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Substituted phenethylamine | |
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Chemical class | Substituted derivatives of phenethylamine |
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In Wikidata |
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. [1] [2] 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.
Chemical Structure | Short Name | RN | Rα | Rβ | R2 | R3 | R4 | R5 | Full Name | Biologic activity |
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meta-Tyramine | OH | 3-hydroxyphenethylamine | Trace amine | |||||||
para-Tyramine | OH | 4-hydroxyphenethylamine | Trace amine | |||||||
Dopamine | OH | OH | 3,4-dihydroxyphenethylamine | Catecholamine neurotransmitter | ||||||
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 | |||||
Norfenefrine | OH | OH | β,3-dihydroxyphenethylamine | Trace amine | ||||||
para-Octopamine | OH | OH | β,4-dihydroxyphenethylamine | Trace aminergic α-adrenoceptor agonist | ||||||
Oxidopamine | 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 | |||||
Isoprenaline | CH(CH3)2 | OH | OH | OH | β,3-dihydroxy-N-isopropylphenethylamine | β-adrenergic agonist; decongestant | ||||
Salbutamol | C(CH3)3 | OH | CH2OH | OH | β,4-dihydroxy-3-hydroxymethyl-N-tert-butylphenethylamine | Short-action β2-adrenergic agonist | ||||
β-Methylphenethylamine | CH3 | β-methylphenethylamine | Stimulant | |||||||
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 | ||||||
Methylphenidate | -CH2-CH2-CH2-CH2- | C(OCH3)=O | N,α-butylene-β-methoxycarbonylphenethylamine | NDRI; Stimulant | ||||||
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 | |||||
Amfepramone (diethylpropion) | C2H5, C2H5 [note 2] | CH3 | =O | N-diethyl-β-ketoamphetamine | Anorectic | |||||
Bupropion | C(CH3)3 | CH3 | =O | Cl | 5-chloro-N-tert-butyl-β-ketoamphetamine | NDRI | ||||
Norfenfluramine | CH3 | CF3 | 3-trifluoromethyl-amphetamine | SSRA | ||||||
Fenfluramine | CH2CH3 | CH3 | CF3 | 3-trifluoromethyl-N-ethylamphetamine | SSRA | |||||
5-APB | CH3 | -CH=CH-O- | 5-(2-aminopropyl)benzofuran | Stimulant, entactogen | ||||||
6-APB | CH3 | -O-CH=CH- | 6-(2-aminopropyl)benzofuran | Stimulant, entactogen | ||||||
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 | |||||
DOM | CH3 | OCH3 | CH3 | OCH3 | 2,5-dimethoxy-4-methylamphetamine | Psychedelic | ||||
DOB | CH3 | OCH3 | Br | OCH3 | 2,5-dimethoxy-4-bromo amphetamine | Psychedelic | ||||
DOC | CH3 | OCH3 | Cl | OCH3 | 2,5-dimethoxy-4-chloro amphetamine | Psychedelic | ||||
DOI | CH3 | OCH3 | I | OCH3 | 2,5-dimethoxy-4-iodo amphetamine | Psychedelic | ||||
DON | CH3 | OCH3 | NO2 | OCH3 | 2,5-dimethoxy-4-nitro amphetamine | Stimulant | ||||
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-C | OCH3 | Cl | OCH3 | 2,5-dimethoxy-4-chlorophenethylamine | Psychedelic | |||||
2C-F | OCH3 | F | OCH3 | 2,5-dimethoxy-4-fluoro phenethylamine | Psychedelic | |||||
2C-I | OCH3 | I | OCH3 | 2,5-dimethoxy-4-iodophenethylamine | Psychedelic, stimulant | |||||
2C-D | OCH3 | CH3 | OCH3 | 2,5-dimethoxy-4-methylphenethylamine | Psychedelic, stimulant | |||||
2C-E | OCH3 | CH2-CH3 | OCH3 | 2,5-dimethoxy-4-ethylphenethylamine | Psychedelic | |||||
2C-P | OCH3 | CH2-CH3-CH3 | OCH3 | 2,5-dimethoxy-4-propylphenethylamine | Entactogen, euphoriant and Psychedelic | |||||
2C-N | OCH3 | NO2 | OCH3 | 2,5-dimethoxy-4-nitrophenethylamine | euphoriant | |||||
2C-T-2 | OCH3 | S-CH2CH3 | OCH3 | 2,5-dimethoxy-4-ethylthio-phenethylamine | Psychedelic | |||||
2C-T-4 | OCH3 | S-CH(CH3)2 | OCH3 | 2,5-dimethoxy-4-isopropyl thio-phenethylamine | Psychedelic | |||||
2C-T-7 | OCH3 | S-CH2CH2CH3 | OCH3 | 2,5-dimethoxy-4-propylthio-phenethylamine | Psychedelic | |||||
2C-T-8 | OCH3 | S-CH2-C3H5 | OCH3 | 2,5-dimethoxy-4-cyclopropyl methylthio-phenethylamine | Psychedelic | |||||
2C-T-19 | OCH3 | S-C(CH3)3 | OCH3 | 2,5-dimethoxy-4-tert-butylthio-phenethylamine | Psychedelic | |||||
2C-T-21 | OCH3 | S-CH2-CH2-F | OCH3 | 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine | Psychedelic and euphoriant | |||||
25B-NBOMe [3] | CH2-C6H4-OCH3 | OCH3 | Br | OCH3 | 2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine | Psychedelic | ||||
25C-NBOMe | CH2-C6H4-OCH3 | OCH3 | Cl | OCH3 | 2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine | Psychedelic | ||||
25F-NBOMe | CH2-C6H4-OCH3 | OCH3 | F | OCH3 | 2-(4-fluoro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine | Psychedelic | ||||
25I-NBOMe | CH2-C6H4-OCH3 | OCH3 | I | OCH3 | 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine | Psychedelic | ||||
25D-NBOMe | CH2-C6H4-OCH3 | OCH3 | CH2 | OCH3 | 2-(4-methyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine | Psychedelic | ||||
25E-NBOMe | CH2-C6H4-OCH3 | OCH3 | CH2-CH3 | OCH3 | 2-(4-ethyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine | Psychedelic | ||||
25P-NBOMe | CH2-C6H4-OCH3 | OCH3 | CH2-CH3-CH3 | OCH3 | 2-(4-propyl-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine | Psychedelic | ||||
Mescaline-NBOMe | CH2-C6H4-OCH3 | OCH3 | OCH3 | OCH3 | N-(2-Methoxybenzyl)-2-(3,4,5-trimethoxyphenyl)ethanamine | Psychedelic | ||||
25B-NBOH | CH2–C6H4–OH | OCH3 | Br | OCH3 | N-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylamine | Psychedelic | ||||
25C-NBOH | CH2–C6H4–OH | OCH3 | Cl | OCH3 | N-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylamine | Psychedelic | ||||
25I-NBOH | CH2–C6H4–OH | OCH3 | I | OCH3 | N-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylamine | Psychedelic | ||||
25I-NBF | CH2–C6H4–F | OCH3 | I | OCH3 | N-(2-fluorobenzyl)-2,5-dimethoxy-4-iodo-phenethylamine | Psychedelic | ||||
Short Name | RN | Rα | Rβ | R2 | R3 | R4 | R5 | Full Name | Biologic activity |
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method | Requirement |
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UV spectrometry | Reagent needed |
Detection of substituted phenethylamines, which include compounds such as 2C-B, MDMA, and other designer drugs, involves various analytical methods aimed at identifying these psychoactive substances. These compounds are structurally similar to amphetamines, making their detection challenging due to potential cross-reactivity in standard drug tests. Techniques like gas chromatography-mass spectrometry (GC-MS), liquid chromatography-mass spectrometry (LC-MS), and immunoassay screenings are commonly employed for accurate identification. Advanced methods like high-performance liquid chromatography (HPLC) allow for precise separation and quantification of these substances even at low concentrations. Given the rising use of these drugs in recreational settings, developing sensitive and specific detection techniques remains crucial in forensic toxicology and clinical diagnostics.
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.
2C-T-2 is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamine compounds. The drug has structural and pharmacodynamic properties similar to those of 2C-T-7.
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.
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.
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.
4'-Methyl-α-pyrrolidinopropiophenone is a stimulant drug and substituted cathinone. It is structurally very similar to α-PPP, with only one added methyl group in the para position on the phenyl ring. 4-MePPP was sold in Germany as a designer drug in the late 1990s and early 2000s, along with a number of other pyrrolidinophenone derivatives. Although it has never achieved the same international popularity as its better-known relations α-PPP and MDPV, 4-MePPP is still sometimes found as an ingredient of grey-market "bath salt" blends such as "NRG-3".
4'-Methoxy-α-pyrrolidinopropiophenone (MOPPP) is a stimulant designer drug of the pyrrolidinophenone class. It has the potential to produce euphoria, an effect shared with other classical stimulants.
These drugs are known in the UK as controlled drug, 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.
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.
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, tranylcypromine, 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.
3-Fluoromethcathinone is a chemical compound of the phenethylamine, amphetamine, and cathinone classes that has been sold online as a designer drug. It is a structural isomer of flephedrone (4-fluoromethcathinone).
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.
βk-2C-B (βeta-keto-4-bromo-2,5-dimethoxyphenylamine), also known as bk-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.
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 potency, unpredictable pharmacokinetics, and sellers passing off the compounds in the series as LSD.