This is an unofficial archive of PsychonautWiki as of 2025-08-11T15:14:44Z. Content on this page may be outdated, incomplete, or inaccurate. Please refer to the original page for the most up-to-date information.
Lysergamides: Difference between revisions
>Tracer Added LAE-32 in List of substituted lysergamides |
>Wk472 added emerging synonym |
||
| (19 intermediate revisions by 11 users not shown) | |||
| Line 2: | Line 2: | ||
[[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 17: | 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]] | |[[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]] | ||
|- | |- | ||
| [[ | |[[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]] | *[[Tryptamine]] | ||
| Line 69: | Line 84: | ||
==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/Lysergamide | |||
*[https://en.wikipedia.org/wiki/Lysergamide Lysergamide (Wikipedia)] | |||
==Literature== | ==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 | |||
*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}} | |||