PRL-8-53

File:PRL-8-53.svg
Systematic (IUPAC) name
Methyl 3-[2-[benzyl(methyl)amino]ethyl]benzoate
Clinical data
Pregnancy category	US: N (Not classified yet)
Legal status	Unscheduled
Routes of administration	Oral
Identifiers
CAS Number	51352-88-6 Template:CAS (HCl)
ATC code	none
PubChem	CID: 39988
ChemSpider	36560
Chemical data
Formula	C18H21NO2
Molecular mass	283.36 g/mol
SMILES CN(CCc1cccc(c1)C(=O)OC)Cc2ccccc2
InChI InChI=1S/C18H21NO2/c1-19(14-16-7-4-3-5-8-16)12-11-15-9-6-10-17(13-15)18(20)21-2/h3-10,13H,11-12,14H2,1-2H3 Key:IGJQEMHBYKNIQR-UHFFFAOYSA-N

PRL-8-53 is a nootropic research chemical derived from benzoic acid and phenylmethylamine (Benzylamine) 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.

Nootropic effects

A single study in humans was reported in 1978. The double-blind trial of PRL-8-53 in 47 healthy volunteers measured its effects on a variety of cognitive measures. 5 mg of the drug was administered orally 2–2.5 hours before the study tasks. Overall improvements in recollection differed based on how many words were recalled under placebo, with the poor performers (six or less words) experiencing a 87.5-105% increase in recollection and the high performers (eight or more words) a 7.9-14% increase which failed to reach statistical significance; when controlling for subjects over the age of 30 only, a 108-152% increase was noted.. No side effects were reported during the trial.

Mechanism of action

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. It displays cholinergic properties, and potentiates dopamine while partially inhibiting serotonin. PRL-8-53 reverses the catatonic and ptotic effects of reserpine.

Toxicity

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 the canine. 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.

Synonyms

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

• Nootropics