Lysergic acid 2,4-dimethylazetidide

Lysergic acid 2,4-dimethylazetidide
Clinical data
Other names	Lysergic acid 2,4-dimethylazetidine, Diazedine, Lambda, LSZ
Routes of; administration	Oral
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Class A; Illegal in Denmark, France, Sweden and Switzerland;
Identifiers
	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;
	freebase: (S,S)-isomer, freebase; tartrate salt: (S,S)-isomer, tartrate salt;
CAS Number	freebase: 470666-31-0 ; tartrate salt: 470666-32-1 ;
PubChem CID	freebase: 71301249;
ChemSpider	freebase: 30773535 ;
UNII	freebase: 8SWJ525W4R;
Chemical and physical data
Formula	C21H25N3O
Molar mass	335.451 g·mol−1
3D model (JSmol)	freebase: Interactive image;
	SMILES freebase: C[C@H]1C[C@@H](N1C(=O)[C@H]2CN([C@@H]3CC4=CNC5=CC=CC(=C45)C3=C2)C)C;
	InChI freebase: InChI=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 ; Key:DUKNIHFTDAXJON-CTQRGLTFSA-N ;
	(what is this?) (verify)

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.^[2]^[3] 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-HT_2A 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.^[4]

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".^[5]^[6]

In 2013 LSZ also appeared on some designer drug and research chemical markets in the UK.^[7] LSZ later gained international popularity through a small cluster of mail-order novel psychedelic shops that appeared in 2012.^[8]

Legal status

On 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.^[7] 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] in Denmark as of May 2015,^[10] and in Sweden as of January 26, 2016.^[11]

References

^ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
^ Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, et al. (January 2017). "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)". Drug Testing and Analysis. 9 (1): 38–50. doi:10.1002/dta.1985. PMC 5411264. PMID 27265891.
^ Schifano F, Orsolini L, Papanti D, Corkery J (June 2016). "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. Springer International Publishing. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. OCLC 643052237. PMID 27272067.
^ Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM (September 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. PMID 12213075.
^ Morris H (1 May 2011). "Life Is a Cosmic Giggle on the Breath of the Universe". Vice Magazine. Retrieved 2011-06-15.
^ Cole K (2005). Lysergic. Indianapolis: Dog Ear Publishing. ISBN 978-1598580075.
^ ^a ^b ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014.
^ Power M (2014-01-29). "The Drug Revolution That No One Can Stop".
^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.
^ "Bekendtgørelse om euforiserende stoffer - ni nye stoffer tilføjet" (in Danish). Lægemiddelstyrelsen. 31 August 2015.
^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.

[1] "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.

[2] Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, et al. (January 2017). "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)". Drug Testing and Analysis. 9 (1): 38–50. doi:10.1002/dta.1985. PMC 5411264. PMID 27265891.

[3] Schifano F, Orsolini L, Papanti D, Corkery J (June 2016). "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. Springer International Publishing. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. OCLC 643052237. PMID 27272067.

[4] Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM (September 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. PMID 12213075.

[hamilton-5] Morris H (1 May 2011). "Life Is a Cosmic Giggle on the Breath of the Universe". Vice Magazine. Retrieved 2011-06-15.

[Lysergic-6] Cole K (2005). Lysergic. Indianapolis: Dog Ear Publishing. ISBN 978-1598580075.

[ACMD_tryptamines-7] ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014.

[8] Power M (2014-01-29). "The Drug Revolution That No One Can Stop".

[9] "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.

[10] "Bekendtgørelse om euforiserende stoffer - ni nye stoffer tilføjet" (in Danish). Lægemiddelstyrelsen. 31 August 2015.

[11] "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.

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Clinical data

Other names	Lysergic acid 2,4-dimethylazetidine, Diazedine, Lambda, LSZ
Routes of administration	Oral
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) UK: Class A Illegal in Denmark, France,^[1] Sweden and Switzerland
Identifiers
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
	freebase: (S,S)-isomer, freebase tartrate salt: (S,S)-isomer, tartrate salt
CAS Number	freebase: 470666-31-0^Y tartrate salt: 470666-32-1^N
PubChem CID	freebase: 71301249
ChemSpider	freebase: 30773535^N
UNII	freebase: 8SWJ525W4R
Chemical and physical data
Formula	C₂₁H₂₅N₃O
Molar mass	335.451 g·mol⁻¹
3D model (JSmol)	freebase: Interactive image
SMILES freebase: C[C@H]1C[C@@H](N1C(=O)[C@H]2CN([C@@H]3CC4=CNC5=CC=CC(=C45)C3=C2)C)C
InChI freebase: InChI=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^N Key:DUKNIHFTDAXJON-CTQRGLTFSA-N^N
^NY (what is this?) (verify)

Lysergic acid 2,4-dimethylazetidide

Legal status

See also

References