Lysergic acid 3-pentyl amide: Difference between revisions

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{{Infobox chemical
{{DISPLAYTITLE:Lysergic acid 3-pentyl amide}}
| Name = Lysergic acid 3-pentyl amide
| Image = Lysergic_acid_3-pentyl_amide.png
| ImageFile1 = Lysergic_acid_3-pentyl_amide_3D_ball.png
| ImageSize1 = 200px
| ImageAlt1 = 3D ball-and-stick model of lysergic acid 3-pentyl amide
| IUPACName = N-[(2S,4aS,8aS)-2-(3-Pentyl-2,3-dihydro-1H-indol-1-yl)-4a,8a-dimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-yl]methanesulfonamide
| OtherNames = LSA, Ergine, D-lysergic acid 3-pentylamide
| CASNumber = 478-94-4
| PubChem = 1312
| ChemSpiderID = 1271
| DrugBank = DB01452
| Chembl = 120160
| C=20|H=27|N=3|O=2|S=1
| MolecularWeight = 369.51 g/mol
| MeltingPoint = 165-166 °C
| BoilingPoint = 520.3 °C at 760 mmHg
| Solubility = Soluble in ethanol, methanol, chloroform
}}


'''Lysergic acid 3-pentyl amide''' (LSA), also known as '''Ergine''' or '''D-lysergic acid 3-pentylamide''', is a naturally occurring psychedelic compound. It belongs to the family of '''ergoline alkaloids''' and is derived from '''lysergic acid''', a compound found in various species of '''ergot fungi'''.
== Lysergic acid 3-pentyl amide ==
[[File:LS3P_structure.png|thumb|right|Chemical structure of Lysergic acid 3-pentyl amide]]


== History ==
'''Lysergic acid 3-pentyl amide''' (LS3P) is a chemical compound belonging to the class of [[lysergamides]], which are derivatives of [[lysergic acid]]. This compound is structurally related to other well-known lysergamides such as [[lysergic acid diethylamide]] (LSD).
Lysergic acid 3-pentyl amide was first isolated and identified in the early 20th century by the Swiss chemist Albert Hofmann. It was later discovered that LSA is a precursor to the synthesis of '''lysergic acid diethylamide''' (LSD), a highly potent hallucinogenic drug.


== Chemical Properties ==
=== Chemical Structure ===
Lysergic acid 3-pentyl amide has a molecular formula of C20H27N3O2S and a molecular weight of 369.51 g/mol. It is a white crystalline solid with a melting point of 165-166 °C. The compound is soluble in ethanol, methanol, and chloroform.
Lysergic acid 3-pentyl amide is characterized by the presence of a lysergic acid core with a 3-pentyl amide substitution. The chemical structure of LS3P is depicted in the adjacent image, showing the lysergic acid moiety linked to a pentyl group via an amide bond.


== Pharmacology ==
=== Pharmacology ===
LSA acts as a '''partial agonist''' at various serotonin receptors, particularly the '''5-HT2A receptor'''. It also interacts with other receptors in the brain, including the '''dopamine''' and '''adrenergic''' receptors. The exact mechanism of action of LSA is not fully understood, but it is believed to modulate the activity of these neurotransmitter systems, leading to its psychedelic effects.
The pharmacological properties of lysergic acid 3-pentyl amide are not as extensively studied as those of LSD. However, as a lysergamide, it is expected to interact with [[serotonin receptors]], particularly the [[5-HT2A receptor]], which is known to play a significant role in the psychedelic effects of related compounds.


== Effects ==
=== Synthesis ===
The effects of LSA are similar to those of LSD, although generally milder and shorter-lasting. Users may experience visual and auditory hallucinations, altered perception of time and space, changes in mood, and enhanced creativity. The intensity and nature of the effects can vary depending on the dose, set, and setting.
The synthesis of lysergic acid 3-pentyl amide involves the reaction of [[lysergic acid]] with a suitable pentylamine. This process typically requires careful control of reaction conditions to ensure the formation of the desired amide bond without degradation of the lysergic acid structure.


== Preparations and Use ==
=== Potential Effects ===
LSA is naturally present in various plants, most notably in the seeds of the '''morning glory''' ('''Ipomoea tricolor''') and the '''Hawaiian baby woodrose''' ('''Argyreia nervosa'''). These seeds can be consumed directly or prepared in various ways, such as grinding and extraction. However, it is important to note that the consumption of LSA-containing plants is illegal in many countries.
While specific studies on LS3P are limited, it is hypothesized that its effects may be similar to those of other lysergamides, potentially inducing alterations in perception, mood, and cognition. The exact potency and duration of effects would depend on its affinity for serotonin receptors and its metabolic stability.


== Safety and Legal Status ==
== Related pages ==
The safety profile of LSA is not well-established, and its use carries potential risks. Users may experience adverse effects such as nausea, vomiting, anxiety, and paranoia. In rare cases, LSA has been associated with more severe reactions, including psychosis and hallucinogen persisting perception disorder (HPPD).
 
The legal status of LSA varies across different jurisdictions. In some countries, it is regulated as a controlled substance, while in others, it may be legal or subject to certain restrictions. It is important to research and comply with the laws of your specific jurisdiction before considering the use of LSA.
 
== See Also ==
* [[Lysergic acid diethylamide]]
* [[Lysergic acid diethylamide]]
* [[Ergotamine]]
* [[Serotonin receptor]]
* [[Psychedelic drug]]
* [[Psychedelic drug]]


== References ==
[[Category:Lysergamides]]
{{Reflist}}
 
[[Category:Psychedelic drugs]]
[[Category:Psychedelic drugs]]
[[Category:Ergoline alkaloids]]

Latest revision as of 05:55, 16 February 2025


Lysergic acid 3-pentyl amide[edit]

Chemical structure of Lysergic acid 3-pentyl amide

Lysergic acid 3-pentyl amide (LS3P) is a chemical compound belonging to the class of lysergamides, which are derivatives of lysergic acid. This compound is structurally related to other well-known lysergamides such as lysergic acid diethylamide (LSD).

Chemical Structure[edit]

Lysergic acid 3-pentyl amide is characterized by the presence of a lysergic acid core with a 3-pentyl amide substitution. The chemical structure of LS3P is depicted in the adjacent image, showing the lysergic acid moiety linked to a pentyl group via an amide bond.

Pharmacology[edit]

The pharmacological properties of lysergic acid 3-pentyl amide are not as extensively studied as those of LSD. However, as a lysergamide, it is expected to interact with serotonin receptors, particularly the 5-HT2A receptor, which is known to play a significant role in the psychedelic effects of related compounds.

Synthesis[edit]

The synthesis of lysergic acid 3-pentyl amide involves the reaction of lysergic acid with a suitable pentylamine. This process typically requires careful control of reaction conditions to ensure the formation of the desired amide bond without degradation of the lysergic acid structure.

Potential Effects[edit]

While specific studies on LS3P are limited, it is hypothesized that its effects may be similar to those of other lysergamides, potentially inducing alterations in perception, mood, and cognition. The exact potency and duration of effects would depend on its affinity for serotonin receptors and its metabolic stability.

Related pages[edit]

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