LBB-66

Pharmaceutical compound From Wikipedia, the free encyclopedia

LBB-66, also known as lysergic acid dibutylamide or as N,N-dibutyllysergamide, is a serotonin receptor modulator of the lysergamide family related to lysergic acid diethylamide (LSD; LSD-25).^[1]^[2]^[3] It is the derivative of LSD in which the N,N-diethyl groups have been replaced with N,N-dibutyl groups.^[1]^[2]^[3]

Other namesLBB66; LA-dibutylamide; Lysergic acid dibutylamide; N,N-Dibutyllysergamide; N,N-Dibutyl-6-methyl-9,10-didehydroergoline-8β-carboxamide

Drug classSerotonin receptor modulator

ATC code

None

PubChem CID

92260373

Quick facts Clinical data, Other names ...

LBB-66
Clinical data

Other names	LBB66; LA-dibutylamide; Lysergic acid dibutylamide; N,N-Dibutyllysergamide; N,N-Dibutyl-6-methyl-9,10-didehydroergoline-8β-carboxamide
Drug class	Serotonin receptor modulator
ATC code	None
Identifiers
IUPAC name (6aR,9R)-N,N-dibutyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID	92260373
ChemSpider	270008
Chemical and physical data
Formula	C₂₄H₃₃N₃O
Molar mass	379.548 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCN(CCCC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
InChI InChI=1S/C24H33N3O/c1-4-6-11-27(12-7-5-2)24(28)18-13-20-19-9-8-10-21-23(19)17(15-25-21)14-22(20)26(3)16-18/h8-10,13,15,18,22,25H,4-7,11-12,14,16H2,1-3H3/t18-,22-/m1/s1 Key:GVTRJLOTMIDJSS-XMSQKQJNSA-N

The drug has about 31% or around one-third of the antiserotonergic activity of LSD in the isolated rat uterus in vitro.^[1]^[4]^[5]^[6] In contrast to other assessed lysergamides, it has been said to bind practically irreversibly in this context.^[5] Unlike LSD, LBB-66 is said to be devoid of psychedelic effects in humans, with a hallucinogenic potency relative to LSD of 0% stated, but the tested doses not given.^[1]

LBB-66 was first described in the scientific literature by Albert Hofmann and colleagues by 1955.^[7]^[8]^[9]^[10]

References

[1]
Fanchamps A (1978). "Some Compounds With Hallucinogenic Activity". Ergot Alkaloids and Related Compounds. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 567–614. doi:10.1007/978-3-642-66775-6_8. ISBN 978-3-642-66777-0. Archived from the original on 30 March 2025. Retrieved 3 June 2025. Lysergic acid dibutylamide (LBB66, No. 73e) is devoid of LSD-like mental effects (Sandoz Res. Lab., 1959). Its antiserotonin effect is 30% of that of LSD (CERLETTI and DOEPFNER, 1958a). [...] Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...] LA dibutylamide (LBB66) [...] Regarding disubstituted ami des, the psychotomimetic activity is reduced by shortening of the chains (DAM 57) and by ring closure (LPD 824 and LSM 775) and suppressed by lengthening (LBB 66).
[2]
Rutschmann J, Stadler PA (1978). "Chemical Background". In Berde B, Schild HO (eds.). Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). Vol. 49. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 29–85. doi:10.1007/978-3-642-66775-6_2. ISBN 978-3-642-66777-0.
[3]
Oberlender RA (May 1989). "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens". Purdue e-Pubs. Purdue University. Table 2. Relative potency values for lysergic acid amides. [...]
[4]
Offermeier J (1965). "Serotonin and its derivatives: a study on structure-activity relations" (PDF). Nijmegen : Thoben. TABLE II Relative anti-5-НТ potency of lysergic acid derivatives on the rat uterus preparation (LSD = 100) [...]
[5]
Cerletti A, Doepfner W (January 1958). "Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids". The Journal of Pharmacology and Experimental Therapeutics. 122 (1): 124–136. doi:10.1016/S0022-3565(25)11933-2. PMID 13502837. Section A of table I summarizes the results obtained by a comparison of the unsubstituted and several disubstituted amides of d-lysergic acid. It shows that the antiserotonin activity of LSD is not reached by any of these compounds. It is, however, interesting to note that the affinity of the compounds to the uterine muscle, estimated from the effect of repeated washing of the preparation, continuously increases from the simple amide to the dibutylamide. This last compound produces a practically irreversible effect. [...] TABLE 1 Antiserotonin potency of 16 amide-derivatives of d-lysergic acid [...]
[6]
Rothlin E (March 1957). "Lysergic acid diethylamide and related substances". Annals of the New York Academy of Sciences. 66 (3): 668–676. Bibcode:1957NYASA..66..668R. doi:10.1111/j.1749-6632.1957.tb40756.x. PMID 13425249. TABLE 1 INHIBITION OF SEROTONIN BY VARIOUS AMIDES OF LYSERGIC ACID [...] Finally, we have the disubstituted amides of d-lysergic acid: the dimethyl, diethyl. di-isopropyl, and dibutyl amides. They are 3 to 5 times weaker than LSD in their antagonism toward serotonin.
[7]
Hofmann A, Stoll A (1955). "Amide der stereoisomeren Lysergsäuren und Dihydro-lysergsäuren. 38. Mitteilung über Mutterkornalkaloide" [Amides of stereoisomeric lysergic and dihydrolysergic acids. 38. Ergot alkaloids]. Helvetica Chimica Acta. 38 (2): 421–433. doi:10.1002/hlca.19550380207. ISSN 0018-019X. Retrieved 5 June 2025.
[8]
Cerletti A (1956). "Lysergic Acid Diethylamide (LSD) and Related Compounds". In Abramson HA (ed.). Neuropharmacology: Transactions of the 2nd Conference, May 25-27, 1955, Princeton, N.J. New York: Josiah Macy. pp. 9–84. Cerletti: I have forgotten to tell you that a whole series of compounds homologous to LSD, such as the diethyl-, the dipropyl-, the di-isopropyland the di-butylamide of lysergic acid, has been prepared by Stoll and Hofmann (6). Besides these, the corresponding monosubstituted amides, for example, lysergic acid methylamide or lysergic acid ethylamide have been studied. The last named substance, known as LAE-32, is of special interest. It is the monothylamide of lysergic acid and is a compound which, when administered in doses about ten times higher than LSD, like LSD, produces very remarkable psychic changes but, in contrast to LSD, seems to be less stimulating and more depressing.
[9]
Hofmann A (1958). "The LSD-Psychosis: III. Lysergic Acid Diethylamide and Related Compounds. Relationship Between Spatial Arrangement and Mental Effects". In Rinkel M (ed.). Chemical Concepts of Psychosis: Proceedings of the Symposium on Chemical Concepts of Psychosis held at the Second International Congress of Psychiatry in Zurich, Switzerland, September 1 to 7, 1957. New York: McDowell, Obolensky. pp. 85–90. doi:10.1037/11190-006. Archived from the original on 4 June 2025. TABLE I Variations in the acid amide group of the LSD molecule. Amides of d-lysergic acid (C15H15N2.COR) prepared for pharmacological investigation. [...]
[10]
Hofmann A (June 1959). "Psychotomimetic drugs; chemical and pharmacological aspects" (PDF). Acta Physiologica et Pharmacologica Neerlandica. 8: 240–258. PMID 13852489. Systematic variations of the substituents in the amide grouping has resulted in the synthesis of a great number of substances (STOLL and HOFMANN, 1955) which are listed in table 1. [...] TABLE 1 Variations in the acid amide group of the LSD molecule Amides of d-lysergic acid (C12H15N2–COR) prepared for pharmacological investigation [...] R: [...] d-lysergic acid pyrrolinide

LBB-66

See also

References

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