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
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 H C3H5 CH2CH3 CH2CH3 -
BU-LAD-2D-skeletal.svg
BU-LAD 96930-87-9 H CH2CH2CH2CH3 CH2CH3 CH2CH3 -
FLUOROETH-LAD structure.png
FLUOROETH-LAD[16] 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[17] COC3H5 CH3 CH2CH3 CH2CH3 -
1D-LSD.svg
1D-LSD COC4H5(CH3)2 CH3 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[18] 50484-99-6 H CH3 CH2CH3 CH2CH3 12-OMe
13-F-LSD structure.png
13-Fluoro-LSD[19] H CH3 CH2CH3 CH2CH3 13-F
14-HO-LSD structure.png
14-Hydroxy-LSD[20] H CH3 CH2CH3 CH2CH3 14-OH

See also

References

  1. ^ Hofmann A (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects". Acta Physiologica et Pharmacologica Neerlandica. 8: 240–58. PMID 13852489.
  2. ^ US patent 2997470, Pioch RP, "LYSERGIC ACID AMIDES", published 1956-03-05, issued 1961-08-22 
  3. ^ Hoffman AJ, Nichols DE (September 1985). "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. doi:10.1021/jm00147a022. PMID 4032428.
  4. ^ Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE (March 1994). "Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives". Pharmacology, Biochemistry, and Behavior. 47 (3): 667–673. doi:10.1016/0091-3057(94)90172-4. PMID 8208787.
  5. ^ Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB (April 1995). "LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors". Psychopharmacology. 118 (4): 401–409. doi:10.1007/BF02245940. PMID 7568626.
  6. ^ Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM (September 2002). "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. doi:10.1021/jm020153s. PMID 12213075.
  7. ^ Schiff PL (October 2006). "Ergot and its alkaloids". American Journal of Pharmaceutical Education. 70 (5): 98. doi:10.5688/aj700598. PMID 17149427.
  8. ^ Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A. "The pharmacology of lysergic acid diethylamide: a review". CNS Neuroscience & Therapeutics. 14 (4): 295–314. doi:10.1111/j.1755-5949.2008.00059.x. PMID 19040555.
  9. ^ Nichols DE. "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. 36: 1–43. doi:10.1007/7854_2017_475. PMID 28401524.
  10. ^ Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Hoang K, et al. (September 2016). "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. doi:10.1002/dta.1884. PMID 26456305.
  11. ^ Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, et al. (January 2017). "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. doi:10.1002/dta.1985. PMID 27265891.
  12. ^ Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Stratford A, et al. (October 2017). "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. doi:10.1002/dta.2196. PMID 28342178.
  13. ^ Brandt SD, Kavanagh PV, Twamley B, Westphal F, Elliott SP, Wallach J, et al. (February 2018). "Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775)". Drug Testing and Analysis. 10 (2): 310–322. doi:10.1002/dta.2222. PMID 28585392.
  14. ^ Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, et al. (August 2019). "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. doi:10.1002/dta.2613. PMID 31083768.
  15. ^ Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, et al. (February 2019). "Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA)". Psychopharmacology. 236 (2): 799–808. doi:10.1007/s00213-018-5055-9. PMID 30298278.
  16. ^ WO 2022/008627, Grill M, "Improved Method for the Production of Lysergic Acid Diethylamide (LSD) and Novel Derivatives thereof." 
  17. ^ Brandt SD, Kavanagh PV, Westphal F, Stratford A, Odland AU, Klein AK, et al. (June 2020). "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. doi:10.1002/dta.2789. PMID 32180350.
  18. ^ Usdin E, Efron DH. Psychotropic Drugs and Related Compounds. (1972) ASIN B002X3CDIY
  19. ^ WO 2021/076572, Olson DE, et al., "Ergoline-like compounds for promoting neural plasticity" 
  20. ^ Libânio Osório Marta RF (August 2019). "Metabolism of lysergic acid diethylamide (LSD): an update". Drug Metabolism Reviews. 51 (3): 378–387. doi:10.1080/03602532.2019.1638931. PMID 31266388.