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

Further information: Serotonergic psychedelic

The psychedelic effects of lysergamides are believed to come from its efficacy at the 5-HT2A 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 Ergotamine.svg
LSA H H H CH3 LSA.svg
LSD CH2CH3 CH2CH3 H CH3 LSD.svg
ALD-52 CH2CH3 CH2CH3 C=OCH3 CH3 ALD-52.svg
1P-LSD CH2CH3 CH2CH3 C=OCH2CH3 CH3 1P-LSD.svg
1B-LSD CH2CH3 CH2CH3 C=OCH2CH2CH3 CH3 1B-LSD.svg
1cP-LSD CH2CH3 CH2CH3 C=OC3H5 CH3 1cP-LSD.svg
1V-LSD CH2CH3 CH2CH3 C=OC3H5 CH3 1V-LSD.svg
ETH-LAD CH2CH3 CH2CH3 H CH2CH3 ETH-LAD.svg
1P-ETH-LAD CH2CH3 CH2CH3 C=OCH2CH3 CH2CH3 1P-ETH-LAD.svg
PRO-LAD CH2CH3 CH2CH3 H CH2CH2CH3 PRO-LAD.svg
AL-LAD CH2CH3 CH2CH3 H CH2CH=CH2 AL-LAD.svg
PARGY-LAD CH2CH3 CH2CH3 H CH2C≡CH PARGY-LAD.svg
iso-LSD CH2CH3 CH2CH3 H CH3 Iso-LSD.svg
LAE-32 CH2CH3 H H CH3 LAE-32.svg
LSH CH2(OH)CH3 H H CH3 LSH.svg
MiPLA CH(CH3)2 CH3 H CH3 MiPLA-skeletal-structure.svg
EiPLA CH(CH3)2 CH2CH3 H CH3 EiPLA.svg
LSZ CH(CH3)CH2- CH(CH3)- H CH3 LSZ.svg
LSM-775 CH2CH2O- CH2CH2- H CH3 LSM-775.svg

See also

External links

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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