The substituted naphthylethylamines are a class of

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

s based on

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 ...

. Many naphthylethylamines are naphthylaminopropanes (also known as naphthylisopropylamines) due to the presence of a

methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated a ...

at the

alpha carbon In the nomenclature of organic chemistry, a locant is a term to indicate the position of a functional group or substituent within a molecule. Numeric locants The International Union of Pure and Applied Chemistry (IUPAC) recommends the use of n ...

of the

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cy ...

chain A chain is a serial assembly of connected pieces, called links, typically made of metal, with an overall character similar to that of a rope in that it is flexible and curved in compression but linear, rigid, and load-bearing in tension. A ...

. The naphthylethylamines are

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

s of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

s, while the naphthylaminopropanes are derivatives of the

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 ...

s. There are two types of naphthylethylamines based on

positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is a compound that contains the same number and type of atoms, but with a different connectivity (i.e. arrangement of bonds) between them. The ...

ism: 1-naphthylethylamines and 2-naphthylethylamines. Examples of these include 1-naphthylaminopropane (1-NAP) and

2-naphthylaminopropane Naphthylaminopropane (NAP; code name PAL-287), also known as naphthylisopropylamine (NIPA), is an experimental drug of the amphetamine and naphthylaminopropane families that was under investigation for the treatment of alcohol and stimulant ad ...

(2-NAP), respectively.

List of substituted naphthylethylamines

The substituted napthylethylamines include the following compounds: Additional naphthylethylamines include

4-NEMD 4-NEMD is a potent sedative drug which acts as a selective alpha-2 adrenergic receptor agonist. It is closely related to dexmedetomidine but is several times more potent. Like other alpha-2 agonists, it produces sedative and muscle relaxant effec ...

, centanafadine (EB-1020), nafimidone,

naphazoline Naphazoline is a medicine used as a decongestant, and a vasoconstrictor added to eye drops to relieve red eye. It has a rapid action in reducing swelling when applied to mucous membranes. It is a sympathomimetic agent with marked alpha adrener ...

, and xaliproden (SR-57746). Some

synthetic cannabinoid Synthetic cannabinoids, or neocannabinoids, are a class of designer drug molecules that Binding affinity, bind to the same receptors to which cannabinoids (Tetrahydrocannabinol, THC, Cannabidiol, CBD and many others) in cannabis plants attach. Th ...

s such as

THJ-018 THJ-018 (SGT-17) is a synthetic cannabinoid that is the indazole analogue of JWH-018 and has been sold online as a designer drug. Pharmacology THJ-018 acts as a full agonist with a binding affinity of 5.84 nM at CB1 and 4.57 nM at C ...

and

THJ-2201 THJ-2201 is an indazole-based synthetic cannabinoid that presumably acts as a potent agonist of the CB1 receptor, CB1 receptor and has been sold online as a designer drug. It is a structural analog of AM-2201 in which the central indole ring h ...

are also naphthylethylamines.

Related compounds

Some related compounds that are not technically naphthylethylamines include 1-naphthylpiperazine and its derivatives like

CSP-2503 CSP-2503 is a potent and selective 5-HT1A receptor agonist, 5-HT2A receptor antagonist, and 5-HT3 receptor antagonist of the naphthylpiperazine class. First synthesized in 2003, it was designed based on computational models and QSAR studi ...

, F-11,461,

S-14506 S-14,506 is a naphthylpiperazine, a 5-HT1A receptor agonist, and a dopamine receptor antagonist. See also * Naphthylpiperazine Naphthylpiperazine (NP) may refer to: * 1-(1-Naphthyl)piperazine (1-NP) * 1-(2-Naphthyl)piperazine (2-NP) Arylpi ...

, and

S-14671 S-14671 is a naphthylpiperazine derivative which acts as a 5-HT1A receptor agonist (pKi = 9.3) with high efficacy and exceptional ''in vivo'' potency, and also as a 5-HT2A and 5-HT2C receptor antagonist (both are pKi = 7.8). It displays only ...

. Another related compound is 2-naphthylpiperazine.

DMNPC ''N'',''O''-Dimethyl-4β-(2-naphthyl)piperidine-3β-carboxylate (DMNPC) is a piperidine based stimulant drug which is synthesised from arecoline. It is similar to nocaine in chemical structure, and has two and a half times more activity than coca ...

is a 2-naphthyl

piperidine Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor de ...

Pharmacology

Many naphthylethylamines, like

and

s, act as

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 ...

s (MRAs),

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 ...

s (MRIs), and/or

monoamine receptor modulator Monoaminergic means "working on monoamine neurotransmitters", which include serotonin, dopamine, norepinephrine, epinephrine, and histamine. A monoaminergic, or monoaminergic drug, is a chemical, which functions to directly modulate the seroton ...

Naphthylpropylaminopentane 1-(2-Naphthyl)-2-propylaminopentane (NPAP), also known as 2-naphthyl-α,''N''-dipropylphenethylamine, is a monoaminergic activity enhancer (MAE) of the α-propylphenethylamine and substituted naphthylaminopropane, naphthylaminopropane families re ...

(NPAP) is a

monoaminergic activity enhancer Monoaminergic activity enhancers (MAE), also known as catecholaminergic/serotonergic activity enhancers (CAE/SAE), are a class of drugs that enhance the action potential-evoked release of monoamine neurotransmitters in the nervous system. MAEs ar ...

(MAE). Some, such as 2-naphthylaminopropane and to a lesser extent 1-naphthylaminopropane, but not others, such as NPAP, are also variably potent

monoamine oxidase inhibitor Monoamine oxidase inhibitors (MAOIs) are a drug class, class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressa ...

s (MAOIs).

References

{{Chemical classes of psychoactive drugs Chemical classes of psychoactive drugs 1-Naphthyl compounds 2-Naphthyl compounds Naphthylethylamines Phenethylamines