Substituted phenethylamine
This article needs additional citations for verification. (August 2014) (Learn how and when to remove this template message) |
Substituted phenethylamine | |
---|---|
Drug class | |
![]() The structural formula of phenethylamine with marked substitution points. Phenethylamine is obtained when
R2=R3=R4=R5=R6=RN=Rα=Rβ=H. |
|
Class identifiers | |
Chemical class | Substituted derivatives of phenethylamine |
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 an ethyl (−CH2–CH2−) 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., dl-2,5-dimethoxy-4-methylamphetamine a.k.a. DOM), entactogens (e.g., 3,4-methylenedioxyamphetamine a.k.a. 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, monoamine neurotransmitters, and many trace amines (e.g., dopamine, norepinephrine, 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.
List of substituted phenethylamines[edit]
Short Name | RN | Rα | Rβ | R2 | R3 | R4 | R5 | Full Name | Biologic activity |
---|---|---|---|---|---|---|---|---|---|
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-methylphenethylamine | Catecholamine neurotransmitter/Fight or Flight hormone | |||
Norepinephrine (Noradrenaline) | OH | OH | OH | β,3,4-trihydroxyphenethylamine | Catecholamine neurotransmitter/Fight or Flight hormone | ||||
meta-Octopamine | OH | OH | β,3-dihydroxyphenethylamine | Trace amine | |||||
para-Octopamine | OH | OH | β,4-dihydroxyphenethylamine | Trace aminergic α-adrenoceptor agonist | |||||
Phenylephrine | CH3 | OH | OH | β,3-dihydroxy-N-methylphenethylamine | α-adrenergic agonist; decongestant | ||||
6-Hydroxydopamine | OH | OH | OH | 2,4,5-trihydroxyphenethylamine | neurotoxic agent for the dopamine and norepinephrine receptors | ||||
Salbutamol | C(CH3)3 | OH | OH | CH2OH | 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 | ||||||
Methamphetamine | CH3 | CH3 | N-methylamphetamine; N,α-dimethylphenethylamine | Monoamine releasing agent; Stimulant; dopaminergic neurotoxin | |||||
Phentermine | 2CH3 | α-methylamphetamine; α,α-dimethylphenethylamine | Stimulant, anorectic | ||||||
Ortetamine | CH3 | CH3 | 2-methylamphetamine; 2,α-dimethylphenethylamine | Stimulant, anorectic | |||||
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 | Somewhat 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 pharmacodynamics actions | |||
Ethcathinone | CH2CH3 | CH3 | =O | N-ethylcathinone | Stimulant and Norepinephrine releasing agent | ||||
Bupropion | C(CH3)3 | CH3 | =O | Cl | 3-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 | |||
Mescaline | OCH3 | OCH3 | OCH3 | 3,4,5-trimethoxyphenethylamine | Serotonergic Psychedelic | ||||
Proscaline | OCH3 | OCH2CH2CH3 | OCH3 | 2-(3,5-dimethoxy-4-propoxyphenyl)ethanamine | Stimulant, entactogen and euphoriant | ||||
Metaescaline | OCH2CH3 | OCH3 | OCH3 | 2-(3-ethoxy-4,5-dimethoxyphenyl)ethanamine | Serotonergic Psychedelic, stimulant, entactogen and euphoriant | ||||
Allylescaline | OCH3 | OCH2CH1CH2 | OCH3 | 4-Allyloxy-3,5-dimethyloxyphenylethylamine | Stimulant, entactogen and euphoriant | ||||
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-bromoamphetamine | Psychedelic | |||
DOI | CH3 | OCH3 | I | OCH3 | 2,5-dimethoxy-4-iodoamphetamine | Psychedelic | |||
DON | CH3 | OCH3 | NO2 | OCH3 | 2,5-dimethoxy-4-nitroamphetamine | Stimulant | |||
DOC | CH3 | OCH3 | Cl | OCH3 | 2,5-dimethoxy-4-chloroamphetamine | Psychedelic | |||
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-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-F | OCH3 | F | OCH3 | 2,5-dimethoxy-4-fluorophenethylamine | None | ||||
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-isopropylthio-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-cyclopropylmethylthio-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 | 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 | |||
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 | |||
25F-NBOMe | CH2-C6H4-OCH3 | OCH3 | F | OCH3 | 2-(4-fluoro-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 | |||
25I-NBOH | CH2–C6H4–OH | OCH3 | I | OCH3 | N-(2-hydroxybenzyl)-2,5-dimethoxy-4-iodo-phenethylamine | Psychedelic | |||
25C-NBOH | CH2–C6H4–OH | OCH3 | Cl | OCH3 | N-(2-hydroxybenzyl)-2,5-dimethoxy-4-chloro-phenethylamine | Psychedelic | |||
25B-NBOH | CH2–C6H4–OH | OCH3 | Br | OCH3 | N-(2-hydroxybenzyl)-2,5-dimethoxy-4-bromo-phenethylamine | Psychedelic | |||
25I-NBF | CH2–C6H4–F | OCH3 | I | OCH3 | N-(2-fluorobenzyl)-2,5-dimethoxy-4-iodo-phenethylamine | Psychedelic | |||
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 |
Detection[edit]
![]() |
This section needs expansion. You can help by adding to it. (December 2015) |
method | Requirement |
---|---|
UV spectrometry | Reagent needed |
See also[edit]
- Substituted amphetamines
- Substituted methylenedioxyphenethylamines
- Substituted cathinones
- Substituted phenylmorpholines
- 2Cs and DOx
- Substituted tryptamines
Notes[edit]
- ^ In other words, all of the compounds that belong to this class are structural analogs of phenethylamine.
- ^ Two ethyl groups attached to the amine group