Lysergamides

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Substitutive structure of a lysergamide

Lysergamides are amides of lysergic acid.

Ergoline refers to a class of compounds derived from alkaloids of a group of fungi known as ergot in the claviceps genus. These compounds typically have strong psychedelic effects.

Chemistry

Lysergamides are polycyclic amides which have both phenethylamine and tryptamine groups embedded within their structure and a carboxamide group attached to carbon number eight.

Varying the substituent attached to the nitrogen atoms has produced a variety of drugs with psychedelic effects as well as prescription drugs for treating headaches and inducing labor.

Hydroxylation of the aromatic ring is one method of metabolizing lysergamides in humans and produces compounds with greater affinity to dopamine receptors.

They can technically be classified as complex tryptamines (like ibogaine).

Pharmacology

The psychedelic effects of lysergamides are believed to come from its efficacy at the 5-HT_2A receptor as a partial agonist. Lysergamides are known to have affinity for a much greater variety of receptors than other psychedelic drugs.

However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

List of substituted lysergamides

Compound	R_N1	R_N2	R₁	R₆
Ergotamine	*	H	H	CH₃
LSA	H	H	H	CH₃
LSD	CH₂CH₃	CH₂CH₃	H	CH₃
ALD-52	CH₂CH₃	CH₂CH₃	C=OCH₃	CH₃
1P-LSD	CH₂CH₃	CH₂CH₃	C=OCH₂CH₃	CH₃
1B-LSD	CH₂CH₃	CH₂CH₃	C=OCH₂CH₂CH₃	CH₃
1cP-LSD	CH₂CH₃	CH₂CH₃	C=OC₃H₅	CH₃
1V-LSD	CH₂CH₃	CH₂CH₃	C=OC₃H₅	CH₃
ETH-LAD	CH₂CH₃	CH₂CH₃	H	CH₂CH₃
1P-ETH-LAD	CH₂CH₃	CH₂CH₃	C=OCH₂CH₃	CH₂CH₃
PRO-LAD	CH₂CH₃	CH₂CH₃	H	CH₂CH₂CH₃
AL-LAD	CH₂CH₃	CH₂CH₃	H	CH₂CH=CH₂
PARGY-LAD	CH₂CH₃	CH₂CH₃	H	CH₂C≡CH
iso-LSD	CH₂CH₃	CH₂CH₃	H	CH₃
LAE-32	CH₂CH₃	H	H	CH₃
LSH	CH₂(OH)CH₃	H	H	CH₃
MiPLA	CH(CH₃)₂	CH₃	H	CH₃
EiPLA	CH(CH₃)₂	CH₂CH₃	H	CH₃
LSZ	CH(CH₃)CH₂-	CH(CH₃)-	H	CH₃
LSM-775	CH₂CH₂O-	CH₂CH₂-	H	CH₃

External links

Lysergamide (Wikipedia)

Literature

Pfaff, R. C., Huang, X., Marona-Lewicka, D., Oberlender, R., & Nichols, D. E. (1994). Lysergamides revisited. NIDA Research Monograph, 146, 52-73. https://doi.org/10.1.1.669.2474
Daniel Wacker, Sheng Wang, John D. McCorvy, Robin M. Betz, A.J. Venkatakrishnan, Anat Levit, Katherine Lansu, Zachary L. Schools, Tao Che, David E. Nichols, Brian K. Shoichet, Ron O. Dror, Bryan L. Roth (2020). Crystal Structure of an LSD-Bound Human Serotonin Receptor. Cell, Volume 168, Issue 3, 377-389. https://doi.org/10.1016/j.cell.2016.12.033

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