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.[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]

General structure of Lysergamides
Lysergamides, tabulated by structure
StructureNameCAS numberR1R6R2R3Other
LSA / LAA478-94-4HCH3HH-
DAM-574238-84-0HCH3CH3CH3-
Ergometrine (Ergonovine)60-79-7HCH3CH(CH3)CH2OHH-
Ergotamine113-15-5HCH3--C17H18N2O4-
Methergine113-42-8HCH3CH(CH2CH3)CH2OHH-
Methysergide361-37-5CH3CH3CH(CH2CH3)CH2OHH-
Amesergide121588-75-8CH(CH3)2CH3C6H11H-
LY-215840137328-52-0CH(CH3)2CH3C5H8OHH-
Cabergoline81409-90-7HH2C=CH-CH2CONHCH2CH3CH2CH2CH2N(CH3)2-
LAE-32478-99-9HCH3CH2CH3H-
LAiPHCH3CH(CH3)2H-
LAtBHCH3C(CH3)3H-
LAcBHCH3(CH2)4H-
CepentilHCH3(CH2)5H-
LSB137765-82-3HCH3CH(CH3)CH2CH3H-
LSPHCH3CH(CH2CH3)CH2CH3H-
DALHCH3H2C=CH-CH2H2C=CH-CH2-
MIPLA100768-08-9HCH3CH(CH3)2CH3-
EIPLAHCH3CH(CH3)2CH2CH3-
ECPLAHCH3C3H5CH2CH3-
ETFELAHCH3CH2CF3CH2CH3-
LAMPA40158-98-3HCH3CH2CH2CH3CH3-
EPLAHCH2CH3CH2CH2CH3CH3-
LSD / LAD50-37-3HCH3CH2CH3CH2CH3-
ETH-LAD65527-62-0HCH2CH3CH2CH3CH2CH3-
PARGY-LADHHC≡C−CH2CH2CH3CH2CH3-
AL-LAD65527-61-9HH2C=CH-CH2CH2CH3CH2CH3-
PRO-LAD65527-63-1HCH2CH2CH3CH2CH3CH2CH3-
IP-LADHCH(CH3)2CH2CH3CH2CH3-
CYP-LAD[16]HC3H5CH2CH3CH2CH3-
BU-LAD96930-87-9HCH2CH2CH2CH3CH2CH3CH2CH3-
FLUORETH-LAD[17]HCH2CH2FCH2CH3CH2CH3-
ALD-523270-02-8COCH3CH3CH2CH3CH2CH3-
1P-LSD2349358-81-0COCH2CH3CH3CH2CH3CH2CH3-
1B-LSD2349376-12-9 COCH2CH2CH3 CH3 CH2CH3 CH2CH3-
1V-LSDCO(CH2)3CH3CH3CH2CH3CH2CH3-
1cP-LSD[18]COC3H5CH3CH2CH3CH2CH3-
1D-LSDCOC4H5(CH3)2CH3CH2CH3CH2CH3-
1P-AL-LADCOCH2CH3H2C=CH-CH2CH2CH3CH2CH3-
1cP-AL-LADCOC3H5H2C=CH-CH2CH2CH3CH2CH3-
1P-ETH-LADCOCH2CH3CH2CH3CH2CH3CH2CH3-
1P-MIPLACOCH2CH3CH3CH(CH3)2CH3-
MLD-414238-85-1CH3CH3CH2CH3CH2CH3-
LSM-7754314-63-0HCH3CH2CH2-O-CH2CH2-
LPD-8242385-87-7HCH3(CH2)4-
LSD-Pip50485-23-9HCH3(CH2)5-
LSD-AzapaneHCH3(CH2)6-
LA-SS-Az470666-31-0HCH3CH2(CHCH3)2CH2-
2-Bromo-LSD478-84-2HCH3CH2CH3CH2CH32-Br
12-Methoxy-LSD[19]50484-99-6HCH3CH2CH3CH2CH312-OMe
13-Fluoro-LSD[20]HCH3CH2CH3CH2CH313-F
14-Hydroxy-LSD[21]HCH3CH2CH3CH2CH314-OH

See also

References

  1. ↑ Hofmann A (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects". Acta Physiologica et Pharmacologica Neerlandica. 8: 240–58. PMID 13852489.
  2. ↑ US patent 2997470, Pioch RP, "LYSERGIC ACID AMIDES", published 1956-03-05, issued 1961-08-22
  3. ↑ Hoffman AJ, Nichols DE (September 1985). "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. doi:10.1021/jm00147a022. PMID 4032428.
  4. ↑ Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE (March 1994). "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". Pharmacology, Biochemistry, and Behavior. 47 (3): 667–673. doi:10.1016/0091-3057(94)90172-4. PMID 8208787. S2CID 16490010.
  5. ↑ Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB (April 1995). "LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors". Psychopharmacology. 118 (4): 401–409. doi:10.1007/BF02245940. PMID 7568626. S2CID 21484356.
  6. ↑ Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM (September 2002). "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. doi:10.1021/jm020153s. PMID 12213075.
  7. ↑ Schiff PL (October 2006). "Ergot and its alkaloids". American Journal of Pharmaceutical Education. 70 (5): 98. doi:10.5688/aj700598. PMC 1637017. PMID 17149427.
  8. ↑ Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A (2008). "The pharmacology of lysergic acid diethylamide: a review". CNS Neuroscience & Therapeutics. 14 (4): 295–314. doi:10.1111/j.1755-5949.2008.00059.x. PMC 6494066. PMID 19040555.
  9. ↑ Nichols DE (2017). "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. 36: 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.
  10. ↑ Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Hoang K, et al. (September 2016). "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. doi:10.1002/dta.1884. PMC 4829483. PMID 26456305.
  11. ↑ Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, et al. (January 2017). "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. doi:10.1002/dta.1985. PMC 5411264. PMID 27265891.
  12. ↑ Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Stratford A, et al. (October 2017). "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. doi:10.1002/dta.2196. PMC 6230477. PMID 28342178.
  13. ↑ Brandt SD, Kavanagh PV, Twamley B, Westphal F, Elliott SP, Wallach J, et al. (February 2018). "Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775)". Drug Testing and Analysis. 10 (2): 310–322. doi:10.1002/dta.2222. PMC 6230476. PMID 28585392.
  14. ↑ Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, et al. (August 2019). "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. doi:10.1002/dta.2613. PMC 6899222. PMID 31083768.
  15. ↑ Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, et al. (February 2019). "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology. 236 (2): 799–808. doi:10.1007/s00213-018-5055-9. PMC 6848745. PMID 30298278.
  16. ↑ Kruegel AC. Novel Ergolines and Methods of Treating Mood Disorders. Patent WO 2022/226408
  17. ↑ WO 2022/008627, Grill M, "Improved Method for the Production of Lysergic Acid Diethylamide (LSD) and Novel Derivatives thereof."
  18. ↑ Brandt SD, Kavanagh PV, Westphal F, Stratford A, Odland AU, Klein AK, et al. (June 2020). "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. doi:10.1002/dta.2789. PMC 9191646. PMID 32180350.
  19. ↑ Usdin E, Efron DH. Psychotropic Drugs and Related Compounds. (1972) ASIN B002X3CDIY
  20. ↑ WO 2021/076572, Olson DE, et al., "Ergoline-like compounds for promoting neural plasticity"
  21. ↑ Libânio Osório Marta RF (August 2019). "Metabolism of lysergic acid diethylamide (LSD): an update". Drug Metabolism Reviews. 51 (3): 378–387. doi:10.1080/03602532.2019.1638931. PMID 31266388.
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