Lysergamides: Difference between revisions

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[[File:Substituted_lysergamide.svg|thumb|right|250px|Substitutive structure of a ''lysergamide'']]

'''Lysergamides''' ~~are amides~~ of ~~lysergic acid~~.

'''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 ~~have~~ have strong [[psychedelic]] effects.

“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==

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==

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{| class="wikitable"

|-

! scope="col" | '''Compound'''

! scope="col" |'''Compound'''

! scope="col" style="width: 50px;" | '''RN1'''

! scope="col" style="width: 50px;" |'''RN1'''

! scope="col" style="width: 50px;" | '''RN2'''

! scope="col" style="width: 50px;" |'''RN2'''

! scope="col" style="width: 50px;" | '''R1'''

! scope="col" style="width: 50px;" |'''R1'''

! scope="col" style="width: 50px;" | '''R6'''

! scope="col" style="width: 50px;" |'''R6'''

! scope="col" | '''Structure'''

! scope="col" |'''Structure'''

|-

| [[~~1B-LSD~~]] || ~~CH2CH3~~ || ~~CH2CH3~~ || ~~C=OCH2CH2CH3~~ || CH3 || [[File:~~1B-LSD~~.svg|170px]]

|[[Ergotamine]]||*||H||H||CH3||[[File:Ergotamine.svg|170px]]

|-

| [[~~1P-ETH-LAD~~]] || ~~CH2CH3~~ || ~~CH2CH3~~ || ~~C=OCH2CH3~~ || ~~CH2~~CH3 || [[File:~~1P-ETH-LAD~~.svg|170px]]

|[[LSA]]||H||H||H||CH3||[[File:LSA.svg|170px]]

|-

| [[~~1P-~~LSD]] || CH2CH3 || CH2CH3 || ~~C=OCH2CH3~~ || CH3 ||[[File:~~1P-~~LSD.svg|~~171px~~]]

|[[LSD]]||CH2CH3||CH2CH3||H||CH3||[[File:LSD.svg|170px]]

|-

| [[ALD-52]] || CH2CH3 || CH2CH3 || C=OCH3 || CH3 || [[File:ALD-52.svg|170px]]

|[[ALD-52]]||CH2CH3||CH2CH3||C=OCH3||CH3||[[File:ALD-52.svg|170px]]

|-

| [[AL-~~LAD~~]] || CH2CH3 || CH2CH3 || ~~H || CH~~2CH=CH2 || [[File:AL-~~LAD~~.svg|~~170px~~]]

|[[1P-LSD]]||CH2CH3||CH2CH3||C=OCH2CH3||CH3||[[File:1P-LSD.svg|171px]]

|-

| [[~~Ergotamine~~]] || * || H || H || CH3 || [[File:~~Ergotamine~~.svg|170px]]

|[[1B-LSD]]||CH2CH3||CH2CH3||C=OCH2CH2CH3||CH3||[[File:1B-LSD.svg|170px]]

|-

| [[~~ETH~~-~~LAD~~]] || CH2CH3 || CH2CH3 || H ~~|| CH~~2CH3 || [[File:~~ETH~~-~~LAD~~.svg|~~170px~~]]

|[[1cP-LSD]]||CH2CH3||CH2CH3||C=OC3H5||CH3||[[File:1cP-LSD.svg|171px]]

|-

| [[~~LSA~~]] || H || H || H || CH3 || [[File:~~LSA~~.svg|~~170px~~]]

|[[1V-LSD]]||CH2CH3||CH2CH3||C=OC3H5||CH3||[[File:1V-LSD.svg|171px]]

|-

| ~~LSH~~ || CH2~~(OH)~~CH3 || H || H || CH3 || [[File:~~LSH~~.svg|170px]]

|[[ETH-LAD]]||CH2CH3||CH2CH3||H||CH2CH3||[[File:ETH-LAD.svg|170px]]

|-

| [[~~LSD~~]] || CH2CH3 || CH2CH3 || H || CH3 || [[File:~~LSD~~.svg|170px]]

|[[1P-ETH-LAD]]||CH2CH3||CH2CH3||C=OCH2CH3||CH2CH3||[[File:1P-ETH-LAD.svg|170px]]

|-

| [[~~iso~~-~~LSD~~]] || CH2CH3 || CH2CH3 || H || CH3 || [[File:~~iso~~-~~LSD~~.~~png~~|170px]]

|[[PRO-LAD]]||CH2CH3||CH2CH3||H||CH2CH2CH3||[[File:PRO-LAD.svg|170px]]

|-

| [[~~LSM~~-~~775~~]] || CH2CH2O- || CH2CH2- || H || CH3 || [[File:~~LSM~~-~~775~~.svg|170px]]

|[[AL-LAD]]||CH2CH3||CH2CH3||H||CH2CH=CH2||[[File:AL-LAD.svg|170px]]

|-

| [[~~LSZ~~]] || ~~CH(~~CH3)CH2- || ~~CH(~~CH3)CH2- || H || CH3 || [[File:~~LSZ~~.svg|170px]]

|[[PARGY-LAD]]||CH2CH3||CH2CH3||H||CH2C≡CH||[[File:PARGY-LAD.svg|170px]]

|-

| [[~~PARGY~~-~~LAD~~]] || CH2CH3 || CH2CH3 || H || CH2~~C≡CH~~ || [[File:~~PARGY~~-~~LAD~~.svg|170px]]

|[[iso-LSD]]||CH2CH3||CH2CH3||H||CH3||[[File:Iso-LSD.svg|170px]]

|-

| [[~~PRO~~-~~LAD~~]] || CH2CH3 || CH2CH3 || H || CH2CH2CH3 || [[File:~~PRO~~-~~LAD~~.svg|170px]]

|[[LAE-32]]||CH2CH3||H||H||CH3||[[File:LAE-32.svg|170px]]

|-

|LSH||CH2(OH)CH3||H||H||CH3||[[File:LSH.svg|170px]]

|-

|[[MiPLA]]||CH(CH3)2||CH3||H||CH3||[[File:MiPLA-skeletal-structure.svg|170px]]

|-

|[[EiPLA]]||CH(CH3)2||CH2CH3||H||CH3||[[File:EiPLA.svg|170px]]

|-

|[[LSZ]]||CH(CH3)CH2-||CH(CH3)-||H||CH3||[[File:LSZ.svg|170px]]

|-

|[[LSM-775]]||CH2CH2O-||CH2CH2-||H||CH3||[[File:LSM-775.svg|170px]]

|-

|}

==See also==

*[[Responsible use]]

*[[Tryptamine]]

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==External links==

*[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

*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==

[[Category:Chemical class]]

[[Category:Lysergamide| ]]

@@ Line 2: / Line 2: @@
 [[File:Substituted_lysergamide.svg|thumb|right|250px|Substitutive structure of a ''lysergamide'']]
-'''Lysergamides''' are amides of lysergic acid.
+'''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 have have strong [[psychedelic]] effects.
+“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==
-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==
@@ Line 17: / Line 25: @@
 {| 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'''
 |-
-| [[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]]
+|[[Ergotamine]]||*||H||H||CH<sub>3</sub>||[[File:Ergotamine.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]]
+|[[LSA]]||H||H||H||CH<sub>3</sub>||[[File:LSA.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]]
+|[[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]]
 |-
-| [[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]]
+|[[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]]
 |-
-| [[Ergotamine]] || * || H || H || CH<sub>3</sub> || [[File:Ergotamine.svg|170px]]
+|[[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]]
 |-
-| [[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]]
+|[[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]]
 |-
-| [[LSA]] || H || H || H || CH<sub>3</sub> || [[File:LSA.svg|170px]]
+|[[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]]
 |-
-| LSH || CH<sub>2</sub>(OH)CH<sub>3</sub> || H || H || CH<sub>3</sub> || [[File:LSH.svg|170px]]
+|[[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]]
 |-
-| [[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]]
+|[[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]]
 |-
-| [[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.png|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]]
 |-
-| [[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]]
+|[[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]]
 |-
-| [[LSZ]] || CH(CH<sub>3</sub>)CH<sub>2</sub>- || CH(CH<sub>3</sub>)CH<sub>2</sub>- || H || CH<sub>3</sub> || [[File:LSZ.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]]
 |-
-| [[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]]
+|[[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==
 *[[Responsible use]]
 *[[Tryptamine]]
@@ Line 65: / Line 84: @@
 ==External links==
-*[https://en.wikipedia.org/wiki/Lysergamide  Lysergamide (Wikipedia)]
+*[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
+*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}}
+[[Category:Chemical class]]
+[[Category:Lysergamide| ]]
+<references />
+{{#set:Featured=true}}