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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>
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>


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 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.
 
As with psychedelics in general, LSZ does not meet the criteria for an addictive substance by the scientific community.<ref>Lüscher, C., & Ungless, M. A. (2006). The Mechanistic Classification of Addictive Drugs, 3(11). https://doi.org/10.1371/journal.pmed.0030437</ref> Nevertheless, unpredictable adverse reactions such as uncontrollable [[anxiety]], [[paranoia]], [[delusions]] and [[psychosis|psychotic breaks]] can always still occur, particularly among those who are predisposed to psychiatric disorders.<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> While these negative reactions or [[bad trip|"bad trips"]] can often be attributed to factors like the user's inexperience or improper preparation of their [[set and setting]], they are known to happen spontaneously among even the most experienced of users as well. This is why despite its low likelihood of displaying any significant toxicity, it is still highly advised to approach this very potent, unpredictable, long-lasting, [[hallucinogenic]] substance with the proper amount of precaution, and [[Harm reduction#Hallucinogens|harm reduction practices]] if choosing to use it.


==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>


==Pharmacology==
==Pharmacology==
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{{#ask: [[Category:LSZ]][[Category:Experience]]|format=ul|Columns=1}}
{{#ask: [[Category:LSZ]][[Category:Experience]]|format=ul|Columns=1}}
Additional experience reports can be found here:
Additional experience reports can be found here:
* [https://www.erowid.org/experiences/subs/exp_LSZ.shtml Erowid Experience Vaults: LSZ]
 
*[https://www.erowid.org/experiences/subs/exp_LSZ.shtml Erowid Experience Vaults: LSZ]


==Toxicity and harm potential==
==Toxicity and harm potential==
{{toxicity}}
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
The toxicity and long-term health effects of recreational LSZ do not seem to have been studied in any scientific context and the exact [[Toxicity::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). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
The toxicity and long-term health effects of recreational LSZ do not seem to have been studied in any scientific context and the exact [[Toxicity::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). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.


It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.


===Tolerance and addiction potential===
===Tolerance and addiction potential===
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 issues==
*'''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>
{{LegalStub}}
*'''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>
*'''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>
*'''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>
*'''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>
*'''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>
*'''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>
*'''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>
*'''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>
*'''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>
*'''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>
*'''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>


==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Research chemical]]
*[[Research chemical]]
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==External links==
==External links==
*[https://en.wikipedia.org/wiki/Lysergic_acid_2,4-dimethylazetidide LSZ (Wikipedia)]
*[https://en.wikipedia.org/wiki/Lysergic_acid_2,4-dimethylazetidide LSZ (Wikipedia)]
*[https://www.erowid.org/chemicals/lsz/lsz.shtml LSZ (Erowid Vault)]
*[https://www.erowid.org/chemicals/lsz/lsz.shtml LSZ (Erowid Vault)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=5363 LSZ (Isomer Design)]
*[https://isomerdesign.com/PiHKAL/explore.php?id=5363 LSZ (Isomer Design)]
*[http://www.bluelight.org/vb/threads/681365-The-Big-amp-Dandy-LSZ-Thread LSZ (Bluelight)]
 
===Discussion===
 
*[http://www.bluelight.org/vb/threads/681365-The-Big-amp-Dandy-LSZ-Thread The Big & Dandy LSZ Thread (Bluelight)]


==References==
==References==
<references />
<references />
[[Category:Substance]]
[[Category:Psychoactive substance]]
[[Category:Psychoactive substance]]
[[Category:Research chemical]]
[[Category:Hallucinogen]]
[[Category:Psychedelic]]
[[Category:Psychedelic]]
[[Category:Lysergamide]]
[[Category:Lysergamide]]
[[Category:Research chemical]]


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{{#set:Featured=true}}
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