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Lysergamides

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Amides of lysergic acid are collectively known as lysergamides or ergoamides,[1][2] 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. [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 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[18] H C3H5 CH2CH3 CH2CH3 -
BU-LAD 96930-87-9 H CH2CH2CH2CH3 CH2CH3 CH2CH3 -
FLUORETH-LAD[19] 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[20] CO(CH2)4CH3 CH3 CH2CH3 CH2CH3 -
1DD-LSD CO(CH2)10CH3 CH3 CH2CH3 CH2CH3 -
1cP-LSD[21] 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[22] 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[23] 50484-99-6 H CH3 CH2CH3 CH2CH3 12-OMe
13-Fluoro-LSD[24] H CH3 CH2CH3 CH2CH3 13-F
14-Hydroxy-LSD[25] H CH3 CH2CH3 CH2CH3 14-OH

See also

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References

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    “There are three main ergot alkaloid classes, clavines, ergoamides (lysergamides), and ergopeptides, with 3 belonging to the ergoamide class.” 2.5 Lysergic acid and LSD, p. 6970
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    “The ergot alkaloids are broadly classified into three groups—the clavines, ergoamides, and the ergopeptines, all of which are distinguished by the different modifications appended to the core ergoline structure.” Results and discussion / Biosynthetic resolution of the ergot alkaloid pathway    {{cite journal}}: CS1 maint: postscript (link)
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  18. ^ Kruegel AC. Novel Ergolines and Methods of Treating Mood Disorders. Patent WO 2022/226408
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