Lysergamides

{{Short description|Class of chemical compounds}} {{cs1 config|name-list-style=vanc|display-authors=6}} thumb|right|150px|class=skin-invert-image|The lysergamide core, with common substitution positions denoted.

'''Lysergamides''', also known as '''ergoamides'''<ref name="JamiesonMisaTang2021">{{Cite journal |last1=Jamieson |first1=Cooper S. |last2=Misa |first2=Joshua |last3=Tang |first3=Yi |last4=Billingsley |first4=John M. |publication-date=2021-04-29 |title=Biosynthesis and synthetic biology of psychoactive natural products |url=https://xlink.rsc.org/?DOI=D1CS00065A |journal=Chemical Society Reviews |language=en |volume=50 |issue=12 |pages=6950–7008 |doi=10.1039/D1CS00065A |issn=0306-0012 |pmc=8217322 |pmid=33908526 | quote=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</ref><ref name="WongLimTan2022">{{Cite journal |last1=Wong |first1=Garrett |last2=Lim |first2=Li Rong |last3=Tan |first3=Yong Quan |last4=Go |first4=Maybelle Kho |last5=Bell |first5=David J. |last6=Freemont |first6=Paul S. |last7=Yew |first7=Wen Shan |date=2022-02-07 |title=Reconstituting the complete biosynthesis of D-lysergic acid in yeast |journal=Nature Communications |language=en |volume=13 |issue=1 |page=712 |doi=10.1038/s41467-022-28386-6 |issn=2041-1723 |pmc=8821704 |pmid=35132076 |bibcode=2022NatCo..13..712W | quote = 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</ref><ref>{{cite web |last=St. Germaine |first=Danielle |title=Psychedelic Therapies Webinar Highlights |website=Cayman Chemical News & Announcements |date=2023-12-14 |url=https://www.caymanchem.com/news/psychedelic-therapies-webinar-highlights |access-date=2025-08-06 | quote=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).}}</ref><ref>{{Cite journal |last=Uhlig |first=Silvio |last2=Rangel-Huerta |first2=Oscar Daniel |last3=Divon |first3=Hege H. |last4=Rolén |first4=Elin |last5=Pauchon |first5=Kari |last6=Sumarah |first6=Mark W. |last7=Vrålstad |first7=Trude |last8=Renaud |first8=Justin B. |date=2021-06-30 |title=Unraveling the Ergot Alkaloid and Indole Diterpenoid Metabolome in the Claviceps purpurea Species Complex Using LC–HRMS/MS Diagnostic Fragmentation Filtering |url=https://pubs.acs.org/doi/10.1021/acs.jafc.1c01973 |journal=Journal of Agricultural and Food Chemistry |language=en |volume=69 |issue=25 |pages=7137–7148 |doi=10.1021/acs.jafc.1c01973 |issn=0021-8561 | quote=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</ref> 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.<ref name="LeePoudelGlinkerman2015">{{Cite journal | last1 = Lee | first1 = K. | last2 = Poudel | first2 = Y. B. | last3 = Glinkerman | first3 = C. M. | last4 = Boger | first4 = D. L. | year = 2015 | title = Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs | journal = Tetrahedron | volume = 71 | issue = 35 | pages = 5897–5905 | doi = 10.1016/j.tet.2015.05.093 | pmid = 26273113 | pmc = 4528678 | quote = Embedded in the structures of the ergot alkaloids are conformationally-restricted variants of the phenethylamine pharmacophores of both dopamine and related biogenic amines as well as that of serotonin.}}</ref>

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.<ref name="US2997470">{{cite patent | country = US | number = 2997470 | status = patent | title = Lysergic Acid Amides | pubdate = 1956-03-05 | gdate = 1961-08-22 | inventor = Pioch RP}}</ref><ref name="HoffmanNichols1985">{{cite journal | vauthors = Hoffman AJ, Nichols DE | title = Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives | journal = Journal of Medicinal Chemistry | volume = 28 | issue = 9 | pages = 1252–1255 | date = September 1985 | pmid = 4032428 | doi = 10.1021/jm00147a022}}</ref><ref name="HuangMarona-LewickaPfaff1994">{{cite journal | vauthors = Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE | title = Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives | journal = Pharmacology, Biochemistry, and Behavior | volume = 47 | issue = 3 | pages = 667–673 | date = March 1994 | pmid = 8208787 | doi = 10.1016/0091-3057(94)90172-4 | s2cid = 16490010}}</ref><ref name="WattsLawlerFox1995">{{cite journal | vauthors = Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB | title = LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors | journal = Psychopharmacology | volume = 118 | issue = 4 | pages = 401–409 | date = April 1995 | pmid = 7568626 | doi = 10.1007/BF02245940 | s2cid = 21484356}}</ref><ref name="NicholsFrescasMarona-Lewicka2002">{{cite journal | vauthors = Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM | title = Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD) | journal = Journal of Medicinal Chemistry | volume = 45 | issue = 19 | pages = 4344–4349 | date = September 2002 | pmid = 12213075 | doi = 10.1021/jm020153s}}</ref><ref name="Schiff2006">{{cite journal | vauthors = Schiff PL | title = Ergot and its alkaloids | journal = American Journal of Pharmaceutical Education | volume = 70 | issue = 5 | page = 98 | date = October 2006 | pmid = 17149427 | doi = 10.5688/aj700598 | doi-broken-date = 6 July 2025 | pmc = 1637017}}</ref><ref name="PassieHalpernStichtenoth2008">{{cite journal | vauthors = Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A | title = The pharmacology of lysergic acid diethylamide: a review | journal = CNS Neuroscience & Therapeutics | year = 2008 | volume = 14 | issue = 4 | pages = 295–314 | pmid = 19040555 | doi = 10.1111/j.1755-5949.2008.00059.x | pmc = 6494066}}</ref><ref name="BrandtKavanaghWestphal2016">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Hoang K, Wallach J, Halberstadt AL | title = Return of the lysergamides. Part I: Analytical and behavioural characterization of 1-propionyl-d-lysergic acid diethylamide (1P-LSD) | journal = Drug Testing and Analysis | volume = 8 | issue = 9 | pages = 891–902 | date = September 2016 | pmid = 26456305 | doi = 10.1002/dta.1884 | pmc = 4829483}}</ref><ref name="BrandtKavanaghWestphal2017a">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, Burrow TE, Chapman SJ, Stratford A, Nichols DE, Halberstadt AL | title = Return of the lysergamides. Part II: Analytical and behavioural characterization of N⁶ -allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ) | journal = Drug Testing and Analysis | volume = 9 | issue = 1 | pages = 38–50 | date = January 2017 | pmid = 27265891 | doi = 10.1002/dta.1985 | pmc = 5411264}}</ref><ref name="BrandtKavanaghWestphal2017b">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Stratford A, Nichols DE, Halberstadt AL | title = Return of the lysergamides. Part III: Analytical characterization of N⁶ -ethyl-6-norlysergic acid diethylamide (ETH-LAD) and 1-propionyl ETH-LAD (1P-ETH-LAD) | journal = Drug Testing and Analysis | volume = 9 | issue = 10 | pages = 1641–1649 | date = October 2017 | pmid = 28342178 | doi = 10.1002/dta.2196 | pmc = 6230477}}</ref><ref name="BrandtKavanaghTwamley2018">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Twamley B, Westphal F, Elliott SP, Wallach J, Stratford A, Klein LM, McCorvy JD, Nichols DE, Halberstadt AL | title = Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775) | journal = Drug Testing and Analysis | volume = 10 | issue = 2 | pages = 310–322 | date = February 2018 | pmid = 28585392 | doi = 10.1002/dta.2222 | pmc = 6230476}}</ref><ref name="BrandtKavanaghWestphal2019">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, Wallach J, Halberstadt AL | title = Return of the lysergamides. Part V: Analytical and behavioural characterization of 1-butanoyl-d-lysergic acid diethylamide (1B-LSD) | journal = Drug Testing and Analysis | volume = 11 | issue = 8 | pages = 1122–1133 | date = August 2019 | pmid = 31083768 | doi = 10.1002/dta.2613 | pmc = 6899222}}</ref><ref name="HalberstadtKleinChatha2019" /> 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.<ref name="BrimblecombePinder1975" /><ref name="Rav2011" /><ref name="SmithTimmis1932" />

Simplified or partial ergolines and lysergamides, such as NDTDI (8,10-seco-LSD), DEMPDHPCA, and ''N''-DEAOP-NMT, are also known.<ref name="Shulgin1976">{{cite book | veditors=Gordon M | title=Psychopharmacological Agents: Use, Misuse and Abuse | series=Medicinal Chemistry: A Series of Monographs | volume=4 | last=Shulgin | first=Alexander T. | chapter=Psychotomimetic Agents | date=1976 | isbn=978-0-12-290559-9 | doi=10.1016/b978-0-12-290559-9.50011-9 | pages=59–146 | publisher=Academic Press | url=https://bitnest.netfirms.com/external/10.1016/B978-0-12-290559-9.50011-9 | quote=The largest number of structural analogs of LSD that have been prepared involve the opening of one or more of the rings of the parent lysergic acid system. The compounds with the piperidine ring (ring D) opened [see (I)] are encountered as natural products in the several Convolvulaceae discussed in Section II,B on ololiuqui. The opening of ring C (by cleavage of the 10-11 bond to the indole "4 position") results in a series of N-α-disubstituted tryptamines. Additionally, analogs are known with the indolic nitrogen replaced with sulfur (benzothiophenes) and with an aliphatic chain (tetralins). A recent review covers this chemistry (Campaigne and Knapp, 1971), but there is apparently no human psychopharmacology as yet known.}}</ref><ref name="Nichols1973">{{cite thesis | vauthors = Nichols DE | title = Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid | date = May 1973 | publisher = University of Iowa | page = 23 | oclc = 1194694085 | url = https://bitnest.netfirms.com/external/Theses/Nichols1973#page=32}}</ref><ref name="CampaigneKnapp1971">{{cite journal | vauthors = Campaigne E, Knapp DR | title = Structural analogs of lysergic acid | journal = J Pharm Sci | volume = 60 | issue = 6 | pages = 809–814 | date = June 1971 | pmid = 4942861 | doi = 10.1002/jps.2600600602 | bibcode = 1971JPhmS..60..809C | url = }}</ref>

==Use and effects== The doses, potencies, durations, and effects of lysergamides have been reviewed by Alexander Shulgin.<ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | chapter=Basic Pharmacology and Effects | pages=67–137 | veditors = Laing RR | title=Hallucinogens: A Forensic Drug Handbook | publisher=Elsevier Science | series=Forensic Drug Handbook Series | year=2003 | isbn=978-0-12-433951-4 | url=https://books.google.com/books?id=l1DrqgobbcwC | chapter-url=https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6}}</ref><ref name="JacobShulgin1994">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Structure-activity relationships of the classic hallucinogens and their analogs | journal = NIDA Res Monogr | volume = 146 | issue = | pages = 74–91 | date = 1994 | pmid = 8742795 | doi = | url = https://bitnest.netfirms.com/external/Books/NIDA146.74}}</ref><ref name="Shulgin1982">{{cite book |vauthors=Shulgin AT | chapter=Chemistry of Psychotomimetics | pages = 3–29 | veditors = Hoffmeister F, Stille G | title=Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs | series=Handbook of Experimental Pharmacology | publisher=Springer Berlin Heidelberg |location=Berlin |date=1982 | volume=55 / 3 |isbn=978-3-642-67772-4 | oclc = 8130916 | doi=10.1007/978-3-642-67770-0_1 | url = https://books.google.com/books?id=mrT8CAAAQBAJ | chapter-url = https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1}}</ref><ref name="Shulgin1980">{{cite book | author = Alexander T. Shulgin | chapter = Hallucinogens | pages = 1109–1137 | chapter-url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5 | veditors = Burger A, Wolf ME | title = Burger's Medicinal Chemistry | edition = 4 | volume = 3 | date = 1980 | publisher = Wiley | location = New York | isbn = 978-0-471-01572-7 | oclc = 219960627 | url = https://books.google.com/books?id=2b3wAAAAMAAJ}}</ref><ref name="TiHKAL1997">{{cite book | author1 = Alexander T. Shulgin | author2 = Ann Shulgin | chapter = #26. LSD-25 Acid; Lysergide; D-Lysergic Acid Diethylamide; Meth-LAD; D-Lysergamide, N,N-Diethyl; N,N-Diethyl-D-Lysergamide; 9,10-Didehydro-N,N-Diethyl-6-Methylergoline-8b-Carboxamide | pages = 490–499 | chapter-url = https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml | title = TiHKAL: The Continuation | publisher = Transform Press | date = 1997 | edition = 1st | location = Berkeley, CA | isbn = 978-0-9630096-9-2 | oclc = 38503252 | quote = The second major location of variations in the structure of LSD has been in the nature of the alkyl groups on the amide nitrogen atom. Some of these are Sandoz syntheses, some are from other research groups, and a few of them are found in nature. Some of these have been studied in man, and some have not. A few of the original clutch of Sandoz compounds have both 1-substituents and amide alkyl (R) group variations: [...] }}</ref> They have also been reviewed by Albert Hofmann,<ref name="Hofmann1959">{{cite journal | vauthors = Hofmann A | title = Psychotomimetic Drugs: Chemical and Pharmacological Aspects | journal = Acta Physiol Pharmacol Neerl | volume = 8 | issue = | pages = 240–258 | date = June 1959 | pmid = 13852489 | doi = | url = https://www.samorini.it/doc1/alt_aut/ek/hofmann-psychotomimetic-drugs.pdf}}</ref> David E. Nichols,<ref name="Nichols2018">{{cite book | vauthors = Nichols DE | title = Chemistry and Structure-Activity Relationships of Psychedelics | series = Current Topics in Behavioral Neurosciences | volume = 36 | pages = 1–43 | date = 2018 | pmid = 28401524 | doi = 10.1007/7854_2017_475 | isbn = 978-3-662-55878-2 | url = https://bitnest.netfirms.com/external/10.1007/7854_2017_475}}</ref> and other researchers.<ref name="RutschmannStadler1978">{{cite book | vauthors = Rutschmann J, Stadler PA | chapter=Chemical Background | veditors=Berde B, Schild HO | title=Ergot Alkaloids and Related Compounds | publisher=Springer Berlin Heidelberg | publication-place=Berlin, Heidelberg | date=1978 | isbn=978-3-642-66777-0 | doi=10.1007/978-3-642-66775-6_2 | pages=29–85 | series=Handbook of Experimental Pharmacology (HEP) | volume=49}}</ref><ref name="Mangner1978">{{cite thesis | vauthors = Mangner TJ | degree = Ph.D. | publisher = University of Michigan | title=Potential Psychotomimetic Antagonists. N,N-Diethyl-1-methyl-3-aryl-1,2,5,6-tetrahydropyridine-5-carboxamides | date=1978 | doi=10.7302/11268 | url=https://www.proquest.com/openview/f845a6810749d00f70305960adfde737/ | archive-url=https://web.archive.org/web/20250330031605/https://media.proquest.com/media/hms/ORIG/2/9yQxJ?cit%3Aauth=MANGNER%2C+THOMAS+JOSEPH&cit%3Atitle=POTENTIAL+PSYCHOTOMIMETIC+ANTAGONISTS.+N%2CN+...&cit%3Apub=ProQuest+Dissertations+and+Theses&cit%3Avol=&cit%3Aiss=&cit%3Apg=&cit%3Adate=1978&ic=true&cit%3Aprod=ProQuest+Dissertations+%26+Theses+Global&_a=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&_s=QP3F3liRMGFAbHtX3wDWE8eO1gs%3D#page=22 | archive-date=30 March 2025 | quote = Table 1. Human psychotomimetic potencies of LSD analogs. [...]}}</ref><ref name="Fanchamps1978">{{cite book | vauthors = Fanchamps A | chapter=Some Compounds With Hallucinogenic Activity | veditors=Berde B, Schild HO | title=Ergot Alkaloids and Related Compounds | publisher=Springer Berlin Heidelberg | publication-place=Berlin, Heidelberg | date=1978 | isbn=978-3-642-66777-0 | doi=10.1007/978-3-642-66775-6_8 | pages=567–614 | series=Handbook of Experimental Pharmacology (HEP) | volume=49 | chapter-url=https://bibliography.maps.org/resources/download/8769#page=30 | archive-url=https://web.archive.org/web/20250330033128/https://bibliography.maps.org/resources/download/8769#page=30 | archive-date=30 March 2025 | quote = Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...]}}</ref><ref name="Rothlin1957">{{cite journal | vauthors = Rothlin E | title = Lysergic acid diethylamide and related substances | journal = Ann N Y Acad Sci | volume = 66 | issue = 3 | pages = 668–676 | date = March 1957 | pmid = 13425249 | doi = 10.1111/j.1749-6632.1957.tb40756.x | bibcode = 1957NYASA..66..668R | url = https://bibliography.maps.org/resources/download/3876| archive-url = https://web.archive.org/web/20250323050424/https://bibliography.maps.org/resources/download/3876 | archive-date = 23 March 2025 }}</ref><ref name="Hoffer1965">{{cite journal | vauthors = Hoffer A | title = D-Lysergic Acid Diethylamide (LSD): A Review of its Present Status | journal = Clin Pharmacol Ther | volume = 6 | issue = 2| pages = 183–255 | date = 1965 | pmid = 14288188 | doi = 10.1002/cpt196562183 | url = https://bibliography.maps.org/resources/download/2117| archive-url = https://web.archive.org/web/20250330030934/https://bibliography.maps.org/resources/download/2117 | archive-date = 30 March 2025 | url-access = subscription }}</ref><ref name="IsbellMinerLogan1959">{{cite journal | vauthors = Isbell H, Miner EJ, Logan CR | title = Relationships of psychotomimetic to anti-serotonin potencies of congeners of lysergic acid diethylamide (LSD-25) | journal = Psychopharmacologia | volume = 1 | issue = | pages = 20–28 | date = 1959 | pmid = 14405872 | doi = 10.1007/BF00408108 | url = https://bibliography.maps.org/resources/download/13773#page=4| archive-url = https://web.archive.org/web/20220407150042/https://bibliography.maps.org/resources/download/13773#page=4 | archive-date = 7 April 2022 | url-access = subscription }}</ref><ref name="Oberlender1989">{{cite web | vauthors = Oberlender RA | title=Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens | publisher=Purdue University | website=Purdue e-Pubs | date=May 1989 | url=https://bitnest.netfirms.com/external/Theses/Oberlender1989#page=49 | quote=Table 2. Relative potency values for lysergic acid amides. [...]}}</ref><ref name="KumbarSankar1973" /><ref name="SankarKumbar1974" />

{{Sticky}} {| class="wikitable sticky-header sortable" |+ 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<ref name="GrumannHenkelBrandt2020" /> |- | 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<ref name="MallaroniMasonVinckenbosch2022" /><ref name="GrumannHenkelBrandt2020">{{cite journal | vauthors = Grumann C, Henkel K, Brandt SD, Stratford A, Passie T, Auwärter V | title = Pharmacokinetics and subjective effects of 1P-LSD in humans after oral and intravenous administration | journal = Drug Test Anal | volume = 12 | issue = 8 | pages = 1144–1153 | date = August 2020 | pmid = 32415750 | doi = 10.1002/dta.2821 | url = }}</ref> |- | 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<ref name="MallaroniMasonVinckenbosch2022" /> |- | 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 |- class="sortbottom" | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''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:'' <ref name="Shulgin2003" /><ref name="JacobShulgin1994" /><ref name="Shulgin1982" /><ref name="Shulgin1980" /><ref name="TiHKAL1997" /><ref name="Abramson1959">{{cite journal | last=Abramson | first=H. A. | title=Lysergic Acid Diethylamide (LSD-25): XXIX. The Response Index as a Measure of Threshold Activity of Psychotropic Drugs in Man | journal=The Journal of Psychology | volume=48 | issue=1 | date=1959 | issn=0022-3980 | doi=10.1080/00223980.1959.9916341 | pages=65–78 | url=https://bibliography.maps.org/resources/download/20361| archive-url=https://web.archive.org/web/20250330025251/https://bibliography.maps.org/resources/download/20361 | archive-date=30 March 2025 | url-access=subscription }}</ref><ref name="HalberstadtChathaKlein2020">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | title = Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species | journal = Neuropharmacology | volume = 167 | issue = | article-number = 107933 | date = May 2020 | pmid = 31917152 | pmc = 9191653 | doi = 10.1016/j.neuropharm.2019.107933 | url = http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf | quote = Table 4 Human potency data for selected hallucinogens. [...] }}</ref><ref name="TittarelliMannocchiPantano2015">{{cite journal | vauthors = Tittarelli R, Mannocchi G, Pantano F, Romolo FS | title = Recreational use, analysis and toxicity of tryptamines | journal = Curr Neuropharmacol | volume = 13 | issue = 1 | pages = 26–46 | date = January 2015 | pmid = 26074742 | doi = 10.2174/1570159X13666141210222409 | pmc = 4462041 | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=90639cbd4ed3fc89df491868f3276f2288f9b1d2 | archive-url = https://web.archive.org/web/20250403082210/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=90639cbd4ed3fc89df491868f3276f2288f9b1d2 | archive-date = 2025-04-03 | quote = Ergine, or lysergic acid amide (LSA), is an alkaloid of the ergoline family closely related to LSD, found in the seeds of Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (Morning Glories). Hallucinogenic activity of LSA occurs with 4-10 seeds of Argyreia nervosa or with 150–200 seeds (3–6 g) of Ipomoea violacea: seeds could be crushed or eaten whole, or also drunk as an extract, after soaking in water [42]. The onset of the hallucinatory effects, after ingestion of Hawaiian Baby Woodrose, is from 20 to 40 minutes and their total duration is from 5 to 8 hours: the plateau is reached after 4-6 hours and the return to normality is after 1-2 hours from the plateau. [...] However, as regards to the assumption of the Morning Glory seeds, the onset of the hallucinatory effects is from 30 to 180 minutes and they last for 4 to 10 hours. The users reported that they return to normality after about 24 hours [67].}}</ref><ref name="KumbarSankar1973">{{cite journal | vauthors = Kumbar M, Sankar DV | title = Quantum chemical studies on drug actions. 3. Correlation of hallucinogenic and anti-serotonin activity of lysergic acid derivatives with quantum chemical data | journal = Res Commun Chem Pathol Pharmacol | volume = 6 | issue = 1 | pages = 65–100 | date = July 1973 | pmid = 4734018 | doi = | url = https://bibliography.maps.org/resources/download/14168 | archive-url = https://web.archive.org/web/20250329003102/https://bibliography.maps.org/resources/download/14168 | archive-date = 29 March 2025 | quote=Table I – Structure and Several Biological Activities of Lysergates [...]}}</ref><ref name="SankarKumbar1974">{{cite journal | vauthors = Sankar DV, Kumbar M | title = Quantum chemical studies on drug actions. IV. Correlation of substituent structures and anti-serotonin activity in lysergamide series | journal = Res Commun Chem Pathol Pharmacol | volume = 7 | issue = 2 | pages = 259–274 | date = February 1974 | pmid = 4818373 | doi = | quote = Table I – Quantum Chemical Data on Lysergamide Derivatives | url = https://bibliography.maps.org/resources/download/20652#page=7| archive-url = https://web.archive.org/web/20250329003312/https://bibliography.maps.org/resources/download/20652#page=7 | archive-date = 29 March 2025 }}</ref><ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | pages = 98–144 | title = Hallucinogenic Agents | date = 1975 | publisher = Wright-Scientechnica | location = Bristol | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://books.google.com/books?id=wU9tQgAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1#page=55 | quote = Table 4.3.—Comparative Hallucinogenic Potencies in Man of Derivatives of D-Lysergic Acid. [...]}}</ref><ref name="Mangner1978" /><ref name="Fanchamps1978" /><ref name="IsbellMinerLogan1959" /><ref name="Hoffer1965" /><ref name="GuptaSinghBindal1983">{{cite journal | last1=Gupta | first1=Satya P. | last2=Singh | first2=Prithvi | last3=Bindal | first3=Mahesh C. | title=QSAR studies on hallucinogens | journal=Chemical Reviews | volume=83 | issue=6 | date=1 December 1983 | issn=0009-2665 | doi=10.1021/cr00058a003 | pages=633–649 | url=https://pubs.acs.org/doi/abs/10.1021/cr00058a003 | quote= TABLE XII. Antiserotonin and Hallucinogenic Activities and Hückel's Total MO Energy of LSD and its Analogues [...] Data collected by Kumbar and Siva Sankar,91,92 from ref 70a, 87, 88, and 90; all activities are relative to that of LSD taken as 100.}}</ref><ref name="MallaroniMasonVinckenbosch2022">{{cite journal | vauthors = Mallaroni P, Mason NL, Vinckenbosch FR, Ramaekers JG | title = The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides | journal = Psychopharmacology (Berl) | volume = 239 | issue = 6 | pages = 1783–1796 | date = June 2022 | pmid = 35487983 | pmc = 9166850 | doi = 10.1007/s00213-022-06142-4 | url = }}</ref> ''Additional:'' <ref name="HalberstadtKleinChatha2019">{{cite journal | vauthors = Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, Nichols DE, Brandt SD | title = Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA) | journal = Psychopharmacology | volume = 236 | issue = 2 | pages = 799–808 | date = February 2019 | pmid = 30298278 | doi = 10.1007/s00213-018-5055-9 | pmc = 6848745 | quote = 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]}}</ref><ref name="GrumannHenkelBrandt2020">{{cite journal | vauthors = Grumann C, Henkel K, Brandt SD, Stratford A, Passie T, Auwärter V | title = Pharmacokinetics and subjective effects of 1P-LSD in humans after oral and intravenous administration | journal = Drug Test Anal | volume = 12 | issue = 8 | pages = 1144–1153 | date = August 2020 | pmid = 32415750 | doi = 10.1002/dta.2821 | url = }}</ref><ref name="ChenDeWitBos2020">{{cite report | last1=Chen | first1=W. | last2=De Wit-Bos | first2=L. | title=Risk assessment of Argyreia nervosa | date=2020 | doi=10.21945/rivm-2019-0210 | url=https://www.rivm.nl/bibliotheek/rapporten/2019-0210.pdf}}</ref><ref name="BigwoodOttThompson1979">{{cite journal | vauthors = Bigwood J, Ott J, Thompson C, Neely P | title = Entheogenic effects of ergonovine | journal = J Psychedelic Drugs | volume = 11 | issue = 1–2 | pages = 147–149 | date = 1979 | pmid = 522166 | doi = 10.1080/02791072.1979.10472099 | url = https://bibliography.maps.org/resources/download/12845 | archive-url = https://web.archive.org/web/20250328185507/https://bibliography.maps.org/resources/download/12845 | archive-date = 28 March 2025 | quote = In 1977 and 1978 Hofmann reported that ergonovine maleate was entheogenic,1 a surprising finding in view of its widespread use in obstetrics (Wasson, Hofmann & Ruck 1978; Hofmann 1977). This report was based on a self-experiment conducted by Hofmann on 1 April 1976, with 2.0 mg of ergonovine maleate taken orally. Hofmann reported that this dose manifested a "slightly hallucinogenic activity" lasting more than five hours.2 [...] Our experiments corroborate Hofmann's report that ergonovine possesses entheogenic properties. We found the active dose to lie between 5.0 and 10.0 mg, peroral. It is interesting to note that Hofmann experienced distinct entheogenic effects at 2.0 mg, while Wasson and Ruck did not. Similarly, J.B. experienced distinct entheogenic effects at 3.0 mg, whereas J.O. and P.N. did not. This underscores the importance of metabolic individuality in the uptake and metabolism of mind-altering drugs. With respect to entheogenic effects 10 mg of ergonovine maleate is roughly equivalent to 50 μg is, ergonovine possesses about that LSD-tartrate, 1/200th the entheogenic potency of LSD.| url-access = subscription }}</ref><ref name="GorodetzkyIsbell1964">{{cite journal | vauthors = Gorodetzky CW, Isbell H | title = A comparison of 2,3-dihydro-lysergic acid diethylamide with LSD-25 | journal = Psychopharmacologia | volume = 6 | issue = 3 | pages = 229–233 | date = September 1964 | pmid = 5319153 | doi = 10.1007/BF00404013 | url = }}</ref><ref name="Sicuteri1963">{{cite journal | vauthors = Sicuteri F | title = Prophylactic Treatment of Migraine by Means of Lysergic Acid Derivatives | journal = Triangle | volume = 6 | issue = | pages = 116–125 | date = October 1963 | pmid = 14087164 | doi = | url = }}</ref> |}

The properties of various additional lysergamides, for instance in terms of serotonin antagonism, have also been described.<ref name="Cerletti1958">{{cite journal | vauthors = Cerletti A, Doepfner W | title = Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 122 | issue = 1 | pages = 124–136 | date = January 1958 | pmid = 13502837 | doi = 10.1016/S0022-3565(25)11933-2 | url = https://bibliography.maps.org/resources/download/19096| archive-url = https://web.archive.org/web/20250630233202/https://bibliography.maps.org/resources/download/19096 | archive-date = 30 June 2025 }}</ref>

==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

==Pharmacology== ===Pharmacodynamics=== {{Sticky}} {| class="wikitable sticky-header" |+ {{Nowrap|Serotonin and dopamine receptor affinities (K_i, nM) of selected lysergamides and related compounds (Jain et al., 2025)<ref name="JainGumpperSlocum2025">{{cite journal | vauthors = Jain MK, Gumpper RH, Slocum ST, Schmitz GP, Madsen JS, Tummino TA, Suomivuori CM, Huang XP, Shub L, DiBerto JF, Kim K, DeLeon C, Krumm BE, Fay JF, Keiser M, Hauser AS, Dror RO, Shoichet B, Gloriam DE, Nichols DE, Roth BL | title = The polypharmacology of psychedelics reveals multiple targets for potential therapeutics | journal = Neuron | volume = 113| issue = 19| pages = 3129–3142.e9| date = July 2025 | pmid = 40683247 | doi = 10.1016/j.neuron.2025.06.012 | url = https://www.cell.com/cms/10.1016/j.neuron.2025.06.012/attachment/7d8365fe-51f3-4a28-bf40-9999bec837f6/mmc11.pdf}}</ref>}} |- ! 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 |}

{{Sticky}} {| class="wikitable sticky-header" |+ {{Nowrap|Serotonin and dopamine receptor affinities (K_i, nM) of selected lysergamides and related compounds (Ray, 2010)<ref name="Ray2010">{{cite journal | vauthors = Ray TS | title = Psychedelics and the human receptorome | journal = PLOS ONE | volume = 5 | issue = 2 | article-number = e9019 | date = February 2010 | pmid = 20126400 | pmc = 2814854 | doi = 10.1371/journal.pone.0009019 | bibcode = 2010PLoSO...5.9019R | doi-access = free | url = }}</ref>}} |- ! 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== [[File:Structural modifications of the psychedelic drug LSD.png|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,<ref name="BrimblecombePinder1975" /><ref name="Rav2011">{{cite book| vauthors = Ravina E |title=The evolution of drug discovery: from traditional medicines to modern drugs|date=2011|publisher=Wiley-VCH|location=Weinheim|isbn=978-3-527-32669-3|page=245|edition= 1st |url=https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA245|url-status=live|archive-url=https://web.archive.org/web/20151226162800/https://books.google.ca/books?id=iDNy0XxGqT8C&pg=PA245|archive-date=2015-12-26}}</ref><ref name="SmithTimmis1932">{{cite journal | vauthors = Smith S, Timmis GM |date=1932 |title=98. The alkaloids of ergot. Part III. Ergine, a new base obtained by the degradation of ergotoxine and ergotinine |url=https://xlink.rsc.org/?DOI=jr9320000763 |journal=Journal of the Chemical Society (Resumed) |language=en |pages=763–766 |doi=10.1039/jr9320000763 |issn=0368-1769|url-access=subscription }}</ref> and LSD was discovered by 1938 and its hallucinogenic effects in 1943 by Albert Hofmann.<ref name="WalkerPullellaPiggott2023">{{cite journal | last1=Walker | first1=Scott R. | last2=Pullella | first2=Glenn A. | last3=Piggott | first3=Matthew J. | last4=Duggan | first4=Peter J. | title=Introduction to the chemistry and pharmacology of psychedelic drugs | journal=Australian Journal of Chemistry | volume=76 | issue=5 | date=5 July 2023 | issn=0004-9425 | doi=10.1071/CH23050 | doi-access=free | pages=236–257 | url=https://www.publish.csiro.au/ch/pdf/CH23050 | access-date=4 April 2025}}</ref><ref name="McKenna1999">{{cite book | last=McKenna | first=Terence | chapter=[Chapter 14:] A Brief History of Psychedelics | pages=223–245 | title=Food of the Gods: The Search for the Original Tree of Knowledge: a Radical History of Plants, Drugs and Human Evolution | publisher=Rider | date=1999 | isbn=978-0-7126-7038-8 | url=https://alquimiahealingarts.com/wp-content/uploads/2020/03/Food-Of-The-Gods-Terence-Mckenna.pdf#page=117}}</ref> 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.<ref name="Hofmann1959" /><ref name="Rothlin1957" /><ref name="Abramson1959" /><ref name="StollHofmann1955">{{cite journal | last1=Stoll | first1=A. | last2=Hofmann | first2=A. | title=Amide der stereoisomeren Lysergsäuren und Dihydro-lysergsäuren. 38. Mitteilung über Mutterkornalkaloide | trans-title=Amides of stereoisomeric lysergic and dihydrolysergic acids. 38. Ergot alkaloids | journal=Helvetica Chimica Acta | volume=38 | issue=2 | date=1955 | issn=0018-019X | doi=10.1002/hlca.19550380207 | pages=421–433 | bibcode=1955HChAc..38..421S | url=https://onlinelibrary.wiley.com/doi/10.1002/hlca.19550380207 | access-date=5 June 2025}}</ref> ''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.<ref name="NicholsOberlenderMcKenna1991">{{cite book | vauthors=Nichols DE, Oberlender R, McKenna DJ | chapter=Stereochemical Aspects of Hallucinogenesis | veditors=Watson RR | title=Biochemistry and Physiology of Substance Abuse | volume=3 | publisher=CRC Press | publication-place=Boca Raton, Fla. | year=1991 | isbn=978-0-8493-4463-3 | oclc=26748320 | pages=1–39 | url=https://archive.org/details/biochemistryphys0003unse/ | chapter-url=https://bitnest.netfirms.com/external/Books/BiochemistryPhysiologySubstanceAbuse3.1 | quote=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}}</ref><ref name="FehrStadlerHofmann1970">{{cite journal | last1=Fehr | first1=T. | last2=Stadler | first2=P. A. | last3=Hofmann | first3=A. | title=Demethylierung des Lysergsäuregerüstes. 73. Mitteilung über Mutterkornalkaloide [1] | journal=Helvetica Chimica Acta | volume=53 | issue=8 | date=1970 | issn=0018-019X | doi=10.1002/hlca.19700530832 | pages=2197–2201 | bibcode=1970HChAc..53.2197F | url=https://onlinelibrary.wiley.com/doi/10.1002/hlca.19700530832 | access-date=29 June 2025}}</ref><ref name="NiwaguchiNakaharaIshii1976">{{cite journal | vauthors = Niwaguchi T, Nakahara Y, Ishii H | title=Lysergic Acid Diethylamideおよび関連化合物に関する研究(第4報)Norlysergic Acidの各種Amide誘導体ならびに関連化合物の合成 | trans-title=Studies on Lysergic Acid Diethylamide and Related Compounds. IV. Syntheses of Various Amide Derivatives of Norlysergic Acid and Related Compounds | journal=Yakugaku Zasshi | volume=96 | issue=5 | date=1976 | issn=0031-6903 | doi=10.1248/yakushi1947.96.5_673 | doi-access=free | pages=673–678 | pmid=987200 | url=https://www.jstage.jst.go.jp/article/yakushi1947/96/5/96_5_673/_pdf | access-date=27 March 2025}}</ref><ref name="HoffmanNichols1985" /> The psychedelic effects of ''N''(6)-substituted lysergamides were reported by Alexander Shulgin in 1986 and thereafter.<ref name="Nichols1986">{{cite journal | vauthors = Nichols DE | title = Studies of the Relationship Between Molecular Structure and Hallucinogenic Activity | journal = Pharmacol Biochem Behav | volume = 24 | issue = 2 | pages = 335–340 | date = February 1986 | pmid = 3952123 | doi = 10.1016/0091-3057(86)90362-x | url = https://bitnest.netfirms.com/external/10.1016/0091-3057(86)90362-X | quote = The ergolines can be viewed as rigid tetracyclic tryptamines. Within this class of compound is found the semisynthetic d-lysergic acid diethylamide (Fig 8) (d-LSD), the most potent of the hallucinogenic drugs. [...] Of the many structural modifications which have been made to the LSD structure, none had yielded a compound more potent than LSD itself. This report will briefly describe some derivatives of LSD which do appear to have somewhat higher potency than LSD. [...] The observations of potency comparable to, or greater than LSD [with N(6)-alkyl-substituted lysergamides] was of great interest. It seemed likely, based on the generalization in the drug discrimination assay and the high potencies of several of the derivatives, that these might well be more potent hallucinogens in man than LSD. Very recently, preliminary studies were carried out (A T Shulgin, personal communication) which indicated that indeed, the N(6)-ethyl and the N(6)-allyl-nor-LSD derivatives are somewhat more potent than LSD, by perhaps a factor of 2–3. Early results also indicated that N(6)-propyl-nor-LSD retains activity comparable to LSD, but with perhaps less visual distortion. These preliminary results were obtained after only a few experiments with each compound and further evaluation to define the potency and character of these lysergamides is underway.| url-access = subscription }}</ref><ref name="Oberlender1989" /><ref name="JacobShulgin1994" /><ref name="TiHKAL1997" /> 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,<ref name="PfaffHuangMarona-Lewicka1994">{{cite journal | vauthors = Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE | title = Lysergamides revisited | journal = NIDA Research Monograph | volume = 146 | pages = 52–73 | date = 1994 | pmid = 8742794 | url = https://bitnest.netfirms.com/external/Books/NIDA146.52 }}</ref><ref name="Oberlender1989" /><ref name="NicholsOberlenderMcKenna1991" /> while LSZ (LA-Azetidine) was described by the same group in 2002.<ref name="NicholsFrescasMarona-Lewicka2002" /> 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.<ref name="Niesporek2022">{{cite AV media | last=Niesporek | first=Tom | title=Der Hype um legales LSD in Deutschland: Wie das Verbot umgangen wird | trans-title=The hype surrounding legal LSD in Germany: How the ban is circumvented | time=2:10–8:12, 20:05–20:41 | language=German | publisher=VICE auf Deutsch | website=YouTube | date=17 August 2022 | url=https://www.youtube.com/watch?v=iVNCt2zyIaQ&t=130 | access-date=29 September 2025}}</ref><ref name="Încrosnatu2023">{{cite web | last=Încrosnatu | first=Dănuț | title=From 1V-LSD to 1D-LSD: The Evolution of Legal Lysergamides | website=Sociedelic | date=17 July 2023 | url=https://www.sociedelic.com/from-1v-lsd-to-1d-lsd-the-evolution-of-legal-lysergamides/}}</ref><ref name="Chiara2022">{{cite web | last=Chiara | first=Jean-Baptiste | title=LSD light: Gobe, c'est du légal ! | trans-title=LSD Light: Swallow It, It's Legal! | website=Technikart | date=27 July 2022 | url=https://www.technikart.com/lsd-light-gobe-cest-du-legal/ | language=fr}}</ref>

==List of lysergamides== {{Sticky}} {| 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)<ref>{{cite web | title=PiHKAL·info | website=Isomer Design | date=12 June 2025 | url=https://isomerdesign.com/pihkal/explore/5321 | access-date=14 May 2026}}</ref> || ? || H || CH₃ || CH(CH₃)C₄H₉ || H || - |- | 125px|class=skin-invert-image || Lysergic acid 2-heptylamide (N2Hp-LA, 2-LSHp)<ref>{{cite web | title=PiHKAL·info | website=Isomer Design | date=12 June 2025 | url=https://isomerdesign.com/pihkal/explore/5323 | access-date=14 May 2026}}</ref> || ? || H || CH₃ || CH(CH₃)C₅H₁₁ || H || - |- | 125px|class=skin-invert-image || Lysergic acid α-methylbenzylamide (''N''-(α-methylbenzyl){{shy}}lysergamide)<ref>{{cite web | title=PiHKAL·info | website=Isomer Design | date=12 June 2025 | url=https://isomerdesign.com/pihkal/explore/9393 | access-date=14 May 2026}}</ref><ref>{{cite web | title=(6aR,9R)-7-methyl-N-(1-phenylethyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/178008029 | access-date=15 May 2026}}</ref> || ? || H || CH₃ || CH(CH₃)C₆H₅ || H || - |- | 125px|class=skin-invert-image || Lysergic acid methyl-2-butylamide<ref>{{cite web | title=N-sec-Butyl-N-methyllysergamide | website=Isomer Design | date=12 June 2025 | url=https://isomerdesign.com/pihkal/explore/9394 | access-date=15 May 2026}}</ref> || ? || H || CH₃ || CH(CH₃)CH₂CH₃ || CH₃ || - |- | 125px|class=skin-invert-image || Lysergic acid ethyl-2-butylamide<ref>{{cite web | title=N-sec-Butyl-N-ethyllysergamide | website=Isomer Design | date=12 June 2025 | url=https://isomerdesign.com/pihkal/explore/9395 | access-date=15 May 2026}}</ref> || ? || 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)<ref>[https://patents.google.com/patent/US20230414583A1 Trachsel D, et al. Lysergic acid derivatives with modified LSD-like action. US 2023/0414583]</ref> || || H || CH₃ || CH₂CH₂F || CH₂CH₃ || - |- | 125px|class=skin-invert-image || DFELA (TRALA-08; WO 2022/226408 Example 29)<ref>[https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022226408 Kruegel AC. Novel Ergolines and Methods of Treating Mood Disorders. Patent WO 2022/226408]</ref> || || 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){{shy}}propionyl)-LSD) || || CO(CH₂)₂PO(CH₃)₂ || CH₃ || CH₂CH₃ || CH₂CH₃ || - |- | 135px|class=skin-invert-image || 1BP-LSD (1-(3-(tetramethyldioxa{{shy}}borolane)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)<ref name="Okada_2024">{{cite journal | vauthors = Okada Y, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Kanamori T, Iwata YT | title = Synthesis and analytical characterization of 1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD) | journal = Drug Testing and Analysis | volume = 17| issue = 4| pages = 494–501| date = June 2024 | pmid = 38922764 | doi = 10.1002/dta.3747}}</ref> || || 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)<ref>{{cite web | title=PiHKAL·info | website=Isomer Design | date=12 June 2025 | url=https://isomerdesign.com/pihkal/explore/5077 | access-date=15 May 2026}}</ref> || ? || 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)<ref>{{cite web | title=LA-2,6-DiMePip | website=Isomer Design | date=12 June 2025 | url=https://isomerdesign.com/pihkal/explore/9396 | access-date=15 May 2026}}</ref> || ? || 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)<ref name="US2997470A">{{cite web | title=Lysergic acid amides | website=Google Patents | date=5 March 1956 | url=https://patents.google.com/patent/US2997470A/en | access-date=5 April 2025 | quote=EXAMPLE 38 Preparation of d-lysergic acid hexamethylene imide: [...]}}</ref> || || H || CH₃ || colspan=2| (CH₂)₆ || - |- | 125px|class=skin-invert-image || 2-Oxa-6-azaspiro[3.3]heptyl-lysergamide (WO 2022/008627 compound)<ref>{{cite patent | url = https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022008627 | inventor = Grill M | title = Improved Method for the Production of Lysergic Acid Diethylamide (LSD) and Novel Derivatives thereof. | country = WO | number = 2022/008627}}</ref> || || 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<ref name="WO2021076572">{{cite patent | country = WO | number = 2021076572 | invent1 = David E. Olson | invent2 = Lee Dunlap | invent3 = Florence Wagner | invent4 = Milan Chytil, Noel Aaron Powell | status = | title = Ergoline-like compounds for promoting neural plasticity | pubdate = 22 April 2021 | gdate = | fdate = 14 October 2020 | pridate = 14 October 2020 | assign1 = Delix Therapeutics, Inc. | assign2 = The Regents of the University of California | url = https://patents.google.com/patent/WO2021076572/ | quote = [0124] In some embodiments, provided herein is a compound, or a pharmaceutically acceptable salt thereof, that is: [...]}}</ref> || || 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<ref name="WO2025019454">{{cite patent | country = WO | number = 2025019454 | invent1 = David Nichols | invent2 = Joel Smith | status = patent | title = Substituted ergolines | pubdate = 23 January 2025 | gdate = | fdate = 15 July 2024 | pridate = 15 July 2024 | assign1 = 2A Biosciences Inc | assign2 = Florida State University Research Foundation | url = https://patentimages.storage.googleapis.com/c8/78/cb/60a8e1e81aa2ca/WO2025019454A2.pdf#page=103}}</ref> || || H || CH₃ || CH₂CH₃ || CH₂CH₃ || 2-Br, 14-Me |}

==Related compounds== {{See also|Substituted ergoline|Partial lysergamide|List of miscellaneous 5-HT2A receptor agonists}}

{{Sticky}} {| 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) || (6a''R'',9''R'',10a''R'')-5-cyclopropyl-''N''-((''S'')-1-hydroxybutan-2-yl)-4,7-dimethyl-4,6,6''a'',7,8,9,10,10''a''-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''-((1''S'',2''R'',3''E'')-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl)-6-methylergoline-8β-carboxamide || 87178-42-5 |- | 85px|class=skin-invert-image || Ergoline || (6a''R'')-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) || (7''S'')-''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 <ref>{{cite web | title=[(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 | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/176977579 | access-date=14 May 2026}}</ref><ref>Sabnis RW. Novel Desamide Isotryptamine Tetracycles as 5‑HT2C Agonists for Treating Brain Disorders. ''ACS Med Chem Lett''. 2025 May 21;16(6):976-977. {{doi|10.1021/acsmedchemlett.5c00286}} {{pmid|40529093}}</ref><ref name="WO2025080608">{{cite patent | country = WO | number = 2025080608 | invent1 = Jeremy R. Tuck | invent2 = David E. Olson | invent3 = Andrian G. Basargin | invent4 = Lee Dunlap | invent5 = Noel Aaron Powell | invent6 = Milan Chytil | invent7 = Manuka Ghosh | status = patent | title = Desamide isotryptamine tetracycles for treating brain disorders | pubdate = 17 April 2025 | gdate = | fdate = 9 October 2024 | pridate = 9 October 2023 | assign1 = Delix Therapeutics Inc | assign2 = University of California Berkeley | assign3 = University of California San Diego | url = }}</ref> || [(4''R'',7''S'')-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== {{Reflist}}

==External links== * [https://tripsitter.com/psychedelics/lysergamides/ Lysergamide Psychedelics - Tripsitter] * [https://tripsitter.substack.com/p/designer-drugs-lysergamides Designer Drug Exposé: Lysergamides - Tripsitter] * [https://pageviews.wmcloud.org/massviews/?platform=all-access&agent=user&source=category&range=latest-365&subjectpage=0&subcategories=1&sort=views&direction=1&view=list&target=https://en.wikipedia.org/wiki/Category:Lysergamides Lysergamides - Wikipedia Massviews Analysis (Wikipedia Page Views of Individual Lysergamides)]

{{Psychedelics}} {{Navboxes | title = Pharmacodynamics | titlestyle = background:#ccccff | list1 = {{Adrenergic receptor modulators}} {{Dopamine receptor modulators}} {{Serotonin receptor modulators}} {{TAAR modulators}} }} {{Ergolines}} {{Chemical classes of psychoactive drugs}}

Category:Lysergamides Category:Chemical classes of psychoactive drugs Category:Alkaloids