-as of [13 APRIL 2024]–

__*TYPES*__

Lysergamides

From Wikipedia, the free encyclopediaJump to navigationJump to search

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

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	CH₂CH₂CH₂CH₂CH₂CH₂
LA-SS-Az	H	CH₃	CH₂(CHCH₃)₂CH₂

References[edit]

^ 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

show v t e Hallucinogens

show Pharmacodynamics

show v t e Ergolines

Categories:

Lysergamides

This page was last edited on 9 June 2020, at 13:50 (UTC).
Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.

240-258(in 9 hours)10:40 PMAmerica/New_York1956-03(in 5 hours)05:56 PMAmerica/New_York1252-5(28 minutes ago)12:52 PMAmerica/New_York401-9(5 hours ago)08:01 AMAmerica/New_York1641-1649(in 15 hours)Next day at 04:30 AMAmerica/New_York310-322(12 hours ago)01:32 AMAmerica/New_York1122-1133(in 5 hours)05:55 PMAmerica/New_York13:50 (UTC)(4 hours ago)08:50 AMAmerica/New_York

*👨‍🔬🕵️‍♀️🙇‍♀️*SKETCHES*🙇‍♂️👩‍🔬🕵️‍♂️*

📚📖|/\-*WIKI-LINK*-/\|📖📚

👈👈👈☜*“AMIDES”* ☞ 👉👉👉

💕💝💖💓🖤💙🖤💙🖤💙🖤❤️💚💛🧡❣️💞💔💘❣️🧡💛💚❤️🖤💜🖤💙🖤💙🖤💗💖💝💘

*🌈✨ *TABLE OF CONTENTS* ✨🌷*

🔥🔥🔥🔥🔥🔥🔥*we won the war* 🔥🔥🔥🔥🔥🔥🔥

-lysergamides-

Lysergamides

See also[edit]

References[edit]

Navigation menu

Search

Contribute

Tools

Print/export

In other projects

Languages