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Lysergamides

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The lysergamide core, with common substitution positions denoted.

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

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.[4][5][6][7][8][9][10][11][12][13][14][15][16] 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.

The lysergamides, such as ergine, isoergine, and ergometrine, were discovered by the early 1930s,[17][18][19] and LSD was discovered by 1938 and its hallucinogenic effects in 1943 by Albert Hofmann.[20][21]

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

Use and effects

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

Doses, potencies, and durations of LSD and its analogues
Common name Code Dose (mg) Potency (×LSD) Duration (h)
Lysergic acid amide (LSA; ergine) LA-111 0.5–6 <0.1 ~4–10
Isolysergic acid amide (iso-LSA; isoergine) Iso-LA-819 2–5 <0.1 ~4–10
Lysergic acid methylamide LAM ~0.5 ≤0.2 ?
Lysergic acid dimethylamide DAM-57 0.5–1.2 0.1 ?
Lysergic acid ethylamide LAE-32 0.5–1.6 ≤0.1 ?
1-Acetyllysergic acid ethylamide ALA-10 ~1.2 ≤0.1 ?
1-Methyllysergic acid ethylamide MLA-74 ~2 0.05 ?
Lysergic acid isopropylamide LAiP ? ? ?
Lysergic acid methylethylamide LME-54 ? ~0.33 ?
Lysergic acid diethylamide LSD-25, METH-LAD 0.05–0.2 1 8–12
Isolysergic acid diethylamide Iso-LSD >0.5 <0.05 ?
2,3-Dihydro-LSD DH-LSD ~0.15–0.4 ~0.15 ~8–12
9,10-Dihydro-LSD – >2.5 <0.02 ?
2-Bromo-LSD BOL-148 >1 (≥6–20) <0.1 (≤0.005–0.02) ?
2-Iodo-LSD IOL ? ? ?
2-Keto-LSD (2-oxy-LSD) ? >0.3 ? ?
1-Acetyl-LSD ALD-52 0.1–0.2 1 ?
1-Methyl-LSD MLD-41 0.2–0.3 0.3 ?
1-Hydroxymethyl-LSD OML-632 ? ~0.7 ?
1-Methyl-2-bromo-LSD MBL-61 >10 <0.01 ?
1-Methyl-2-iodo-LSD MIL ? ? ?
Lysergic acid propylamide LAP >0.5 <0.2 ?
Lysergic acid methylpropylamide LMP >0.1 <1 ?
Lysergic acid ethylpropylamide LEP-57 ? ~0.33 ?
Lysergic acid dipropylamide DPL >1 <0.1 ?
Lysergic acid dibutylamide LBB-66 ? 0 ?
Lysergic acid diallylamide DAL >1 <0.1 ?
Lysergic acid 2,4-dimethylazetidide LA-SS-Az, LSZ 0.1–0.3 0.5 ?
Ergonovine (ergometrine)a – 5–10 ≤0.01 ?
Methylergonovine (methylergometrine)b – 2 0.05 ?
Methysergidec UML-491 4–8 0.02 ?
Lysergic acid piperidide LSD-Pip ? ? ?
Lysergic acid pyrrolide LPD-824 ~0.8 0.05–0.1 ?
1-Methyllysergic acid pyrrolide MPD-75 >1.6 ≤0.1 ?
Lysergic acid pyrrolinide – ? 0.1 ?
Lysergic acid morpholide LSM-775 0.3–0.6 0.1–0.3 ?
Nor-LSD (6-nor-LSD) – >0.5 <0.2 ?
6-Ethyl-nor-LSD ETH-LAD 0.04–0.15 2 8–12
6-Propyl-nor-LSD PRO-LAD 0.08–0.2 1 6–8
6-Allyl-nor-LSD AL-LAD, ALLY-LAD 0.05–0.16 1 6–8
6-n-Butyl-nor-LSD BU-LAD ≥0.4–0.5 <0.3 ?
6-Propynyl-nor-LSD PARGY-LAD 0.16–0.5 0.2–0.6 ?
6-(β-Phenethyl)-nor-LSD PHENETHY-LAD >0.35–0.5 <0.3 ?
Footnotes: a = Ergonovine is lysergic acid hydroxyisopropylamide. b = Methylergonovine is lysergic acid hydroxy-sec-butylamide. c = Methysergide is 1-methylmethylergonovine (1-methyllysergic acid hydroxy-sec-butylamide). Refs: [25][26][27][28][29][41][42][43][39][40][17][33][34][44][45][46]

List of lysergamides

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Lysergamides, tabulated by structure
Structure Name (synonyms) CAS # R1 R6 R2 R3 Other
Ergine (lysergic acid amide, lysergamide) 478-94-4 H CH3 H H -
Isoergine (isolysergic acid amide, isolysergamide) 2889-26-1 H CH3 H H 8-epi
DAM-57 (lysergic acid dimethylamide) 4238-84-0 H CH3 CH3 CH3 -
Ergometrine (ergonovine; lysergic acid propanolamide) 60-79-7 H CH3 CH(CH3)CH2OH H -
Propisergide (1-methylergonovine) 5793-04-4 CH3 CH3 CH(CH3)CH2OH H -
Ergotamine (an ergopeptine) 113-15-5 H CH3 -- C17H18N2O4 -
Methylergometrine (methylergonovine; lysergic acid butanolamide) 113-42-8 H CH3 CH(CH2CH3)CH2OH H -
Methysergide (1-methyl-lysergic acid butanolamide) 361-37-5 CH3 CH3 CH(CH2CH3)CH2OH H -
Amesergide (9,10-dihydro-11-isopropyllysergic acid cyclohexylamide) 121588-75-8 CH(CH3)2 CH3 C6H11 H -
LY-215840 (1-isopropyl-9,10-dihydro-N-(2-hydroxycyclopent-anyl)lysergamide) 137328-52-0 CH(CH3)2 CH3 C5H8OH H -
Cabergoline (N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-(prop-2-en-1-yl)-9,10-dihydrolysergamide) 81409-90-7 H H2C=CH-CH2 CONHCH2CH3 CH2CH2CH2N(CH3)2 -
LAE-32 (lysergic acid ethylamide) 478-99-9 H CH3 CH2CH3 H -
LAiP (lysergic acid isopropylamide) H CH3 CH(CH3)2 H -
LAtB (lysergic acid tert-butylamide) H CH3 C(CH3)3 H -
LAcB (lysergic acid cyclobutylamide) H CH3 (CH2)4 H -
Cepentil (lysergic acid cyclopentylamide) H CH3 (CH2)5 H -
LSB (lysergic acid 2-butylamide) 137765-82-3 H CH3 CH(CH3)CH2CH3 H -
LSP (lysergic acid 3-pentylamide) H CH3 CH(CH2CH3)CH2CH3 H -
DPL (lysergic acid dipropylamide) H CH3 CH2CH2CH3 CH2CH2CH3 -
DAL (lysergic acid diallylamide) H CH3 H2C=CH-CH2 H2C=CH-CH2 -
MIPLA (lysergic acid methylisopropylamide) 100768-08-9 H CH3 CH(CH3)2 CH3 -
EIPLA (lysergic acid ethylisopropylamide) H CH3 CH(CH3)2 CH2CH3 -
ECPLA (lysergic acid ethylcyclopropylamide) H CH3 C3H5 CH2CH3 -
ETFELA (lysergic acid N-ethyl-N-(2,2,2-trifluoroethyl)amide) H CH3 CH2CF3 CH2CH3 -
LAMPA (lysergic acid methylpropylamide) 40158-98-3 H CH3 CH2CH2CH3 CH3 -
EPLA (lysergic acid ethylpropylamide; LEP-57) H CH2CH3 CH2CH2CH3 CH3 -
LSD (lysergic acid diethylamide; LAD) 50-37-3 H CH3 CH2CH3 CH2CH3 -
ETH-LAD (6-ethyl-6-nor-LSD) 65527-62-0 H CH2CH3 CH2CH3 CH2CH3 -
PARGY-LAD (6-propynyl-6-nor-LSD) H HC≡C−CH2 CH2CH3 CH2CH3 -
AL-LAD (6-allyl-6-nor-LSD) 65527-61-9 H H2C=CH-CH2 CH2CH3 CH2CH3 -
PRO-LAD (6-propyl-6-nor-LSD) 65527-63-1 H CH2CH2CH3 CH2CH3 CH2CH3 -
IP-LAD (6-isopropyl-6-nor-LSD) H CH(CH3)2 CH2CH3 CH2CH3 -
CYP-LAD (6-cyclopropyl-6-nor-LSD) H C3H5 CH2CH3 CH2CH3 -
BU-LAD (6-butyl-6-nor-LSD) 96930-87-9 H CH2CH2CH2CH3 CH2CH3 CH2CH3 -
FLUORETH-LAD (FE-LAD; 6-(2-fluoroethyl)-6-nor-LSD) H CH2CH2F CH2CH3 CH2CH3 -
CE-LAD (CHLORETH-LAD; 6-(2-chloroethyl)-6-nor-LSD) H CH2CH2Cl CH2CH3 CH2CH3 -
ALD-52 (1-acetyl-LSD) 3270-02-8 COCH3 CH3 CH2CH3 CH2CH3 -
1P-LSD (1-propionyl-LSD) 2349358-81-0 COCH2CH3 CH3 CH2CH3 CH2CH3 -
1B-LSD (1-butanoyl-LSD) 2349376-12-9 COCH2CH2CH3 CH3 CH2CH3 CH2CH3 -
1V-LSD (1-valeryl-LSD) CO(CH2)3CH3 CH3 CH2CH3 CH2CH3 -
1H-LSD (1-hexanoyl-LSD) CO(CH2)4CH3 CH3 CH2CH3 CH2CH3 -
1DD-LSD (1-dodecanoyl-LSD) CO(CH2)10CH3 CH3 CH2CH3 CH2CH3 -
1cP-LSD (1-cyclopropylmethanoyl-LSD) COC3H5 CH3 CH2CH3 CH2CH3 -
1D-LSD (1-(1,2-dimethylcyclobutane-1-carbonyl)-LSD) COC4H5(CH3)2 CH3 CH2CH3 CH2CH3 -
1T-LSD (1-(thiophene-2-carbonyl)-LSD) COC4H3S CH3 CH2CH3 CH2CH3 -
1S-LSD (1-(3-(trimethylsilyl)propionyl)-LSD) CO(CH2)2Si(CH3)3 CH3 CH2CH3 CH2CH3 -
1P-AL-LAD (1-propionyl-6-allyl-6-nor-LSD) COCH2CH3 H2C=CH-CH2 CH2CH3 CH2CH3 -
1cP-AL-LAD (1-cyclopropylmethanoyl-6-allyl-6-nor-LSD) COC3H5 H2C=CH-CH2 CH2CH3 CH2CH3 -
1T-AL-LAD (1-(2-thienoyl)-6-allyl-6-nor-LSD)[47] COC4H3S H2C=CH-CH2 CH2CH3 CH2CH3 -
1P-ETH-LAD (1-propionyl-6-ethyl-6-nor-LSD) COCH2CH3 CH2CH3 CH2CH3 CH2CH3 -
1P-MIPLA (1-propionyl-lysergic acid methylisopropylamide) COCH2CH3 CH3 CH(CH3)2 CH3 -
MLD-41 (1-methyl-LSD) 4238-85-1 CH3 CH3 CH2CH3 CH2CH3 -
OML-632 (1-hydroxymethyl-LSD) 114004-70-5 CH2OH CH3 CH2CH3 CH2CH3 -
LSM-775 (lysergic acid morpholide) 4314-63-0 H CH3 CH2CH2-O-CH2CH2 -
LPD-824 (lysergic acid pyrrolidide) 2385-87-7 H CH3 (CH2)4 -
LSD-Pip (lysergic acid piperidide) 50485-23-9 H CH3 (CH2)5 -
LSD-Azepane (lysergic acid azepane)[48][49][50] H CH3 (CH2)6 -
Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) 470666-31-0 H CH3 CH2(CHCH3)2CH2 -
2-Bromo-LSD (BOL-148; bromolysergide) 478-84-2 H CH3 CH2CH3 CH2CH3 2-Br
1P-BOL-148 (1-propionyl-2-bromo-LSD) COCH2CH3 CH3 CH2CH3 CH2CH3 2-Br
12-Hydroxy-LSD (12-OH-LSD) 60573-89-9 H CH3 CH2CH3 CH2CH3 12-OH
12-Methoxy-LSD (12-MeO-LSD) 50484-99-6 H CH3 CH2CH3 CH2CH3 12-OMe
13-Fluoro-LSD[51] H CH3 CH2CH3 CH2CH3 13-F
14-Hydroxy-LSD[52] H CH3 CH2CH3 CH2CH3 14-OH
2,3-Dihydro-LSD (2,3-DH-LSD) ? H CH3 CH2CH3 CH2CH3 2,3-Dihydro
9,10-Dihydro-LSD (9,10-DH-LSD) 3031-47-8 H CH3 CH2CH3 CH2CH3 9,10-Dihydro
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See also: List of miscellaneous 5-HT2A receptor agonists
Structure Name Chemical name CAS #
Bromerguride 1,1-diethyl-3-(2-bromo-9,10-didehydro-6-methyl-8α-ergolinyl)urea 83455-48-5
Descarboxylysergic acid 6-methyl-9,10-didehydroergoline 51867-17-5
Disulergine 59032-40-5
Dosergoside[53] N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-6-methylergoline-8-carboxamide 87178-42-5
Ergoline (6aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline 478-88-6
Etisulergine[54] N,N-diethyl-N'-(6-methylergolin-8α-yl)sulfamide 64795-23-9
GYKI-32887 78463-86-2
JRT (7S)-N,N-diethyl-6-methyl-6,9-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,10,12(16),13-pentaene-4-carboxamide ?
Lysergine 9,10-didehydro-6,8β-dimethylergoline 519-10-8
Lysergol (6-methyl-9,10-didehydroergolin-8β-yl)methanol 1413-67-8
Lysergic acid 6-methyl-9,10-didehydroergoline-8β-carboxylic acid 82-58-6
Lergotrile 2-[(6aR,9S,10aR)-5-chloro-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]acetonitrile 36945-03-6
Lisuride 1,1-diethyl-3-(6-methyl-9,10-didehydroergolin-8α-yl)urea 18016-80-3
Proteguride[55][56] 1,1-diethyl-3-(6-n-propyl-8α-ergolinyl)urea ?
Terguride N,N-diethyl-N'-[(8α)-6-methylergolin-8-yl]urea 37686-84-3

See also

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References

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  29. ^ a b Alexander T. Shulgin, Ann Shulgin (1997). "#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". TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press. pp. 490–499. ISBN 978-0-9630096-9-2. OCLC 38503252. 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: [...]
  30. ^ Hofmann A (June 1959). "Psychotomimetic Drugs: Chemical and Pharmacological Aspects" (PDF). Acta Physiol Pharmacol Neerl. 8: 240–258. PMID 13852489.
  31. ^ Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.
  32. ^ Rutschmann J, Stadler PA (1978). "Chemical Background". In Berde B, Schild HO (eds.). Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). Vol. 49. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 29–85. doi:10.1007/978-3-642-66775-6_2. ISBN 978-3-642-66777-0.
  33. ^ a b Mangner TJ (1978). Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides (Ph.D. thesis). University of Michigan. doi:10.7302/11268. Archived from the original on 30 March 2025. Table 1. Human psychotomimetic potencies of LSD analogs. [...]
  34. ^ a b Fanchamps A (1978). "Some Compounds With Hallucinogenic Activity". In Berde B, Schild HO (eds.). Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). Vol. 49. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 567–614. doi:10.1007/978-3-642-66775-6_8. ISBN 978-3-642-66777-0. Archived from the original on 30 March 2025. Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...]
  35. ^ Rothlin E (March 1957). "Lysergic acid diethylamide and related substances". Ann N Y Acad Sci. 66 (3): 668–676. Bibcode:1957NYASA..66..668R. doi:10.1111/j.1749-6632.1957.tb40756.x. PMID 13425249. Archived from the original on 23 March 2025.
  36. ^ Hoffer A (1965). "D-Lysergic Acid Diethylamide (LSD): A Review of its Present Status". Clin Pharmacol Ther. 6 (2): 183–255. doi:10.1002/cpt196562183. PMID 14288188. Archived from the original on 30 March 2025.
  37. ^ Isbell H, Miner EJ, Logan CR (1959). "Relationships of psychotomimetic to anti-serotonin potencies of congeners of lysergic acid diethylamide (LSD-25)". Psychopharmacologia. 1: 20–28. doi:10.1007/BF00408108. PMID 14405872. Archived from the original on 7 April 2022.
  38. ^ Oberlender RA (May 1989). "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens". Purdue e-Pubs. Purdue University. Table 2. Relative potency values for lysergic acid amides. [...]
  39. ^ a b Kumbar M, Sankar DV (July 1973). "Quantum chemical studies on drug actions. 3. Correlation of hallucinogenic and anti-serotonin activity of lysergic acid derivatives with quantum chemical data". Res Commun Chem Pathol Pharmacol. 6 (1): 65–100. PMID 4734018. Archived from the original on 29 March 2025. Table I – Structure and Several Biological Activities of Lysergates [...]
  40. ^ a b Sankar DV, Kumbar M (February 1974). "Quantum chemical studies on drug actions. IV. Correlation of substituent structures and anti-serotonin activity in lysergamide series". Res Commun Chem Pathol Pharmacol. 7 (2): 259–274. PMID 4818373. Archived from the original on 29 March 2025. Table I – Quantum Chemical Data on Lysergamide Derivatives
  41. ^ Abramson HA (1959). "Lysergic Acid Diethylamide (LSD-25): XXIX. The Response Index as a Measure of Threshold Activity of Psychotropic Drugs in Man". The Journal of Psychology. 48 (1): 65–78. doi:10.1080/00223980.1959.9916341. ISSN 0022-3980. Archived from the original on 30 March 2025.
  42. ^ Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167: 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Table 4 Human potency data for selected hallucinogens. [...]
  43. ^ Tittarelli R, Mannocchi G, Pantano F, Romolo FS (January 2015). "Recreational use, analysis and toxicity of tryptamines". Curr Neuropharmacol. 13 (1): 26–46. doi:10.2174/1570159X13666141210222409. PMC 4462041. PMID 26074742. 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].
  44. ^ Chen W, De Wit-Bos L (2020). Risk assessment of Argyreia nervosa (PDF) (Report). doi:10.21945/rivm-2019-0210.
  45. ^ Bigwood J, Ott J, Thompson C, Neely P (1979). "Entheogenic effects of ergonovine". J Psychedelic Drugs. 11 (1–2): 147–149. doi:10.1080/02791072.1979.10472099. PMID 522166. Archived from the original on 28 March 2025. 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.
  46. ^ Gorodetzky CW, Isbell H (September 1964). "A comparison of 2,3-dihydro-lysergic acid diethylamide with LSD-25". Psychopharmacologia. 6 (3): 229–233. doi:10.1007/BF00404013. PMID 5319153.
  47. ^ Okada Y, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Kanamori T, et al. (June 2024). "Synthesis and analytical characterization of 1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD)". Drug Testing and Analysis. doi:10.1002/dta.3747. PMID 38922764.
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  49. ^ Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X. TABLE 1 5-HT2A Receptor Affinity and Functional Effects of Selected Lysergamides [...]
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  55. ^ "Тергурид и протергурид отдельно и в комбинации в качестве средства при изготовлении лекарства для лечения постоянной боли и фармацевтическая композиция, изготовленная с их помощью" [TERGURIDE AND PROTEGURIDE, SEPARATELY AND IN COMBINATION, AS A MEANS FOR THE PRODUCTION OF MEDICINE FOR TREATMENT OF PERMANENT PAIN AND PHARMACEUTICAL COMPOSITION, PRODUCED WITH THEIR HELP]. Google Patents. 21 March 2007. Retrieved 18 April 2025.
  56. ^ "Pharmaceutical composition having a cystostatic activity". Google Patents. 29 April 1983. Retrieved 18 April 2025.
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