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|Chemical class||Substituted derivatives of phenethylamine|
Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; [note 1] 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.
The structural formula of any substituted phenethylamine contains a phenyl ring that is joined to an amino (NH) group via a two-carbon sidechain. Hence, any substituted phenethylamine can be classified according to the substitution of hydrogen (H) atoms on phenethylamine's phenyl ring, sidechain, or amino group with a specific group of atoms.
Many substituted phenethylamines are psychoactive drugs which belong to a variety of different drug classes, including central nervous system stimulants (e.g., amphetamine), hallucinogens (e.g., 3,4,5-trimethoxyphenethylamine a.k.a. mescaline), 2,5-dimethoxy-4-methylamphetamine a.k.a. DOM), entactogen (e.g., , MDA), appetite suppressants (e.g. phentermine), nasal decongestants and bronchodilators (e.g., levomethamphetamine and pseudoephedrine), antidepressants (e.g. bupropion and phenelzine), antiparkinson agents (e.g., selegiline), and vasopressors (e.g., ephedrine), among others.[ medical citation needed ] Many of these psychoactive compounds exert their pharmacological effects primarily by modulating monoamine neurotransmitter systems; however, there is no mechanism of action or biological target that is common to all members of this subclass.[ medical citation needed ]
Numerous endogenous compounds – including hormones, catecholamines such as dopamine and noradrenaline, and many trace amines (e.g. adrenaline, phenethylamine itself, tyramine, thyronamine, and iodothyronamine) – are substituted phenethylamines. Several notable recreational drugs, such as MDMA (ecstasy), methamphetamine, and cathinone, are also members of the class. All of the substituted amphetamines and substituted methylenedioxyphenethylamines are substituted phenethylamines as well.
|Short Name||RN||Rα||Rβ||R2||R3||R4||R5||Full Name||Biologic activity|
|Epinephrine (Adrenaline)||CH3||OH||OH||OH||β,3,4-trihydroxy-N-methyl phenethylamine||Catecholamine neurotransmitter/Fight or Flight hormone|
|Norepinephrine (Noradrenaline)||OH||OH||OH||β,3,4-trihydroxyphenethylamine||Catecholamine neurotransmitter/Fight or Flight hormone|
|para-Octopamine||OH||OH||β,4-dihydroxyphenethylamine||Trace aminergic α-adrenoceptor agonist|
|6-Hydroxydopamine||OH||OH||OH||2,4,5-trihydroxyphenethylamine||neurotoxic agent for the dopamine and norepinephrine receptors|
|Phenylephrine||CH3||OH||OH||β,3-dihydroxy-N-methylphenethylamine||α-adrenergic agonist; decongestant|
|Isoproterenol||CH(CH3)2||OH||OH||OH||β,3-dihydroxy-N-methylphenethylamine||β-adrenergic agonist; decongestant|
|Salbutamol||C(CH3)3||OH||CH2OH||OH||β,4-dihydroxy-3-hydroxymethyl-N-tert-butylphenethylamine||Short-action β2-adrenergic agonist|
|Amphetamine||CH3||α-methylphenethylamine||Monoamine releasing agent; Stimulant|
|N-Methylphenethylamine||CH3||N-methylphenethylamine||Trace amine; endogenous amphetamine isomer|
|N,N-Dimethylphenethylamine||(CH3)2||N,N-dimethylphenethylamine||Trivial effects (used as a food additive and flavoring agent)|
|Methamphetamine||CH3||CH3||N-methylamphetamine; N,α-dimethylphenethylamine||Monoamine releasing agent; stimulant; neurotoxin|
|Phentermine||(CH3)2||α-methylamphetamine; α,α-dimethylphenethylamine||Stimulant, anorectic|
|Ortetamine||CH3||CH3||2-methylamphetamine; 2,α-dimethylphenethylamine||Stimulant, anorectic|
|Phenelzine||NH2||β-phenylethylhydrazine||Monoamine oxidase inhibitor|
|Tranylcypromine||-CH2-||2-phenylcyclopropylamine||Monoamine oxidase inhibitor|
|Selegiline||-CH2-C≡CH||CH3||N,α-dimethyl-N-2-propynylphenethylamine||MAO-B selective monoamine oxidase inhibitor|
|Ephedrine / Pseudoephedrine||CH3||CH3||OH||N-methyl-β-hydroxyamphetamine||Releasing agent; stimulant; decongestant|
|Cathine||CH3||OH||d-β-hydroxyamphetamine||Moderately selective norepinephrine releasing agent|
|Cathinone||CH3||=O||β-ketoamphetamine||Selective norepinephrine and dopamine releasing agent|
|Methcathinone||CH3||CH3||=O||N-methylcathinone||Selective norepinephrine and dopamine releasing agent|
|Mephedrone||CH3||CH3||=O||CH3||4-methylmethcathinone||Stimulant, unknown pharmacodynamic actions|
|Ethcathinone||CH2CH3||CH3||=O||N-ethylcathinone||Stimulant and norepinephrine releasing agent|
|MDA||CH3||-O-CH2-O-||3,4-methylenedioxy-amphetamine||Stimulant, psychedelic, entactogen|
|MDEA||CH2CH3||CH3||-O-CH2-O-||3,4-methylenedioxy-N-ethylamphetamine||Psychedelic, entactogen, and releasing agent|
|MDMA||CH3||CH3||-O-CH2-O-||3,4-methylenedioxy-N-methylamphetamine||Psychedelic, entactogen, and releasing agent|
|MDMC||CH3||CH3||=O||-O-CH2-O-||3,4-methylenedioxymethcathinone||Psychedelic, entactogen, and releasing agent|
|MMDA||CH3||-O-CH2-O-||OCH3||5-methoxy-3,4-methylenedioxy-amphetamine||Stimulant, psychedelic and entactogen|
|MMDMA||CH3||CH3||-O-CH2-O-||OCH3||5-methoxy-3,4-methylenedioxy-N-methylamphetamine||Psychedelic, entactogen, and releasing agent|
|Lophophine||-O-CH2-O-||OCH3||5-methoxy-3,4-methylenedioxyphenethylamine||Psychedelic and entactogen|
|Mescaline||OCH3||OCH3||OCH3||3,4,5-trimethoxy phenethylamine||Psychedelic and entactogen|
|Proscaline||OCH3||OCH2CH2CH3||OCH3||2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine||Psychedelic and entactogen|
|Metaescaline||OCH2CH3||OCH3||OCH3||2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine||Psychedelic and entactogen|
|Allylescaline||OCH3||OCH2CH1CH2||OCH3||4-Allyloxy-3,5-dimethyloxyphenylethylamine||Psychedelic and entactogen|
|Methallylescaline||OCH3||OCH2C(CH2CH3)||OCH3||4-Methallyloxy-3,5-dimethoxyphenethylamine||Psychedelic and entactogen|
|Asymbescaline||OCH2CH3||OCH2CH3||OCH3||3,4-Diethoxy-5-methoxyphenethylamine||Psychedelic and euphoriant|
|2C-B||OCH3||Br||OCH3||2,5-dimethoxy-4-bromophenethylamine||Psychedelic, stimulant, entactogen and euphoriant|
|βk-2C-B||=O||OCH3||Br||OCH3||2,5-dimethoxy-4-bromo-β-ketophenethylamine||Psychedelic, stimulant, entactogen and euphoriant|
|2C-P||OCH3||CH2-CH3-CH3||OCH3||2,5-dimethoxy-4-propylphenethylamine||Entactogen, euphoriant and Psychedelic|
|2C-T-21||OCH3||S-CH2-CH2-F||OCH3||2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine||Psychedelic and euphoriant|
|Amfepramone (diethylpropion)||C2H5, C2H5 [note 2]||CH3||=O||N-diethyl-β-ketoamphetamine||Anorectic|
|Short Name||RN||Rα||Rβ||R2||R3||R4||R5||Full Name||Biologic activity|
This section needs expansion. You can help by adding to it. (December 2015)
|UV spectrometry||Reagent needed|
In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.
PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved."
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.
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.
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.
2C (2C-x) is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting compounds. Most of the currently known 2C compounds were first synthesized by Alexander Shulgin in the 1970s and 1980s and published in his book PiHKAL. Shulgin also coined the term 2C, being an acronym for the 2 carbon atoms between the benzene ring and the amino group.
β-Methylphenethylamine is an organic compound of the phenethylamine class, and a positional isomer of the drug amphetamine, with which it shares some properties. In particular, both amphetamine and β-methylphenethylamine are human TAAR1 agonists. In appearance, it is a colorless or yellowish liquid.
Substituted methylenedioxy- phenethylamines (MDxx) are a large chemical class of derivatives of the phenethylamines, which includes many psychoactive drugs that act as entactogens, psychedelics, and/or stimulants, as well as entheogens. These agents are used as research chemicals, designer drugs and as recreational substances.
These drugs are known in the UK as controlled drugs, because this is the term by which the act itself refers to them. In more general terms, however, many of these drugs are also controlled by the Medicines Act 1968, there are many other drugs which are controlled by the Medicines Act but not by the Misuse of Drugs Act, and some other drugs are controlled by other laws.
Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).
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.
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.
Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.
6-(2-Aminopropyl)indole is an indole derivative which was first identified being sold on the designer drug market by a laboratory in the Czech Republic in July 2016.
βk-2C-B is a novel psychedelic substance. It is the beta (β) ketone structural analogue of 2C-B, a psychedelic drug of the 2C family. It is used as a recreational drug, usually taken orally. βk-2C-B is a controlled substance in Canada, Germany, Switzerland, and the United Kingdom.
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.
N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC50 values of 0.0978 and 0.0467 μM, respectively. N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV). Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug. In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.
To combat the illicit synthetic cannabinoid industry many jurisdictions have created a system to control these cannabinoids through their general structure as opposed to their specific identity. In this way new analogs are already controlled before they are even created. A large number of cannabinoids have been grouped into classes based on similarities in their chemical structure, and these classes have been widely adopted across a variety of jurisdictions.
The 25-NB (25x-NBx) series, sometimes alternatively referred to as the NBOMe compounds, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. They act as selective agonists of the serotonin 5-HT2A receptor. The 25-NB family is unique relative to other classes of psychedelics in that they are, generally speaking, extremely potent and relatively selective for the 5-HT2A receptor. Use of NBOMe series drugs has caused many deaths and hospitalisations since the drugs popularisation in the 2010s. This is primarily due to their high overdose potential and sellers passing off the compounds in the series as LSD.