Substituted amphetamines

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Amphetamine is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy; it is also used to treat binge eating disorder in the form of lisdexamfetamine. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant

Dextroamphetamine is a central nervous system (CNS) stimulant and enantiomer of amphetamine that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used illicitly to enhance cognitive and athletic performance, and recreationally as an aphrodisiac and euphoriant. Dextroamphetamine is generally regarded as the prototypical stimulant.

Sibutramine, formerly sold under the brand name Meridia among others, is an appetite suppressant which has been discontinued in many countries. It works as a serotonin–norepinephrine reuptake inhibitor (SNRI) similar to certain antidepressants. Until 2010, it was widely marketed and prescribed as an adjunct in the treatment of obesity along with diet and exercise.

Fenethylline (BAN, USAN) or fenetylline (INN) is a codrug of amphetamine and theophylline and so a mutual prodrug of both. It is also spelled phenethylline; other names for it are amphetaminoethyltheophylline and amfetyline. The drug was marketed for use as a psychostimulant under the brand names Captagon, Biocapton, and Fitton. The brand name "Captagon" (or in lowercase as "captagon") is often used generically to describe illicitly produced fenethylline.

Lisdexamfetamine, sold under the brand names Vyvanse (, ) and Elvanse among others, is a stimulant medication that is used as a treatment for attention deficit hyperactivity disorder (ADHD) in both children and adults, and for moderate-to-severe binge eating disorder in adults. A prodrug of dextroamphetamine, lisdexamfetamine is taken by mouth. Its effects generally begin within 90 minutes and last for up to 14 hours.

thumb|Tamsulosin – ARISTO Pharma – 0.4 mg prolonged-release tablets – Urologikum

Formoterol, also known as eformoterol, is a long-acting β2 agonist (LABA) used as a bronchodilator in the management of asthma and chronic obstructive pulmonary disease (COPD). Formoterol has an extended duration of action (up to 12&nbsp;h) compared to short-acting β2 agonists such as salbutamol (albuterol), which are effective for 4&nbsp;h to 6&nbsp;h. Formoterol has a relatively rapid onset of action compared to other LABAs, and is effective within 2-3&nbsp;minutes. The 2022 Global Initiative for Asthma report recommends a combination formoterol/inhaled corticosteroid inhaler as both a preve

Tranylcypromine, sold under the brand name Parnate among others, is a monoamine oxidase inhibitor (MAOI). More specifically, tranylcypromine acts as nonselective and irreversible inhibitor of the enzyme monoamine oxidase (MAO). It is used as an antidepressant and anxiolytic agent in the clinical treatment of mood and anxiety disorders, respectively. It is also effective in the treatment of ADHD.

Adderall is the brand name of a fixed-dose combination medication used for the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy. It is also used as an athletic performance enhancer, cognitive enhancer, appetite suppressant, and recreationally as a euphoriant. Such uses are illegal in many countries. It is a central nervous system (CNS) stimulant of the phenethylamine class. It contains the amphetamines dextroamphetamine saccharate, amphetamine aspartate, dextroamphetamine sulfate, and amphetamine sulfate. It is taken by mouth.

Silodosin, sold under the brand name Urief among others, is a medication used for the symptomatic treatment of benign prostatic hyperplasia. It acts as an alpha-1 adrenergic receptor antagonist.

Fenoterol is a β2-adrenergic receptor agonist and bronchodilator medication used in the treatment of asthma.

any chemical compound that is a substituted amphetamine (1-phenylpropane-2-amine)

Fenfluramine, sold under the brand name Fintepla, is a serotonergic medication used for the treatment of seizures associated with Dravet syndrome and Lennox–Gastaut syndrome. It was formerly used as an appetite suppressant in the treatment of obesity, but was discontinued for this use due to cardiovascular toxicity before being repurposed for new indications. Fenfluramine was used for weight loss both alone under the brand name Pondimin and in combination with phentermine commonly known as fen-phen.

Benzphetamine, sold under the brand name Didrex among others, is an amphetamine-type stimulant and appetite suppressant used short-term for weight loss along with a doctor-approved, reduced-calorie diet, exercise, and behavioral program. It is prescribed for obesity to people who have been unable to lose weight through exercise and dieting alone. It is a prodrug of dextromethamphetamine and dextroamphetamine.

'''para-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA'''), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogenic effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties.

Levoamphetamine is a stimulant medication which is used in the treatment of certain medical conditions. It was previously marketed by itself under the brand name Cydril, but is now available only in combination with dextroamphetamine in varying ratios under brand names such as Adderall. The drug is known to increase wakefulness and concentration in association with decreased appetite and fatigue. Pharmaceuticals that contain levoamphetamine are currently indicated and prescribed for the treatment of attention deficit hyperactivity disorder (ADHD), obesity, and narcolepsy in some countries. Lev

4-Fluoroamphetamine (4-FA; 4-FMP; PAL-303; "Flux"), also known as '''para-fluoroamphetamine (PFA'''), is a psychoactive research chemical of the phenethylamine and substituted amphetamine chemical classes. It produces stimulant and entactogenic effects. As a recreational drug, 4-FA is sometimes sold along with related compounds such as 2-fluoroamphetamine and 4-fluoromethamphetamine.

4-Methylthioamphetamine (4-MTA), also known as '''para-methylthioamphetamine (MTA'''), is a designer drug of the substituted amphetamine class developed in the 1990s by a team led by David E. Nichols, an American pharmacologist and medical chemist, at Purdue University. It acts as a non-neurotoxic highly selective serotonin releasing agent (SSRA) in animals. 4-MTA is the methylthio derivative of amphetamine.

Mefenorex (marketed as Rondimen, Pondinil, Anexate) is an amphetamine derivative with a relatively mild psychostimulant profile. Developed in the 1960s, it was used throughout the 1970s as an appetite suppressant for treating obesity. Mefenorex is a prodrug of amphetamine; upon ingestion, the compound will begin to metabolize into, as well as promote the production of, the active metabolites levoamphetamine and dextroamphetamine. Multiple sources have noted the substance as exerting "mild stimulant effects....[and having] relatively little abuse potential."

Benfluorex, sold under the brand name Mediator, is an anorectic and hypolipidemic agent that is structurally related to fenfluramine (a substituted amphetamine). It acts mostly as a prodrug of norfenfluramine. It was fraudulently claimed to improve glycemic control and decrease insulin resistance in people with poorly controlled type-2 diabetes through norfenfluramine acting as a 5-HT2B receptor agonist

Arformoterol, sold under the brand name Brovana among others, is a medication used for the treatment of chronic obstructive pulmonary disease (COPD).

Lefetamine (Santenol) is a drug which is a stimulant and also an analgesic with effects comparable to codeine.

Levomethamphetamine (INN: levmetamfetamine) is an optical isomer of methamphetamine primarily used as a topical nasal decongestant. Levomethamphetamine is used to treat nasal congestion from allergies and the common cold. It was first used medically as decongestant beginning in 1958 and has been used for such purposes, primarily in the United States, since then.

Solriamfetol, sold under the brand name Sunosi, is a wakefulness-promoting medication used in the treatment of excessive sleepiness related to narcolepsy and sleep apnea. It is taken by mouth.

Fenproporex (Perphoxene) (N-2-Cyanoethylamphetamine) (3-(1-phenylpropan-2-ylamino)propanenitrile) (3-[(1-Methyl-2-Phenylethyl)amino]propiononitrile) is a stimulant drug of the phenethylamine and amphetamine chemical classes that was developed in the 1960s. It is used as an appetite suppressant for the treatment of obesity.

Mesocarb, sold under the brand name Sidnocarb or Sydnocarb and known by the developmental code name MLR-1017, is a psychostimulant medication which has been used in the treatment of psychiatric disorders and for a number of other indications in the Soviet Union and Russia. It is currently under development for the treatment of Parkinson's disease and sleep disorders. It is taken by mouth.

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.

Pheniprazine, formerly sold under the brand names Catron and Cavodil, is an irreversible and non-selective monoamine oxidase inhibitor (MAOI) of the hydrazine group that was used as an antidepressant to treat depression in the 1960s. It was also used in the treatment of angina pectoris and schizophrenia. Pheniprazine has been largely discontinued due to toxicity concerns such as jaundice, amblyopia, and optic neuritis.

Amfetaminil (also known as amphetaminil, '''N-cyanobenzylamphetamine, and AN-1; brand name Aponeuron''') is a stimulant drug derived from amphetamine, which was developed in the 1970s and used for the treatment of obesity, ADHD, and narcolepsy. It has largely been withdrawn from clinical use following problems with abuse. The drug is a prodrug to amphetamine.

4-Methylamphetamine (4-MA) or para-methylamphetamine, 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).

Hydroxyamphetamine, also known as 4-hydroxyamphetamine or norpholedrine and sold under the brand names Paredrine and Paremyd among others, is a sympathomimetic medication used in eye drops to dilate the pupil for eye examinations.

Methoxyphenamine (trade names ASMI, Euspirol, Orthoxine, Ortodrinex, Proasma), also known as '2-methoxy-N-methylamphetamine (OMMA'), is a β-adrenergic receptor agonist of the amphetamine class used as a bronchodilator.

6-APB, also known as 6-(2-aminopropyl)benzofuran, is an entactogen of the phenethylamine, amphetamine, and benzofuran families. 6-APB and related drugs are sometimes informally called "Benzofury" in media reports. It is similar in structure to MDA, but differs in that the 3,4-methylenedioxyphenyl ring system has been replaced with a benzofuran ring. 6-APB is also the unsaturated benzofuran derivative of 6-APDB. It may appear as a tan or brown grainy powder.

Propylamphetamine (code name PAL-424; also known as '''N-propylamphetamine or NPA''') 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.

chemical compound

Xylopropamine, also known as 3,4-dimethylamphetamine (DMeA) and sold under the brand names Perhedrin and Esanin, is a stimulant drug of the phenethylamine and amphetamine families which was developed and marketed as an appetite suppressant in the 1950s.

'''para-Chloroamphetamine (PCA), also known as 4-chloroamphetamine (4-CA'''), is a serotonin–norepinephrine–dopamine releasing agent (SNDRA) and serotonergic neurotoxin of the amphetamine family. It is used in scientific research in the study of the serotonin system, as a serotonin releasing agent (SRA) at lower doses to produce serotonergic effects, and as a serotonergic neurotoxin at higher doses to produce long-lasting depletions of serotonin.

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.

5-(2-Aminopropyl)indole (5-API or 5-IT), also known as 3,4-pyrrolo[b]amphetamine or by the code name PAL-571, is an indole and amphetamine derivative with stimulant effects. Its preparation was first reported by Albert Hofmann in 1962. It is a designer drug that has been openly sold as a recreational drug by online vendors since 2011.

thumb|1 gram of 2-FA

Ortetamine (INN), also known as 2-methylamphetamine, is a stimulant drug of the amphetamine class. In animal drug discrimination tests it substituted for dextroamphetamine more closely than either 3- or 4-methylamphetamine, although with only around 1/10 the potency of dextroamphetamine itself.

'α-Methyl-p-tyrosine (AMPT), or simply α-methyltyrosine', also known in its chiral 2-(S) form as metirosine, is a tyrosine hydroxylase enzyme inhibitor and is therefore a drug involved in inhibiting the catecholamine biosynthetic pathway. AMPT inhibits tyrosine hydroxylase whose enzymatic activity is normally regulated through the phosphorylation of different serine residues in regulatory domain sites. Catecholamine biosynthesis starts with dietary tyrosine, which is hydroxylated by tyrosine hydroxylase and it is hypothesized that AMPT competes with tyrosine at the tyrosine-binding site, causi

Dimethylamphetamine (Metrotonin), also known as dimetamfetamine (INN), dimephenopan and '''N,N-dimethylamphetamine''', is a stimulant drug of the phenethylamine and amphetamine chemical classes. Dimethylamphetamine has weaker stimulant effects than amphetamine or methamphetamine and is considerably less addictive and less neurotoxic compared to methamphetamine. However, it still retains some mild stimulant effects and abuse potential, and is illegal in both the United States and Australia.

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 addiction.

Zylofuramine is a stimulant drug. It was developed in 1961, and was intended for use as an appetite suppressant and for the treatment of senile dementia in the elderly, but there is little information about it and it does not appear to have ever been marketed.

chemical compound

'''para-Iodoamphetamine (PIA), also known as 4-iodoamphetamine (4-IA'), is a monoamine releasing agent (MRA) and serotonergic neurotoxin of the amphetamine family related to para''-chloroamphetamine (PCA).

MEDA, also known as 3-methoxy-4,5-ethylenedioxyamphetamine or as 5-methoxy-EDA, is a chemical compound of the phenethylamine, amphetamine, and EDxx families. It is the EDxx analogue of the MDxx psychedelic and entactogen MMDA (5-methoxy-MDA). In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MEDA's dose as greater than 200mg orally and its duration as unknown. MEDA produced few to no effects at tested doses. The chemical synthesis of MEDA has been described. MEDA was first described in the scientific literature by Shulgin in 1964. Subsequently, it was describ

'5-(2-Aminopropyl)-2,3-dihydro-1H-indene (5-APDI), also known as indanylaminopropane (IAP), 2-aminopropylindane (2-API), indanametamine, and, incorrectly, as indanylamphetamine', is an entactogen and psychedelic drug of the amphetamine family. It has been sold by online vendors through the Internet and has been encountered as a designer drug since 2003, but its popularity and availability has diminished in recent years.

Prenylamine (Segontin) is a calcium channel blocker of the amphetamine chemical class that was used as a vasodilator in the treatment of angina pectoris. It produces amphetamine as a metabolite.

'''para-Bromoamphetamine (PBA), also known as 4-bromoamphetamine (4-BA'''), is an amphetamine derivative which acts as a serotonin-norepinephrine-dopamine releasing agent (SNDRA) and produces stimulant effects.

Clobenzorex is a central nervous system stimulant and anorectic drug, chemically classified as an N-substituted amphetamine and a phenethylamine. Marketed by Aventis under the trade name Asenlix in India, Mexico, Honduras, and other parts of Latin America.

EDMA, also known as '3,4-ethylenedioxy-N-methylamphetamine or as MDMC', is a psychoactive drug of the phenethylamine, amphetamine, and EDxx families. It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring.

drug chemical compound

Bis-TOM, or 2,5-TOM, also known as 4-methyl-2,5-dimethylthioamphetamine or as 2,5-dithio-DOM, is a chemical compound of the phenethylamine and amphetamine families related to DOM. It is the analogue of DOM in which the methoxy groups at the 2 and 5 positions have been replaced with methylthio groups.

3-Methylamphetamine (3-MeA; PAL-314) is a stimulant drug from the amphetamine family. It is self-administered by mice to a similar extent to 4-fluoroamphetamine and has comparable properties as a monoamine releaser, although with a more balanced release of all three monoamines, as opposed to the more dopamine/noradrenaline selective fluoro analogues.

'''para-Methoxyethylamphetamine (PMEA''') is a stimulant drug related to PMA. PMEA reputedly produces similar effects to PMA, but is considerably less potent and seems to have slightly less tendency to produce severe hyperthermia, at least at low doses. At higher doses however the side effects and danger of death approach those of PMA itself, and PMEA should still be considered a potentially dangerous drug. Investigation of a drug-related death in Japan in 2005 showed PMEA to be present in the body and was thought to be responsible for the death.

Gepefrine, also known as 3-hydroxyamphetamine or 'α-methyl-meta-tyramine and sold under the brand names Pressionorm and Wintonin', is a sympathomimetic medication used as an antihypotensive agent which has been marketed in Germany.