Lysergamides

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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][16][17]

General structure of Lysergamides
Lysergamides, tabulated by structure
Structure Name R1 R6 R2 R3
Ergine.svg LSA / LAA H CH3 H H
DAM-57.svg DAM-57 H CH3 CH3 CH3
Ergonovine-skeletal.svg Ergometrine (Ergonovine) H CH3 CH(CH3)CH2OH H
Ergotamine-skeletal.svg Ergotamine H CH3 -- C17H18N2O4
Methylergometrin.svg Methergine H CH3 CH(CH2CH3)CH2OH H
Methylsergide Structural Formula V1.svg Methysergide CH3 CH3 CH(CH2CH3)CH2OH H
Amesergide.svg Amesergide CH(CH3)2 CH3 C6H11 H
LY-215840 structure.png LY-215840 CH(CH3)2 CH3 C5H8OH H
Cabergoline.svg Cabergoline H H2C=CH-CH2 CONHCH2CH3 CH2CH2CH2N(CH3)2
LAE-32.svg LAE-32 H CH3 CH2CH3 H
LAiP structure.png LAiP H CH3 CH(CH3)2 H
LAtB structure.png LAtB H CH3 C(CH3)3 H
LAcB structure.png LAcB H CH3 (CH2)4 H
LAcPe structure.png LAcPe H CH3 (CH2)5 H
SBULSD.svg LSB H CH3 CH(CH3)CH2CH3 H
LS3P structure.png LSP H CH3 CH(CH2CH3)CH2CH3 H
DALAD.svg DAL H CH3 H2C=CH-CH2 H2C=CH-CH2
MIPLSD.svg MIPLA H CH3 CH(CH3)2 CH3
EiPLA structure.png EIPLA H CH3 CH(CH3)2 CH2CH3
ECPLA structure.png ECPLA H CH3 C3H5 CH2CH3
ETFELA structure.png ETFELA H CH3 CH2CF3 CH2CH3
MPLA structure.png MPLA H CH3 CH2CH2CH3 CH3
LSD structural formulae v.1.png LSD / LAD H CH3 CH2CH3 CH2CH3
ETH-LAD structure.png ETH-LAD H CH2CH3 CH2CH3 CH2CH3
PARGY-LAD.svg PARGY-LAD H HC≡C−CH2 CH2CH3 CH2CH3
AL-LAD structure.svg AL-LAD H H2C=CH-CH2 CH2CH3 CH2CH3
PRO-LAD structure.png PRO-LAD H CH2CH2CH3 CH2CH3 CH2CH3
IP-LAD structure.png IP-LAD H CH(CH3)2 CH2CH3 CH2CH3
CYP-LAD.svg CYP-LAD H C3H5 CH2CH3 CH2CH3
BU-LAD-2D-skeletal.svg BU-LAD H CH2CH2CH2CH3 CH2CH3 CH2CH3
ALD-52 image.svg ALD-52 COCH3 CH3 CH2CH3 CH2CH3
1P-LSD Structural Formulae V.1.svg 1P-LSD COCH2CH3 CH3 CH2CH3 CH2CH3
1B-LSD structure.png 1B-LSD COCH2CH2CH3 CH3 CH2CH3 CH2CH3
1cP-LSD structure.png 1cP-LSD COC3H5 CH3 CH2CH3 CH2CH3
1P-ETH-LAD Structural Formulae V2.svg 1P-ETH-LAD COCH2CH3 CH2CH3 CH2CH3 CH2CH3
1P-MIPLA structure.png 1P-MIPLA COCH2CH3 CH3 CH(CH3)2 CH3
MLD-41.svg MLD-41 CH3 CH3 CH2CH3 CH2CH3
LSM-775.svg LSM-775 H CH3 CH2CH2-O-CH2CH2
LPD-824-2d-skeletal.svg LPD-824 H CH3 CH2CH2

CH2CH2

LSD-Pip.svg LSD-Pip H CH3 CH2CH2

CH2CH2CH2

LSD Azapane structure.png LSD-Azapane H CH3 CH2CH2CH2

CH2CH2CH2

LSD-azetidine.svg LA-SS-Az H CH3 CH2(CHCH3)2CH2

See also[edit]

References[edit]

  1. ^ Hofmann A. Psychotomimetic Drugs: Chemical and Pharmacological Aspects. Acta. Physiol. Pharmacol. Neerlandica. 1959;8:240-258.
  2. ^ US patent 2997470, Richard P. Pioch, "LYSERGIC ACID AMIDES", published 1956-03-05, issued 1961-08-22 
  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. J Med Chem. 1985 Sep;28(9):1252-5. PMID 4032428 doi:10.1021/jm00147a022
  4. ^ Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE. Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives. Pharmacol Biochem Behav. 1994 Mar;47(3):667-73. PMID 8208787
  5. ^ Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB. LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors. Psychopharmacology (Berl). 1995 Apr;118(4):401-9. PMID 7568626
  6. ^ David E. Nichols. LSD and Its Lysergamide Cousins. The Heffter Review of Psychedelic Research. 2001;2:80-87.
  7. ^ 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). J Med Chem. 2002 Sep 12;45(19):4344-9. PMID 12213075
  8. ^ Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. PMID 17149427
  9. ^ Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A. The pharmacology of lysergic acid diethylamide: a review. CNS Neurosci Ther. 2008 Winter;14(4):295-314. doi:10.1111/j.1755-5949.2008.00059.x PMID 19040555
  10. ^ Nichols DE. Structure-activity relationships of serotonin 5-HT2A agonists. WIREs Membr. Transp. Signal, 2012; 1(5): 559-579. doi:10.1002/wmts.42
  11. ^ Nichols DE. Chemistry and Structure-Activity Relationships of Psychedelics. Curr Top Behav Neurosci. 2018;36:1-43. doi:10.1007/7854_2017_475 PMID 28401524
  12. ^ 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 Test Anal. 2016 Sep;8(9):891-902. doi:10.1002/dta.1884 PMID 26456305
  13. ^ 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 Test Anal. 2017 Jan;9(1):38-50. doi:10.1002/dta.1985 PMID 27265891
  14. ^ 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 Test Anal. 2017 Oct;9(10):1641-1649. doi:10.1002/dta.2196 PMID 28342178
  15. ^ 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 Test Anal. 2018 Feb;10(2):310-322. doi:10.1002/dta.2222 PMID 28585392
  16. ^ 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 Test Anal. 2019 Aug;11(8):1122-1133. doi:10.1002/dta.2613 PMID 31083768
  17. ^ 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 (Berl). 2019 Feb;236(2):799-808. doi:10.1007/s00213-018-5055-9 PMID 30298278