| 词条 | Lysergic acid 2,4-dimethylazetidide |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 452018128 | IUPAC_name = [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl]-[(2S,4S)-2,4-dimethylazetidin-1-yl]methanone | image = LSD-azetidine.svg | width = 130 | tradename = | legal_AU = | legal_CA = | legal_UK = Class A | legal_US = | legal_status = Illegal in Sweden and Switzerland | dependency_liability = | routes_of_administration = Oral | metabolism = | excretion = | index_comment = (S,S)-isomer, freebase | index2_comment = (S,S)-isomer, tartrate salt | index_label = freebase | index2_label= tartrate salt | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 470666-31-0 | CAS_number2_Ref = {{cascite|changed|??}} | CAS_number2= 470666-32-1 | PubChem = 71301249 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 30773535 | ChEMBL = | C=21 | H=25 | N=3 | O=1 | molecular_weight = 335.442 g/mol | smiles = C[C@H]1C[C@@H](N1C(=O)[C@H]2CN([C@@H]3CC4=CNC5=CC=CC(=C45)C3=C2)C)C | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C21H25N3O/c1-12-7-13(2)24(12)21(25)15-8-17-16-5-4-6-18-20(16)14(10-22-18)9-19(17)23(3)11-15/h4-6,8,10,12-13,15,19,22H,7,9,11H2,1-3H3/t12-,13-,15+,19+/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = DUKNIHFTDAXJON-CTQRGLTFSA-N | synonyms = Lysergic acid 2,4-dimethylazetidine, Diazedine, Lambda, LSZ }}Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) is an analog of LSD developed by the team led by David E. Nichols at Purdue University.[1][2] It was developed as a rigid analog of LSD with the diethylamide group constrained into an azetidine ring in order to map the binding site at the 5-HT2A receptor. There are three possible stereoisomers around the azetidine ring, with the (S,S)-(+) isomer being the most active, slightly more potent than LSD itself in drug discrimination tests using trained rats.[3] There have been several unconfirmed reports of lysergic acid 2,4-dimethylazetidide being synthesized in illicit laboratories and distributed on blotter paper or in liquid solution under names such as "diazedine" and "λ".[4][5] In 2013 LSZ also appeared on some designer drug and research chemical markets in the UK.[6]{{unreliable source?|date=April 2014}}[7] LSZ later gained international popularity through a small cluster of mail-order novel psychedelic shops that appeared in 2012.[7] Legal statusOn June 10, 2014 the UK Advisory Council on the Misuse of Drugs (ACMD) recommended that LSZ be specifically named in the UK Misuse of Drugs Act as a class A drug despite not identifying any harm associated with its use.[8] The UK Home office accepted this advice and announced a ban of the substance to be enacted on 6 January 2015 as part of The Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2014. LSZ is illegal in Switzerland as of December 2015[9] and in Sweden as of January 26, 2016.[10] See also
References1. ^{{cite journal | author1=Simon D. Brandt | author10=David E. Nichols | author11=Adam L. Halberstadt | url=https://www.erowid.org/references/texts/show/9058docid7821 | format=PDF | title=Return of the lysergamides. Part II: Analytical and behavioural characterization of N6-allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ) | date=June 2016 | author2=Pierce V. Kavanagh | author3=Folker Westphal | author4=Simon P. Elliott | author5=Jason Wallach | author6=Tristan Colestock | author7=Timothy E. Burrow | author8=Stephen J. Chapman | author9=Alexander Stratford | journal=Drug Testing and Analysis | volume=9 | issue=1 | pages=38–50 | doi=10.1002/dta.1985 | pmid=27265891| pmc=5411264 }} {{Hallucinogens}}{{Serotonergics}}{{Ergolines}}{{DEFAULTSORT:LSZ}}2. ^{{cite book | url=https://link.springer.com/bookseries/7854 | chapter-url=https://link.springer.com/chapter/10.1007/7854_2016_15 | doi=10.1007/7854_2016_15 | pmid=27272067 | title=Current Topics in Behavioral Neurosciences | journal=Current Topics in Behavioral Neurosciences | volume=32 | publisher=Springer International Publishing | author=Fabrizio Schifano | author2=Laura Orsolini | author3=Duccio Papanti | author4=John Corkery | date=June 2016 | pages=351–380 | oclc=643052237 | chapter=NPS: Medical Consequences Associated with Their Intake| isbn=978-3-319-52442-9 }} 3. ^{{ cite journal |author1=Nichols, D. E. |author2=Frescas, S. |author3=Marona-Lewicka, D. |author4=Kurrasch-Orbaugh, D. M. | 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 |date=September 2002 | volume = 45 | issue = 19 | pages = 4344–4349 | doi = 10.1021/jm020153s | pmid = 12213075 | url = https://www.erowid.org/references/texts/show/6524docid6053 | format = PDF }} 4. ^{{cite web|url=https://www.vice.com/en_ca/read/life-is-a-cosmic-giggle-803-v18n5/page/3 |title=Life Is a Cosmic Giggle on the Breath of the Universe |last=Morris|first=H. |publisher=Vice Magazine |date=1 May 2011|accessdate=2011-06-15}} 5. ^{{cite book | last = Cole | first = Krystle | year = 2005 | title = Lysergic | publisher = Dog Ear Publishing | location = Indianapolis | isbn = 978-1598580075}} 6. ^[https://www.ukchemicalresearch.org/Thread-LSZ LSZ Thread. UKChemicalResearch.org]{{unreliable source?|date=April 2014}} 7. ^{{cite web|url=https://medium.com/matter/the-drug-revolution-that-no-one-can-stop-19f753fb15e0|title=The Drug Revolution That No One Can Stop|author=Mike Power|date=2014-01-29}} 8. ^1 {{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}} 9. ^{{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=Der Bundesrat | language=German}} 10. ^{{cite web | url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/november/31-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/ | title=31 nya ämnen kan klassas som narkotika eller hälsofarlig vara | publisher=Folkhälsomyndigheten | language=Swedish | date=November 2015}} 5 : Lysergamides|Azetidines|Designer drugs|Psychedelia|Serotonin receptor agonists |
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