Lysergamides

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Lysergamides are amides of lysergic acid.

Substitutive structure of a *lysergamide*

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 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.

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
1P-ETH-LAD	CH₂CH₃	CH₂CH₃	C=OCH₂CH₃	CH₂CH₃
1P-LSD	CH₂CH₃	CH₂CH₃	C=OCH₂CH₃	CH₃
ALD-52	CH₂CH₃	CH₂CH₃	C=OCH₃	CH₃
AL-LAD	CH₂CH₃	CH₂CH₃	H	CH₂CH=CH₂
Ergotamine	*	H	H	CH₃
ETH-LAD	CH₂CH₃	CH₂CH₃	H	CH₂CH₃
LSA	H	H	H	CH₃
LSH	CH₂(OH)CH₃	H	H	CH₃
LSD	CH₂CH₃	CH₂CH₃	H	CH₃
iso-LSD	CH₂CH₃	CH₂CH₃	H	CH₃
LSM-775	CH₂CH₂O-	CH₂CH₂-	H	CH₃
LSZ	CH(CH₃)CH₂-	CH(CH₃)CH₂-	H	CH₃
PARGY-LAD	CH₂CH₃	CH₂CH₃	H	CH₂C≡CH
PRO-LAD	CH₂CH₃	CH₂CH₃	H	CH₂CH₂CH₃

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

References

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