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Other names | AMAPN |
Drug class | Serotonin–norepinephrine–dopamine releasing agent |
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Chemical and physical data | |
Formula | C14H15NO |
Molar mass | 213.280 g·mol−1 |
3D model (JSmol) | |
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1-Naphthylmethcathinone (AMAPN) is a monoamine releasing agent of the cathinone and naphthylaminopropane families. [1] [2] It is an analogue of methcathinone in which the phenyl ring has been replaced with a 1-naphthalene ring. [1] [2]
The drug acts as a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA). [1] [2] Its EC50 values for induction of monoamine release are 21.6 nM for serotonin and 55.2 nM for dopamine, whereas the EC50 for norepinephrine was not reported. [1] However, AMAPN induced 92% release of norepinephrine at a concentration of 10,000 nM, indicating that it is an effective norepinephrine releaser as well. [1]
para-Methoxymethamphetamine (PMMA), also known as 4-methoxy-N-methylamphetamine (4-MMA), is a serotonergic drug of the amphetamine family related to para-methoxyamphetamine (PMA). It is the 4-methoxy analogue of methamphetamine. Little is known about the pharmacological properties, metabolism, and toxicity of PMMA; because of its structural similarity to PMA, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA.
Naphthylaminopropane, 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 addiction.
A dopamine releasing agent (DRA) is a type of drug which induces the release of dopamine in the body and/or brain.
A serotonin–dopamine releasing agent (SDRA) is a type of drug which induces the release of serotonin and dopamine in the body and/or brain.
4-Methylamphetamine (4-MA), also known by the former proposed brand name Aptrol, is a stimulant and anorectic drug of the amphetamine family. It is structurally related to mephedrone (4-methylmethcathinone).
4-Methylmethamphetamine (4-MMA), also known as mephedrine, is a putative stimulant and entactogen drug of the amphetamine family. It acts as a serotonin–norepinephrine–dopamine releasing agent (SNDRA). The drug is the β-deketo analogue of mephedrone and the N-methyl analogue of 4-methylamphetamine (4-MA).
Substituted cathinones, or simply cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along with additional substitutions. Cathinone occurs naturally in the plant khat whose leaves are chewed as a recreational drug.
1-Phenylpiperazine is a simple chemical compound and drug featuring a phenyl group bound to a piperazine ring. The suffix ‘-piprazole’ is sometimes used in the names of drugs to indicate they belong to this class.
Methamnetamine is a triple monoamine releasing agent of the amphetamine and naphthylaminopropane families. It is the N-methyl analog of the non-neurotoxic experimental drug naphthylaminopropane and the naphthalene analog of methamphetamine. It has been sold online as a designer drug.
3-Chloromethcathinone (3-CMC), also known as clophedrone, is a synthetic substance belonging to the cathinone class of psychoactive compounds. It is very similar in structure to other methcathinone derivatives such as 3-MMC and 4-CMC. Unlike cathinone, which occurs naturally in the khat plant Catha edulis, 3-CMC is not found in nature and is solely produced through chemical synthesis.
2-Naphthylmethcathinone (BMAPN), also known as βk-methamnetamine, is a stimulant drug of the cathinone and naphthylaminopropane families. It inhibits dopamine reuptake and has rewarding and reinforcing properties in animal studies. It is banned under drug analogue legislation in a number of jurisdictions. The drug was at one point marketed under the name NRG-3, although only a minority of samples of substances sold under this name have been found to actually contain BMAPN, with most such samples containing mixtures of other cathinone derivatives.
3-Methoxymethcathinone (3-MeOMC), also known as meta-methoxymethcathinone (m-MeOMC), is a designer drug of the substituted cathinone family described as a stimulant.
2-Aminoacetophenone, also known as β-ketophenethylamine, α-desmethylcathinone, or phenacylamine, is a substituted phenethylamine derivative. It is the phenethylamine homologue of cathinone (β-ketoamphetamine) and hence is a parent compound of a large number of stimulant and entactogen drugs.
BK-NM-AMT, or βk-NM-αMT, also known as β-keto-N-methyl-αMT or α,N-dimethyl-β-ketotryptamine, as well as 3-indoylmethcathinone, is a serotonin–dopamine releasing agent (SDRA) and putative entactogen of the tryptamine, α-alkyltryptamine, and β-ketotryptamine families. Along with certain other tryptamines, such as α-ethyltryptamine (αET), 5-chloro-αMT and 5-fluoro-αET, it is one of the few SDRAs known.
2-Fluoromethcathinone (2-FMC), also known as 2-flephedrone, is a psychostimulant and designer drug of the cathinone family. It acts as a dopamine and norepinephrine releasing agent (NDRA).
Ethylnaphthylaminopropane is a monoamine releasing agent (MRA) of the amphetamine and naphthylaminopropane families that is related to naphthylaminopropane and methamnetamine. It acts specifically as a serotonin–norepinephrine–dopamine releasing agent (SNDRA). However, ENAP is unusual in being a partial releaser of serotonin and dopamine and a full releaser of norepinephrine.
Naphthylmetrazine, also known as 3-methyl-2-(2′-naphthyl)morpholine, is a monoamine releasing agent (MRA) and monoamine reuptake inhibitor (MRI) of the phenylmorpholine and naphthylaminopropane families related to phenmetrazine. It is a analogue of phenmetrazine in which the phenyl ring has been replaced with a naphthalene ring.
3,4-Ethylenedioxymethcathinone (EDMC), or 3,4-ethylenedioxy-N-methylcathinone, is a monoamine releasing agent (MRA) of the cathinone family related to methylone. It is the β-keto or cathinone analogue of 3,4-ethylenedioxymethamphetamine (EDMA).
The substituted naphthylethylamines are a class of chemical compounds based on naphthalene. Many naphthylethylamines are naphthylaminopropanes due to the presence of a methyl group at the alpha carbon of the alkyl chain. The naphthylethylamines are derivatives of the phenethylamines, while the naphthylaminopropanes are derivatives of the amphetamines.
Naphthylmorpholine, also known as 2-(2′-naphthyl)morpholine, is a monoamine releasing agent of the arylmorpholine and naphthylethylamine families. It is the derivative of 2-phenylmorpholine with a 2-naphthalene ring instead of a phenyl ring. Naphthylmorpholine is a close analogue of naphthylmetrazine, but lacks naphthylmetrazine's methyl group at the 3 position of the morpholine ring.