Chemistry:Lysergic acid amylamide

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Lysergic acid amylamide
Clinical data
Other namesLysergic acid pentylamide; N-Pentyllysergamide; N-Amyllysergamide; NPe-LA; 6-Methyl-N-pentyl-9,10-didehydroergoline-8β-carboxamide
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
Chemical and physical data
FormulaC21H27N3O
Molar mass337.467 g·mol−1
3D model (JSmol)

Lysergic acid amylamide, also known as lysergic acid pentylamide or as N-pentyllysergamide (NPe-LA), is a serotonin receptor modulator of the lysergamide family related to the psychedelic drug 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-pentyl group (amyl group) and is also the N-pentyl derivative of ergine (lysergic acid amide; LSA).[1][2][3] The drug shows 75.1% of the antiserotonergic activity of LSD in the isolated rat uterus in vitro.[2][3] However, activity in this assay does not correlate with hallucinogenic activity.[4] 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.[5][6] Lysergic acid amylamide was first described in the scientific literature by 1958.[3]

See also

References

  1. ↑ 1.0 1.1 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml.  https://erowid.org/library/books_online/tihkal/tihkal26.shtml [...] "N-Pentyllysergamide" [...]
  2. ↑ 2.0 2.1 2.2 "Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens". Purdue University. May 1989. https://bitnest.netfirms.com/external/Theses/Oberlender1989#page=49. "Table 2. Relative potency values for lysergic acid amides. [...]" 
  3. ↑ 3.0 3.1 3.2 3.3 "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. January 1958. doi:10.1016/S0022-3565(25)11933-2. PMID 13502837. https://bibliography.maps.org/resources/download/19096. 
  4. ↑ "Some Compounds With Hallucinogenic Activity". Ergot Alkaloids and Related Compounds. Handbook of Experimental Pharmacology (HEP). 49. Berlin, Heidelberg: Springer Berlin Heidelberg. 1978. pp. 567–614. doi:10.1007/978-3-642-66775-6_8. ISBN 978-3-642-66777-0. https://bibliography.maps.org/resources/download/8769#page=30. "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." 
  5. ↑ "Lysergic acid diethylamide and related substances". Annals of the New York Academy of Sciences 66 (3): 668–676. March 1957. doi:10.1111/j.1749-6632.1957.tb40756.x. PMID 13425249. Bibcode: 1957NYASA..66..668R. "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, [butyl, or pentyl/amyl 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.". 
  6. ↑ "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6. 



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