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Lysergic acid propylamide

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Lysergic acid propylamide
Clinical data
Other namesLAP; Lysergic acid monopropylamide; NP-LA; N-Propyllysergamide; N-Propylergine; N-Propyl-LSA; 6-Methyl-N-propyl-9,10-didehydroergoline-8β-carboxamide
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • (6aR,9R)-7-methyl-N-propyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
PubChem CID
Chemical and physical data
FormulaC19H23N3O
Molar mass309.413 g·mol−1
3D model (JSmol)
  • CCCNC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3
  • InChI=1S/C19H23N3O/c1-3-7-20-19(23)13-8-15-14-5-4-6-16-18(14)12(10-21-16)9-17(15)22(2)11-13/h4-6,8,10,13,17,21H,3,7,9,11H2,1-2H3,(H,20,23)/t13-,17-/m1/s1
  • Key:VHECNRXVHIGFCO-CXAGYDPISA-N

Lysergic acid propylamide (LAP), also known as N-propyllysergamide (NP-LA), is a serotonin receptor modulator of the lysergamide family related to lysergic acid diethylamide (LSD).[1][2][3] It is the analogue of LSD in which the N,N-diethyl groups have been replaced with an N-propyl group and is also the N-propyl derivative of ergine (lysergic acid amide; LSA).[1][2]

Pharmacology

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The drug had about 40% of the antiserotonergic activity of LSD in the isolated rat uterus in vitro.[2][3][4] The potency of LSD analogues in this assay increased with length or size of the monoalkyl chain: ergine (4.3%) < lysergic acid methylamide (6.3%) < lysergic acid ethylamide (11.9%) < lysergic acid isopropylamide (22.2%) < LAP (40.0%) < lysergic acid butylamide (64.9%) < lysergic acid amylamide (75.1%).[2][3][4] However, activity in this assay does not correlate with hallucinogenic activity.[5]

It was initially reported that LAP was inactive as a hallucinogen in humans but produced autonomic effects at relatively low doses in both animals and humans, with no other details, such as doses, provided.[4] Subsequently, Alexander Shulgin reported that LAP was inactive at a psychedelic at doses of up to 500 μg and had less than 20% of the hallucinogenic potency of LSD.[1]

History

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LAP was first described in the scientific literature by Albert Hofmann and colleagues by 1955.[6][4][3]

See also

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References

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  1. ^ a b c 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.
  2. ^ a b c d 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. ^ a b c d 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.
  4. ^ a b c d 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. In this connection, 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.
  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. ^ Stoll A, Hofmann 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.
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