Lysergamides

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Substitutive structure of a lysergamide

Lysergamides or ergoamides 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

Further information: Serotonergic psychedelic

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	RN1	RN2	R1	R6	Structure
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

See also

• Responsible use
• Tryptamine
• LSD
• LSA
• AL-LAD
• ETH-LAD

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

References

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