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'''Lysergic acid 2,4-dimethylazetidide''' (also known as '''λ''', '''Lambda''', and '''LSZ''') is a synthetic [[Psychoactive class::psychedelic]] of the [[chemical class::lysergamide]] chemical class which produces [[LSD#Subjective effects|LSD-like]] [[psychedelic]] effects when [[Routes of administration|administered]].
'''Lysergic acid 2,4-dimethylazetidide''' (also known as '''λ''', '''Lambda''', and '''LSZ''') is a synthetic [[Psychoactive class::psychedelic]] of the [[chemical class::lysergamide]] chemical class which produces [[LSD#Subjective effects|LSD-like]] [[psychedelic]] effects when [[Routes of administration|administered]].
In the 2000s, a team led by [https://en.wikipedia.org/wiki/David_E._Nichols David E. Nichols] at Purdue University set to develop a rigid analog of [[LSD]] with the diethylamide group constrained into an azetidine ring in order to map the binding site at the [[Serotonin#The_5-HT_system|5-HT<sub>2A</sub>]] [[receptor]].<ref>Nichols, D.E., Frescas S., Marona-Lewicka D., and Kurrasch-Orbaugh D.M. (2002). Lysergamides of Isomeric 2,4-Dimethylazetidines Map the Binding Orientation of the Diethylamide Moiety in the Potent Hallucinogenic Agent N,N-Diethyllysergamide (LSD). Journal of Medicinal Chemistry 2002 45 (19), 4344-4349. DOI: 10.1021/jm020153s</ref>
In the 2000s, a team led by [https://en.wikipedia.org/wiki/David_E._Nichols David E. Nichols] at Purdue University set to develop a rigid analog of [[LSD]] with the diethylamide group constrained into an azetidine ring in order to map the binding site at the [[Serotonin#The_5-HT_system|5-HT<sub>2A</sub>]] [[receptor]].<ref name="Nichols2002">{{cite journal|last1=Nichols|first1=D. E.|author-link1=David E. Nichols|last2=Frescas|first2=S.|last3=Marona-Lewicka|first3=D.|last4=Kurrasch-Orbaugh|first4=D. M.|year=2002|title=Lysergamides of Isomeric 2,4-Dimethylazetidines Map the Binding Orientation of the Diethylamide Moiety in the Potent Hallucinogenic Agent ''N'',''N''-Diethyllysergamide (LSD)|journal=Journal of Medicinal Chemistry|volume=45|issue=19|pages=4344-4349|doi=10.1021/jm020153s|issn=0022-2623|eissn=1520-4804|oclc=39480771|pmid=12213075}}</ref>
LSZ has little to no history of human usage prior to 2012 when it appeared on some [[research chemical]] markets in the UK.<ref name="ACMD">http://www.ukchemicalresearch.org/Thread-LSZ</ref><ref>ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" | https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/318693/UpdateGenericDefinitionTryptamines.pdf</ref> LSZ later gained international popularity through a small cluster of mail-order novel psychedelic shops that appeared in 2012.<ref>The Drug Revolution That No One Can Stop | https://medium.com/matter/the-drug-revolution-that-no-one-can-stop-19f753fb15e0#.fupvbuawp</ref> There have also been several unconfirmed reports of LSZ being synthesized in illicit laboratories and distributed on blotter paper or in liquid solution under names such as "Diazedine" and "λ" (or "Lambda").<ref>Life Is a Cosmic Giggle on the Breath of the Universe | http://www.vice.com/en_ca/read/life-is-a-cosmic-giggle-803-v18n5?Contentpage=3</ref><ref>Cole, Krystle (2005). Lysergic. Indianapolis: Dog Ear Publishing. ISBN 1-59858-007-8.</ref>
LSZ has little to no history of human usage prior to 2012 when it appeared on some [[research chemical]] markets in the UK.<ref name="ACMD2014">{{cite web|url=https://assets.publishing.service.gov.uk/government/uploads/system/uploads/attachment_data/file/318693/UpdateGenericDefinitionTryptamines.pdf|title=Update of the generic definition for tryptamines|date=June 10, 2014|access-date=January 1, 2020|publisher=Government Digital Service|page=12|author=Advisory Council on the Misuse of Drugs (ACMD)}}</ref> LSZ later gained international popularity through a small cluster of mail-order novel psychedelic shops that appeared in 2012.<ref>{{cite news|url=https://medium.com/matter/the-drug-revolution-that-no-one-can-stop-19f753fb15e0#.fupvbuawp|title=The Drug Revolution That No One Can Stop|author=Mike Power|date=January 29, 2014|access-date=January 7, 2020|publisher=Medium|work=Matter}}</ref> There have also been several unconfirmed reports of LSZ being synthesized in illicit laboratories and distributed on blotter paper or in liquid solution under names such as "Diazedine" and "λ" (or "Lambda").<ref>{{cite book|last=Cole|first=Krystle|year=2005|location=Indianapolis|publisher=Dog Ear Publishing|isbn=1-59858-007-8|title=Lysergic}}</ref><ref>{{cite news|url=http://www.vice.com/en_ca/read/life-is-a-cosmic-giggle-803-v18n5?Contentpage=3|title=Life Is a Cosmic Giggle on the Breath of the Universe|author=Hamilton Morris|date=May 1, 2011|access-date=January 7, 2020|publisher=VICE}}</ref>
LSZ is not considered to be addictive or physiologically toxic.<ref>Lüscher, C., & Ungless, M. A. (2006). The Mechanistic Classification of Addictive Drugs, 3(11). https://doi.org/10.1371/journal.pmed.0030437</ref><ref>Nichols, D. E. (2016). "Psychedelics." Pharmacological Reviews, 68(2), 264-355. https://doi.org/10.1124/pr.115.011478</ref> Nevertheless, adverse psychological reactions such as severe [[anxiety]], [[paranoia]] and [[psychosis]] are always possible, particularly among those predisposed to mental illness.<ref>Strassman, R. J. (1984). Adverse Reactions to Psychedelic Drugs: A Review of the Literature. The Journal of Nervous and Mental Disease, 172(10), 577-595. PMID: 6384428</ref> It is highly advised to use [[Harm reduction#Hallucinogens|harm reduction practices]] if using this substance.
LSZ is not considered to be addictive or physiologically toxic.<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|eissn=1549-1676}}</ref><ref name="Nichols2016">{{cite journal|last=Nichols|first=David E.|author-link=David E. Nichols|editor-last=Barker|editor-first=Eric L.|title=Psychedelics|journal=Pharmacological Reviews|volume=68|issue=2|pages=264-355|doi=10.1124/pr.115.011478|year=2016|issn=0031-6997|eissn=1521-0081}}</ref> Nevertheless, adverse psychological reactions such as severe [[anxiety]], [[paranoia]] and [[psychosis]] are always possible, particularly among those predisposed to mental illness.<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 highly advised to use [[Harm reduction#Hallucinogens|harm reduction practices]] if using this substance.
==Chemistry==
==Chemistry==
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The structure contains a bicyclic hexahydroindole fused to a bicyclic quinoline group (lysergic acid). At carbon 8 of the quinoline, an amide group is bound. Additionally, the substitutions of the terminal nitrogen atom of the amide group form a 2,4-dimethylazetidide group. LSZ is additionally substituted at carbon 6 with a methyl group.
The structure contains a bicyclic hexahydroindole fused to a bicyclic quinoline group (lysergic acid). At carbon 8 of the quinoline, an amide group is bound. Additionally, the substitutions of the terminal nitrogen atom of the amide group form a 2,4-dimethylazetidide group. LSZ is additionally substituted at carbon 6 with a methyl group.
There are three possible stereoisomers around the azetidine ring with the (S,S)-(+) isomer being the most active. It is slightly more potent than LSD itself in drug discrimination tests using trained rats.<ref>Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD) (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/12213075</ref>
There are three possible stereoisomers around the azetidine ring with the (S,S)-(+) isomer being the most active. It is slightly more potent than LSD itself in drug discrimination tests using trained rats.<ref name="Nichols2002"></ref>
LSZ is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating.
LSZ is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating.
Tolerance to the effects of LSZ are built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). LSZ presents cross-tolerance with all [[psychedelic]]s, meaning that all psychedelics will have a reduced effect after the consumption of LSZ.
Tolerance to the effects of LSZ is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). LSZ presents cross-tolerance with all [[psychedelic]]s, meaning that all psychedelics will have a reduced effect after the consumption of LSZ.
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Psychedelics}}
==Legal status==
==Legal status==
*'''Denmark:''' As of August 25th, 2015, LSZ is specifically named on the list of illegal substances in Denmark.<ref><nowiki>https://laegemiddelstyrelsen.dk/da/nyheder/2015/bekendtgoerelse-om-euforiserende-stoffer-ni-nye-stoffer-tilfoejet/</nowiki></ref>
*'''Latvia:''' LSZ is illegal in Latvia. Although it isn't officially scheduled, it is controlled as an LSD structural analog due to an amendment made on June 1th, 2015.<ref>Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2.4.punkts) | http://likumi.lv/doc.php?id=121086</ref>
*'''Denmark''': As of August 25, 2015, LSZ is specifically named on the list of illegal substances in Denmark.<ref>{{cite web|url=https://laegemiddelstyrelsen.dk/da/nyheder/2015/bekendtgoerelse-om-euforiserende-stoffer-ni-nye-stoffer-tilfoejet|title=Bekendtgørelse om euforiserende stoffer - ni nye stoffer tilføjet|publisher=Danish Medicines Ageny|date=August 31, 2015|access-date=January 1, 2020|language=da}}</ref>
*'''Sweden:''' Following its sale as a [[designer drug]], LSZ was made illegal in Sweden on 26 January 2016.<ref>(in Swedish) Folkhälsomyndigheten. | https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2016/januari/31-nya-substanser-klassas-som-narkotika-eller-halsofarlig-vara/</ref>
*'''Germany''': LSZ 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>
*'''Switzerland:''' LSZ was added to the list of controlled substances on the 1st of December 2015.<ref>https://www.admin.ch/opc/de/official-compilation/2015/5093.pdf</ref>
*'''Japan''': LSZ is controlled by the Pharmaceutical Affairs Law in Japan, making it illegal to possess or sell.<ref>{{cite web|title=危険ドラッグの成分３物質を新たに指定薬物に指定|language=ja|url=https://www.mhlw.go.jp/stf/houdou/0000212475_00035.html|publisher=厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]|access-date=December 2, 2022}}</ref>
*'''United Kingdom:''' As of January 7th, 2015, LSZ is specifically named in the U.K. Misuse of Drugs Act as a Class A drug.<ref name="ACMD tryptamines">{{cite web | url=https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/318693/UpdateGenericDefinitionTryptamines.pdf | title=Update of the Generic Definition for Tryptamines | publisher=UK Home Office | date=10 June 2014 | accessdate=10 June 2014 | author=ACMD|page=12}}</ref>
*'''Latvia''': LSZ is illegal in Latvia. Although it isn't officially scheduled, it is controlled as an LSD structural analog due to an amendment made on June 1, 2015.<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>
*'''Sweden''': Following its sale as a [[designer drug]], LSZ was made illegal in Sweden on January 26, 2016.<ref>{{cite web|url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2016/januari/31-nya-substanser-klassas-som-narkotika-eller-halsofarlig-vara|title=31 nya substanser klassas som narkotika eller hälsofarlig vara|publisher=Folkhälsomyndigheten [Public Health Agency of Sweden]|access-date=January 1, 2020|publication-date=January 26, 2016|language=sv}}</ref>
*'''Switzerland''': LSZ is a controlled substance specifically named under Verzeichnis E. It was added to the list of controlled substances on the December 1, 2015.<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>
*'''Turkey:''' LSZ is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="Bakanlar Kurulu Kararı - Karar Sayısı : 2016/9712">https://resmigazete.gov.tr/eskiler/2017/01/20170112-8.pdf</ref>
*'''United Kingdom''': As of January 7, 2015, LSZ is specifically named in the U.K. Misuse of Drugs Act as a Class A drug.<ref name="ACMD2014"></ref>
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
In the 2000s, a team led by David E. Nichols at Purdue University set to develop a rigid analog of LSD with the diethylamide group constrained into an azetidine ring in order to map the binding site at the 5-HT2Areceptor.[1]
LSZ has little to no history of human usage prior to 2012 when it appeared on some research chemical markets in the UK.[2] LSZ later gained international popularity through a small cluster of mail-order novel psychedelic shops that appeared in 2012.[3] There have also been several unconfirmed reports of LSZ being synthesized in illicit laboratories and distributed on blotter paper or in liquid solution under names such as "Diazedine" and "λ" (or "Lambda").[4][5]
LSZ is not considered to be addictive or physiologically toxic.[6][7] Nevertheless, adverse psychological reactions such as severe anxiety, paranoia and psychosis are always possible, particularly among those predisposed to mental illness.[8] It is highly advised to use harm reduction practices if using this substance.
LSZ, or d-lysergic acid 2,4-dimethylazetidide, is a semi-synthethic alkaloid of the lysergamide famiy. It contains a core structure of lysergic acid with an amine functional group bound to RN of the chemical structure. This core polycyclic structure is an indole derivative, and has tryptamine and phenethylamine groups embedded within it.
The structure contains a bicyclic hexahydroindole fused to a bicyclic quinoline group (lysergic acid). At carbon 8 of the quinoline, an amide group is bound. Additionally, the substitutions of the terminal nitrogen atom of the amide group form a 2,4-dimethylazetidide group. LSZ is additionally substituted at carbon 6 with a methyl group.
There are three possible stereoisomers around the azetidine ring with the (S,S)-(+) isomer being the most active. It is slightly more potent than LSD itself in drug discrimination tests using trained rats.[1]
LSZ likely acts as a 5-HT2Apartial agonist. The psychedelic effects are believed to come from LSZ's efficacy at the 5-HT2A receptors. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWikicontributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
This toxicity and harm potential section is a stub.
As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it. Note: Always conduct independent research and use harm reduction practices if using this substance.
The toxicity and long-term health effects of recreational LSZ do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because LSZ is a research chemical with very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried LSZ suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.
LSZ is not habit-forming and the desire to use it can actually decrease with use. It is most often self-regulating.
Tolerance to the effects of LSZ is built almost immediately after ingestion. After that, it takes about 3 days for the tolerance to be reduced to half and 7 days to be back at baseline (in the absence of further consumption). LSZ presents cross-tolerance with all psychedelics, meaning that all psychedelics will have a reduced effect after the consumption of LSZ.
Dangerous interactions
Warning:Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
[[Wikipedia:Lithium_(medication)|DangerousInteraction::Lithium]] - Lithium is commonly prescribed for the treatment of bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.
"[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Cannabis may have an unexpectedly strong and unpredictable synergy with the effects of LSZ. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid unintentional overdose.
"[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Tramadol is well-documented to lower the seizure threshold[9] and psychedelics may act to trigger seizures in susceptible individuals.[citation needed]
Legal status
Denmark: As of August 25, 2015, LSZ is specifically named on the list of illegal substances in Denmark.[10]
Germany: LSZ is controlled under the NpSG (New Psychoactive Substances Act)[11] as of July 18, 2019.[12] 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.[13]
Japan: LSZ is controlled by the Pharmaceutical Affairs Law in Japan, making it illegal to possess or sell.[14]
Latvia: LSZ is illegal in Latvia. Although it isn't officially scheduled, it is controlled as an LSD structural analog due to an amendment made on June 1, 2015.[15]
Sweden: Following its sale as a designer drug, LSZ was made illegal in Sweden on January 26, 2016.[16]
Switzerland: LSZ is a controlled substance specifically named under Verzeichnis E. It was added to the list of controlled substances on the December 1, 2015.[17]
Turkey: LSZ is a classed as drug and is illegal to possess, produce, supply, or import.[18]
United Kingdom: As of January 7, 2015, LSZ is specifically named in the U.K. Misuse of Drugs Act as a Class A drug.[2]
↑ 1.01.1Nichols, D. E.; Frescas, S.; Marona-Lewicka, D.; Kurrasch-Orbaugh, D. M. (2002). "Lysergamides of Isomeric 2,4-Dimethylazetidines Map the Binding Orientation of the Diethylamide Moiety in the Potent Hallucinogenic Agent N,N-Diethyllysergamide (LSD)". Journal of Medicinal Chemistry. 45 (19): 4344–4349. doi:10.1021/jm020153s. eISSN1520-4804. ISSN0022-2623. OCLC39480771. PMID12213075.
↑Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. doi:10.1007/BF03161089. ISSN1556-9039.
↑"Anlage NpSG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
↑"§ 4 NpSG" (in Deutsch). Bundesministerium der Justiz und für Verbraucherschutz [Federal Ministry of Justice and Consumer Protection]. Retrieved December 10, 2019.
↑"危険ドラッグの成分３物質を新たに指定薬物に指定" (in 日本語). 厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)]. Retrieved December 2, 2022.
