PRL-8-53
| File:PRL-8-53.svg | |
| Clinical data | |
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| Routes of administration | Oral |
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| E number | {{#property:P628}} |
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| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C18H21NO2 |
| Molar mass | 283.371 g·mol−1 |
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PRL-8-53 is a nootropic substituted phenethylamine that has been shown to act as a hypermnesic drug in humans; it was first synthesized by medical chemistry professor Nikolaus Hansl at Creighton University in the 1970s as part of his work on amino ethyl meta benzoic acid esters.[1][2]
Mechanism of action
[edit | edit source]The exact mechanism of action of PRL-8-53 remains unknown. Doses up to 200 mg/kg are not observed to have stimulant properties, and a dosage of 20 mg/kg does not potentiate the effects of dextroamphetamine in rats.[1] It displays possible cholinergic properties, and potentiates dopamine while partially inhibiting serotonin.[1] PRL-8-53 reverses the catatonic and ptotic effects of reserpine.[1][3]
Toxicity
[edit | edit source]PRL-8-53 is relatively non-toxic, with an oral LD50 in mice of 860 mg/kg, giving the drug a high therapeutic index. Doses above 8 mg/kg have brief hypotensive effects in canines. High doses depress motor activity in the rat and mouse, with the ED50 for a 50% reduction in motor activity of mice at 160 mg/kg. PRL-8-53 displays spasmolytic effects.[3]
Reasons for discontinuation
[edit | edit source]PRL-8-53's development was not pursued further, despite not exhibiting side effects in human or animal trials that would warrant discontinuation. Termination of further research may have been due to factors including the retirement of Dr. Nikolaus Hansl and a lawsuit filed between Hansl and Creighton University in 1985.
Hansl v. Creighton University
[edit | edit source]On July 1, 1985 Dr. Nikolaus Hansl entered into a settlement agreement with Creighton University.[4] The terms of the agreement guaranteed Dr. Hansl access to his laboratory facilities and office space at the university for a period of 2 years.[4] Upon returning from a 4-month absence. Hansl found that the refrigerator he had used to store various experimental compounds had been unplugged, purportedly rendering the compounds unusable.[4]
Patent
[edit | edit source]Dr. Hansl's patent for the synthesis of PRL-8-53 has expired.[5]
Synonyms
[edit | edit source]Methyl 3-(2-(benzylmethylamino)ethyl)benzoate hydrochloride
3-(2-benzylmethylaminoethyl) benzoic acid methyl ester hydrochloride
3-(2-(Methyl(phenylmethyl)amino)ethyl)benzoic acid methyl ester hydrochloride
See also
[edit | edit source]References
[edit | edit source]- ^ a b c d Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ US Patent 3870715 A: Substituted amino ethyl meta benzoic acid esters
- ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ a b c Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Nikolaus R. Hansl; Process for hydrolyzing 3-trifluoromethyl phenethylamines (US patent 3 792 048) 1974