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] |
Methcathinone is a monoamine alkaloid and psychoactive stimulant, a substituted cathinone. It is used as a recreational drug due to its potent stimulant and euphoric effects and is considered to be addictive, with both physical and psychological withdrawal occurring if its use is discontinued after prolonged or high-dosage administration. It is usually snorted, but can be smoked, injected, or taken orally.
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.
Aminorex, sold under the brand names Menocil and Apiquel among others, is a weight loss (anorectic) stimulant drug. It was withdrawn from the market after it was found to cause pulmonary hypertension (PPH). In the United States, aminorex is a Schedule I controlled substance.
Chlorphentermine, sold under the brand names Apsedon, Desopimon, and Lucofen, is a serotonergic appetite suppressant of the amphetamine family. Developed in 1962, it is the para-chloro derivative of the better-known appetite suppressant phentermine, which is still in current use.
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 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.
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.
4,4'-Dimethylaminorex, sometimes referred to by the street name "Serotoni", is a psychostimulant and entactogen designer drug related to aminorex, 4-methylaminorex, and pemoline. It was first detected in the Netherlands in December 2012, and has been sold as a designer drug around Europe since mid-2013.
4-Methylcathinone (4-MC), also known as normephedrone is a stimulant drug of the cathinone group. It is an active metabolite of the better known drug mephedrone.
3',4'-Methylenedioxy-4-methylaminorex (MDMAR) is a recreational designer drug from the substituted aminorex family, with monoamine-releasing effects. It is a potent serotonin–norepinephrine–dopamine releasing agent (SNDRA).
Butylamphetamine is a psychostimulant of the substituted amphetamine family which was never marketed.
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).