Substituted amphetamine

Last updated

Substituted amphetamine
Drug class
Racemic amphetamine.svg
Class identifiers
Chemical class Substituted derivatives of amphetamine
Legal status
In Wikidata
Optical isomers of amphetamine
L-amphetamine.svg D-amphetamine.svg
L-amphetamine-3D-vdW.png D-amphetamine-3D-vdW.png
L-amphetamine D-amphetamine

Substituted amphetamines are a class of compounds based upon the amphetamine structure; [1] it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. [1] [2] [3] [4] The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. [2] Examples of substituted amphetamines are amphetamine (itself), [1] [2] methamphetamine, [1] ephedrine, [1] cathinone, [1] phentermine, [1] mephentermine, [1] tranylcypromine, [5] bupropion, [1] methoxyphenamine, [1] selegiline, [1] amfepramone (diethylpropion), [1] pyrovalerone, [1] MDMA (ecstasy), and DOM (STP).

Contents

Some of amphetamine's substituted derivatives occur in nature, for example in the leaves of Ephedra and khat plants. [1] Amphetamine was first produced at the end of the 19th century. By the 1930s, amphetamine and some of its derivative compounds found use as decongestants in the symptomatic treatment of colds and also occasionally as psychoactive agents. Their effects on the central nervous system are diverse, but can be summarized by three overlapping types of activity: psychoanaleptic, hallucinogenic and empathogenic. Various substituted amphetamines may cause these actions either separately or in combination.

Partial list of substituted amphetamines

Generic or Trivial NameChemical Name# of Subs
Amphetamine α-Methyl-phenethylamine0
Methamphetamine N-Methylamphetamine1
Ethylamphetamine N-Ethylamphetamine1
Propylamphetamine N-Propylamphetamine1
Isopropylamphetamine N-iso-Propylamphetamine1
Phentermine α-Methylamphetamine1
Phenylpropanolamine (PPA)β-Hydroxyamphetamine, (1R,2S)-1
Cathine β-Hydroxyamphetamine, (1S,2S)-1
Cathinone β-Ketoamphetamine1
Ortetamine 2-Methylamphetamine1
2-Fluoroamphetamine (2-FA)2-Fluoroamphetamine1
3-Methylamphetamine (3-MA)3-Methylamphetamine1
2-Phenyl-3-aminobutane 2-Phenyl-3-aminobutane1
Tranylcypromine Trans-2-phenylcyclopropylamine 
3-Fluoroamphetamine (3-FA)3-Fluoroamphetamine1
Norfenfluramine 3-Trifluoromethylamphetamine1
4-Methylamphetamine (4-MA)4-Methylamphetamine1
para-Methoxyamphetamine (PMA)4-Methoxyamphetamine1
para-Ethoxyamphetamine 4-Ethoxyamphetamine1
4-Methylthioamphetamine (4-MTA)4-Methylthioamphetamine1
Norpholedrine (α-Me-TRA)4-Hydroxyamphetamine1
para-Bromoamphetamine (PBA, 4-BA)4-Bromoamphetamine1
para-Chloroamphetamine (PCA, 4-CA)4-Chloroamphetamine1
para-Fluoroamphetamine (PFA, 4-FA, 4-FMP)4-Fluoroamphetamine1
para-Iodoamphetamine (PIA, 4-IA)4-Iodoamphetamine1
Clobenzorex N-(2-chlorobenzyl)-1-phenylpropan-2-amine1
Dimethylamphetamine N,N-Dimethylamphetamine2
Benzphetamine N-Benzyl-N-methylamphetamine2
D-Deprenyl N-Methyl-N-propargylamphetamine, (S)-2
Selegiline N-Methyl-N-propargylamphetamine, (R)-2
Mephentermine N-Methyl-α-methylamphetamine2
Phenpentermine α,β-Dimethylamphetamine2
Ephedrine β-Hydroxy-N-methylamphetamine, (1R,2S)-2
Pseudoephedrine (PSE)β-Hydroxy-N-methylamphetamine, (1S,2S)-2
Methcathinone β-Keto-N-methylamphetamine2
Ethcathinone β-Keto-N-ethylamphetamine2
Clortermine 2-Chloro-α-methylamphetamine2
Methoxymethylamphetamine (MMA)3-Methoxy-4-methylamphetamine2
Fenfluramine 3-Trifluoromethyl-N-ethylamphetamine2
Dexfenfluramine 3-Trifluoromethyl-N-ethylamphetamine, (S)-2
4-Methylmethamphetamine (4-MMA)4-Methyl-N-methylamphetamine2
para-Methoxymethamphetamine (PMMA)4-Methoxy-N-methylamphetamine2
para-Methoxyethylamphetamine (PMEA)4-Methoxy-N-ethylamphetamine2
Pholedrine 4-Hydroxy-N-methylamphetamine2
Chlorphentermine 4-Chloro-α-methylamphetamine2
para-Fluoromethamphetamine (PFMA, 4-FMA)4-Fluoro-N-methylamphetamine2
Xylopropamine 3,4-Dimethylamphetamine2
α-Methyldopamine (α-Me-DA)3,4-Dihydroxyamphetamine2
3,4-Methylenedioxyamphetamine (MDA)3,4-Methylenedioxyamphetamine2
Dimethoxyamphetamine (DMA)X,X-Dimethoxyamphetamine2
6-APB 6-(2-aminopropyl)benzofuran2
Nordefrin (α-Me-NE)β,3,4-Trihydroxyamphetamine, (R)-3
Oxilofrine β,4-Dihydroxy-N-methylamphetamine3
Aleph 2,5-dimethoxy-4-methylthioamphetamine3
Dimethoxybromoamphetamine (DOB)2,5-Dimethoxy-4-bromoamphetamine3
Dimethoxychloroamphetamine (DOC)2,5-Dimethoxy-4-chloroamphetamine3
Dimethoxyfluoroethylamphetamine (DOEF)2,5-Dimethoxy-4-fluoroethylamphetamine3
Dimethoxyethylamphetamine (DOET)2,5-Dimethoxy-4-ethylamphetamine3
Dimethoxyfluoroamphetamine (DOF)2,5-Dimethoxy-4-fluoroamphetamine3
Dimethoxyiodoamphetamine (DOI)2,5-Dimethoxy-4-iodoamphetamine3
Dimethoxymethylamphetamine (DOM)2,5-Dimethoxy-4-methylamphetamine3
Dimethoxynitroamphetamine (DON)2,5-Dimethoxy-4-nitroamphetamine3
Dimethoxypropylamphetamine (DOPR)2,5-Dimethoxy-4-propylamphetamine3
Dimethoxytrifluoromethylamphetamine (DOTFM)2,5-Dimethoxy-4-trifluoromethylamphetamine3
Methylenedioxymethamphetamine (MDMA)3,4-Methylenedioxy-N-methylamphetamine3
Methylenedioxyethylamphetamine (MDEA)3,4-Methylenedioxy-N-ethylamphetamine3
Methylenedioxyhydroxyamphetamine (MDOH)3,4-Methylenedioxy-N-hydroxyamphetamine3
2-Methyl-MDA 3,4-Methylenedioxy-2-methylamphetamine3
5-Methyl-MDA 4,5-Methylenedioxy-3-methylamphetamine3
Methoxymethylenedioxyamphetamine (MMDA)3-Methoxy-4,5-methylenedioxyamphetamine3
Trimethoxyamphetamine (TMA)X,X,X-Trimethoxyamphetamine3
Dimethylcathinone β-Keto-N,N-dimethylamphetamine3
Diethylcathinone β-Keto-N,N-diethylamphetamine3
Bupropion β-Keto-3-chloro-N-tert-butylamphetamine3
Mephedrone (4-MMC)β-Keto-4-methyl-N-methylamphetamine3
Methedrone (PMMC)β-Keto-4-methoxy-N-methylamphetamine3
Brephedrone (4-BMC)β-Keto-4-bromo-N-methylamphetamine3
Flephedrone (4-FMC)β-Keto-4-fluoro-N-methylamphetamine3

Prodrugs of amphetamine/methamphetamine

A variety of prodrugs of amphetamine and/or methamphetamine exist, and include amfecloral, amphetaminil, benzphetamine, clobenzorex, D-deprenyl, dimethylamphetamine, ethylamphetamine, fencamine, fenethylline, fenproporex, furfenorex, lisdexamfetamine, mefenorex, prenylamine, and selegiline. [6]

Structure

This shows phenethylamine in blue with its substitution points marked. Amphetamine and its substituted derivatives contain a CH3 group at the alpha-position (R ). Phenylethyl Amine General Formula V1.svg
This shows phenethylamine in blue with its substitution points marked. Amphetamine and its substituted derivatives contain a CH3 group at the alpha-position (R ).
This shows amphetamine with its substitution points marked, excluding the N-position at the NH2 group which is unmarked. The wavy line between a carbon and CH3 group indicates isomerism; the CH3 group may either be towards or away from the viewer. Amphetamine numbered.svg
This shows amphetamine with its substitution points marked, excluding the N-position at the NH2 group which is unmarked. The wavy line between α carbon and CH3 group indicates isomerism; the CH3 group may either be towards or away from the viewer.

Amphetamines are a subgroup of the substituted phenethylamine class of compounds. Substitution of hydrogen atoms results in a large class of compounds. Typical reaction is substitution by methyl and sometimes ethyl groups at the amine and phenyl sites: [8] [9] [10]

SubstanceSubstituentsStructureSources
Nαβ phenyl group
2345
Phenethylamine Phenethylamine2DCSD.svg
Amphetamine (α-methylphenylethylamine)-CH3 Racemic amphetamine 2.svg [7]
Methamphetamine (N-methylamphetamine)-CH3-CH3 Methamphetamine.svg [7]
Phentermine (α-methylamphetamine)-(CH3)2 Fentermina.svg [7]
Ephedrine -CH3-CH3-OH (+)-Ephedrin.svg [7]
Pseudoephedrine -CH3-CH3-OH (+)-Pseudoephedrin.svg [7]
Cathinone -CH3=O S-Cathinone.svg [7]
Methcathinone (ephedrone)-CH3-CH3=O Methcathinone skeletal.svg [7]
MDA (3,4-methylenedioxyamphetamine)-CH3-O-CH2-O- MDA-2D-skeletal.svg [7]
MDMA (3,4-methylenedioxymethamphetamine)-CH3-CH3-O-CH2-O- MDMA (simple).svg [7]
MDEA (3,4-methylenedioxy-N-ethylamphetamine)-CH2-CH3-CH3-O-CH2-O- MDEA.svg [7]
EDMA (3,4-ethylenedioxy-N-methylamphetamine)-CH3-CH3-O-CH2-CH2-O- EDMA.svg
MBDB (N-methyl-1,3-benzodioxolylbutanamine)-CH3-CH2-CH3-O-CH2-O- MBDB.svg
PMA (para-methoxyamphetamine)-CH3-O-CH3 PMA.svg
PMMA (para-methoxymethamphetamine)-CH3-CH3-O-CH3 4-Methoxymethamphetamine.svg
4-MTA (4-methylthioamphetamine)-CH3-S-CH3 4-methylthioamphetamine.svg
3,4-DMA (3,4-dimethoxyamphetamine)-CH3-O-CH3-O-CH3 3,4-dma.png
3,4,5-Trimethoxyamphetamine (α-methylmescaline)-CH3-O-CH3-O-CH3-O-CH3 Trimethoxyamphetamine structure.svg
DOM (2,5-dimethoxy-4-methylamphetamine)-CH3-O-CH3-CH3-O-CH3 2,5-Dimethoxy-4-methylamphetamine.svg
DOB (2,5-dimethoxy-4-bromoamphetamine)-CH3-O-CH3-Br-O-CH3 R-DOB.svg

History

Ephedra was used 5000 years ago in China as a medicinal plant; its active ingredients are alkaloids ephedrine, pseudoephedrine, norephedrine (phenylpropanolamine) and norpseudoephedrine (cathine). Natives of Yemen and Ethiopia have a long tradition of chewing khat leaves to achieve a stimulating effect. The active substances of khat are cathinone and, to a lesser extent, cathine. [11]

Amphetamine was first synthesized in 1887 by Romanian chemist Lazăr Edeleanu, although its pharmacological effects remained unknown until the 1930s. [12] MDMA was produced in 1912 (in 1914, according to other sources [13] ) as an intermediate product. However, this synthesis also went largely unnoticed. [14] In the 1920s, both methamphetamine and the dextrorotatory optical isomer of amphetamine, dextroamphetamine, were synthesized. This synthesis was a by-product of a search for ephedrine, a bronchodilator used to treat asthma extracted exclusively from natural sources. Over-the-counter use of substituted amphetamines was initiated in the early 1930s by the pharmaceutical company Smith, Kline & French (now part of GlaxoSmithKline), as a medicine (Benzedrine) for colds and nasal congestion. Subsequently, amphetamine was used in the treatment of narcolepsy, obesity, hay fever, orthostatic hypotension, epilepsy, Parkinson's disease, alcoholism and migraine. [12] [15] The "reinforcing" effects of substituted amphetamines were quickly discovered, and the misuse of substituted amphetamines had been noted as far back as 1936. [15]

Amphetamine pills Amph salts.jpg
Amphetamine pills

During World War II, amphetamines were used by the German military to keep their tank crews awake for long periods, and treat depression. It was noticed that extended rest was required after such artificially induced activity. [12] The widespread use of substituted amphetamines began in postwar Japan and quickly spread to other countries. Modified "designer amphetamines", such as MDA and PMA, have gained in popularity since the 1960s. [15] In 1970, the United States adopted "the Controlled Substances Act" that limited non-medical use of substituted amphetamines. [15] Street use of PMA was noted in 1972. [16] MDMA emerged as a substitute for MDA in the early 1970s. [17] American chemist Alexander Shulgin first synthesized the drug in 1976 and through him the drug was briefly introduced into psychotherapy. [18] Recreational use grew and in 1985 MDMA was banned by the US authorities in an emergency scheduling initiated by the Drug Enforcement Administration. [19]

Since the mid-1990s, MDMA has become a popular entactogenic drug among the youth and quite often non-MDMA substances were sold as ecstasy. [20] Ongoing trials are investigating its efficacy as an adjunct to psychotherapy in the management of treatment-resistant post-traumatic stress disorder (PTSD). [21]

AgentsLegal status by 2009. [22] [23] [24] [25]
USRussia Australia
Amphetamine (racemic)Schedule IISchedule IISchedule IISchedule 8
Dextroamphetamine (D-amphetamine)Schedule IISchedule IISchedule ISchedule 8
Levoamphetamine (L-amphetamine)Schedule IISchedule IISchedule IIISchedule 8
Methamphetamine Schedule IISchedule IISchedule ISchedule 8
Cathinone Methcathinone Schedule ISchedule ISchedule ISchedule 9
MDA, MDMA, MDEA Schedule ISchedule ISchedule ISchedule 9
PMA Schedule ISchedule ISchedule ISchedule 9
DOB, DOM, 3,4,5-TMA Schedule ISchedule ISchedule ISchedule 9

See also

Related Research Articles

<span class="mw-page-title-main">MDMA</span> Psychoactive drug, often called ecstasy

3,4-Methyl​enedioxy​methamphetamine (MDMA), commonly known as ecstasy, and molly or mandy, is a potent empathogen–entactogen with stimulant and minor psychedelic properties. Investigational indications include as an adjunct to psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder. The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.

<span class="mw-page-title-main">Stimulant</span> Drug that increases activity of central nervous system

Stimulants are a class of drugs that increase the activity of the brain and the spinal cord. They are used for various purposes, such as enhancing alertness, attention, motivation, cognition, mood, and physical performance. Some of the most common stimulants are caffeine, nicotine, amphetamines, cocaine, and modafinil.

<span class="mw-page-title-main">Methcathinone</span> Psychoactive stimulant

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.

<span class="mw-page-title-main">Phenethylamine</span> Organic compound, a stimulant in humans

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 amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation.

<span class="mw-page-title-main">Empathogen–entactogen</span> Class of psychoactive drugs that produce empathic experiences

Empathogens or entactogens are a class of psychoactive drugs that induce the production of experiences of emotional communion, oneness, relatedness, emotional openness—that is, empathy or sympathy—as particularly observed and reported for experiences with 3,4-methylenedioxymethamphetamine (MDMA). This class of drug is distinguished from the classes of hallucinogen or psychedelic, and amphetamine or stimulants. Major members of this class include MDMA, MDA, MDEA, MDOH, MBDB, 5-APB, 5-MAPB, 6-APB, 6-MAPB, methylone, mephedrone, GHB, αMT, and αET, MDAI among others. Most entactogens are phenethylamines and amphetamines, although several, such as αMT and αET, are tryptamines. When referring to MDMA and its counterparts, the term MDxx is often used. Entactogens are sometimes incorrectly referred to as hallucinogens or stimulants, although many entactogens such as ecstasy exhibit psychedelic or stimulant properties as well.

<span class="mw-page-title-main">Cathine</span> Chemical compound

D-norpseudoephedrine, also known as cathine and (+)-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine chemical classes which acts as a stimulant. Along with cathinone, it is found naturally in Catha edulis (khat), and contributes to its overall effects. It has approximately 7-10% the potency of amphetamine.

<span class="mw-page-title-main">Cathinone</span> Chemical compound

Cathinone is a monoamine alkaloid found in the shrub Catha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to the stimulant effect of Catha edulis, also known as khat. Cathinone differs from many other amphetamines in that it has a ketone functional group. Other phenethylamines that share this structure include the stimulants methcathinone, MDPV, mephedrone and the antidepressant bupropion.

<span class="mw-page-title-main">Phenylpropanolamine</span> Sympathomimetic agent

Phenylpropanolamine (PPA) is a sympathomimetic agent which is used as a decongestant and appetite suppressant. It was commonly used in prescription and over-the-counter cough and cold preparations. In veterinary medicine, it is used to control urinary incontinence in dogs.

<span class="mw-page-title-main">3,4-Methylenedioxyamphetamine</span> Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

<span class="mw-page-title-main">Phenylacetone</span> Chemical compound

Phenylacetone, also known as phenyl-2-propanone, is an organic compound with the chemical formula C6H5CH2COCH3. It is a colorless oil that is soluble in organic solvents. It is a mono-substituted benzene derivative, consisting of an acetone attached to a phenyl group. As such, its systematic IUPAC name is 1-phenyl-2-propanone.

<span class="mw-page-title-main">Methylone</span> Group of stereoisomers

Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

<span class="mw-page-title-main">Substituted methylenedioxyphenethylamine</span> Class of psychoactive drugs

The substituted methylenedioxyphenethylamines represent a diverse chemical class of compounds derived from phenethylamines. This category encompasses numerous psychoactive substances with entactogenic, psychedelic, and/or stimulant properties, in addition to entheogens. These compounds find application as research chemicals, designer drugs, and recreational substances.

<span class="mw-page-title-main">Convention on Psychotropic Substances</span> 1971 UN treaty to regulate recreational drugs

The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamine-type stimulants, barbiturates, benzodiazepines, and psychedelics signed in Vienna, Austria on 21 February 1971. The Single Convention on Narcotic Drugs of 1961 did not ban the many newly discovered psychotropics, since its scope was limited to drugs with cannabis, coca and opium-like effects.

<span class="mw-page-title-main">MDAI</span> Chemical compound

MDAI (5,6-methylenedioxy-2-aminoindane) is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in vitro and produces entactogen effects in humans.

<span class="mw-page-title-main">Substituted phenethylamine</span> Chemical class of organic compounds

Substituted phenethylamines are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents.

DO<em>x</em> Class of chemical compounds

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonists. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT2 receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects.

<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

Substituted 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.

<span class="mw-page-title-main">Substituted benzofuran</span> Class of chemical compounds

The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Many medicines use the benzofuran core as a scaffold, but most commonly the term is used to refer to the simpler compounds in this class which include numerous psychoactive drugs, including stimulants, psychedelics and empathogens. In general, these compounds have a benzofuran core to which a 2-aminoethyl group is attached, and combined with a range of other substituents. Some psychoactive derivatives from this family have been sold under the name Benzofury.

Amphetamine type stimulants (ATS) are a group of synthetic drugs that are chemical derivatives of the parent compound alpha-methylphenethylamine, also known as amphetamine. Common ATS includes amphetamine, methamphetamine, ephedrine, pseudoephedrine, 3,4-methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxyethylamphetamine (MDEA). ATS when used illicitly has street names including ice, meth, crystal, crank, bennies, and speed. Within the group of amphetamine-type stimulants, there are also prescription drugs including mixed amphetamine salts, dextroamphetamine, and lisdexamfetamine.

<span class="mw-page-title-main">Dimethylone</span> Stimulant and empathogenic drug

Dimethylone (βk-MDDMA) is a substituted cathinone derivative with stimulant and empathogenic effects. Unlike the corresponding amphetamine derivative MDDM which is thought to be practically inactive, dimethylone substitutes for methamphetamine and MDMA in animal studies and has been sold as a designer drug.

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Hagel JM, Krizevski R, Marsolais F, Lewinsohn E, Facchini PJ (2012). "Biosynthesis of amphetamine analogs in plants". Trends Plant Sci. 17 (7): 404–412. doi:10.1016/j.tplants.2012.03.004. PMID   22502775. Substituted amphetamines, which are also called phenylpropylamino alkaloids, are a diverse group of nitrogen-containing compounds that feature a phenethylamine backbone with a methyl group at the α-position relative to the nitrogen (Figure 1). Countless variation in functional group substitutions has yielded a collection of synthetic drugs with diverse pharmacological properties as stimulants, empathogens and hallucinogens [3]. ... Beyond (1R,2S)-ephedrine and (1S,2S)-pseudoephedrine, myriad other substituted amphetamines have important pharmaceutical applications. The stereochemistry at the α-carbon is often a key determinant of pharmacological activity, with (S)-enantiomers being more potent. For example, (S)-amphetamine, commonly known as d-amphetamine or dextroamphetamine, displays five times greater psychostimulant activity compared with its (R)-isomer [78]. Most such molecules are produced exclusively through chemical syntheses and many are prescribed widely in modern medicine. For example, (S)-amphetamine (Figure 4b), a key ingredient in Adderall and Dexedrine, is used to treat attention deficit hyperactivity disorder (ADHD) [79]. ...
    [Figure 4](b) Examples of synthetic, pharmaceutically important substituted amphetamines.
  2. 1 2 3 Glennon RA (2013). "Phenylisopropylamine stimulants: amphetamine-related agents". In Lemke TL, Williams DA, Roche VF, Zito W (eds.). Foye's principles of medicinal chemistry (7th ed.). Philadelphia, USA: Wolters Kluwer Health/Lippincott Williams & Wilkins. pp. 646–648. ISBN   9781609133450. The simplest unsubstituted phenylisopropylamine, 1-phenyl-2-aminopropane, or amphetamine, serves as a common structural template for hallucinogens and psychostimulants. Amphetamine produces central stimulant, anorectic, and sympathomimetic actions, and it is the prototype member of this class (39).
  3. Lillsunde P, Korte T (March 1991). "Determination of ring- and N-substituted amphetamines as heptafluorobutyryl derivatives". Forensic Sci. Int. 49 (2): 205–213. doi:10.1016/0379-0738(91)90081-s. PMID   1855720.
  4. Custodio, Raly James Perez; Botanas, Chrislean Jun; Yoon, Seong Shoon; Peña, June Bryan de la; Peña, Irene Joy dela; Kim, Mikyung; Woo, Taeseon; Seo, Joung-Wook; Jang, Choon-Gon; Kwon, Yong Ho; Kim, Nam Yong (1 November 2017). "Evaluation of the Abuse Potential of Novel Amphetamine Derivatives with Modifications on the Amine (NBNA) and Phenyl (EDA, PMEA, 2-APN) Sites". Biomolecules & Therapeutics. 25 (6): 578–585. doi:10.4062/biomolther.2017.141. ISSN   2005-4483. PMC   5685426 . PMID   29081089.
  5. Ulrich S, Ricken R, Adli M (2017). "Tranylcypromine in mind (Part I): Review of pharmacology". European Neuropsychopharmacology. 27 (8): 697–713. doi: 10.1016/j.euroneuro.2017.05.007 . PMID   28655495. S2CID   4913721.
  6. Reinhard Dettmeyer; Marcel A. Verhoff; Harald F. Schütz (9 October 2013). Forensic Medicine: Fundamentals and Perspectives. Springer Science & Business Media. pp. 519–. ISBN   978-3-642-38818-7.
  7. 1 2 3 4 5 6 7 8 9 10 11 Barceloux DG (February 2012). "Chapter 1: Amphetamine and Methamphetamine". Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants (First ed.). John Wiley & Sons. p. 5. ISBN   9781118106051 . Retrieved 16 February 2019.
  8. Goldfrank, pp. 1125–1127
  9. Glennon, pp. 184–187
  10. Schatzberg, p.843
  11. Paul M Dewick (2002). Medicinal Natural Products. A Biosynthetic Approach. Second Edition. Wiley. pp. 383–384. ISBN   978-0-471-49640-3.
  12. 1 2 3 Snow, p. 1
  13. A. Richard Green, et al. (2003). "The Pharmacology and Clinical Pharmacology of 3,4-Methylenedioxymethamphetamine (MDMA, Ecstasy)". Pharmacological Reviews. 55 (3): 463–508. doi:10.1124/pr.55.3.3. PMID   12869661. S2CID   1786307.
  14. Goldfrank, p. 1125
  15. 1 2 3 4 Goldfrank, p. 1119
  16. Liang Han Ling, et al. (2001). "Poisoning with the recreational drug paramethoxyamphetamine ("death" )". The Medical Journal of Australia. 174 (9): 453–5. doi:10.5694/j.1326-5377.2001.tb143372.x. hdl: 2440/14508 . PMID   11386590. S2CID   37596142. Archived from the original on 26 November 2009.
  17. Foderaro, Lisa W. (11 December 1988). "Psychedelic Drug Called Ecstasy Gains Popularity in Manhattan Nightclubs". The New York Times. Archived from the original on 17 November 2015. Retrieved 27 August 2015.
  18. Benzenhöfer, Udo; Passie, Torsten (9 July 2010). "Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin". Addiction. 105 (8): 1355–1361. doi:10.1111/j.1360-0443.2010.02948.x. PMID   20653618.
  19. Snow, p. 71
  20. Goldfrank, p. 1121
  21. Mithoefer M., et al. (2011). "The safety and efficacy of ±3,4-methylenedioxymethamphetamine-assisted psychotherapy in subjects with chronic, treatment-resistant posttraumatic stress disorder: the first randomized controlled pilot study". Journal of Psychopharmacology. 25 (4): 439–52. doi:10.1177/0269881110378371. PMC   3122379 . PMID   20643699.
  22. "List of psychotropic substances under international control" (PDF). International Narcotics Control Board. August 2003. Archived from the original on 25 November 2010.{{cite web}}: CS1 maint: unfit URL (link) May 2010 Edition Archived 24 December 2012 at the Wayback Machine
  23. "DEA Drug Scheduling". U.S. Drug Enforcement Administration. Archived from the original on 7 February 2011. Retrieved 17 November 2009.
  24. "Resolution of RF Government of 30 June 1998 N 681 "On approval of list of drugs psychotropic substances and their precursors subject to control in the Russian Federation"". garant.ru (in Russian). Archived from the original on 20 January 2012. Retrieved 15 November 2009.
  25. "The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP)". Australian Therapeutic Goods Administration (TGA). Archived from the original on 27 June 2015. Retrieved 26 June 2015.
  26. "Convention on Psychotropic Substances, 1971" (PDF). United Nations. Archived from the original on 25 November 2010.{{cite web}}: CS1 maint: unfit URL (link)

Bibliography