsley JM (2021-04-29). "Biosynthesis and synthetic biology of psychoactive natural products". Chemical Society Reviews. 50 (12): 6950–7008. doi:10.1039/D1CS00065A. ISSN 0306-0012. PMC 8217322. PMID 33908526. There are three main ergot alkaloid classes, clavines, ergoamides (lysergamides), and ergopeptides, with [LSD] belonging to the ergoamide class.  2.5 Lysergic acid and LSD, page 6970
  2. ^ Wong G, Lim LR, Tan YQ, Go MK, Bell DJ, Freemont PS, et al. (2022-02-07). "Reconstituting the complete biosynthesis of D-lysergic acid in yeast". Nature Communications. 13 (1): 712. Bibcode:2022NatCo..13..712W. doi:10.1038/s41467-022-28386-6. ISSN 2041-1723. PMC 8821704. PMID 35132076. The ergot alkaloids are broadly classified into three groups—the clavines, ergoamides, and the ergopeptines, all of which are distinguished by the different modifications appended to the core ergoline structure. Results and discussion § Biosynthetic resolution of the ergot alkaloid pathway
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  4. ^ Uhlig S, Rangel-Huerta OD, Divon HH, Rolén E, Pauchon K, Sumarah MW, et al. (2021-06-30). "Unraveling the Ergot Alkaloid and Indole Diterpenoid Metabolome in the Claviceps purpurea Species Complex Using LC–HRMS/MS Diagnostic Fragmentation Filtering". Journal of Agricultural and Food Chemistry. 69 (25): 7137–7148. doi:10.1021/acs.jafc.1c01973. ISSN 0021-8561. The m/z 251, 223, and 208 series of ions is well-conserved across the ergoamides, ergopeptines, and their corresponding lactam variants and therefore are diagnostic for the detection of both known and unknown peptide ergot alkaloids (Figure 4). RESULTS AND DISCUSSION, page 7141
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  18. ^ a b Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, et al. (February 2019). "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology. 236 (2): 799–808. doi:10.1007/s00213-018-5055-9. PMC 6848745. PMID 30298278. Importantly, MIPLA has been reported to have about one-third the potency of LSD as a psychedelic in man (Shulgin 2016); recent online postings indicate that MIPLA is available as an NPS (Anonymous 2018). By contrast, little is known about the pharmacology of LAMPA. In a study conducted in six hallucinogen-experienced subjects, administration of LAMPA (100 μg p.o.) had no effect in four subjects and produced effects consistent with a threshold dose of LSD in two subjects (Abramson and Rolo 1967). [...] According to Shulgin, human subjects administered MIPLA at doses of 180–300 μg experienced LSD-like psychedelic effects, making it about two- to threefold less potent than LSD (Shulgin 2016). [...] Shulgin AT (2016) Pharmacology Notebook 9. Available online: [...] [Accessed: January 20, 2018]
  19. ^ a b c Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. Table 4.3.—Comparative Hallucinogenic Potencies in Man of Derivatives of D-Lysergic Acid. [...]
  20. ^ a b Ravina E (2011). The evolution of drug discovery: from traditional medicines to modern drugs (1st ed.). Weinheim: Wiley-VCH. p. 245. ISBN 978-3-527-32669-3. Archived from the original on 2015-12-26.
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  47. ^ Chen W, De Wit-Bos L (2020). Risk assessment of Argyreia nervosa (PDF) (Report). doi:10.21945/rivm-2019-0210.
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  56. ^ Stoll A, Hofmann A (1955). "Amide der stereoisomeren Lysergsäuren und Dihydro-lysergsäuren. 38. Mitteilung über Mutterkornalkaloide" [Amides of stereoisomeric lysergic and dihydrolysergic acids. 38. Ergot alkaloids]. Helvetica Chimica Acta. 38 (2): 421–433. Bibcode:1955HChAc..38..421S. doi:10.1002/hlca.19550380207. ISSN 0018-019X. Retrieved 5 June 2025.
  57. ^ a b Nichols DE, Oberlender R, McKenna DJ (1991). "Stereochemical Aspects of Hallucinogenesis". In Watson RR (ed.). Biochemistry and Physiology of Substance Abuse. Vol. 3. Boca Raton, Fla.: CRC Press. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320. Chemical transformations at N(6) were not accomplished until after clinical studies had been terminated. Initial work in this area was reported in 1970 by Fehr et al.184 who synthesized d-lysergic acid with various N(6) alkyl groups from 6-nor-d-lysergic acid methyl ester.151 Similar chemistry was first applied to LSD by Nakahara and Niwaguchi,185 then by Niwaguchi et al.,186 and most recently by Hoffman and Nichols.162 Initial pharmacological studies identified high activity in the isolated rat uterus preparation for the ethyl, propyl, and allyl analogues, from which high potency in the CNS was predicted.161
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[edit]
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Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the List of trace amines, TAAR, and TAAR1 pages.
See also: Receptor/signaling modulators
Ergolines
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