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LSA: Difference between revisions
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LSA is chemically related to [[LSD]] and is said to produce similar effects, although the extent to which it does is unclear. | LSA is chemically related to [[LSD]] and is said to produce similar effects, although the extent to which it does is unclear. | ||
LSA was first described in 1932 as part of an investigation into the alkaloids found in ergot.<ref>Smith | LSA was first described in 1932 as part of an investigation into the alkaloids found in ergot.<ref>{{cite journal|last1=Smith|first1=Sydney|last2=Timmis|first2=Geoffrey M.|title=The alkaloids of ergot. Part III. Ergine, a new base obtained by the degradation of ergotoxine and ergotinine|journal=Journal of the Chemical Society (Resumed)|year=1932|issue=98|edition=1932|pages=763-766|doi=10.1039/JR9320000763}}</ref> In 1947, it was synthesized and tested for human activity by [[Albert Hofmann]]. The [[intramuscular]] administration of a 500 microgram dose produced a "tired, dreamy state with an inability to maintain clear thoughts."<ref name="TiKHAL">{{cite book|title=TiHKAL: The Continuation|title-link=TiHKAL|last1=Shulgin|first1=Alexander|last2=Shulgin|first2=Ann|author-link1=Alexander Shulgin|year=1997|publisher=Transform Press|location=United States|isbn=0-9630096-9-9|oclc=38503252|chapter-url=https://erowid.org/library/books_online/tihkal/tihkal26.shtml|chapter=#26. LSD-25}}</ref> | ||
In 1947, it was synthesized and tested for human activity by [[Albert Hofmann]]. The [[intramuscular]] administration of a 500 microgram dose produced a "tired, dreamy state with an inability to maintain clear thoughts."<ref> | In 1970, LSA was detected as a constituent in Hawaiian baby woodrose seeds, which were being ground up into capsules and sold on the street as "mescaline".<ref>{{cite journal|last1=Miller|first1=Michael D.|title=Isolation and Identification of Lysergic Acid Amide and Isolysergic Acid Amide as the Principal Ergoline Alkaloids in ''Argyreia nervosa'', a Tropical Wood Rose|journal=Journal of the AOAC|year=1970|volume=53|issue=1|pages=123-128|issn=1060-3271|url=https://chemistry.mdma.ch/hiveboard/rhodium/pdf/forensic/lsa.hbwr.jaoac.pdf}}</ref> Today, LSA is typically consumed via [[LSA#Morning_glory_seeds_.28MGS.29|morning glory]] and [[LSA#Hawaiian_baby_woodrose_seeds_.28HBWR.29|Hawaiian baby woodrose]] seeds.<ref>{{cite journal|last1=Borsutzky|first1=M.|last2=Passie|first2=T.|last3=Paetzold|first3=W.|last4=Schneider|first4=U.|title=Hawaiian baby woodrose: (Psycho-) Pharmacological effects of the seeds of Argyreia nervosa. A case-orientated demonstration|journal=Der Nervenarzt|issn=0028-2804|doi=10.1007/s00115-002-1374-4|pmid=12215884|year=2002|volume=73|issue=9|pages=892-896}}</ref> | ||
In 1970, LSA was detected as a constituent in Hawaiian baby woodrose seeds, which were being ground up into capsules and sold on the street as "mescaline".<ref>Miller | |||
Today, LSA is typically consumed via [[LSA#Morning_glory_seeds_.28MGS.29|morning glory]] and [[LSA#Hawaiian_baby_woodrose_seeds_.28HBWR.29|Hawaiian baby woodrose]] seeds.<ref>Borsutzky | |||
User reports describe the effects of LSA as primarily sedating and dream-like, with a mild to moderate psychedelic component. The psychedelic effects of LSA occur inconsistently and are not directly comparable to the effects of classical psychedelics like [[LSD]], [[psilocybin mushrooms]], or [[mescaline]]. LSA is described as primarily bodily and cognitive with little visual effects. Many users report serious [[nausea]] and bodily discomfort ("body load") when taking LSA-containing seeds. | User reports describe the effects of LSA as primarily sedating and dream-like, with a mild to moderate psychedelic component. The psychedelic effects of LSA occur inconsistently and are not directly comparable to the effects of classical psychedelics like [[LSD]], [[psilocybin mushrooms]], or [[mescaline]]. LSA is described as primarily bodily and cognitive with little visual effects. Many users report serious [[nausea]] and bodily discomfort ("body load") when taking LSA-containing seeds. | ||
Like other psychedelics, LSA is not considered to be addictive.<ref>Lüscher | Like other [[psychedelics]], LSA is not considered to be addictive.<ref>{{cite journal|last1=Lüscher|first1=Christian|last2=Ungless|first2=Mark A.|title=The Mechanistic Classification of Addictive Drugs|year=2006|journal=PLOS Medicine|volume=3|issue=11|doi=10.1371/journal.pmed.0030437|pmid=17105338|issn=1549-1277}}</ref> However, adverse reactions such as severe [[anxiety]], [[paranoia]], and [[psychosis]] are always possible, particularly among those who are predisposed to psychiatric disorders.<ref>{{cite journal|last=Strassmann|first=Rick|title=Adverse reactions to psychedelic drugs. A review of the literature|journal=Journal of Nervous and Mental Disease|volume=172|issue=10|pages=577–595|doi=10.1097/00005053-198410000-00001|pmid=6384428|year=1984|issn=0022-3018|oclc=1754691}}</ref> It is therefore highly advised to use [[harm reduction practices]] if using this substance. | ||
==Chemistry== | ==Chemistry== | ||
LSA, or d-lysergic acid amide, is an organic alkaloid belonging to the [[lysergamide]] class. The chemical structure of LSA contains a core structure of lysergic acid with an amine functional group bound to R<sub>N</sub>. The structure of lysergic acid is composed of a bicyclic hexahydroindole fused to a bicyclic quinoline group (lysergic acid). At carbon 8 of the quinoline, an acetamide group is bound. LSA is additionally substituted at carbon 6 with a methyl group. | LSA, or d-lysergic acid amide, is an organic [[alkaloid]] belonging to the [[lysergamide]] class. The chemical structure of LSA contains a core structure of lysergic acid with an amine functional group bound to R<sub>N</sub>. The structure of lysergic acid is composed of a bicyclic hexahydroindole fused to a bicyclic quinoline group (lysergic acid). At carbon 8 of the quinoline, an acetamide group is bound. LSA is additionally substituted at carbon 6 with a methyl group. | ||
LSA is a chiral compound with two stereocenters at R<sub>5</sub> and R<sub>8</sub>. LSA, also called (+)-D-LSA, has an absolute configuration of (5''R'', 8''R''). The three other stereoisomers of LSA do not have psychoactive properties. LSA is structurally analogous to LSD, with the exception being that LSA lacks the diethyl substitution of LSD at R<sub>N</sub> of its carboxamide group. It can be used as a precursor to LSD. | LSA is a chiral compound with two stereocenters at R<sub>5</sub> and R<sub>8</sub>. LSA, also called (+)-D-LSA, has an absolute configuration of (5''R'', 8''R''). The three other stereoisomers of LSA do not have psychoactive properties. LSA is structurally analogous to [[LSD]], with the exception being that LSA lacks the diethyl substitution of LSD at R<sub>N</sub> of its carboxamide group. It can be used as a precursor to LSD. | ||
==Pharmacology== | ==Pharmacology== | ||
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*'''[[Effect::Vasoconstriction]]'''{{citation needed}} - LSA is commonly reported to produce strong and pronounced feelings of vasoconstriction. This varies in its intensity between individuals but is often considered moderately to extremely uncomfortable in comparison to other [[psychedelics]]. This effect is commonly reported to cause joint and limb pains. | *'''[[Effect::Vasoconstriction]]'''{{citation needed}} - LSA is commonly reported to produce strong and pronounced feelings of vasoconstriction. This varies in its intensity between individuals but is often considered moderately to extremely uncomfortable in comparison to other [[psychedelics]]. This effect is commonly reported to cause joint and limb pains. | ||
*'''[[Effect::Increased heart rate]]''' | *'''[[Effect::Increased heart rate]]''' | ||
*'''[[Effect::Increased blood pressure]]''' or '''[[Effect::Decreased blood pressure]]'''{{citation needed}} - LSA has been reported as being capable of producing both an increase and a decrease in blood pressure, sometimes alternating at different points in the experience, such as during the [[come up]] or [[offset]], although it is unclear how much of this is dependent on the seeds and variations in alkaloid contents. | *'''[[Effect::Increased blood pressure]]''' or '''[[Effect::Decreased blood pressure]]'''{{citation needed}} - LSA has been reported as being capable of producing both an increase and a decrease in blood pressure, sometimes alternating at different points in the experience, such as during the [[come up]] or [[offset]], although it is unclear how much of this is dependent on the seeds and variations in [[alkaloid]] contents. | ||
*'''[[Effect::Muscle contractions]]''' & '''[[Effect::Muscle relaxation]]''' | *'''[[Effect::Muscle contractions]]''' & '''[[Effect::Muscle relaxation]]''' | ||
*'''[[Effect::Muscle spasms]]''' | *'''[[Effect::Muscle spasms]]''' | ||
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==Natural plant sources== | ==Natural plant sources== | ||
{{main|Morning glory}} | {{main|Morning glory}} | ||
Although LSA is illegal in some countries, various seeds which contain it are readily available in many gardening stores. However, the seeds from commercial sources are often coated in some form of | Although LSA is illegal in some countries, various seeds which contain it are readily available in many gardening stores. However, the seeds from commercial sources are often coated in some form of seed treatment or fungicide which can result in extreme nausea, bodily discomfort, or (in the case of organomercury compounds) long-term neurological damage and cognitive impairment if ingested. Methods for cleaning or de-coating the seeds are available, but are typically ineffective (organomercury compounds penetrate the entire seed). Therefore it is important to only purchase untreated seeds from reliable, trusted vendors. Heavy metal testing kits can be purchased online to test seed extracts for mercury content prior to ingestion. | ||
===Morning glory seeds (MGS)=== | ===Morning glory seeds (MGS)=== | ||
{{main|Ipomoea tricolor (botany)}} | {{main|Ipomoea tricolor (botany)}} | ||
[[File:Lsa_-_morning_glory_seedsgck.jpg|thumb|right|upright|200px|Morning glory seeds]] | [[File:Lsa_-_morning_glory_seedsgck.jpg|thumb|right|upright|200px|Morning glory seeds]] | ||
The seeds of many species of morning glory are known to contain [[lysergamide]] [[alkaloids]] such LSA.<ref> | The seeds of many species of morning glory are known to contain [[lysergamide]] [[alkaloids]] such as LSA.<ref>{{cite journal|last1=Ingram Jr.|first1=Albert L.|title=Morning Glory Seed Reaction|year=1964|journal=JAMA: The Journal of the American Medical Association|issn=0098-7484|doi=10.1001/jama.1964.03070260045019|volume=190|issue=13|pages=1133–1134}}</ref> Typical oral doses of morning glory seeds are as follows: | ||
*'''Threshold:''' ''[[Oral threshold dose::20]] - 50 seeds / 1.5 g'' | *'''Threshold:''' ''[[Oral threshold dose::20]] - 50 seeds / 1.5 g'' | ||
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{{main|Argyreia nervosa (botany)}} | {{main|Argyreia nervosa (botany)}} | ||
[[File:Hawaiin_baby_woodrose.jpg|thumb|right|upright|200px|Hawaiian baby woodrose seeds]] | [[File:Hawaiin_baby_woodrose.jpg|thumb|right|upright|200px|Hawaiian baby woodrose seeds]] | ||
Hawaiian baby woodrose is a perennial climbing vine that is native to the Indian subcontinent and has since been introduced to numerous areas worldwide including Hawaii, Africa and the Caribbean. Its seeds may be consumed for their various [[lysergamide|lysergamide alkaloids]] such as LSA.<ref> | Hawaiian baby woodrose is a perennial climbing vine that is native to the Indian subcontinent and has since been introduced to numerous areas worldwide including Hawaii, Africa and the Caribbean. Its seeds may be consumed for their various [[lysergamide|lysergamide alkaloids]] such as LSA.<ref>{{cite journal|last1=Klinke|first1=Helene B.|last2=Müller|last3=Steffenrud|first3=S.|last4=Dahl-Sørensen|first4=R.|title=Two cases of lysergamide intoxication by ingestion of seeds from Hawaiian Baby Woodrose|year=2010|journal=Forensic Science International|volume=197|issue=1–3|pages=e1-e5|issn=0379-0738|doi=10.1016/j.forsciint.2009.11.017}}</ref> Typical oral doses for Hawaiian baby woodrose seeds are as follows: | ||
*'''Threshold:''' ''[[Sublingual threshold dose::1]] - 3 [[Sublingual dose units::seeds]]'' | *'''Threshold:''' ''[[Sublingual threshold dose::1]] - 3 [[Sublingual dose units::seeds]]'' | ||
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===Vasoconstriction=== | ===Vasoconstriction=== | ||
LSA should not be used regularly for long periods of time. When used repeatedly over a short period of time, LSA's [[vasoconstriction|vasoconstrictive]] effects build up while the psychoactive effects get weaker. A common sign of vasoconstriction build up can be described as a feeling of painful or uncomfortable legs.<ref> | LSA should not be used regularly for long periods of time. When used repeatedly over a short period of time, LSA's [[vasoconstriction|vasoconstrictive]] effects build up while the psychoactive effects get weaker. A common sign of vasoconstriction build up can be described as a feeling of painful or uncomfortable legs.<ref>{{cite journal|last1=Iemitsu|first1=M.|last2=Itoh|first2=M.|last3=Fujimoto|first3=T.|last4=Tashiro|first4=M.|last5=Nagatomi|first5=R.|last6=Ohmori|first6=H.|last7=Ishii|first7=K.|journal=Medicine & Science in Sports & Exercise|year=2000|title=Whole-body energy mapping under physical exercise using positron emission tomography|volume=32|issue=12|pages=2067-2070|issn=0195-9131|pmid=11128853|doi=10.1097/00005768-200012000-00016}}</ref> This happens as a result of an insufficient amount of blood getting to the muscles. The upper leg muscles are the largest, most energy consuming muscles in the body and will feel sore if blood flow to them is lowered even slightly. | ||
When HBWR, morning glory seeds or pure LSA seeds are consumed and sore legs are experienced, a break has been reported to be helpful. With LSA it can take up to 3 days of abstinence to get back to vasoconstriction baseline. | When HBWR, morning glory seeds or pure LSA seeds are consumed and sore legs are experienced, a break has been reported to be helpful. With LSA it can take up to 3 days of abstinence to get back to vasoconstriction baseline. | ||
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===Dangerous interactions=== | ===Dangerous interactions=== | ||
{{DangerousInteractions/Intro}} | {{DangerousInteractions/Intro}} | ||
{{DangerousInteractions/Psychedelics}} | |||
===Other interactions=== | ===Other interactions=== | ||
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*'''Australia''': LSA is illegal to produce, sell, and consume in Australia.{{citation needed}} | *'''Australia''': LSA is illegal to produce, sell, and consume in Australia.{{citation needed}} | ||
*'''Austria''': LSA containing seeds are not regulated, thus are legal to possess, produce and sell.{{citation needed}} | *'''Austria''': LSA containing seeds are not regulated, thus are legal to possess, produce and sell.{{citation needed}} | ||
*'''Germany''': LSA is controlled under the NpSG (New Psychoactive Substances Act) | *'''Germany''': LSA is controlled under the NpSG (''New Psychoactive Substances Act'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]|access-date=December 10, 2019|language=de}}</ref> as of July 18, 2019.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl119s1083.pdf|title=Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Jahrgang 2019 Teil I Nr. 27|pages=1083-1094|publication-date=July 17, 2019|access-date=January 1, 2020|language=de}}</ref> Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]|access-date=December 10, 2019|language=de}}</ref> Plant parts containing LSA are not covered by the law.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__2.html|title=§ 2 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]|access-date=December 10, 2019|language=de}}</ref> | ||
*'''Latvia''': LSA itself is controlled as a structural analog of LSD. However, there is no information about LSA-containing seeds. In Latvia, plants are only illegal if they contain Schedule I controlled substances and LSA is not a Schedule 1 controlled substance.<ref> | *'''Latvia''': LSA itself is controlled as a structural analog of LSD. However, there is no information about LSA-containing seeds. In Latvia, plants are only illegal if they contain Schedule I controlled substances and LSA is not a Schedule 1 controlled substance.<ref>{{cite web|url=http://likumi.lv/doc.php?id=121086|title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem|publisher=VSIA Latvijas Vēstnesis|access-date=January 1, 2020|publication-date=November 10, 2005|language=lv}}</ref> | ||
*'''The Netherlands''': LSA is illegal to consume, sell, | *'''The Netherlands''': LSA is illegal. However, Hawaiian Baby Woodrose and Morning Glory seeds are not illegal to consume, sell or posses, like other entheogens.{{citation needed}} | ||
*'''New Zealand''': LSA is illegal to consume, sell, and possess. The plants and seeds of morning glory species are legal to possess, cultivate, buy and distribute.{{citation needed}} | *'''New Zealand''': LSA is illegal to consume, sell, and possess. The plants and seeds of morning glory species are legal to possess, cultivate, buy and distribute.{{citation needed}} | ||
*'''Sweden''': LSA is illegal | *'''Sweden''': LSA is being researched by health authorities and there is a risk in near future for LSA to become illegal. <ref>{{cite web|url=https://www.folkhalsomyndigheten.se/livsvillkor-levnadsvanor/andts/vad-vi-gor-inom-andts/narkotika-och-halsofarliga-varor/substanser-under-utredning/|publisher=Folkhälsomyndigheten |access-date=August 15, 2020|language=sv|publication-date=June 17, 2020|title=Substanser under utredning/ yttranden}}</ref> | ||
*''' | *'''Switzerland''': As a chemical, LSA can be considered a controlled substance as a defined derivative of Lysergic Acid under Verzeichnis E point 263. It is legal when used for scientific or industrial use.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>. Plant matter is not illegal. | ||
*'''United Kingdom''': LSA is a Class A | *'''Türkiye''': LSA is illegal to consume, sell, and possess. <ref>{{cite web|url=https://www.resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf|publisher=Resmi Gazete |access-date=January 16, 2020|language=tr|publication-date=December 16, 2013|title=Karar Sayısı : 2013/5742}}</ref> The plants and seeds of morning glory species are legal to possess, cultivate, buy and distribute.{{citation needed}} | ||
*'''United States''': As a precursor to LSD, LSA is a DEA Schedule III | *'''United Kingdom''': LSA is a Class A controlled substance and categorized as a precursor to [[LSD]].{{citation needed}} | ||
*'''United States''': As a precursor to LSD, LSA is a DEA Schedule III controlled substance.{{citation needed}} However, seeds containing LSA can be purchased legally on the internet and from gardening stores. | |||
*'''Poland''': ''Argyreia nervosa'' (Hawaiian baby woodrose) and ''Rivea corymbosa'' are illegal (I-N) with penalty for posession of up to 3 years in prison. LSA itself is covered by analogue law (VI-NPS) and therefore illegal with posession punishable by fine. Morning glory seeds are legal and openly sold in gargening shops.<ref>[https://isap.sejm.gov.pl/isap.nsf/DocDetails.xsp?id=WDU20240001139 Announcement of the Minister of Health of 17 June 2024 on the announcement of the uniform text of the regulation of the Minister of Health on the list of psychotropic substances, narcotic drugs and new psychoactive substances]</ref> | |||
==See also== | ==See also== | ||
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*[http://www.erowid.org/chemicals/lsa/lsa.shtml LSA (Erowid Vault)] | *[http://www.erowid.org/chemicals/lsa/lsa.shtml LSA (Erowid Vault)] | ||
*[https://isomerdesign.com/PiHKAL/explore.php?id=5309 LSA (Isomer Design)] | *[https://isomerdesign.com/PiHKAL/explore.php?id=5309 LSA (Isomer Design)] | ||
*[https://drugs-forum.com/wiki/LSA LSA (Drugs-Forum)] | |||
===Discussion=== | ===Discussion=== | ||
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==References== | ==References== | ||
<references /> | <references /> | ||
[[Category:Alkaloid]] | |||
[[Category:Lysergamide]] | [[Category:Lysergamide]] | ||
[[Category:Psychedelic]] | [[Category:Psychedelic]] | ||
[[Category:Entheogen]] | [[Category:Entheogen]] | ||