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Lysergamides: Difference between revisions
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[[File:Substituted_lysergamide.svg|thumb|right|250px|Substitutive structure of a ''lysergamide'']] | [[File:Substituted_lysergamide.svg|thumb|right|250px|Substitutive structure of a ''lysergamide'']] | ||
'''Lysergamides''' | '''Lysergamides''' or ergoamides<ref>Jamieson CS, Misa J, Tang Y, Billingsley JM (2021-04-29). "Biosynthesis and synthetic biology of psychoactive natural products". ''Chemical Society Reviews''. '''50''' (12): 6950–7008. DOI: 10.1039/D1CS00065A. [[ISSN (identifier)|ISSN]] 0306-0012. [[PMC (identifier)|PMC]] 8217322. [[PMID (identifier)|PMID]] 33908526. | ||
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 | “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</ref> 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== | ==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. | 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== | ==Pharmacology== | ||
| Line 16: | Line 25: | ||
{| class="wikitable" | {| class="wikitable" | ||
|- | |- | ||
! scope="col" | '''Compound''' | ! scope="col" |'''Compound''' | ||
! scope="col" style="width: 50px;" | '''R<sub>N1</sub>''' | ! scope="col" style="width: 50px;" |'''R<sub>N1</sub>''' | ||
! scope="col" style="width: 50px;" | '''R<sub>N2</sub>''' | ! scope="col" style="width: 50px;" |'''R<sub>N2</sub>''' | ||
! scope="col" style="width: 50px;" | '''R<sub>1</sub>''' | ! scope="col" style="width: 50px;" |'''R<sub>1</sub>''' | ||
! scope="col" style="width: 50px;" | '''R<sub>6</sub>''' | ! scope="col" style="width: 50px;" |'''R<sub>6</sub>''' | ||
! scope="col" | '''Structure''' | ! scope="col" |'''Structure''' | ||
|- | |- | ||
| [[ | |[[Ergotamine]]||*||H||H||CH<sub>3</sub>||[[File:Ergotamine.svg|170px]] | ||
|- | |- | ||
| [[ | |[[LSA]]||H||H||H||CH<sub>3</sub>||[[File:LSA.svg|170px]] | ||
|- | |- | ||
| [[ | |[[LSD]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||CH<sub>3</sub>||[[File:LSD.svg|170px]] | ||
|- | |- | ||
| [[ | |[[ALD-52]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||C=OCH<sub>3</sub>||CH<sub>3</sub>||[[File:ALD-52.svg|170px]] | ||
|- | |- | ||
| [[ | |[[1P-LSD]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||C=OCH<sub>2</sub>CH<sub>3</sub>||CH<sub>3</sub>||[[File:1P-LSD.svg|171px]] | ||
|- | |- | ||
| [[ | |[[1B-LSD]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||C=OCH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||CH<sub>3</sub>||[[File:1B-LSD.svg|170px]] | ||
|- | |- | ||
| [[ | |[[1cP-LSD]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||C=OC<sub>3</sub>H<sub>5</sub>||CH<sub>3</sub>||[[File:1cP-LSD.svg|171px]] | ||
|- | |- | ||
| | |[[1V-LSD]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||C=OC<sub>3</sub>H<sub>5</sub>||CH<sub>3</sub>||[[File:1V-LSD.svg|171px]] | ||
|- | |- | ||
| [[ | |[[ETH-LAD]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||CH<sub>2</sub>CH<sub>3</sub>||[[File:ETH-LAD.svg|170px]] | ||
|- | |- | ||
| [[ | |[[1P-ETH-LAD]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||C=OCH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||[[File:1P-ETH-LAD.svg|170px]] | ||
|- | |- | ||
| [[ | |[[PRO-LAD]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>||[[File:PRO-LAD.svg|170px]] | ||
|- | |- | ||
| [[ | |[[AL-LAD]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||CH<sub>2</sub>CH=CH<sub>2</sub>||[[File:AL-LAD.svg|170px]] | ||
|- | |- | ||
| [[PARGY-LAD]] || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || H || CH<sub>2</sub>C≡CH || [[File:PARGY-LAD.svg|170px]] | |[[PARGY-LAD]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||CH<sub>2</sub>C≡CH||[[File:PARGY-LAD.svg|170px]] | ||
|- | |- | ||
| [[ | |[[iso-LSD]]||CH<sub>2</sub>CH<sub>3</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||CH<sub>3</sub>||[[File:Iso-LSD.svg|170px]] | ||
|- | |||
|[[LAE-32]]||CH<sub>2</sub>CH<sub>3</sub>||H||H||CH<sub>3</sub>||[[File:LAE-32.svg|170px]] | |||
|- | |||
|LSH||CH<sub>2</sub>(OH)CH<sub>3</sub>||H||H||CH<sub>3</sub>||[[File:LSH.svg|170px]] | |||
|- | |||
|[[MiPLA]]||CH(CH<sub>3</sub>)<sub>2</sub>||CH<sub>3</sub>||H||CH<sub>3</sub>||[[File:MiPLA-skeletal-structure.svg|170px]] | |||
|- | |||
|[[EiPLA]]||CH(CH<sub>3</sub>)<sub>2</sub>||CH<sub>2</sub>CH<sub>3</sub>||H||CH<sub>3</sub>||[[File:EiPLA.svg|170px]] | |||
|- | |||
|[[LSZ]]||CH(CH<sub>3</sub>)CH<sub>2</sub>-||CH(CH<sub>3</sub>)-||H||CH<sub>3</sub>||[[File:LSZ.svg|170px]] | |||
|- | |||
|[[LSM-775]]||CH<sub>2</sub>CH<sub>2</sub>O-||CH<sub>2</sub>CH<sub>2</sub>-||H||CH<sub>3</sub>||[[File:LSM-775.svg|170px]] | |||
|- | |- | ||
|} | |} | ||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Tryptamine]] | |||
*[[LSD]] | *[[LSD]] | ||
*[[LSA]] | *[[LSA]] | ||
*[[ | *[[AL-LAD]] | ||
*[[ | *[[ETH-LAD]] | ||
==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/Lysergamide | |||
*[https://en.wikipedia.org/wiki/Lysergamide 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== | ==References== | ||
{{references}} | {{references}} | ||
[[Category:Chemical class]] | |||
[[Category:Lysergamide| ]] | |||
<references /> | |||
{{#set:Featured=true}} | |||
Latest revision as of 07:26, 30 November 2024
 |
This article is a stub. As such, it may contain incomplete or wrong information. You can help by expanding it. |
Lysergamides or ergoamides[1] 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 | 
|
| 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
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
 |
This article does not cite enough references. You can help by adding some. |
- ↑ Jamieson CS, Misa J, Tang Y, Billingsley JM (2021-04-29). "Biosynthesis and synthetic biology of psychoactive natural products". Chemical Society Reviews. 50 (12): 6950–7008. DOI: 10.1039/D1CS00065A. ISSN 0306-0012. PMC 8217322. PMID 33908526. “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