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Lysergamides

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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. Lysergamides contain an embedded tryptamine structure, and as a result can produce similar, often psychedelic, effects to those of the true tryptamines. [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
LSA / LAA 478-94-4 H CH3 H H -
DAM-57 4238-84-0 H CH3 CH3 CH3 -
Ergometrine (Ergonovine) 60-79-7 H CH3 CH(CH3)CH2OH H -
Ergotamine 113-15-5 H CH3 -- C17H18N2O4 -
Methergine 113-42-8 H CH3 CH(CH2CH3)CH2OH H -
Methysergide 361-37-5 CH3 CH3 CH(CH2CH3)CH2OH H -
Amesergide 121588-75-8 CH(CH3)2 CH3 C6H11 H -
LY-215840 137328-52-0 CH(CH3)2 CH3 C5H8OH H -
Cabergoline 81409-90-7 H H2C=CH-CH2 CONHCH2CH3 CH2CH2CH2N(CH3)2 -
LAE-32 478-99-9 H CH3 CH2CH3 H -
LAiP H CH3 CH(CH3)2 H -
LAtB H CH3 C(CH3)3 H -
LAcB H CH3 (CH2)4 H -
Cepentil H CH3 (CH2)5 H -
LSB 137765-82-3 H CH3 CH(CH3)CH2CH3 H -
LSP H CH3 CH(CH2CH3)CH2CH3 H -
DAL H CH3 H2C=CH-CH2 H2C=CH-CH2 -
MIPLA 100768-08-9 H CH3 CH(CH3)2 CH3 -
EIPLA H CH3 CH(CH3)2 CH2CH3 -
ECPLA H CH3 C3H5 CH2CH3 -
ETFELA H CH3 CH2CF3 CH2CH3 -
LAMPA 40158-98-3 H CH3 CH2CH2CH3 CH3 -
EPLA H CH2CH3 CH2CH2CH3 CH3 -
LSD / LAD 50-37-3 H CH3 CH2CH3 CH2CH3 -
ETH-LAD 65527-62-0 H CH2CH3 CH2CH3 CH2CH3 -
PARGY-LAD H HC≡C−CH2 CH2CH3 CH2CH3 -
AL-LAD 65527-61-9 H H2C=CH-CH2 CH2CH3 CH2CH3 -
PRO-LAD 65527-63-1 H CH2CH2CH3 CH2CH3 CH2CH3 -
IP-LAD H CH(CH3)2 CH2CH3 CH2CH3 -
CYP-LAD[16] H C3H5 CH2CH3 CH2CH3 -
BU-LAD 96930-87-9 H CH2CH2CH2CH3 CH2CH3 CH2CH3 -
FLUORETH-LAD[17] H CH2CH2F CH2CH3 CH2CH3 -
ALD-52 3270-02-8 COCH3 CH3 CH2CH3 CH2CH3 -
1P-LSD 2349358-81-0 COCH2CH3 CH3 CH2CH3 CH2CH3 -
1B-LSD 2349376-12-9 COCH2CH2CH3 CH3 CH2CH3 CH2CH3 -
1V-LSD CO(CH2)3CH3 CH3 CH2CH3 CH2CH3 -
1H-LSD[18] CO(CH2)4CH3 CH3 CH2CH3 CH2CH3 -
1DD-LSD CO(CH2)10CH3 CH3 CH2CH3 CH2CH3 -
1cP-LSD[19] COC3H5 CH3 CH2CH3 CH2CH3 -
1D-LSD COC4H5(CH3)2 CH3 CH2CH3 CH2CH3 -
1T-LSD COC4H3S CH3 CH2CH3 CH2CH3 -
1S-LSD CO(CH2)2Si(CH3)3 CH3 CH2CH3 CH2CH3 -
1P-AL-LAD COCH2CH3 H2C=CH-CH2 CH2CH3 CH2CH3 -
1cP-AL-LAD COC3H5 H2C=CH-CH2 CH2CH3 CH2CH3 -
1T-AL-LAD[20] COC4H3S H2C=CH-CH2 CH2CH3 CH2CH3 -
1P-ETH-LAD COCH2CH3 CH2CH3 CH2CH3 CH2CH3 -
1P-MIPLA COCH2CH3 CH3 CH(CH3)2 CH3 -
MLD-41 4238-85-1 CH3 CH3 CH2CH3 CH2CH3 -
LSM-775 4314-63-0 H CH3 CH2CH2-O-CH2CH2 -
LPD-824 2385-87-7 H CH3 (CH2)4 -
LSD-Pip 50485-23-9 H CH3 (CH2)5 -
LSD-Azapane H CH3 (CH2)6 -
LA-SS-Az 470666-31-0 H CH3 CH2(CHCH3)2CH2 -
2-Bromo-LSD 478-84-2 H CH3 CH2CH3 CH2CH3 2-Br
12-Methoxy-LSD[21] 50484-99-6 H CH3 CH2CH3 CH2CH3 12-OMe
13-Fluoro-LSD[22] H CH3 CH2CH3 CH2CH3 13-F
14-Hydroxy-LSD[23] H CH3 CH2CH3 CH2CH3 14-OH

See also

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References

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  2. ^ US patent 2997470, Pioch RP, "LYSERGIC ACID AMIDES", published 1956-03-05, issued 1961-08-22 
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  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. PMC 4829483. 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. PMC 5411264. 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. PMC 6230477. 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. PMC 6230476. 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. PMC 6899222. 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. PMC 6848745. PMID 30298278.
  16. ^ Kruegel AC. Novel Ergolines and Methods of Treating Mood Disorders. Patent WO 2022/226408
  17. ^ WO 2022/008627, Grill M, "Improved Method for the Production of Lysergic Acid Diethylamide (LSD) and Novel Derivatives thereof." 
  18. ^ Brandt SD, Kavanagh PV, Gare S, Stratford A, Halberstadt AL. Analytical and behavioral characterization of 1-hexanoyl-LSD (1H-LSD). Drug Test Anal. 2024 Jul 4. doi:10.1002/dta.3767 PMID 38965834
  19. ^ 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. PMC 9191646. PMID 32180350.
  20. ^ Okada Y, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Kanamori T, et al. (June 2024). "Synthesis and analytical characterization of 1-(2-thienoyl)-6-allyl-nor-d-lysergic acid diethylamide (1T-AL-LAD)". Drug Testing and Analysis. doi:10.1002/dta.3747. PMID 38922764.
  21. ^ Usdin E, Efron DH. Psychotropic Drugs and Related Compounds. (1972) ASIN B002X3CDIY
  22. ^ WO 2021/076572, Olson DE, et al., "Ergoline-like compounds for promoting neural plasticity" 
  23. ^ 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.
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