Chemistry:Lysergamides

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Short description: Class of chemical compounds

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
Structure Name CAS number R1 R6 R2 R3 Other
Ergine.svg LSA / LAA 478-94-4 H CH3 H H -
DAM-57.svg DAM-57 4238-84-0 H CH3 CH3 CH3 -
Ergonovine-skeletal.svg Ergometrine (Ergonovine) 60-79-7 H CH3 CH(CH3)CH2OH H -
Ergotamine-skeletal.svg Ergotamine 113-15-5 H CH3 -- C17H18N2O4 -
Methylergometrin.svg Methergine 113-42-8 H CH3 CH(CH2CH3)CH2OH H -
Methylsergide Structural Formula V1.svg Methysergide 361-37-5 CH3 CH3 CH(CH2CH3)CH2OH H -
Amesergide.svg Amesergide 121588-75-8 CH(CH3)2 CH3 C6H11 H -
LY-215840 structure.png LY-215840 137328-52-0 CH(CH3)2 CH3 C5H8OH H -
Cabergoline.svg Cabergoline 81409-90-7 H H2C=CH-CH2 CONHCH2CH3 CH2CH2CH2N(CH3)2 -
LAE-32.svg LAE-32 478-99-9 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 Cepentil H CH3 (CH2)5 H -
SBULSD.svg LSB 137765-82-3 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 100768-08-9 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 LAMPA 40158-98-3 H CH3 CH2CH2CH3 CH3 -
EPLA structure.png EPLA H CH2CH3 CH2CH2CH3 CH3 -
LSD structural formulae v.1.png LSD / LAD 50-37-3 H CH3 CH2CH3 CH2CH3 -
ETH-LAD structure.png ETH-LAD 65527-62-0 H CH2CH3 CH2CH3 CH2CH3 -
PARGY-LAD.svg PARGY-LAD H HC≡C−CH2 CH2CH3 CH2CH3 -
AL-LAD structure.svg AL-LAD 65527-61-9 H H2C=CH-CH2 CH2CH3 CH2CH3 -
PRO-LAD structure.png PRO-LAD 65527-63-1 H CH2CH2CH3 CH2CH3 CH2CH3 -
IP-LAD structure.png IP-LAD H CH(CH3)2 CH2CH3 CH2CH3 -
CYP-LAD.svg CYP-LAD[16] H C3H5 CH2CH3 CH2CH3 -
BU-LAD-2D-skeletal.svg BU-LAD 96930-87-9 H CH2CH2CH2CH3 CH2CH3 CH2CH3 -
FLUOROETH-LAD structure.png FLUORETH-LAD[17] H CH2CH2F CH2CH3 CH2CH3 -
ALD-52 image.svg ALD-52 3270-02-8 COCH3 CH3 CH2CH3 CH2CH3 -
1P-LSD Structural Formulae V.1.svg 1P-LSD 2349358-81-0 COCH2CH3 CH3 CH2CH3 CH2CH3 -
1B-LSD Structure.svg 1B-LSD 2349376-12-9 COCH2CH2CH3 CH3 CH2CH3 CH2CH3 -
1V-LSD structure.svg 1V-LSD CO(CH2)3CH3 CH3 CH2CH3 CH2CH3 -
1CP-LSD structure.svg 1cP-LSD[18] COC3H5 CH3 CH2CH3 CH2CH3 -
1D-LSD.svg 1D-LSD COC4H5(CH3)2 CH3 CH2CH3 CH2CH3 -
1P-AL-LAD structure.png 1P-AL-LAD COCH2CH3 H2C=CH-CH2 CH2CH3 CH2CH3 -
1CP-AL-LAD structure.png 1cP-AL-LAD COC3H5 H2C=CH-CH2 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 4238-85-1 CH3 CH3 CH2CH3 CH2CH3 -
LSM-775.svg LSM-775 4314-63-0 H CH3 CH2CH2-O-CH2CH2 -
LPD-824-2d-skeletal.svg LPD-824 2385-87-7 H CH3 (CH2)4 -
LSD-Pip.svg LSD-Pip 50485-23-9 H CH3 (CH2)5 -
LSD Azapane structure.png LSD-Azapane H CH3 (CH2)6 -
LSD-azetidine.svg LA-SS-Az 470666-31-0 H CH3 CH2(CHCH3)2CH2 -
2-bromo-LSD structure.svg 2-Bromo-LSD 478-84-2 H CH3 CH2CH3 CH2CH3 2-Br
12-MeO-LSD structure.png 12-Methoxy-LSD[19] 50484-99-6 H CH3 CH2CH3 CH2CH3 12-OMe
13-F-LSD structure.png 13-Fluoro-LSD[20] H CH3 CH2CH3 CH2CH3 13-F
14-HO-LSD structure.png 14-Hydroxy-LSD[21] H CH3 CH2CH3 CH2CH3 14-OH

See also

References

  1. ↑ "Psychotomimetic drugs; chemical and pharmacological aspects". Acta Physiologica et Pharmacologica Neerlandica 8: 240–58. June 1959. PMID 13852489. 
  2. ↑ Pioch RP, "LYSERGIC ACID AMIDES", US patent 2997470, published 1956-03-05, issued 1961-08-22
  3. ↑ "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. September 1985. doi:10.1021/jm00147a022. PMID 4032428. 
  4. ↑ "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". Pharmacology, Biochemistry, and Behavior 47 (3): 667–673. March 1994. doi:10.1016/0091-3057(94)90172-4. PMID 8208787. 
  5. ↑ "LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors". Psychopharmacology 118 (4): 401–409. April 1995. doi:10.1007/BF02245940. PMID 7568626. 
  6. ↑ "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. September 2002. doi:10.1021/jm020153s. PMID 12213075. 
  7. ↑ "Ergot and its alkaloids". American Journal of Pharmaceutical Education 70 (5): 98. October 2006. doi:10.5688/aj700598. PMID 17149427. 
  8. ↑ "The pharmacology of lysergic acid diethylamide: a review". CNS Neuroscience & Therapeutics 14 (4): 295–314. 2008. doi:10.1111/j.1755-5949.2008.00059.x. PMID 19040555. 
  9. ↑ "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences 36: 1–43. 2017. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524. 
  10. ↑ "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. September 2016. doi:10.1002/dta.1884. PMID 26456305. 
  11. ↑ "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. January 2017. doi:10.1002/dta.1985. PMID 27265891. 
  12. ↑ "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. October 2017. doi:10.1002/dta.2196. PMID 28342178. 
  13. ↑ "Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775)". Drug Testing and Analysis 10 (2): 310–322. February 2018. doi:10.1002/dta.2222. PMID 28585392. 
  14. ↑ "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. August 2019. doi:10.1002/dta.2613. PMID 31083768. 
  15. ↑ "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology 236 (2): 799–808. February 2019. doi:10.1007/s00213-018-5055-9. PMID 30298278. 
  16. ↑ Kruegel AC. Novel Ergolines and Methods of Treating Mood Disorders. Patent WO 2022/226408
  17. ↑ Grill M, "Improved Method for the Production of Lysergic Acid Diethylamide (LSD) and Novel Derivatives thereof.", WO patent 2022/008627
  18. ↑ "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. June 2020. doi:10.1002/dta.2789. PMID 32180350. 
  19. ↑ Usdin E, Efron DH. Psychotropic Drugs and Related Compounds. (1972) ASIN B002X3CDIY
  20. ↑ Olson DE, et al., "Ergoline-like compounds for promoting neural plasticity", WO patent 2021/076572
  21. ↑ "Metabolism of lysergic acid diethylamide (LSD): an update". Drug Metabolism Reviews 51 (3): 378–387. August 2019. doi:10.1080/03602532.2019.1638931. PMID 31266388. 



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