Lysergic acid 2,4-dimethylazetidide

Lysergic acid 2,4-dimethylazetidide
Systematic (IUPAC) name
(8β)-8- {[(2S,4S)- 2,4-dimethylazetidin- 1-yl] carbonyl}- 6-methyl- 9,10- didehydroergoline
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 470666-31-0 (S,S) isomer, freebase
470666-32-1 (S,S) isomer, tartrate salt
ATC code  ?
PubChem CID 10472143
Synonyms Lysergic acid 2,4-dimethylazetidine
Chemical data
Formula C21H25N3O 
Mol. mass 335.442 g/mol
SMILES eMolecules & PubChem
 Y(what is this?)  (verify)

Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) is an analogue of LSD developed by the team led by David E. Nichols at Purdue University. It was developed as a rigid analogue 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.[1]

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".[2][3][4]

References

  1. ^ Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM. 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 Sep 12;45(19):4344-9. doi:10.1021/jm020153s PMID 12213075 http://www.erowid.org/archive/rhodium/pdf/azetidine-lsd.pdf
  2. ^ Morris, H. (1 May 2011). "A Tour of Gordon Todd Skinner’s Subterranean LSD Palace". Vice Magazine. http://www.viceland.com/int/v18n5/htdocs/life-is-a-cosmic-giggle-803.php?page=3. Retrieved 2011-06-15. 
  3. ^ Cole, Krystle (2005). Lysergic. Indianapolis: Dog Ear Publishing. ISBN 1-59858-007-8. 
  4. ^ "Lysergic acid 2,4-dimethylazetidide". Bluelight.ru. 26 May 2009. http://www.bluelight.ru/vb/showpost.php?p=7176694&postcount=4. Retrieved 2011-06-15. 
Psychedelics
5-HT2AR agonists
Dissociatives
NMDAR antagonists
Deliriants
mAChR antagonists
Miscellaneous
Others
Lysergic acid derivatives
2-Bromo-LSD (BOL-148) • Bromocriptine • Cabergoline • Dihydroergocornine • Dihydroergocristine • Dihydroergocryptine • Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) • Dihydroergotamine • Dihydroergotoxine • Ergine (LSA; LA-111; Lysergamide) • Ergocornine • Ergocristine • Ergocryptine • Ergoloid • Ergometrine (Ergonovine, Ergobasine) • Ergometrinine • Ergotamine • Ergotoxine • Ergovaline • Lisuride • LSD • LSH • Lysergic Acid • Lysergic acid cyclobutylamide • Lysergic acid cyclopentylamide • Lysergic Acid Methyl Ester • Lysergol • Mesulergine • Metergoline • Methergine (Methylergometrine, Methylergonovine, Methylergobasine) • Methysergide • Pergolide • Syntometrine
Psychedelic lysergamides
AL-LAD • ALD-52 • BU-LAD • CYP-LAD • DAL • DAM-57 • Ergonovine • ETH-LAD • IP-LAD • LAE-32 • LSD • LPD-824 • LSM-775 • LSH • LSD-Pip • Lysergic Acid 2-Butylamide • Lysergic Acid 2,4-Dimethylazetidide • Lysergic Acid 3-Pentylamide • Methylergonovine • Methylisopropyllysergamide • MLD-41 • PARGY-LAD • PRO-LAD
Other ergolines
Natural sources
Achnatherum robustum (Sleepy Grass) • Argyreia nervosa (Hawaiian Baby Woodrose) • Claviceps spp. (Ergot) • Ipomoea spp. (Morning Glory, Tlitliltzin, Badoh Negro) • Rivea corymbosa (Coaxihuitl, Ololiúqui)