Lysergic acid tert-butylamide

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-HT_2A 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]

Other namesLAtB; N-tert-Butyllysergamide; NtB-LA

Drug classSerotonin receptor modulator; Serotonin 5-HT_2A receptor agonist; Serotonergic psychedelic; Hallucinogen

ATC code

• None

PubChem CID

• 154273364

Quick facts Clinical data, Other names ...

LAtB

Clinical data
Other names	LAtB; N-tert-Butyllysergamide; NtB-LA
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name (6aR,9R)-N-tert-butyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID	154273364
Chemical and physical data
Formula	C20H25N3O
Molar mass	323.440 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)(C)NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
InChI 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

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