Lysergic acid butylamide

Lysergic acid butylamide, also known as N-butyllysergamide (NB-LA), is a serotonin receptor modulator of the lysergamide family related to the psychedelic drug lysergic acid diethylamide (LSD).^[1]^[2]^[3]^[4] It is the analogue of LSD in which the N,N-diethyl groups have been replaced with an N-butyl group and is also the N-butyl derivative of ergine (lysergic acid amide; LSA).^[1]^[2]^[3]^[4] The drug shows 64.9% of the antiserotonergic activity of LSD in the isolated rat uterus in vitro.^[2]^[3]^[4] However, activity in this assay does not correlate with hallucinogenic activity.^[5] In addition, unlike LSD and lysergic acid ethylamide (LAE-32), the lower homologue lysergic acid propylamide is known to be inactive as a psychedelic in humans at doses of up to 500 μg orally.^[3]^[6] Lysergic acid butylamide was first described in the scientific literature by 1957.^[3]^[4]

Other namesLAB; N-Butyllysergamide; NB-LA; N-Butyl-9,10-didehydro-6-methylergoline-8β-carboxamide

Drug classSerotonin receptor modulator

ATC code

None

CAS Number

50583-88-5

Quick facts Clinical data, Other names ...

Lysergic acid butylamide
Clinical data

Other names	LAB; N-Butyllysergamide; NB-LA; N-Butyl-9,10-didehydro-6-methylergoline-8β-carboxamide
Drug class	Serotonin receptor modulator
ATC code	None
Identifiers
IUPAC name (6aR,9R)-N-butyl-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number	50583-88-5
PubChem CID	3039392
ChemSpider	2302861
Chemical and physical data
Formula	C₂₀H₂₅N₃O
Molar mass	323.440 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCNC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
InChI InChI=1S/C20H25N3O/c1-3-4-8-21-20(24)14-9-16-15-6-5-7-17-19(15)13(11-22-17)10-18(16)23(2)12-14/h5-7,9,11,14,18,22H,3-4,8,10,12H2,1-2H3,(H,21,24)/t14-,18-/m1/s1 Key:PZRGRDXQFPWKCS-RDTXWAMCSA-N

References

[1]
Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. https://erowid.org/library/books_online/tihkal/tihkal26.shtml [...] "N-Butyllysergamide" [...]
[2]
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. [...]
[3]
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. The fourth group comprises compounds having a single substituent at the amide nitrogen. These compounds form a homologous series in which the substituent is a methyl, ethyl, isopropyl, propyl, or butyl group. All these compounds are weaker antagonists of serotonin than is LSD, the comparative figures being in the same sequence: 15.5., 8.5, 5, 2.5, and 1.5 times weaker than LSD. We see here a significant increase of action with the length of the side chain. [...] it may be mentioned that the monomethylamide and dimethylamide and the monopropylamide and dipropylamide do not possess any psychic action. On the other hand, both in animals and in man the 4 latter compounds are capable of eliciting autonomic actions in doses in which the monoethylamide, for example, is completely inactive.
[4]
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. Archived from the original on 2025-06-30.
[5]
Fanchamps A (1978). "Some Compounds With Hallucinogenic Activity". In Berde B, Schild HO (eds.). Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). Vol. 49. 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. The hypothesis that brain serotonin plays a role in maintaining normal mental processes, and that the hallucinogenic effect of LSD and of other psychotomimetic compounds might be connected with their serotonin antagonism has been proposed by various authors, especially by WOOLLEY (WOOLLEY and SHAW, 1954; WOOLLEY, 1958). However, CERLETTI and ROTHLIN (1955) concluded from the lack of LSD-like activity of BOL 148 that such a correlation is not very likely; according to these authors, it cannot be argued that BOL 148 does not penetrate into the brain, since it produces sedation, which is a central effect, and has been detected in the brain in the same amounts as LSD after intravenous injection to mice. Their conclusion is further supported by the complete absence of parallelism between the psychotomimetic activity and the anti serotonin potency, as evidenced by Table 2; very weak as well as very strong serotonin antagonists may be found side by side in the group of compounds with medium as well as in the group with no LSD-like properties.
[6]
Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4.

Lysergic acid butylamide

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References

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