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Lysergamides

Class of chemical compounds

Lysergamides

Class of chemical compounds

The lysergamide core, with common substitution positions denoted.

Lysergamides, also known as ergoamides "More recently, ergot alkaloids, in particular ergoamides, also known as lysergic acid amides, have gained notoriety through their use as synthetic precursors for lysergic acid diethylamide (LSD)." 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. 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.

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

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.

Common nameCodeDosePotency (×LSD)Duration
Lysergic acid amide (LSA; ergine)LA-111500–6,000 μg≤10%~4–10 hours
Isolysergic acid amide (iso-LSA; isoergine)Iso-LA-8192,000–5,000 μg~4–10 hours
Lysergic acid methylamideLAM~500 μg≤20%Unknown
Lysergic acid dimethylamideDAM-57500–1,200 μg10%Unknown
Lysergic acid ethylamide (LAE)LAE-32500–1,600 μg≤10%Unknown
[1-Acetyl-LAE](1-acetyllysergic-acid-ethylamide)ALA-10, 1A-LAE~1,200 μg≤10%Unknown
[1-Methyl-LAE](1-methyllysergic-acid-ethylamide)MLA-74~2,000 μg5%Unknown
Lysergic acid methylethylamideLME-54Unknown~33%Unknown
Lysergic acid diethylamide (LSD)LSD-25, METH-LAD50–200 μg100%8–12 hours
Isolysergic acid diethylamideIso-LSD4,000 μgUnknown
*l*-Lysergic acid diethylamide*l*-LSD10,000 μgUnknown
*l*-Isolysergic acid diethylamide*l*-Iso-LSD500 μgUnknown
[2,3-Dihydro-LSD](2-3-dihydro-lsd)2,3-DH-LSD~150–400 μg~15%~8–12 hours
[9,10-Dihydro-LSD](9-10-dihydro-lsd)9,10-DH-LSD2,500 μgUnknown
10-Hydroxy-9,10-dihydro-LSDLumi-LSDUnknownUnknown
[2-Bromo-LSD](2-bromo-lsd)BOL-1481,000 μg (≥6,000 μg)Unknown
[2-Iodo-LSD](2-iodo-lsd)IOLUnknownUnknownUnknown
[2-Oxo-LSD](2-oxo-lsd) (2-oxy-LSD)–300 μgUnknownUnknown
[1-Acetyl-LSD](1-acetyl-lsd)ALD-52, 1A-LSD100–200 μg100%~8–12 hours
[1-Methyl-LSD](1-methyl-lsd)MLD-41200–300 μg30%Unknown
[1-Hydroxymethyl-LSD](1-hydroxymethyl-lsd)OML-632Unknown~70%Unknown
[1-Propionyl-LSD](1-propionyl-lsd)1P-LSD100–200 μg100%vauthors = Grumann C, Henkel K, Brandt SD, Stratford A, Passie T, Auwärter Vtitle = Pharmacokinetics and subjective effects of 1P-LSD in humans after oral and intravenous administrationjournal = Drug Test Analvolume = 12issue = 8pages = 1144–1153date = August 2020pmid = 32415750doi = 10.1002/dta.2821url = }}
[1-Methyl-2-bromo-LSD](1-methyl-2-bromo-lsd)MBL-61, MOB-6110,000 μgUnknown
[1-Methyl-2-iodo-LSD](1-methyl-2-iodo-lsd)MILUnknownUnknownUnknown
Lysergic acid propylamideLAP500 μgUnknown
Lysergic acid methylpropylamideLMP-55; LAMPA; MPLA100 μgUnknown
Lysergic acid ethylpropylamideLEP-57; EPLAUnknown~33%Unknown
Lysergic acid methylisopropylamideMiPLA180–300 μg~33–50%Unknown
Lysergic acid dipropylamideDPL1,000 μgUnknown
Lysergic acid dibutylamideLBB-66Unknown0%Unknown
Lysergic acid diallylamideDAL1,000 μgUnknown
Ergonovine (ergometrine)a–5,000–10,000 μg≤1%Unknown
Methylergonovine (methylergometrine)b–2,000 μg5%Unknown
PropisergidecPML-9463,000 μgUnknownUnknown
MethysergidedUML-4914,000–8,000 μg2%Unknown
Lysergic acid piperidideLA-PipUnknownUnknownUnknown
Lysergic acid pyrrolidide (LPD)LPD-824~800 μg5–10%Unknown
Lysergic acid pyrrolinideLPNUnknownUnknownUnknown
[1-Methyl-LPD](1-methyllysergic-acid-pyrrolidide)MPD-751,600 μg≤10%Unknown
Lysergic acid morpholideLSM-775, SLM300–600 μg10–30%Unknown
Lysergic acid 2,4-dimethylazetidideLA-SS-Az, LSZ100–300 μg50%~4–10 hours
Nor-LSD (6-nor-LSD)H-LAD500 μgUnknown
[6-Ethyl-nor-LSD](6-ethyl-nor-lsd)ETH-LAD40–150 μg200%8–12 hours
[6-Propyl-nor-LSD](6-propyl-nor-lsd)PRO-LAD80–200 μg100%6–8 hours
[6-Allyl-nor-LSD](6-allyl-nor-lsd)AL-LAD, ALLY-LAD50–160 μg100%6–8 hours
[6-n-Butyl-nor-LSD](6-n-butyl-nor-lsd)BU-LAD≥400–500 μgUnknown
[6-Propynyl-nor-LSD](6-propynyl-nor-lsd)PARGY-LAD160–500 μg20–60%Unknown
[6-(β-Phenethyl)-nor-LSD](6-b-phenethyl-nor-lsd)PHENETH-LAD350–500 μgUnknown
**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:* *Additional:*

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

Interactions

Pharmacology

Pharmacodynamics

Compound[5-HT1A](5-ht1a)[5-HT1B](5-ht1b)[5-HT1D](5-ht1d)[5-HT1E](5-ht1e)[5-HT2A](5-ht2a)[5-HT2B](5-ht2b)[5-HT2C](5-ht2c)[5-HT3](5-ht3)[5-HT5A](5-ht5a)[5-HT6](5-ht6)[5-HT7](5-ht7)D1D2D3D4D5
LSD5.9213.51358.55.517–1.8168.528820437112955
DAM-5714181756121687–421923676–3099552,000
DiPLA5889254571517234–17492613523425219316
LAMPA13276.6–114.958–19356.53392043532794
LSZ2.36318224163.515–3218354681159.11291,150
NorLSD7.8141374071554525–1001451––76275–
ETH-LAD3.53215859.31856–21211141715881240891
AL-LAD6.027578479171468–115042–26927155–
MAL-LAD174–295–2854479–891,050200––3633,240–
BU-LAD212,1901291,350211625–9126123417813916613,630
Lisuride4.1631393251650–5.6189.5174105.6101,050
Compound[5-HT1A](5-ht1a)[5-HT1B](5-ht1b)[5-HT1D](5-ht1d)[5-HT1E](5-ht1e)[5-HT2A](5-ht2a)[5-HT2B](5-ht2b)[5-HT2C](5-ht2c)[5-HT3](5-ht3)[5-HT5A](5-ht5a)[5-HT6](5-ht6)[5-HT7](5-ht7)D1D2D3D4D5
LSD7.33.97.89311303110,00096.96.617711027158344
LSZ0.42.4?27619273710,00027151429274696402
Lisuride0.31610,000445.42.910,00010,0003.17.36.810,0006.71363.877

History

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. The psychedelic effects of N(6)-substituted lysergamides were reported by Alexander Shulgin in 1986 and thereafter. 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, while LSZ (LA-Azetidine) was described by the same group in 2002. 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.

List of lysergamides

StructureName (synonyms)CAS #R1R6R2R3Other
[[File:Ergine.svg125pxclass=skin-invert-image]]Ergine (lysergic acid amide, lysergamide)478-94-4HCH3HH-
[[File:Isoergine.svg125pxclass=skin-invert-image]]Isoergine (isolysergic acid amide, isolysergamide)2889-26-1HCH3HH8-epi
[[File:LA-methylamide_structure.png125pxclass=skin-invert-image]]LAM (lysergic acid methylamide)50485-06-8HCH3CH3H-
[[File:DAM-57.svg125pxclass=skin-invert-image]]DAM-57 (lysergic acid dimethylamide)4238-84-0HCH3CH3CH3-
[[File:Ergonovine-skeletal.svg125pxclass=skin-invert-image]]Ergometrine (ergonovine; lysergic acid propanolamide)60-79-7HCH3CH(CH3)CH2OHH-
[[File:Propisergide.svg125pxclass=skin-invert-image]]Propisergide (1-methylergonovine; PML-946)5793-04-4CH3CH3CH(CH3)CH2OHH-
[[File:Methylergometrin.svg125pxclass=skin-invert-image]]Methylergometrine (methylergonovine; lysergic acid butanolamide)113-42-8HCH3CH(CH2CH3)CH2OHH-
[[File:Methysergide.svg125pxclass=skin-invert-image]]Methysergide (1-methyl-lysergic acid butanolamide; UML-491)361-37-5CH3CH3CH(CH2CH3)CH2OHH-
[[File:Amesergide.svg125pxclass=skin-invert-image]]Amesergide (LY-237733; 9,10-dihydro-11-isopropyllysergic acid cyclohexylamide)121588-75-8CH(CH3)2CH3C6H11H-
[[File:LY-215840_structure.png125pxclass=skin-invert-image]]LY-215840 (1-isopropyl-9,10-dihydro-*N*-(2-hydroxycyclopent-anyl)lysergamide)137328-52-0CH(CH3)2CH3C5H8OHH-
[[File:Cabergoline.svg125pxclass=skin-invert-image]]Cabergoline (*N*-[3-(dimethylamino)propyl]-*N*-(ethylcarbamoyl)-6-(prop-2-en-1-yl)-9,10-dihydrolysergamide)81409-90-7HH2C=CH-CH2CONHCH2CH3CH2CH2CH2N(CH3)2-
[[File:LAE-32.svg125pxclass=skin-invert-image]]LAE-32 (lysergic acid ethylamide)478-99-9HCH3CH2CH3H-
[[File:LA-propylamide_structure.png125pxclass=skin-invert-image]]LAP (lysergic acid propylamide)?HCH3CH2CH2CH3H-
[[File:LAiP_structure.png125pxclass=skin-invert-image]]iPLA (lysergic acid isopropylamide; LAiP)HCH3CH(CH3)2H-
[[File:LAtB structure.png125pxclass=skin-invert-image]]LAtB (lysergic acid *tert*-butylamide)HCH3C(CH3)3H-
[[File:LAcB_structure.png125pxclass=skin-invert-image]]LAcB (lysergic acid cyclobutylamide)HCH3(CH2)4H-
[[File:LAcPe_structure.png125pxclass=skin-invert-image]]Cepentil (lysergic acid cyclopentylamide)HCH3(CH2)5H-
[[File:SBULSD.svg125pxclass=skin-invert-image]]LSB (lysergic acid 2-butylamide)137765-82-3HCH3CH(CH3)CH2CH3H-
[[File:LS3P_structure.png125pxclass=skin-invert-image]]LSP (lysergic acid 3-pentylamide)HCH3CH(CH2CH3)CH2CH3H-
[[File:Lysergic acid dipropylamide.svg125pxclass=skin-invert-image]]DPL (lysergic acid dipropylamide)HCH3CH2CH2CH3CH2CH2CH3-
[[File:N,N-Diisopropyllysergamide.svg125pxclass=skin-invert-image]]DiPLA (lysergic acid diisopropylamide)HCH3CH(CH3)2CH(CH3)2-
[[File:LA-dibutylamide_structure.png125pxclass=skin-invert-image]]LBB-66 (lysergic acid dibutylamide)HCH3CH2CH2CH2CH3CH2CH2CH2CH3-
[[File:DALAD.svg125pxclass=skin-invert-image]]DAL (lysergic acid diallylamide)HCH3H2C=CH-CH2AllylH2C=CH-CH2-
[[File:MIPLSD.svg125pxclass=skin-invert-image]]MiPLA (lysergic acid methylisopropylamide)100768-08-9HCH3CH(CH3)2CH3-
[[File:EiPLA_structure.png125pxclass=skin-invert-image]]EiPLA (lysergic acid ethylisopropylamide)HCH3CH(CH3)2CH2CH3-
[[File:ECPLA_structure.png125pxclass=skin-invert-image]]EcPLA (lysergic acid ethylcyclopropylamide)HCH3C3H5CH2CH3-
[[File:Lysergic acid ethyl-2-hydroxyethylamide.svg125pxclass=skin-invert-image]]LEO (lysergic acid ethyl-2-hydroxyethylamide)65527-58-4HCH3CH2CH2OHCH2CH3-
[[File:LA-MeO_structure.png150pxclass=skin-invert-image]]LA-MeO (lysergic acid ethyl-2-methoxyethylamide)HCH3CH2CH2OCH3CH2CH3-
[[File:ETFELA.svg125pxclass=skin-invert-image]]ETFELA (lysergic acid *N*-ethyl-*N*-(2,2,2-trifluoroethyl)amide)HCH3CH2CF3CH2CH3-
[[File:WO22-008627-4_structure.png125pxclass=skin-invert-image]]WO 2022/008627 Compound 4; TRALA-04HCH3CH2CH2FCH2CH3-
[[File:WO22-226408-29_structure.png125pxclass=skin-invert-image]]WO 2022/226408 Example 29; TRALA-08HCH3CH2CH2FCH2CH2F-
[[File:LA-3Cl-SB_structure.png125pxclass=skin-invert-image]]LA-3Cl-SB (lysergic acid *N*-(3-chloro-*sec*-butyl)amide)HCH3CH(CH3)CClHCH3H-
[[File:LA-methylethylamide_structure.png125pxclass=skin-invert-image]]LME-54 (lysergic acid methylethylamide)HCH3CH2CH3CH3-
[[File:MPLA_structure.png125pxclass=skin-invert-image]]LAMPA (LMP-55; lysergic acid methylpropylamide)40158-98-3HCH3CH2CH2CH3CH3-
[[File:EPLA_structure.png125pxclass=skin-invert-image]]EPLA (lysergic acid ethylpropylamide; LEP-57)HCH2CH3CH2CH2CH3CH3-
[[File:LSD skeletal formula.svg125pxclass=skin-invert-image]]**LSD** (lysergic acid diethylamide; LAD)50-37-3HCH3CH2CH3CH2CH3-
[[File:Iso-LSD_structure.png125pxclass=skin-invert-image]]Iso-LSD2126-78-5HCH3CH2CH3CH2CH38-epi
[[File:(-)-LSD.svg125pxclass=skin-invert-image]]*l*-LSD3184-49-4HCH3CH2CH3CH2CH35,8-epi
[[File:(-)-iso-LSD.svg125pxclass=skin-invert-image]]*l*-Iso-LSDHCH3CH2CH3CH2CH35-epi
[[File:Nor-LSD_structure.png125pxclass=skin-invert-image]]Nor-LSD (6-nor-LSD)35779-43-2HHCH2CH3CH2CH3-
[[File:ETH-LAD v2.svg125pxclass=skin-invert-image]]ETH-LAD (6-ethyl-6-nor-LSD)65527-62-0HCH2CH3CH2CH3CH2CH3-
[[File:PARGY-LAD.svg125pxclass=skin-invert-image]]PARGY-LAD (6-propynyl-6-nor-LSD)2767597-51-1HHC≡C−CH2CH2CH3CH2CH3-
[[File:AL-LAD v2.svg125pxclass=skin-invert-image]]AL-LAD (6-allyl-6-nor-LSD)65527-61-9HH2C=CH-CH2CH2CH3CH2CH3-
[[File:PRO-LAD v2.svg125pxclass=skin-invert-image]]PRO-LAD (6-propyl-6-nor-LSD)65527-63-1HCH2CH2CH3CH2CH3CH2CH3-
[[File:IP-LAD.svg125pxclass=skin-invert-image]]IP-LAD (6-isopropyl-6-nor-LSD)HCH(CH3)2CH2CH3CH2CH3-
[[File:MAL-LAD.svg125pxclass=skin-invert-image]]MAL-LAD (METAL-LAD; 6-methallyl-6-nor-LSD)HCH2=C(CH3)CH2CH2CH3CH2CH3-
[[File:CYP-LAD.svg125pxclass=skin-invert-image]]CYP-LAD (TRALA-22; 6-cyclopropyl-6-nor-LSD)HC3H5CH2CH3CH2CH3-
[[File:WO22-226408-13_structure.png125pxclass=skin-invert-image]]CPM-LAD (6-cyclopropylmethyl-6-nor-LSD)HCH2C3H5CH2CH3CH2CH3-
[[File:BU-LAD-2D-skeletal.svg125pxclass=skin-invert-image]]BU-LAD (6-butyl-6-nor-LSD)96930-87-9HCH2CH2CH2CH3CH2CH3CH2CH3-
[[File:PHENETHY-LAD_structure.png150pxclass=skin-invert-image]]PHENETH-LAD (6-(phenethyl)-6-nor-LSD)HCH2CH2C6H5CH2CH3CH2CH3-
[[File:WO22-226408-10_structure.png150pxclass=skin-invert-image]]NBOMe-LAD (6-(2-methoxybenzyl)-LAD)HCH2C6H4-*o*-OCH3CH2CH3CH2CH3-
[[File:FLUOROETH-LAD_structure.png125pxclass=skin-invert-image]]FLUORETH-LAD (FE-LAD; TRALA-15; 6-(2-fluoroethyl)-6-nor-LSD)HCH2CH2FCH2CH3CH2CH3-
[[File:WO22-226408-2_structure.png125pxclass=skin-invert-image]]FP-LAD (WO 2022/226408 Example 2; TRALA-16; 6-(3-fluoropropyl)-6-nor-LSD)HCH2CH2CH2FCH2CH3CH2CH3-
[[File:CE-LAD.svg125pxclass=skin-invert-image]]CE-LAD (CHLORETH-LAD; 6-(2-chloroethyl)-6-nor-LSD)HCH2CH2ClCH2CH3CH2CH3-
[[File:1F-LSD.svg125pxclass=skin-invert-image]][1-Formyl-LSD](1-formyl-lsd) (1F-LSD)CH=OCH3CH2CH3CH2CH3-
[[File:ALD-52_image.svg125pxclass=skin-invert-image]]ALD-52 (1-acetyl-LSD; 1A-LSD)3270-02-8COCH3CH3CH2CH3CH2CH3-
[[File:ALA-10.svg125pxclass=skin-invert-image]]ALA-10 (1-acetyl-LAE; 1A-LAE)50485-03-5COCH3CH3CH2CH3H-
[[File:1P-LSD.svg125pxclass=skin-invert-image]][1P-LSD](1p-lsd) (1-propionyl-LSD)2349358-81-0COCH2CH3CH3CH2CH3CH2CH3-
[[File:1B-LSD.svg125pxclass=skin-invert-image]][1B-LSD](1b-lsd) (1-butanoyl-LSD)2349376-12-9COCH2CH2CH3CH3CH2CH3CH2CH3-
[[File:1V-LSD_structure.svg125pxclass=skin-invert-image]][1V-LSD](1v-lsd) (1-valeryl-LSD)CO(CH2)3CH3CH3CH2CH3CH2CH3-
[[File:1H-LSD_structure.png125pxclass=skin-invert-image]][1H-LSD](1h-lsd) (1-hexanoyl-LSD)CO(CH2)4CH3CH3CH2CH3CH2CH3-
[[File:1DD-LSD_structure.png125pxclass=skin-invert-image]][1DD-LSD](1dd-lsd) (1-dodecanoyl-LSD)CO(CH2)10CH3CH3CH2CH3CH2CH3-
[[File:1cP-LSD.svg125pxclass=skin-invert-image]][1cP-LSD](1cp-lsd) (1-cyclopropylmethanoyl-LSD)COC3H5CH3CH2CH3CH2CH3-
[[File:1D-LSD.svg125pxclass=skin-invert-image]][1D-LSD](1d-lsd) (1-(1,2-dimethylcyclobutane-1-carbonyl)-LSD)COC4H5(CH3)2CH3CH2CH3CH2CH3-
[[File:1F-LSD_structure.png125pxclass=skin-invert-image]][1F-LSD](1f-lsd) (1-(furan-2-carbonyl)-LSD; 1-(2-furoyl)-LSD; SYN-L-005)COC4H3OCH3CH2CH3CH2CH3-
[[File:1T-LSD_structure.png125pxclass=skin-invert-image]][1T-LSD](1t-lsd) (1-(thiophene-2-carbonyl)-LSD)COC4H3SCH3CH2CH3CH2CH3-
[[File:1Bz-LSD.svg125pxclass=skin-invert-image]][1Bz-LSD](1bz-lsd) (1-benzoyl-LSD; SYN-L-018)COC6H5CH3CH2CH3CH2CH3-
[[File:1N-LSD_structure.png125pxclass=skin-invert-image]]1N-LSD (1-(pyridin-3-ylcarbonyl)-LSD)COC5H4NCH3CH2CH3CH2CH3-
[[File:1CPP-LSD_structure.png125pxclass=skin-invert-image]]1C-LSD (1-(cypionyl)-LSD)CO(CH2)2C5H8CH3CH2CH3CH2CH3-
[[File:1PP-LSD_structure.png125pxclass=skin-invert-image]]1PP-LSD (1-(phenylpropionyl)-LSD)CO(CH2)2C6H5CH3CH2CH3CH2CH3-
[[File:1MS-LSD_structure.png125pxclass=skin-invert-image]]1MS-LSD (1-(methylsuccinyl)-LSD)CO(CH2)2COOCH3CH3CH2CH3CH2CH3-
[[File:1OX-LSD_structure.png125pxclass=skin-invert-image]]1OX-LSD (1-(oxetan-3-yl)-LSD)COCH(CH2)2OCH3CH2CH3CH2CH3-
[[File:1E-LSD_structure.png125pxclass=skin-invert-image]]1E-LSD (1-(enacarbil)-LSD)COOCH(CH3)OCOCH(CH3)2CH3CH2CH3CH2CH3-
[[File:1S-LSD_structure.png135pxclass=skin-invert-image]][1S-LSD](1s-lsd) (1-(3-(trimethylsilyl)propionyl)-LSD)CO(CH2)2Si(CH3)3CH3CH2CH3CH2CH3-
[[File:1SB-LSD_structure.png145pxclass=skin-invert-image]][1SB-LSD](1sb-lsd) (1BS-LSD; 1-(4-(trimethylsilyl)benzoyl)-LSD)CO(C6H4)-*p*-Si(CH3)3CH3CH2CH3CH2CH3-
[[File:1DP-LSD_structure.png135pxclass=skin-invert-image]]1DP-LSD (1-(3-(dimethylphosphoryl)propionyl)-LSD)CO(CH2)2PO(CH3)2CH3CH2CH3CH2CH3-
[[File:1BP-LSD_structure.png135pxclass=skin-invert-image]][1BP-LSD](1bp-lsd) (1-(3-(tetramethyldioxaborolane)propionyl)-LSD)CO(CH2)2BO2(C(CH3)2)2CH3CH2CH3CH2CH3-
[[File:1Fe-LSD_structure.png135pxclass=skin-invert-image]][1Fe-LSD](1fe-lsd) (1-(ferrocenecarbonyl)-LSD)CO(C5H4)FeC5H5CH3CH2CH3CH2CH3-
[[File:1P-AL-LAD_structure.png125pxclass=skin-invert-image]][1P-AL-LAD](1p-al-lad) (1-propionyl-6-allyl-6-nor-LSD)COCH2CH3H2C=CH-CH2CH2CH3CH2CH3-
[[File:1CP-AL-LAD_structure.png125pxclass=skin-invert-image]][1cP-AL-LAD](1cp-al-lad) (1-cyclopropylmethanoyl-6-allyl-6-nor-LSD)COC3H5H2C=CH-CH2CH2CH3CH2CH3-
[[File:1D-AL-LAD.svg125pxclass=skin-invert-image]][1D-AL-LAD](1d-al-lad) (1-(1,2-dimethylcyclobutane-1-carbonyl)-AL-LAD)COC4H5(CH3)2H2C=CH-CH2CH2CH3CH2CH3-
[[File:1T-AL-LAD_structure.png125pxclass=skin-invert-image]]vauthors = Okada Y, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Kanamori T, Iwata YTtitle = Synthesis and analytical characterization of 1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD)journal = Drug Testing and Analysisvolume = 17issue = 4pages = 494–501date = June 2024pmid = 38922764doi = 10.1002/dta.3747}}COC4H3SH2C=CH-CH2CH2CH3CH2CH3-
[[File:1P-ETH-LAD.svg125pxclass=skin-invert-image]][1P-ETH-LAD](1p-eth-lad) (1-propionyl-6-ethyl-6-nor-LSD)COCH2CH3CH2CH3CH2CH3CH2CH3-
[[File:1P-MIPLA_structure.png125pxclass=skin-invert-image]][1P-MiPLA](1p-mipla) (1-propionyl-lysergic acid methylisopropylamide)COCH2CH3CH3CH(CH3)2CH3-
[[File:1cP-MIPLA.svg125pxclass=skin-invert-image]][1cP-MiPLA](1cp-mipla) (1-cyclopropionyl-lysergic acid methylisopropylamide)3028950-74-2COC3H5CH3CH(CH3)2CH3-
[[File:MLD-41.svg125pxclass=skin-invert-image]]MLD-41 (1-methyl-LSD)4238-85-1CH3CH3CH2CH3CH2CH3-
[[File:MLA-74.svg125pxclass=skin-invert-image]]MLA-74 (1-methyl-LAE)7240-57-5CH3CH3CH2CH3H-
[[File:1-Hydroxymethyl-LSD.svg125pxclass=skin-invert-image]]OML-632 (1-hydroxymethyl-LSD)114004-70-5CH2OHCH3CH2CH3CH2CH3-
[[File:1-Dimethylaminomethyl-LSD.svg125pxclass=skin-invert-image]][1-Dimethylaminomethyl-LSD](1-dimethylaminomethyl-lsd)?CH2NCH2CH2CH3CH2CH3CH2CH3-
[[File:LSM-775.svg125pxclass=skin-invert-image]]LSM-775 (lysergic acid morpholide)4314-63-0HCH3CH2CH2-O-CH2CH2-
[[File:LPD-824-2d-skeletal.svg125pxclass=skin-invert-image]]LPD-824 (lysergic acid pyrrolidide)2385-87-7HCH3(CH2)4-
[[File:MPD-75_structure.png125pxclass=skin-invert-image]]MPD-75 (1-methyllysergic acid pyrrolidide)7221-79-6CH3CH3(CH2)4-
[[File:LA-pyrrolinide_structure.png125pxclass=skin-invert-image]]Lysergic acid pyrrolinide?HCH3CH2-CH=CH-CH2-
[[File:LA-Cispyr_structure.png125pxclass=skin-invert-image]]LA-Cispyr?HCH3*cis*-CH(CH3)-CH2CH2-CH(CH3)-
[[File:LSD-Pip.svg125pxclass=skin-invert-image]]LA-Pip (lysergic acid piperidide)50485-23-9HCH3(CH2)5-
[[File:LSD Azapane structure.png125pxclass=skin-invert-image]]title=Lysergic acid amideswebsite=Google Patentsdate=5 March 1956url=https://patents.google.com/patent/US2997470A/enaccess-date=5 April 2025quote=EXAMPLE 38 Preparation of d-lysergic acid hexamethylene imide: [...]}}HCH3(CH2)6-
[[File:LSD-azetidine.svg125pxclass=skin-invert-image]]Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ, LA-Azetidine)470666-31-0HCH3CH2(CHCH3)2CH2-
[[File:WO22-008627-1_structure.png150pxclass=skin-invert-image]]WO 2022/008627 Compound 1HCH3(CH2)2C(CH2)2O-
[[File:LA-Aziridine structure.png125pxclass=skin-invert-image]]Lysergic acid-(2,3-dimethylaziridinyl)amide (LA-Aziridine)?HCH3?-
[[File:2-bromo-LSD_structure.svg125pxclass=skin-invert-image]][2-Bromo-LSD](2-bromo-lsd) (BOL-148; bromolysergide)478-84-2HCH3CH2CH3CH2CH32-Br
[[File:2-iodo-LSD_structure.png125pxclass=skin-invert-image]][2-Iodo-LSD](2-iodo-lsd) (IOL)3712-25-2HCH3CH2CH3CH2CH32-I
[[File:2-oxo-LSD_structure.png125pxclass=skin-invert-image]][2-Oxo-LSD](2-oxo-lsd) (2-oxy-LSD)?HCH3CH2CH3CH2CH32-Oxo
[[File:3-OH-2-oxo-LSD_structure.png125pxclass=skin-invert-image]][2-Oxo-3-hydroxy-LSD](2-oxo-3-hydroxy-lsd)?HCH3CH2CH3CH2CH32-Oxo, 3-OH
[[File:1-Methyl-2-bromo-LSD.svg125pxclass=skin-invert-image]]MBL-61 (MOB-61; 1-methyl-2-bromo-LSD)50484-98-5CH3CH3CH2CH3CH2CH32-Br
[[File:1-Methyl-2-iodo-LSD.svg125pxclass=skin-invert-image]][MIL](1-methyl-2-iodo-lsd) (1-methyl-2-iodo-LSD)97165-34-9CH3CH3CH2CH3CH2CH32-I
[[File:1P-BOL-148_structure.png125pxclass=skin-invert-image]][1P-BOL-148](1p-bol-148) (1-propionyl-2-bromo-LSD)COCH2CH3CH3CH2CH3CH2CH32-Br
[[File:12-Hydroxy-LSD.svg125pxclass=skin-invert-image]][12-Hydroxy-LSD](12-hydroxy-lsd) (12-OH-LSD)60573-89-9HCH3CH2CH3CH2CH312-OH
[[File:12-MeO-LSD_structure.png125pxclass=skin-invert-image]][12-Methoxy-LSD](12-methoxy-lsd) (12-MeO-LSD)50484-99-6HCH3CH2CH3CH2CH312-OMe
[[File:13-F-LSD_structure.png125pxclass=skin-invert-image]]country = WOnumber = 2021076572invent1 = David E. Olsoninvent2 = Lee Dunlapinvent3 = Florence Wagnerinvent4 = Milan Chytil, Noel Aaron Powellstatus =title = Ergoline-like compounds for promoting neural plasticitypubdate = 22 April 2021gdate =fdate = 14 October 2020pridate = 14 October 2020assign1 = Delix Therapeutics, Inc.assign2 = The Regents of the University of Californiaurl = https://patents.google.com/patent/WO2021076572/quote = [0124] In some embodiments, provided herein is a compound, or a pharmaceutically acceptable salt thereof, that is: [...]}}HCH3CH2CH3CH2CH313-F
[[File:13-Hydroxy-LSD.svg125pxclass=skin-invert-image]][13-Hydroxy-LSD](13-hydroxy-lsd)HCH3CH2CH3CH2CH313-OH
[[File:13-MeO-LSD_structure.png125pxclass=skin-invert-image]][13-Methoxy-LSD](13-methoxy-lsd)HCH3CH2CH3CH2CH313-OMe
[[File:14-HO-LSD_structure.png125pxclass=skin-invert-image]][14-Hydroxy-LSD](14-hydroxy-lsd)HCH3CH2CH3CH2CH314-OH
[[File:14-MeO-LSD_structure.png125pxclass=skin-invert-image]][14-Methoxy-LSD](14-methoxy-lsd)HCH3CH2CH3CH2CH314-OMe

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