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
| Structure | Name | R1 | R6 | R2 | R3 |
|---|---|---|---|---|---|
) | LSA / LAA | H | CH3 | H | H |
) | DAM-57 | H | CH3 | CH3 | CH3 |
) | Ergometrine (Ergonovine) | H | CH3 | CH(CH3)CH2OH | H |
) | Ergotamine | H | CH3 | -- | C17H18N2O4 |
) | Methergine | H | CH3 | CH(CH2CH3)CH2OH | H |
) | Methysergide | CH3 | CH3 | CH(CH2CH3)CH2OH | H |
) | Amesergide | CH(CH3)2 | CH3 | C6H11 | H |
) | LY-215840 | CH(CH3)2 | CH3 | C5H8OH | H |
) | Cabergoline | H | H2C=CH-CH2 | CONHCH2CH3 | CH2CH2CH2N(CH3)2 |
) | LAE-32 | H | CH3 | CH2CH3 | H |
) | LAiP | H | CH3 | CH(CH3)2 | H |
) | LAtB | H | CH3 | C(CH3)3 | H |
) | LAcB | H | CH3 | (CH2)4 | H |
) | LAcPe | H | CH3 | (CH2)5 | H |
) | LSB | H | CH3 | CH(CH3)CH2CH3 | H |
) | LSP | H | CH3 | CH(CH2CH3)CH2CH3 | H |
) | DAL | H | CH3 | H2C=CH-CH2 | H2C=CH-CH2 |
) | MIPLA | H | CH3 | CH(CH3)2 | CH3 |
) | EIPLA | H | CH3 | CH(CH3)2 | CH2CH3 |
) | ECPLA | H | CH3 | C3H5 | CH2CH3 |
) | ETFELA | H | CH3 | CH2CF3 | CH2CH3 |
) | MPLA | H | CH3 | CH2CH2CH3 | CH3 |
) | LSD / LAD | H | CH3 | CH2CH3 | CH2CH3 |
) | ETH-LAD | H | CH2CH3 | CH2CH3 | CH2CH3 |
) | PARGY-LAD | H | HC≡C−CH2 | CH2CH3 | CH2CH3 |
) | AL-LAD | H | H2C=CH-CH2 | CH2CH3 | CH2CH3 |
) | PRO-LAD | H | CH2CH2CH3 | CH2CH3 | CH2CH3 |
) | IP-LAD | H | CH(CH3)2 | CH2CH3 | CH2CH3 |
) | CYP-LAD | H | C3H5 | CH2CH3 | CH2CH3 |
) | BU-LAD | H | CH2CH2CH2CH3 | CH2CH3 | CH2CH3 |
) | ALD-52 | COCH3 | CH3 | CH2CH3 | CH2CH3 |
) | 1P-LSD | COCH2CH3 | CH3 | CH2CH3 | CH2CH3 |
) | 1B-LSD | COCH2CH2CH3 | CH3 | CH2CH3 | CH2CH3 |
) | 1cP-LSD[18] | COC3H5 | CH3 | CH2CH3 | CH2CH3 |
) | 1P-ETH-LAD | COCH2CH3 | CH2CH3 | CH2CH3 | CH2CH3 |
) | 1P-MIPLA | COCH2CH3 | CH3 | CH(CH3)2 | CH3 |
) | MLD-41 | CH3 | CH3 | CH2CH3 | CH2CH3 |
) | LSM-775 | H | CH3 | CH2CH2-O-CH2CH2 | |
) | LPD-824 | H | CH3 | CH2CH2 | |
) | LSD-Pip | H | CH3 | CH2CH2 | |
) | LSD-Azapane | H | CH3 | CH2CH2CH2 CH2CH2CH2 | |
) | LA-SS-Az | H | CH3 | CH2(CHCH3)2CH2 | |
See also
- Ergoline
- BOL-148
- Bromocriptine
- Fumigaclavine C
- Hydergine
- Lisuride
- Pergolide
References
- ^ Hofmann A. Psychotomimetic Drugs: Chemical and Pharmacological Aspects. Acta. Physiol. Pharmacol. Neerlandica. 1959;8:240-258.
- ^ US patent 2997470, Richard P. Pioch, "LYSERGIC ACID AMIDES", published 1956-03-05, issued 1961-08-22
- ^ 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
- ^ 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
- ^ 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
- ^ David E. Nichols. LSD and Its Lysergamide Cousins. The Heffter Review of Psychedelic Research. 2001;2:80-87.
- ^ 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
- ^ Schiff PL. Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. PMID 17149427
- ^ 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
- ^ Nichols DE. Structure-activity relationships of serotonin 5-HT2A agonists. WIREs Membr. Transp. Signal, 2012; 1(5): 559-579. doi:10.1002/wmts.42
- ^ 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
- ^ 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
- ^ 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
- ^ 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
- ^ 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
- ^ 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
- ^ 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
- ^ 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 Test Anal. 2020 Mar 16. doi:10.1002/dta.2789 PMID 32180350