Lysergic acid tert-butylamide

Last updated

LAtB
LAtB structure.png
LAtB 3D.png
Clinical data
Other namesLAtB; N-tert-Butyllysergamide; NtB-LA
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • (6aR,9R)-N-tert-butyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID
Chemical and physical data
Formula C20H25N3O
Molar mass 323.440 g·mol−1
3D model (JSmol)
  • CC(C)(C)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
  • InChI=1S/C20H25N3O/c1-20(2,3)22-19(24)13-8-15-14-6-5-7-16-18(14)12(10-21-16)9-17(15)23(4)11-13/h5-8,10,13,17,21H,9,11H2,1-4H3,(H,22,24)/t13-,17-/m1/s1
  • Key:UTEDIDSANBDUDS-CXAGYDPISA-N

Lysergic acid tert-butylamide (LAtB), also known as N-tert-butyllysergamide (NtB-LA), is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD). [1] [2] [3] It was described in an early patent as reportedly being psychoactive and hallucinogenic and as producing hypothermia and "anti-hypothalamic" effects presumably in animals. [2] The drug shows activity at serotonin receptors, but is a very low-potency agonist of the serotonin 5-HT2A receptor. [1] The chemical synthesis of LAtB has been described [2] and analytical characterization has been described. [3] It was first described in the literature in a patent by Richard P. Pioch at Eli Lilly and Company in 1961 (filed in 1956). [2] The drug's pharmacology was later studied by David E. Nichols and colleagues. [1]

Contents

See also

References

  1. 1 2 3 Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN   978-3-662-55878-2. PMID   28401524.
  2. 1 2 3 4 US 2997470,Pioch RP,"Lysergic acid amides",issued 1961-08-22, assigned to Eli Lilly and Company
  3. 1 2 Clark CC (1 May 1989). "The Differentiation of Lysergic Acid Diethylamide (LSD) from N -Methyl- N -Propyl and N -Butyl Amides of Lysergic Acid" . Journal of Forensic Sciences. 34 (3): 532–546. doi:10.1520/JFS12674J. ISSN   0022-1198 . Retrieved 15 October 2025.
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