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AWD 52-39

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Pharmaceutical compound
AWD 52-39
Clinical data
Other namesAWD-5239; AWD5239; N,N-Diacetoxyethyl-9,10-dihydrolysergamide
Routes of
administration 		Unknown[1]
Drug class Nootropic; Serotonin receptor modulator; Serotonin 5-HT2 receptor antagonist
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
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C24H31N3O5
Molar mass 441.528g·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, or AWD-5239, also known as N,N-diacetoxyethyl-9,10-dihydrolysergamide, is a drug described as a "nootropic" (cognitive enhancer) of the lysergamide family related to lysergic acid diethylamide (LSD) that was never marketed.[1] [2] [3] [4] [5] It was under development by Arzneimittelwerk Dresden, but development was discontinued.[4] The effects of AWD 52-39 in preclinical studies have been reported.[5] [6] [7] [8] It has been described as a serotonin 5-HT2 receptor antagonist.[1] [2] The drug has been found to enhance learning and memory and to produce antidepressant-like effects in rodents.[3] It appears to act upon vascular serotonin receptors.[7] The chemical synthesis and stereochemistry of AWD 52-39 have been described.[9] The drug was first described in the scientific literature by 1989.[5] It reached phase 2 clinical trials for the treatment of cognition disorders prior to the discontinuation of its development.[1] [2]

See also

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References

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  1. 1 2 3 4 "AWD 5239". AdisInsight. 31 July 1995. Retrieved 4 June 2026.
  2. 1 2 3 "Delving into the Latest Updates on AWD-5239 with Synapse". Synapse. 16 May 2026. Retrieved 4 June 2026.
  3. 1 2 Hoffmann 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 . Retrieved 15 October 2025.
  4. 1 2 Froestl 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.
  5. 1 2 3 Hoffman 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.
  6. ↑ 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.
  7. 1 2 Müller 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.
  8. ↑ 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.
  9. ↑ 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.

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