Naphthylmetrazine (code name PAL-704), also known as 3-methyl-2-(2′-naphthyl)morpholine, is a

monoamine releasing agent A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrati ...

(MRA) and

monoamine reuptake inhibitor A monoamine reuptake inhibitor (MRI) is a drug that acts as a reuptake inhibitor of one or more of the three major monoamine neurotransmitters serotonin, norepinephrine, and dopamine by blocking the action of one or more of the respective monoamin ...

(MRI) of the phenylmorpholine and naphthylaminopropane families related to

phenmetrazine Phenmetrazine, sold under the brand name Preludin among others, is a stimulant drug first chemical synthesis, synthesized in 1952 and originally used as an appetite suppressant, but withdrawn drug, withdrawn from the market in the 1980s due to ...

. It is a analogue of phenmetrazine in which the

phenyl ring In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...

has been replaced with a

naphthalene Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white Crystal, crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 Parts-per notation ...

ring. The drug acts as a hybrid

norepinephrine–dopamine releasing agent A norepinephrine–dopamine releasing agent (NDRA) is a type of drug which induces the synapse, release of norepinephrine (and epinephrine) and dopamine in the body and/or brain. Many of these are amphetamine type stimulants. Examples Examples ...

(NDRA) and

serotonin reuptake inhibitor A serotonin reuptake inhibitor (SRI) is a type of drug which acts as a reuptake inhibitor of the neurotransmitter serotonin (5-hydroxytryptamine, or 5-HT) by blocking the drug action, action of the serotonin transporter (SERT). This in turn lea ...

(SRI). Its values for induction of monoamine release are 111nM for

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. It is an amine synthesized ...

, 203nM for

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...

, and inactive for

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

in rat brain

synaptosome A synaptosome is an isolated synaptic terminal from a neuron. Synaptosomes are obtained by mild homogenization of nervous tissue under isotonic conditions and subsequent fractionation using differential and density gradient centrifugation. Liquid ...

s, whereas its for serotonin reuptake inhibition is 105nM. Hence, it is about

equipotent In mathematics, two set (mathematics), sets or class (mathematics), classes ''A'' and ''B'' are equinumerous if there exists a one-to-one correspondence (or bijection) between them, that is, if there exists a function (mathematics), function from ...

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 A chemical structure of a molecule is a spatial arrangement of its atoms and their chemical bonds. Its determination includes a chemist's specifying the molecular geometry and, when feasible and necessary, the electronic structure of the target m ...

, naphthylmetrazine is to phenmetrazine as

naphthylisopropylamine Naphthylaminopropane (NAP; code name PAL-287), also known as naphthylisopropylamine (NIPA), is an research chemical, experimental drug of the substituted amphetamine, amphetamine and substituted naphthylaminopropane, naphthylaminopropane famili ...

(PAL-287) is to

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

. Other naphthyl analogues of

s and related compounds include

methamnetamine Methamnetamine (also known as methylnaphetamine, MNA, MNT, MNAP, PAL-1046, and MY-10) is a triple monoamine releasing agent of the amphetamine and naphthylaminopropane families. It is the ''N''-methyl analog of the non-neurotoxic experimental d ...

(PAL-1046; "naphthylmethamphetamine"),

ethylnaphthylaminopropane Ethylnaphthylaminopropane (ENAP; developmental code name PAL-1045) is a monoamine releasing agent (MRA) of the amphetamine and naphthylaminopropane families that is related to naphthylaminopropane (NAP; PAL-287) and methamnetamine (MNAP; PAL-1 ...

(ENAP; PAL-1045; "naphthylethylamphetamine"), BMAPN (βk-methamnetamine; "naphthylmethcathinone"),

methylnaphthidate HDMP-28 or methylnaphthidate is a stimulant drug of the piperidine and naphthylaminopropane groups, closely related to methylphenidate (Ritalin), but with the benzene ring replaced by naphthalene. It is a potent dopamine reuptake inhibitor, wit ...

(HDMP-28; "naphthylmethylphenidate"),

ethylnaphthidate HDEP-28 or ethylnaphthidate is a stimulant drug of the piperidine and naphthylaminopropane groups, closely related to ethylphenidate, but with the benzene ring replaced by naphthalene. It is even more closely related to HDMP-28, which acts as a ...

(HDEP-28; "naphthylethylphenidate"), and

naphyrone Naphyrone, also known as O-2482 and naphthylpyrovalerone, is a stimulant drug of the cathinone and naphthylaminopropane families. It was derived from pyrovalerone and acts as a serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI). ...

("naphthyl-α-PVP" or "naphthylpyrovalerone"; O-2482). A closely related compound to naphthylmetrazine is naphthylmorpholine (PAL-678), the naphthyl analogue of the phenmetrazine parent compound 2-phenylmorpholine (PAL-632).

References

{{Phenethylamines Beta-Hydroxyamphetamines 2-Naphthyl compounds Naphthylethylamines Norepinephrine-dopamine releasing agents Phenylmorpholines Serotonin reuptake inhibitors Stimulants