Lysergamides Explained

Amides of lysergic acid are collectively known as lysergamides, and include a number of compounds with potent agonist and/or antagonist activity at various serotonin and dopamine receptors. Lysergamides contain an embedded tryptamine structure, and as a result can produce similar, often psychedelic, effects to those of the true tryptamines. [1] [2] [3] [4] [5] [6] [7] [8] [9] [10] [11] [12] [13] [14] [15]

Lysergamides, tabulated by structure
Structure Name CAS number R1 R6 R2 R3 Other
478-94-4 H H H -
4238-84-0 H CH3 CH3 CH3 -
Ergometrine (Ergonovine) 60-79-7 H CH3 CH(CH3)CH2OH H -
113-15-5 H CH3 -- C17H18N2O4 -
113-42-8 H CH3 CH(CH2CH3)CH2OH H -
361-37-5 CH3 CH3 CH(CH2CH3)CH2OH H -
121588-75-8 CH(CH3)2 CH3 H -
137328-52-0 CH(CH3)2 CH3 C5H8OH H -
81409-90-7 H H2C=CH-CH2 CONHCH2CH3 CH2CH2CH2N(CH3)2 -
478-99-9 H CH3 H -
LAiP H CH3 CH(CH3)2 H -
LAtB H CH3 C(CH3)3 H -
LAcB H CH3 (CH2)4 H -
H CH3 (CH2)5 H -
137765-82-3 H CH3 CH(CH3)CH2CH3 H -
H CH3 CH(CH2CH3)CH2CH3 H -
H CH3 AllylH2C=CH-CH2 -
100768-08-9 H CH3 CH3 -
H CH3 CH(CH3)2 CH2CH3 -
H CH3 C3H5 CH2CH3 -
H CH3 CH2CF3 CH2CH3 -
40158-98-3 H CH3 CH2CH2CH3 CH3 -
EPLA H CH2CH3 CH2CH2CH3 CH3 -
50-37-3 H CH3 CH2CH3 CH2CH3 -
65527-62-0 H CH2CH3 CH2CH3 CH2CH3 -
H CH2CH3 CH2CH3 -
65527-61-9 H H2C=CH-CH2 CH2CH3 CH2CH3 -
65527-63-1 H CH2CH3 CH2CH3 -
H CH(CH3)2 CH2CH3 CH2CH3 -
CYP-LAD[16] H CH2CH3 CH2CH3 -
96930-87-9 H CH2CH3 CH2CH3 -
FLUORETH-LAD[17] H CH2CH2F CH2CH3 CH2CH3 -
3270-02-8 CH3 CH2CH3 CH2CH3 -
2349358-81-0 CH3 CH2CH3 CH2CH3 -
2349376-12-9COCH2CH2CH3CH3CH2CH3CH2CH3 -
CO(CH2)3CH3 CH3 CH2CH3 CH2CH3 -
CO(CH2)10CH3 CH3 CH2CH3 CH2CH3 -
1cP-LSD[18] COC3H5 CH3 CH2CH3 CH2CH3 -
COC4H5(CH3)2 CH3 CH2CH3 CH2CH3 -
COC4H3S CH3 CH2CH3 CH2CH3 -
1S-LSD CO(CH2)2Si(CH3)3 CH3 CH2CH3 CH2CH3 -
COCH2CH3 H2C=CH-CH2 CH2CH3 CH2CH3 -
COC3H5 H2C=CH-CH2 CH2CH3 CH2CH3 -
1T-AL-LAD[19] COC4H3S H2C=CH-CH2 CH2CH3 CH2CH3 -
COCH2CH3 CH2CH3 CH2CH3 CH2CH3 -
1P-MIPLA COCH2CH3 CH3 CH3 -
4238-85-1 CH3 CH3 CH2CH3 CH2CH3 -
4314-63-0 H CH3 -
2385-87-7 H CH3 -
50485-23-9 H CH3 -
LSD-Azapane H CH3 (CH2)6 -
470666-31-0 H CH3 CH2(CHCH3)2CH2 -
478-84-2 H CH3 CH2CH3 CH2CH3 2-Br
12-Methoxy-LSD[20] 50484-99-6 H CH3 CH2CH3 CH2CH3 12-OMe
13-Fluoro-LSD[21] H CH3 CH2CH3 CH2CH3 13-F
14-Hydroxy-LSD[22] H CH3 CH2CH3 CH2CH3 14-OH

See also

Notes and References

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  2. US . 2997470 . patent . LYSERGIC ACID AMIDES . 1956-03-05 . 1961-08-22 . Pioch RP .
  3. Hoffman AJ, Nichols DE . Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives . Journal of Medicinal Chemistry . 28 . 9 . 1252–1255 . September 1985 . 4032428 . 10.1021/jm00147a022 .
  4. Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE . Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives . Pharmacology, Biochemistry, and Behavior . 47 . 3 . 667–673 . March 1994 . 8208787 . 10.1016/0091-3057(94)90172-4 . 16490010 .
  5. Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB . LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors . Psychopharmacology . 118 . 4 . 401–409 . April 1995 . 7568626 . 10.1007/BF02245940 . 21484356 .
  6. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM . Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD) . Journal of Medicinal Chemistry . 45 . 19 . 4344–4349 . September 2002 . 12213075 . 10.1021/jm020153s .
  7. Schiff PL . Ergot and its alkaloids . American Journal of Pharmaceutical Education . 70 . 5 . 98 . October 2006 . 17149427 . 10.5688/aj700598 . 1637017 .
  8. Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A . The pharmacology of lysergic acid diethylamide: a review . CNS Neuroscience & Therapeutics . 2008 . 14 . 4 . 295–314 . 19040555 . 10.1111/j.1755-5949.2008.00059.x . 6494066 .
  9. Nichols DE . Chemistry and Structure-Activity Relationships of Psychedelics . Current Topics in Behavioral Neurosciences . 2017 . 36 . 1–43 . 28401524 . 10.1007/7854_2017_475 . 978-3-662-55878-2 .
  10. Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Hoang K, Wallach J, Halberstadt AL . Return of the lysergamides. Part I: Analytical and behavioural characterization of 1-propionyl-d-lysergic acid diethylamide (1P-LSD) . Drug Testing and Analysis . 8 . 9 . 891–902 . September 2016 . 26456305 . 10.1002/dta.1884 . 4829483 .
  11. Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, Burrow TE, Chapman SJ, Stratford A, Nichols DE, Halberstadt AL . 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) . Drug Testing and Analysis . 9 . 1 . 38–50 . January 2017 . 27265891 . 10.1002/dta.1985 . 5411264 .
  12. Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Stratford A, Nichols DE, Halberstadt AL . 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) . Drug Testing and Analysis . 9 . 10 . 1641–1649 . October 2017 . 28342178 . 10.1002/dta.2196 . 6230477 .
  13. Brandt SD, Kavanagh PV, Twamley B, Westphal F, Elliott SP, Wallach J, Stratford A, Klein LM, McCorvy JD, Nichols DE, Halberstadt AL . Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775) . Drug Testing and Analysis . 10 . 2 . 310–322 . February 2018 . 28585392 . 10.1002/dta.2222 . 6230476 .
  14. Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, Wallach J, Halberstadt AL . Return of the lysergamides. Part V: Analytical and behavioural characterization of 1-butanoyl-d-lysergic acid diethylamide (1B-LSD) . Drug Testing and Analysis . 11 . 8 . 1122–1133 . August 2019 . 31083768 . 10.1002/dta.2613 . 6899222 .
  15. Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, Nichols DE, Brandt SD . Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA) . Psychopharmacology . 236 . 2 . 799–808 . February 2019 . 30298278 . 10.1007/s00213-018-5055-9 . 6848745 .
  16. https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2022226408 Kruegel AC. Novel Ergolines and Methods of Treating Mood Disorders. Patent WO 2022/226408
  17. Improved Method for the Production of Lysergic Acid Diethylamide (LSD) and Novel Derivatives thereof.. Grill M . WO . 2022/008627 .
  18. Brandt SD, Kavanagh PV, Westphal F, Stratford A, Odland AU, Klein AK, Dowling G, Dempster NM, Wallach J, Passie T, Halberstadt AL . Return of the lysergamides. Part VI: Analytical and behavioural characterization of 1-cyclopropanoyl-d-lysergic acid diethylamide (1CP-LSD) . Drug Testing and Analysis . 12 . 6 . 812–826 . June 2020 . 32180350 . 10.1002/dta.2789 . 9191646 .
  19. Okada Y, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Kanamori T, Iwata YT . Synthesis and analytical characterization of 1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD) . Drug Testing and Analysis . June 2024 . 38922764 . 10.1002/dta.3747 .
  20. Usdin E, Efron DH. Psychotropic Drugs and Related Compounds. (1972)
  21. Ergoline-like compounds for promoting neural plasticity . Olson DE, et al. . WO . 2021/076572.
  22. Libânio Osório Marta RF . Metabolism of lysergic acid diethylamide (LSD): an update . Drug Metabolism Reviews . 51 . 3 . 378–387 . August 2019 . 31266388 . 10.1080/03602532.2019.1638931 .

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