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Clinical data | |
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Other names | 3-Phenyl-1-propylamine |
Drug class | Norepinephrine–dopamine releasing agent |
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ECHA InfoCard | 100.016.376 |
Chemical and physical data | |
Formula | C9H13N |
Molar mass | 135.210 g·mol−1 |
3D model (JSmol) | |
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Phenylpropylamine, also known as 3-phenylpropylamine, is a monoamine releasing agent (MRA) related to phenethylamine (2-phenylethylamine). [1] [2] It is the analogue of phenethylamine in which the ethylamine side chain has been lengthened by one carbon atom to instead be a propylamine chain. [1] [2]
Phenylpropylamine was synthesized and characterized during investigations of the structure–activity relationships (SAR) of phenethylamine and amphetamine MRAs. [1] [2] It acts as a norepinephrine–dopamine releasing agent (NDRA). [1] [2] However, phenylpropylamine is dramatically less potent than phenethylamine as an NDRA in rat brain synaptosomes in vitro and shows ~7-fold preference for induction of norepinephrine release over dopamine release. [1] [2]
The analogue of phenethylamine with the ethylamine side chain shortened by one carbon atom to instead be a methylamine chain is benzylamine (phenylmethylamine). [3] In contrast to phenethylamine and phenylpropylamine, benzylamine is said to be inactive as a norepinephrine releasing agent (NRA). [3] However, certain derivatives of benzylamine have nonetheless been found to show MRA-like effects in animals. [4] [5] In addition, benzylpiperazine, an analogue of benzylamine with a methylamine-like side chain, is a potent MRA and psychostimulant. [6] [2] [7]
Compound | NE | DA | 5-HT | Ref |
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Phenethylamine (2-phenylethylamine) | 10.9 | 39.5 | >10,000 | [8] [1] [2] |
Phenylpropylamine (3-phenylpropylamine) | 222 | 1,491 | ND | [1] [2] |
β-Methylphenethylamine (2-phenylpropylamine) | 126 | 627 | ND | [9] |
Dextroamphetamine (d-phenylisopropylamine) | 6.6–7.2 | 5.8–24.8 | 698–1,765 | [10] [11] |
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: [12] [6] |
Phentermine, sold under the brand name Adipex-P among others, is a medication used together with diet and exercise to treat obesity. It is available by itself or as the combination phentermine/topiramate. Phentermine is taken by mouth.
Phenmetrazine, sold under the brand name Preludin among others, is a stimulant drug first synthesized in 1952 and originally used as an appetite suppressant, but withdrawn from the market in the 1980s due to widespread misuse. It was initially replaced by its analogue phendimetrazine which functions as a prodrug to phenmetrazine, but now it is rarely prescribed, due to concerns of misuse and addiction. Chemically, phenmetrazine is a substituted amphetamine containing a morpholine ring or a substituted phenylmorpholine.
4-Methylaminorex is a stimulant drug of the 2-amino-5-aryloxazoline group that was first synthesized in 1960 by McNeil Laboratories. It is also known by its street name "U4Euh" ("Euphoria"). It is banned in many countries as a stimulant. 4-Methylaminorex has effects comparable to methamphetamine but with a longer duration.
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.
Etilamfetamine, also known as N-ethylamphetamine and formerly sold under the brand names Apetinil and Adiparthrol, is a stimulant drug of the amphetamine family. It was invented in the early 20th century and was subsequently used as an anorectic or appetite suppressant in the 1950s, but was not as commonly used as other amphetamines such as amphetamine, methamphetamine, and benzphetamine, and was largely discontinued once newer drugs such as phenmetrazine were introduced.
Propylamphetamine is a psychostimulant of the amphetamine family which was never marketed. It was first developed in the 1970s, mainly for research into the metabolism of, and as a comparison tool to, other amphetamines.
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.
Norfenfluramine, or 3-trifluoromethylamphetamine, is a never-marketed drug of the amphetamine family and a major active metabolite of the appetite suppressants fenfluramine and benfluorex. The compound is a racemic mixture of two enantiomers with differing activities, dexnorfenfluramine and levonorfenfluramine.
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 concentrations of the neurotransmitters and hence enhanced signaling by those neurotransmitters. The monoamine neurotransmitters include serotonin, norepinephrine, and dopamine; MRAs can induce the release of one or more of these neurotransmitters.
A dopamine releasing agent (DRA) is a type of drug which induces the release of dopamine in the body and/or brain.
A norepinephrine–dopamine releasing agent (NDRA) is a type of drug which induces the release of norepinephrine and dopamine in the body and/or brain.
3-Fluoroamphetamine is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.
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.
Pseudophenmetrazine is a psychostimulant of the phenylmorpholine group. It is the N-demethylated and cis-configured analogue of phendimetrazine as well as the cis-configured stereoisomer of phenmetrazine. In addition, along with phenmetrazine, it is believed to be one of the active metabolites of phendimetrazine, which itself is inactive and behaves merely as a prodrug.
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.
Butylamphetamine is a psychostimulant of the substituted amphetamine family which was never marketed.
Substituted β-hydroxyamphetamines, or simply β-hydroxyamphetamines, also known as phenylisopropanolamines, phenylpropanolamines, norephedrines, or cathinols, are derivatives of β-hydroxyamphetamine with one or more chemical substituents. They are substituted phenethylamines, phenylethanolamines (β-hydroxyphenethylamines), and amphetamines (α-methylphenethylamines), and are closely related to but distinct from the substituted cathinones (β-ketoamphetamines). Examples of β-hydroxyamphetamines include the β-hydroxyamphetamine stereoisomers phenylpropanolamine and cathine and the stereospecific N-methylated β-hydroxyamphetamine derivatives ephedrine and pseudoephedrine, among many others.
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.
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.
The β-phenethylamine skeleton is a critical feature of the molecule since either increasing or decreasing the number of carbons between the phenyl ring and the nitrogen reduced or abolished the activity. Both the γ-phenylpropylamines (e.g., 1-phenyl-3-aminobutane, γ-phenylpropylamine, γ-phenyl-N,N-dimethylpropylamine) and the benzylamines (e.g., α-methylbenzylamine, N,N-diethylbenzylamine, benzylamine) were found to be inactive as releasers of norepinephrine (Daly et al., 1966).