Substituted phenethylamine
Encyclopedia
The substituted phenethylamines are chemical compound
s with the 2-phenethylamine chemical structure
modified at the phenyl ring
, sidechain, and/or amino group. Some of them are psychoactive drug
s, including stimulant
s, psychedelic
s, opioid
s, and entactogens, which exert their effects primarily through modulation of the monoamine neurotransmitter
systems. Other substituted phenethylamines, such as dopamine
and epinephrine
are neurotransmitter
s. The substituted phenethylamines encompass the substituted amphetamine
s, the substituted methylenedioxyphenethylamines as well as a very large group of alkaloid
s derived from phenethylamines, including but by no means limited to tetrahydroisoquinoline
s, benzylisoquinoline
s, protoberberines, aporphine
s, morphinan
s, protopine
s and narcotine.p. 74
Substituted phenethylamines fall into a wide variety of therapeutic classes, including but not limited to psychotropic drugs (including hallucinogens such as dl-2,5-dimethoxy-4-methylamphetamine
a.k.a. DOM), central nervous system stimulants (e.g. amphetamine
), appetite depressants (e.g. phentermine
), antilipemic agents, vasoconstrictors (including nasal decongestants such as levomethamphetamine and pseudoephedrine
), bronchodilators, cardiotonic agents, vasodilators, calcium channel blockers, antidepressants (e.g. bupropion
, phenelzine
, and tranylcypromine
), neuroprotective agents and Antiparkinson agents.
Substituted phenethylamines are known to act as adrenergic
agents (including adrenergic uptake inhibitors such as methamphetamine
, adrenergic beta-agonists like methoxyphenamine
and the adrenergic alpha-agonist mephentermine
), antilipemic agents (e.g. benfluorex
), dopamine agents (including dopamine uptake inhibitors such as bupropion
), serotonin agents (including serotonin agonists such as 2,5-dimethoxy-4-bromoamphetamine
and the serotonin uptake inhibitor fenfluramine
), calcium channel blockers (e.g. prenylamine
and verapamil
) and monoamine oxidase inhibitors (e.g. selegiline
).
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
s with the 2-phenethylamine chemical structure
Chemical structure
A chemical structure includes molecular geometry, electronic structure and crystal structure of molecules. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. Molecular geometry can range from the very simple, such as...
modified at the phenyl ring
Phenyl group
In organic chemistry, the phenyl group or phenyl ring is a cyclic group of atoms with the formula C6H5. Phenyl groups are closely related to benzene. Phenyl groups have six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the...
, sidechain, and/or amino group. Some of them are psychoactive drug
Psychoactive drug
A psychoactive drug, psychopharmaceutical, or psychotropic is a chemical substance that crosses the blood–brain barrier and acts primarily upon the central nervous system where it affects brain function, resulting in changes in perception, mood, consciousness, cognition, and behavior...
s, including stimulant
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
s, psychedelic
Psychedelic
The term psychedelic is derived from the Greek words ψυχή and δηλοῦν , translating to "soul-manifesting". A psychedelic experience is characterized by the striking perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly...
s, opioid
Opioid
An opioid is a psychoactive chemical that works by binding to opioid receptors, which are found principally in the central and peripheral nervous system and the gastrointestinal tract...
s, and entactogens, which exert their effects primarily through modulation of the monoamine neurotransmitter
Neurotransmitter
Neurotransmitters are endogenous chemicals that transmit signals from a neuron to a target cell across a synapse. Neurotransmitters are packaged into synaptic vesicles clustered beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to...
systems. Other substituted phenethylamines, such as dopamine
Dopamine
Dopamine is a catecholamine neurotransmitter present in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this substituted phenethylamine functions as a neurotransmitter, activating the five known types of dopamine receptors—D1, D2, D3, D4, and D5—and their...
and epinephrine
Epinephrine
Epinephrine is a hormone and a neurotransmitter. It increases heart rate, constricts blood vessels, dilates air passages and participates in the fight-or-flight response of the sympathetic nervous system. In chemical terms, adrenaline is one of a group of monoamines called the catecholamines...
are neurotransmitter
Neurotransmitter
Neurotransmitters are endogenous chemicals that transmit signals from a neuron to a target cell across a synapse. Neurotransmitters are packaged into synaptic vesicles clustered beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to...
s. The substituted phenethylamines encompass the substituted amphetamine
Substituted amphetamine
Substituted amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions...
s, the substituted methylenedioxyphenethylamines as well as a very large group of alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
s derived from phenethylamines, including but by no means limited to tetrahydroisoquinoline
Tetrahydroisoquinoline
Tetrahydroisoquinoline is a secondary amine with the chemical formula C9H11N.-Reactions:Like other secondary amines, tetrahydroisoquinoline can be oxidized to the corresponding nitrone using hydrogen peroxide, catalyzed by selenium dioxide....
s, benzylisoquinoline
Benzylisoquinoline
1-Benzylisoquinoline is a chemical compound, and the structural backbone of many alkaloids with a wide variety of structures, including papaverine, noscapine, codeine, morphine, apomorphine, berberine, protopine and tubocurarine.-Biosynthesis:...
s, protoberberines, aporphine
Aporphine
Aporphine is one of a class of quinoline alkaloids. Many different relatives of this compound have been purified from plants.One commonly-used aporphine derivative is apomorphine....
s, morphinan
Morphinan
Morphinan is the base chemical structure of a large chemical class of psychoactive drugs, consisting of opioid analgesics, cough suppressants, and dissociative hallucinogens, among others.- Chemical Derivatives :Immediate derivatives of morphinan include:...
s, protopine
Protopine
Protopine is a benzylisoquinoline alkaloid occurring in opium poppy, corydalis tubers and other plants of the family papaveraceae. It has been found to inhibit histamine H1 receptors and platelet aggregation, and acts as an opioid analgesic....
s and narcotine.p. 74
Substituted phenethylamines fall into a wide variety of therapeutic classes, including but not limited to psychotropic drugs (including hallucinogens such as dl-2,5-dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine...
a.k.a. DOM), central nervous system stimulants (e.g. amphetamine
Amphetamine
Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,...
), appetite depressants (e.g. phentermine
Phentermine
Phentermine, a contraction of "phenyl-tertiary-butylamine", is a psychostimulant drug of the phenethylamine class, chemically related to amphetamine. It is used medically as an appetite suppressant....
), antilipemic agents, vasoconstrictors (including nasal decongestants such as levomethamphetamine and pseudoephedrine
Pseudoephedrine
Pseudoephedrine is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It is used as a nasal/sinus decongestant and stimulant, or as a wakefulness-promoting agent....
), bronchodilators, cardiotonic agents, vasodilators, calcium channel blockers, antidepressants (e.g. bupropion
Bupropion
Bupropion is an atypical antidepressant and smoking cessation aid. The drug is a non-tricyclic antidepressant and differs from most commonly prescribed antidepressants such as SSRIs, as its primary pharmacological action is thought to be norepinephrine-dopamine reuptake inhibition...
, phenelzine
Phenelzine
Phenelzine is a non-selective and irreversible monoamine oxidase inhibitor of the hydrazine class which is used as an antidepressant and anxiolytic...
, and tranylcypromine
Tranylcypromine
Tranylcypromine is a drug of the substituted phenethylamine and amphetamine classes which acts as a monoamine oxidase inhibitor —it is a non-selective and irreversible inhibitor of the enzyme monoamine oxidase...
), neuroprotective agents and Antiparkinson agents.
Substituted phenethylamines are known to act as adrenergic
Adrenergic
An adrenergic agent is a drug, or other substance, which has effects similar to, or the same as, epinephrine . Thus, it is a kind of sympathomimetic agent...
agents (including adrenergic uptake inhibitors such as methamphetamine
Methamphetamine
Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs...
, adrenergic beta-agonists like methoxyphenamine
Methoxyphenamine
Methoxyphenamine , also known as 2-methoxy-N-methylamphetamine , is a β-adrenergic receptor agonist of the amphetamine class used as a bronchodilator....
and the adrenergic alpha-agonist mephentermine
Mephentermine
Mephentermine is a cardiac stimulant. It was formerly used in Wyamine nasal decongestant inhalers and before that as a stimulant in psychiatry.It has been used as a treatment for hypotension.-References:...
), antilipemic agents (e.g. benfluorex
Benfluorex
Benfluorex is an anorectic and hypolipidemic agent that is structurally related to fenfluramine. Two clinical studies have shown it may improve glycemic control and decrease insulin resistance in people with poorly controlled type 2 diabetes; However Servier is suspected of having marketed Mediator...
), dopamine agents (including dopamine uptake inhibitors such as bupropion
Bupropion
Bupropion is an atypical antidepressant and smoking cessation aid. The drug is a non-tricyclic antidepressant and differs from most commonly prescribed antidepressants such as SSRIs, as its primary pharmacological action is thought to be norepinephrine-dopamine reuptake inhibition...
), serotonin agents (including serotonin agonists such as 2,5-dimethoxy-4-bromoamphetamine
2,5-Dimethoxy-4-bromoamphetamine
DOB, also known as Brolamfetamine and Bromo-DMA, is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. DOB was first synthesized by Alexander Shulgin in 1967...
and the serotonin uptake inhibitor fenfluramine
Fenfluramine
Fenfluramine is a drug that was part of the Fen-Phen anti-obesity medication . Fenfluramine was introduced on the U.S. market in 1973. It is the racemic mixture of two enantiomers, dextrofenfluramine and levofenfluramine...
), calcium channel blockers (e.g. prenylamine
Prenylamine
Prenylamine is a calcium channel blocker of the amphetamine chemical class which is used as a vasodilator in the treatment of angina pectoris. It has been shown to partially metabolize to amphetamine and can cause false positives for it in drug tests...
and verapamil
Verapamil
Verapamil is an L-type calcium channel blocker of the phenylalkylamine class. It has been used in the treatment of hypertension, angina pectoris, cardiac arrhythmia, and most recently, cluster headaches. It is also an effective preventive medication for migraine...
) and monoamine oxidase inhibitors (e.g. selegiline
Selegiline
Selegiline is a drug used for the treatment of early-stage Parkinson's disease, depression and senile dementia. In normal clinical doses it is a selective irreversible MAO-B inhibitor, however in larger doses it loses its specificity and also inhibits MAO-A...
).
List of substituted phenethylamines
| Short Name | RN | Rα | Rβ | R2 | R3 | R4 | R5 | Full Name |
|---|---|---|---|---|---|---|---|---|
| meta-Tyramine Tyramine Tyramine is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine. Tyramine acts as a catecholamine releasing agent... |
OH Hydroxyl A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in... |
3-hydroxyphenethylamine | ||||||
| para-Tyramine Tyramine Tyramine is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine. Tyramine acts as a catecholamine releasing agent... |
OH | 4-hydroxyphenethylamine | ||||||
| Dopamine Dopamine Dopamine is a catecholamine neurotransmitter present in a wide variety of animals, including both vertebrates and invertebrates. In the brain, this substituted phenethylamine functions as a neurotransmitter, activating the five known types of dopamine receptors—D1, D2, D3, D4, and D5—and their... |
OH | OH | 3,4-dihydroxyphenethylamine | |||||
| Epinephrine Epinephrine Epinephrine is a hormone and a neurotransmitter. It increases heart rate, constricts blood vessels, dilates air passages and participates in the fight-or-flight response of the sympathetic nervous system. In chemical terms, adrenaline is one of a group of monoamines called the catecholamines... (Adrenaline) |
CH3 Methyl group Methyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion... |
OH | OH | OH | β,3,4-trihydroxy-N-methyl Methyl group Methyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion... |
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| Norepinephrine Norepinephrine Norepinephrine is the US name for noradrenaline , a catecholamine with multiple roles including as a hormone and a neurotransmitter... (Noradrenaline) |
OH | OH | OH | β,3,4-trihydroxyphenethylamine | ||||
| meta-Octopamine Octopamine Octopamine is an endogenous biogenic amine that is closely related to norepinephrine, and has effects on the adrenergic and dopaminergic systems. It is also found naturally in numerous plants, including bitter orange. Biosynthesis of the D--enantiomer of octopamine is by β-hydroxylation of... |
OH | OH | β,3-dihydroxyphenethylamine | |||||
| para-Octopamine Octopamine Octopamine is an endogenous biogenic amine that is closely related to norepinephrine, and has effects on the adrenergic and dopaminergic systems. It is also found naturally in numerous plants, including bitter orange. Biosynthesis of the D--enantiomer of octopamine is by β-hydroxylation of... |
OH | OH | β,4-dihydroxyphenethylamine | |||||
| Phenylephrine Phenylephrine Phenylephrine is a selective α1-adrenergic receptor agonist used primarily as a decongestant, as an agent to dilate the pupil, and to increase blood pressure... |
CH3 | OH | OH | β,3-dihydroxy-N-methylphenethylamine | ||||
| 6-Hydroxydopamine | OH | OH | OH | 2,4,5-trihydroxyphenethylamine | ||||
| Salbutamol Salbutamol Salbutamol or albuterol is a short-acting β2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and chronic obstructive pulmonary disease. It is marketed as Ventolin among other brand names.... |
C(CH3)3 | OH | OH | CH2OH | β,4-dihydroxy-3-hydroxymethyl-N-tert-butylphenethylamine | |||
| β-Methylphenethylamine | CH3 | β-methylphenethylamine | ||||||
| Amphetamine Amphetamine Amphetamine or amfetamine is a psychostimulant drug of the phenethylamine class which produces increased wakefulness and focus in association with decreased fatigue and appetite.Brand names of medications that contain, or metabolize into, amphetamine include Adderall, Dexedrine, Dextrostat,... |
CH3 | α-methylphenethylamine | ||||||
| Methamphetamine Methamphetamine Methamphetamine is a psychostimulant of the phenethylamine and amphetamine class of psychoactive drugs... |
CH3 | CH3 | N-methylamphetamine | |||||
| Methylphenidate Methylphenidate Methylphenidate is a psychostimulant drug approved for treatment of attention-deficit hyperactivity disorder, postural orthostatic tachycardia syndrome and narcolepsy. It may also be prescribed for off-label use in treatment-resistant cases of lethargy, depression, neural insult and obesity... |
-CH2-CH2-CH2-CH2- | C(OCH3)=O | N,α-butylene-β-methoxycarbonylphenethylamine | |||||
| Ephedrine Ephedrine Ephedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia.... / Pseudoephedrine Pseudoephedrine Pseudoephedrine is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It is used as a nasal/sinus decongestant and stimulant, or as a wakefulness-promoting agent.... |
CH3 | CH3 | OH | N-methyl-β-hydroxyamphetamine | ||||
| Cathine Cathine Cathine, also known as d-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine chemical classes which acts as a stimulant... |
CH3 | OH | β-hydroxy-amphetamine | |||||
| Cathinone Cathinone Cathinone, or Benzoylethanamine, is a monoamine alkaloid found in the shrub Catha edulis and is chemically similar to ephedrine, cathine and other amphetamines. Cathinone induces the release of dopamine from striatal preparations that are prelabelled either with dopamine or its precursors. It is... |
CH3 | =O | β-keto-amphetamine | |||||
| Methcathinone Methcathinone Methcathinone , is a psychoactive stimulant, sometimes used as a recreational drug and considered addictive. It is usually snorted, but can be smoked, injected, or taken orally... |
CH3 | CH3 | =O | N-methylcathinone | ||||
| Mephedrone | CH3 | CH3 | =O | CH3 | 4-methylmethcathinone | |||
| Ethcathinone Ethcathinone Ethcathinone, also known as ethylpropion, is a stimulant drug of the phenethylamine, amphetamine, and cathinone chemical classes. It is an active metabolite of the prodrug diethylcathinone and is fully responsible for its effects... |
CH2CH3 | CH3 | =O | N-ethylcathinone | ||||
| Bupropion Bupropion Bupropion is an atypical antidepressant and smoking cessation aid. The drug is a non-tricyclic antidepressant and differs from most commonly prescribed antidepressants such as SSRIs, as its primary pharmacological action is thought to be norepinephrine-dopamine reuptake inhibition... |
C(CH3)3 | CH3 | =O | Cl Chlorine Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine... |
3-chloro-N-tert-butyl-β-ketoamphetamine | |||
| Norfenfluramine Norfenfluramine Norfenfluramine is a psychoactive drug which functions as a serotonin releasing agent and potent 5HT2B receptor agonist. The action of norfenfluramine on 5HT2B receptors on heart valves leads to a characteristic pattern of heart failure following proliferation of cardiac fibroblasts on the... |
CH3 | CF3 Trifluoromethyl Trifluoromethyl is a functional group in organofluorines that has the formula -CF3. The naming of is group is derived from the methyl group , by replacing each hydrogen atom by a fluorine atom. The trifluomethyl group has a significant electronegativity that is often described as being... |
3-trifluoromethyl Trifluoromethyl Trifluoromethyl is a functional group in organofluorines that has the formula -CF3. The naming of is group is derived from the methyl group , by replacing each hydrogen atom by a fluorine atom. The trifluomethyl group has a significant electronegativity that is often described as being... -amphetamine |
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| Fenfluramine Fenfluramine Fenfluramine is a drug that was part of the Fen-Phen anti-obesity medication . Fenfluramine was introduced on the U.S. market in 1973. It is the racemic mixture of two enantiomers, dextrofenfluramine and levofenfluramine... |
CH2CH3 | CH3 | CF3 | 3-trifluoromethyl-N-ethyl Ethyl group In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5.... -amphetamine |
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| Phentermine Phentermine Phentermine, a contraction of "phenyl-tertiary-butylamine", is a psychostimulant drug of the phenethylamine class, chemically related to amphetamine. It is used medically as an appetite suppressant.... |
2CH3 | α,α-dimethylphenethylamine | ||||||
| Mescaline Mescaline Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally occurring psychedelic alkaloid of the phenethylamine class used mainly as an entheogen.... |
OCH3 Methoxy In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether... |
OCH3 | OCH3 | 3,4,5-trimethoxy Methoxy In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether... |
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| MDA 3,4-Methylenedioxyamphetamine 3,4-Methylenedioxyamphetamine , also known as tenamfetamine , is a psychedelic and entactogenic drug of the phenethylamine and amphetamine chemical classes... |
CH3 | -O-CH2-O- | 3,4-methylenedioxy Methylenedioxy Methylenedioxy in the field of chemistry, particularly in organic chemistry, is the name for a functional group with the structural formula R-O-CH2-O-R' which is connected to the rest of a molecule by two chemical bonds. The methylenedioxy group consists of two oxygen atoms connected to a methylene... |
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| MDEA Methylenedioxyethylamphetamine 3,4-Methylenedioxy-N-ethylamphetamine is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes.... |
CH2CH3 | CH3 | -O-CH2-O- | 3,4-methylenedioxy-N-ethylamphetamine | ||||
| MDMA | CH3 | CH3 | -O-CH2-O- | 3,4-methylenedioxy-N-methylamphetamine | ||||
| MDMC | CH3 | CH3 | =O | -O-CH2-O- | 3,4-methylenedioxymethcathinone | |||
| DOM 2,5-Dimethoxy-4-methylamphetamine 2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine... |
CH3 | OCH3 | CH3 | OCH3 | 2,5-dimethoxy-4-methylamphetamine | |||
| DOB 2,5-Dimethoxy-4-bromoamphetamine DOB, also known as Brolamfetamine and Bromo-DMA, is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. DOB was first synthesized by Alexander Shulgin in 1967... |
CH3 | OCH3 | Br Bromine Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826... |
OCH3 | 2,5-dimethoxy-4-bromo |
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| DOI 2,5-Dimethoxy-4-iodoamphetamine 2,5-dimethoxy-4-iodoamphetamine is a psychedelic drug and a substituted amphetamine of the phenethylamine family. It is also a powerful anti-inflammatory that is effective at doses on the order of 100 micrograms in humans, far below its effective dose as a psychedelic. Despite being a substituted... |
CH3 | OCH3 | I Iodine Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor.... |
OCH3 | 2,5-dimethoxy-4-iodo Iodo Iodo may refer to;*Socotra Rock*Iodo , South Korean film directed by Kim Ki-young*Iodine, chemical element... |
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| DON 2,5-Dimethoxy-4-nitroamphetamine 2,5-Dimethoxy-4-nitroamphetamine is an analogue of DOM and DOB. It is also closely related to 2C-N, and produces hallucinogenic, psychedelic, and entheogenic effects.-Chemistry:... |
CH3 | OCH3 | NO2 Nitro compound Nitro compounds are organic compounds that contain one or more nitro functional groups . They are often highly explosive, especially when the compound contains more than one nitro group and is impure. The nitro group is one of the most common explosophores used globally... |
OCH3 | 2,5-dimethoxy-4-nitro Nitro compound Nitro compounds are organic compounds that contain one or more nitro functional groups . They are often highly explosive, especially when the compound contains more than one nitro group and is impure. The nitro group is one of the most common explosophores used globally... |
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| DOC | CH3 | OCH3 | Cl Chlorine Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine... |
OCH3 | 2,5-dimethoxy-4-chloro |
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| 2C-B 2C-B 2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book PiHKAL, the dosage range is listed as 16–24 mg. 2C-B is sold as a white powder sometimes pressed in tablets or gel caps and is referred... |
OCH3 | Br | OCH3 | 2,5-dimethoxy-4-bromophenethylamine | ||||
| 2C-C 2C-C 2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. The full name of the chemical is 2,5-dimethoxy-4-chlorophenethylamine. In his book PiHKAL , Shulgin lists the dosage range as 20–40 mg. 2C-C is usually taken orally,... |
OCH3 | Cl | OCH3 | 2,5-dimethoxy-4-chlorophenethylamine | ||||
| 2C-I 2C-I 2C-I or 2,5-dimethoxy-4-iodophenethylamine is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. It was described in Shulgin’s book PiHKAL: A Chemical Love Story. The drug is used recreationally for its psychedelic and entactogenic effects... |
OCH3 | I | OCH3 | 2,5-dimethoxy-4-iodophenethylamine | ||||
| 2C-D 2C-D 2C-D is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity was subsequently investigated in humans by Alexander Shulgin. The full name of the chemical is... |
OCH3 | CH3 | OCH3 | 2,5-dimethoxy-4-methylphenethylamine | ||||
| 2C-E 2C-E 2C-E is a psychedelic and phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. 2C-E is typically found as a white crystalline powder.... |
OCH3 | CH2-CH3 | OCH3 | 2,5-dimethoxy-4-ethylphenethylamine | ||||
| 2C-P 2C-P 2C-P is a psychedelic phenethylamine and 2C compound first synthesized by Alexander Shulgin.-Chemistry:2C-P is 2,5-dimethoxy-4--propylphenethylamine. The full name of the chemical is 2-ethanamine.-Dosage:... |
OCH3 | CH2-CH3-CH3 | OCH3 | 2,5-dimethoxy-4-propylphenethylamine | ||||
| 2C-F 2C-F 2C-F, or 4-fluoro-2,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 250 mg... |
OCH3 | F Fluorine Fluorine is the chemical element with atomic number 9, represented by the symbol F. It is the lightest element of the halogen column of the periodic table and has a single stable isotope, fluorine-19. At standard pressure and temperature, fluorine is a pale yellow gas composed of diatomic... |
OCH3 | 2,5-dimethoxy-4-fluoro |
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| 2C-N 2C-N 2C-N, or 2,5-Dimethoxy-4-nitrophenethylamine, is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin.-Chemistry:The full name of the chemical is 2-ethanamine.... |
OCH3 | NO2 | OCH3 | 2,5-dimethoxy-4-nitrophenethylamine | ||||
| 2C-T-2 2C-T-2 2C-T-2, or 2,5-dimethoxy-4-ethylthiophenethylamine is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin. The drug has structural and pharmacodynamic properties similar to the drug 2C-T-7 .-Dosage:In Alexander Shulgin's book... |
OCH3 | S Thio The prefix thio-, when applied to a chemical, such as an ion, means that an oxygen atom in the compound has been replaced by a sulfur atom. This meaning is especially valid in organic chemistry. For example, the word ether refers to an oxygen-containing compound having the general chemical... -CH2CH3 |
OCH3 | 2,5-dimethoxy-4-ethylthio Thio The prefix thio-, when applied to a chemical, such as an ion, means that an oxygen atom in the compound has been replaced by a sulfur atom. This meaning is especially valid in organic chemistry. For example, the word ether refers to an oxygen-containing compound having the general chemical... -phenethylamine |
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| 2C-T-4 2C-T-4 2C-T-4 or 2,5-dimethoxy-4-isopropylthiophenethylamine is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.-Chemistry:... |
OCH3 | S-CH(CH3)2 Isopropyl In organic chemistry, isopropyl is a propyl with a group attached to the secondary carbon. If viewed as a functional group an isopropyl is an organic compound with a propyl group attached at its secondary carbon.The bond is therefore on the middle carbon.... |
OCH3 | 2,5-dimethoxy-4-isopropyl Isopropyl In organic chemistry, isopropyl is a propyl with a group attached to the secondary carbon. If viewed as a functional group an isopropyl is an organic compound with a propyl group attached at its secondary carbon.The bond is therefore on the middle carbon.... |
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| 2C-T-7 2C-T-7 2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book PiHKAL: A Chemical Love Story, Alexander Shulgin lists the dosage range as 10 to 30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic effects that last 8 to 15 hours... |
OCH3 | S-CH2CH2CH3 | OCH3 | 2,5-dimethoxy-4-propylthio-phenethylamine | ||||
| 2C-T-8 2C-T-8 2C-T-8 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.-Chemistry:The full name of the chemical is 2,5-dimethoxy-4-cyclopropylmethylthiophenethylamine... |
OCH3 | S-CH2-C3H5 | OCH3 | 2,5-dimethoxy-4-cyclopropyl |
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| 2C-T-9 2C-T-9 2C-T-9 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.-Chemistry:2C-T-9 is 2,5-dimethoxy-4--butylthiophenethylamine.... |
OCH3 | S-C(CH3)3 | OCH3 | 2,5-dimethoxy-4-tert-butylthio-phenethylamine | ||||
| 2C-T-21 2C-T-21 2C-T-21 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. It was the first psychedelic drug known to contain six different chemical elements in the structure.-Chemistry:... |
OCH3 | S-CH2-CH2-F | OCH3 | 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine | ||||
| Short Name | RN | Rα | Rβ | R2 | R3 | R4 | R5 | Full Name |