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AWD 52-39

From Wikipedia, the free encyclopedia

Pharmaceutical compound
AWD 52-39
Clinical data
Other namesN,N-Diacetoxyethyl-9,10-dihydrolysergamide
Drug classNootropic;Serotonin receptor modulator
ATC code
  • None
Identifiers
  • 2-[2-acetyloxyethyl-[(6aR,9R)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carbonyl]amino]ethyl acetate
CAS Number
PubChemCID
ChemSpider
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC24H31N3O5
Molar mass441.528 g·mol−1
3D model (JSmol)
  • CC(=O)OCCN(CCOC(=O)C)C(=O)[C@@H]1CC2[C@@H](CC3=CNC4=CC=CC2=C34)N(C1)C
  • InChI=1S/C24H31N3O5/c1-15(28)31-9-7-27(8-10-32-16(2)29)24(30)18-11-20-19-5-4-6-21-23(19)17(13-25-21)12-22(20)26(3)14-18/h4-6,13,18,20,22,25H,7-12,14H2,1-3H3/t18-,20?,22-/m1/s1
  • Key:LXWNLFQDQZPCPP-HCNFZCTASA-N

AWD 52-39, also known asN,N-diacetoxyethyl-9,10-dihydrolysergamide, is adrug described as a "nootropic" (cognitive enhancer) of thelysergamide family related tolysergic acid diethylamide (LSD) that was never marketed.[1][2][3] It was under development byArzneimittelwerk Dresden, but development was discontinued.[2] The effects of AWD 52-39 inpreclinical studies have been reported.[3][4][5][6] The drug has been found to enhancelearning andmemory and to produceantidepressant-like effects in rodents.[1] It appears to act uponvascularserotonin receptors.[5] Thechemical synthesis andstereochemistry of AWD 52-39 have been described.[7] The drug was first described in thescientific literature by 1989.[3]

See also

[edit]

References

[edit]
  1. ^abHoffmann W, Rostock A, Siegemund C, Bartsch R (1990)."Effects of the novel compound AWD 52-39 on behavioral test methods for evaluation of memory-enhancing drugs".European Journal of Pharmacology.183 (4): 1480.doi:10.1016/0014-2999(90)94625-8. Retrieved15 October 2025.
  2. ^abFroestl W, Pfeifer A, Muhs A (2013)."Cognitive enhancers (nootropics). Part 3: drugs interacting with targets other than receptors or enzymes. disease-modifying drugs".Journal of Alzheimer's Disease.34 (1):1–114.doi:10.3233/JAD-121729.PMID 23186990.
  3. ^abcHoffman W, Rostock A, Siegemund C, Bartsch R (April 1989). "AWD 52-39, an ergot derivative with potential nootropic activity".Activitas Nervosa Superior.31 (1):56–57.PMID 2782003.
  4. ^Brust P, Jordan K (August 1992). "Effects of the nootropic AWD 52-39 on the blood-brain transfer of leucine, choline and glucose in rats after 14-d exposure to ethanol".Die Pharmazie.47 (8):616–620.PMID 1438514.
  5. ^abMüller H, Glusa E (February 1992). "Effect of AWD 52-39 on vasoconstriction induced by noradrenaline and 5-hydroxytryptamine in vitro and in vivo in rats".Die Pharmazie.47 (2):137–139.PMID 1635923.
  6. ^Brust P (1991). "Blood-brain barrier transport under different physiological and pathophysiological circumstances including ischemia".Experimental Pathology.42 (4):213–219.doi:10.1016/s0232-1513(11)80068-x.PMID 1959581.
  7. ^Dopke W, Heidenbluth K, Hempel R, Zeigan D, Mugge C (1995)."Synthese und Stereochemie von AWD 52-39" [Synthesis and Stereochemistry of AWD-52-39.].Pharmazie (in German).50 (5):351–354.
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Ergolines
(incl.lysergines)
Clavines
(6,8-dimethylergolines)
Lysergamides
(lysergic acid amides)
Ergopeptines
(peptide ergolines)
Partial ergolines
Related compounds
Natural sources
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