Lysergamides

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
	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 CH2CH2
	LSD-Pip	H	CH3	CH2CH2 CH2CH2CH2
	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

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
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 Test Anal. 2020 Mar 16. doi:10.1002/dta.2789 PMID 32180350