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ALA-10

From Wikipedia, the free encyclopedia

Pharmaceutical compound
ALA-10
Clinical data
Other namesALA10; 1-Acetyl-LAE; 1A-LAE; 1-Acetyl-LAE-32; 1A-LAE-32; 1-Acetyllysergic acid ethylamide; 1-Acetyl-N-ethyllysergamide; 1-Acetyl-N-ethyl-6-methyl-9,10-didehydroergoline-8β-carboxamide
Routes of
administration
Oral
Drug classSerotonin receptor modulator;Serotonergic psychedelic;Hallucinogen
ATC code
  • None
Identifiers
  • (6aR,9R)-4-acetyl-N-ethyl-7-methyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChemCID
ChemSpider
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H23N3O2
Molar mass337.423 g·mol−1
3D model (JSmol)
  • CCNC(=O)[C@H]1CN([C@@H]2CC3=CN(C4=CC=CC(=C34)C2=C1)C(=O)C)C
  • InChI=1S/C20H23N3O2/c1-4-21-20(25)14-8-16-15-6-5-7-17-19(15)13(11-23(17)12(2)24)9-18(16)22(3)10-14/h5-8,11,14,18H,4,9-10H2,1-3H3,(H,21,25)/t14-,18-/m1/s1
  • Key:UKRWCEJTOPSTEC-RDTXWAMCSA-N

ALA-10, also known as1-acetyl-LAE (1A-LAE), is apsychedelic drug of thelysergamide family related tolysergic acid diethylamide (LSD).[1][2][3] It is the 1-acetylderivative ofLAE-32.[2][3][4][5] 1-Acetylated lysergamides likeALD-52 (1-acetyl-LSD; 1A-LSD) are thought to function asprodrugs viadeacetylation to the 1-unsubstitutedanalogues, which in the case of ALD-52 is LSD.[6][7][8]

Use and effects

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ALA-10 is active at a dose of approximately 1.2 mgorally in humans and has around 7 to 10% of thepotency ofLSD.[1][2][3][9][10] It produces LSD-like psychic effects.[2][10] It is said to have a quickeronset and shorterduration than LSD.[2][10] For comparison,LAE-32, has a dose range of 0.5 to 1.6 mg, about 5 to 10% of the activity of LSD, and a likewise faster onset and shorter duration than LSD.[1][2][3][9] Both ALA-10 and LAE-32 are said to produce only slight or weakhallucinogenic effects.[11] ALA-10 is around 15-fold less potent thanALD-52 (1-acetyl-LSD), which is roughlyequipotent with LSD.[1][2][3]

Interactions

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See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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ALA-10 showsantiserotonergic activity in the isolated ratuterus of about 39% of that of LSD but about 3 times stronger than that ofLAE-32.[1][10] Itspyretogenicpotency in rabbits is only about 1% of that of LSD.[1]

History

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ALA-10 was first described in thescientific literature by the late 1950s.[1][10]

See also

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References

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  1. ^abcdefgFanchamps 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 fromthe original on 30 March 2025.I-Acetyl-lysergic acid ethylamide (ALA 10, No. 36g), the acetylated analogue of LAE 32, exhibits 7% of the psychotomimetic effect of LSD (ISBELL et a!., 1959a). Its antiserotonin potency on the isolated rat uterus is 40% of that of LSD (thus three times stronger than LAE 32), whereas its pyretogenic effect in rabbits is only 1 % of the LSD action (Sandoz Res. Lab., 1958). [...] Also if applied to the less potent lysergic acid ethylamide or pyrrolidide, the 1-substitution (ALA 10, MLA 74, MPD75) only slightly affects the psychotomimetic activity of the parent compounds LAE 32 and LPD 824. [...] Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...] The monosubstituted ethyl-analogues LAE32, ALA 10, MLA 74 are psychotomimetic, but about 10-20 times weaker than the corresponding diethylamides LSD, ALD 52, and MLD41. [...]
  2. ^abcdefgBrimblecombe RW, Pinder RM (1975)."Indolealkylamines and Related Compounds".Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144.ISBN 978-0-85608-011-1.OCLC 2176880.OL 4850660M.Table 4.3.—Comparative Hallucinogenic Potencies in Man of Derivatives of D-Lysergic Acid. [...]
  3. ^abcdeShulgin 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.
  4. ^Shulgin AT,Shulgin A (1997)."#26. LSD-25 Acid; Lysergide; D-Lysergic Acid Diethylamide; Meth-LAD; D-Lysergamide, N,N-Diethyl; N,N-Diethyl-D-Lysergamide; 9,10-Didehydro-N,N-Diethyl-6-Methylergoline-8b-Carboxamide".TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press. pp. 490–499.ISBN 978-0-9630096-9-2.OCLC 38503252.
  5. ^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.
  6. ^Elliott SP, Holdbrook T, Brandt SD (May 2020). "Prodrugs of New Psychoactive Substances (NPS): A New Challenge".Journal of Forensic Sciences.65 (3):913–920.doi:10.1111/1556-4029.14268.PMID 31943218.Recently, a number of LSD derivatives and analogues have been investigated, namely 1-acetyl-LSD (1A-LSD, ALD-52), [...] (46-52) (Figure 1B). A biotransformation has been observed in lysergamides acylated at the indole nitrogen that in turn produce the corresponding "core" drug of LSD or ETH-LAD (52). Therefore, 1P-LSD, 1B-LSD and ALD-52 are all prodrugs of LSD and 1P-ETH-LAD is a prodrug of ETH-LAD. All of these drugs have been discussed in Internet drug forums and are currently available for purchase online (53-56). Although ALD-52 was known to be psychoactive in humans for a long time (57), the formation of LSD both in vitro and in vivo (rats) has only been confirmed recently (51,57).
  7. ^Ponce JD (2024)."The use of prodrugs as drugs of abuse".WIREs Forensic Science.6 (3) e1514.doi:10.1002/wfs2.1514.ISSN 2573-9468.
  8. ^Schifano F, Vento A, Scherbaum N, Guirguis A (2023). "Stimulant and hallucinogenic novel psychoactive substances; an update".Expert Review of Clinical Pharmacology.16 (11):1109–1123.doi:10.1080/17512433.2023.2279192.hdl:2299/27223.PMID 37968919.
  9. ^abJacob P, Shulgin AT (1994). "Structure-activity relationships of the classic hallucinogens and their analogs".NIDA Research Monograph.146:74–91.PMID 8742795.
  10. ^abcdeIsbell H, Miner EJ, Logan CR (1959)."Relationships of psychotomimetic to anti-serotonin potencies of congeners of lysergic acid diethylamide (LSD-25)".Psychopharmacologia.1:20–28.doi:10.1007/BF00408108.PMID 14405872. Archived fromthe original on 7 April 2022.
  11. ^Keup W (1970)."Structure-Activity Relationship among Hallucinogenic Agents".Origin and Mechanisms of Hallucinations. Boston, MA: Springer US. pp. 345–376.doi:10.1007/978-1-4615-8645-6_29.ISBN 978-1-4615-8647-0. Retrieved12 October 2025.A relation in the same direction might exist between the two N-monoethyl analogues ALA-10 and MLA-74, if judged by their LD50; both are only slightly psychotomimetic. The unsubstituted N-monoethyl analogue of LSD itself is a weak hallucinogen only [122].

External links

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