Naphthylmetrazine
Naphthylmetrazine, also known as 3-methyl-2-morpholine, is a monoamine releasing agent and monoamine reuptake inhibitor of the phenylmorpholine and naphthylaminopropane families related to phenmetrazine. It is an analogue of phenmetrazine in which the phenyl ring has been replaced with a naphthalene ring.
The drug acts as a hybrid norepinephrine–dopamine releasing agent and serotonin reuptake inhibitor. Its values for induction of monoamine release are 111nM for dopamine, 203nM for norepinephrine, and inactive for serotonin in rat brain synaptosomes, whereas its for serotonin reuptake inhibition is 105nM. Hence, it is about equipotent in inducing dopamine release and inhibiting serotonin reuptake and is about 2-fold more potent in these actions than in inducing norepinephrine release.
In terms of chemical structure, naphthylmetrazine is to phenmetrazine as naphthylisopropylamine is to amphetamine. Other naphthyl analogues of amphetamines and related compounds include methamnetamine, ethylnaphthylaminopropane, BMAPN, methylnaphthidate, ethylnaphthidate, and naphyrone.
A closely related compound to naphthylmetrazine is naphthylmorpholine, the naphthyl analogue of the phenmetrazine parent compound 2-phenylmorpholine.