Phenethylamine

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Phenethylamine

Phenethylamine, or ß-phenylethylamine or 2-phenylethylamine, is an alkaloid

Alkaloid

Alkaloids are naturally occurring chemical compounds containing base nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base....
and monoamine. Phenethylamine also has a constitutional isomer a-phenylethylamine (1-phenylethylamine

1-Phenylethylamine

1-Phenylethylamine, or alpha-phenethylamine, is an amine. Individual enantiomers of this base compound are useful for performing chiral resolution of acidic compounds by forming diastereomeric salts....
), which has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine. In the human brain, 2-phenethylamine is believed to function as a neuromodulator or neurotransmitter

Neurotransmitter

Neurotransmitters are chemistry which relay, amplify and modulate signals between a neuron and another cell . Neurotransmitters are packaged into vesicles that cluster beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to receptors in the membrane on the postsynaptic side of...
(trace amine

Trace amine

Trace amines are endogenous compounds structurally related to classical biogenic amines, such as catecholamines, serotonin and histamine. Trace amines include p-tyramine, ?-phenylethylamine, tryptamine, octopamine, and 3-iodothyronamine, and are found in the nervous systems of animals from insects to mammals....
). Phenethylamine is a natural compound biosynthesized from the amino acid

Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
phenylalanine

Phenylalanine

Phenylalanine is an a-amino acid with the chemical formula HO2CCHCH2C6H5, which is found naturally in the breast milk of mammals and manufactured for food and drink products and are also sold as nutritional supplements for their reputed analgesic and antidepressant effects....
by enzymatic decarboxylation

Decarboxylation

Decarboxylation is any chemical reaction in which a carboxyl group is split off from a compound as carbon dioxide ....
.

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Encyclopedia

Phenethylamine, or ß-phenylethylamine or 2-phenylethylamine, is an alkaloid

Alkaloid

1-Phenylethylamine

Neurotransmitter

Trace amine

Amino acid

Phenylalanine

Decarboxylation

Decarboxylation is any chemical reaction in which a carboxyl group is split off from a compound as carbon dioxide ....
. It is also found in many foods such as chocolate

Chocolate

Microorganism

A microorganism or microbe is an organism that is microscopic . The study of microorganisms is called microbiology, a subject that began with Anton van Leeuwenhoek's discovery of microorganisms in 1675, using a microscope of his own design....
fermentation

Fermentation (food)

Fermentation in food processing typically refers to the conversion of sugar to alcohol using yeast under anaerobic conditions. A more general definition of fermentation is the chemical conversion of carbohydrates into alcohols or acids....
. However trace amounts from food are quickly metabolized by the enzyme

Enzyme

Enzymes are biomolecules that catalysis chemical reactions. Almost all enzymes are proteins. In enzymatic reactions, the molecules at the beginning of the process are called Substrate , and the enzyme converts them into different molecules, the products....
MAO-B, preventing significant concentrations from reaching the brain.

Phenylethylamine is a precursor to the neurotransmitter phenylethanolamine.

D-Phenylalanine increases the brain content of phenylethylamine. Phenylethylamine has been shown at least indirectly to satisfy the four main criteria required to demonstrate that a neuroamine sustains mood and that its deficit can be responsible for depression. Antidepressant drug therapy is an indirect (pharmacological) "replacement" of brain phenylethylamine.

Substituted phenethylamines are a broad and diverse class of compounds that include stimulant

Stimulant

Stimulant drugs are drugs that temporarily increase alertness and awareness. They usually have increased side-effects with increased effectiveness, and the more powerful variants are therefore often prescription medicines or illegal drugs....
s, hallucinogens

Psychedelics, dissociatives and deliriants

The general group of pharmacology agents commonly known as hallucinogens can be divided into three broad categories: Psychedelic drugs, dissociatives, and deliriants....
, entactogen

Empathogen-entactogen

The terms empathogen and entactogen are different terms used to describe a class of psychoactive drugs that produce distinctive emotional and social effects similar to those of methylenedioxymethamphetamine ....
s, anorectic

Anorectic

Anorexics, anorexigenics or appetite suppressants are substances that reduce the appetite and cause a person to eat less....
s, bronchodilator

Bronchodilator

A bronchodilator is a substance that Wiktionary:dilate#Verb the Bronchus and bronchioles, decreasing airway resistance and thereby facilitating airflow....
s, and antidepressant

Antidepressant

An antidepressant is a psychiatric medication used for alleviating major depressive disorder or dysthymia. Drug groups known as MAOIs, tricyclics, and second-generation antidepressants such as SSRIs, and serotonin-norepinephrine reuptake inhibitors are particularly associated with the term....
s.

Chemistry

Phenethylamine is an aromatic amine, which is a colorless liquid at room temperature. It is soluble in water, ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
, and ether

Diethyl ether

Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic odor....
. Similar to other low-molecular-weight amines, it has a fishy odor. Upon exposure to air, it forms a solid carbonate

Carbonate

In chemistry, a carbonate is a salt or ester of carbonic acid....
salt

Salt

A salt, in chemistry, is defined as the product formed from the neutralisation reaction of acids and base . Salts are ionic compounds composed of cations and anions so that the product is electrically electric charge ....
with carbon dioxide

Carbon dioxide

Carbon dioxide is a chemical compound composed of two oxygen atoms covalent bond to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state....
. Phenethylamine is strongly basic

Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
and forms a stable crystalline hydrochloride

Hydrochloride

In chemistry, hydrochlorides are salt s resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic Base . This is also known as muriate, derived from hydrochloric acid's other name: muriatic acid....
salt with a melting point of 217 °C. Phenethylamine is also a skin irritant and possible sensitizer.

Neurochemistry

Infusion of phenylethylamine increased extracellular levels of dopamine while at the same time inhibiting DA neuron firings. It also modulates noradrenergic transmission. Phenethylamine, along with tyramine

Tyramine

In organic chemistry chemistry tyramine is a monoamine Chemical compound derived from the amino acid tyrosine. Tyramine can cause the release of stored monoamines, such as dopamine, norepinephrine, and epinephrine....
, reversibly depresses the slow GABA_B receptor inhibitory post-synaptic potential in midbrain dopaminergic cells.

Low levels are found in those suffering from attention deficit disorder and often in depression, while levels are elevated in schizophrenia. This is associated with low dopamine in ADHD and depression and high dopamine in schizophrenia.

Chocolate theory of love

In the early 1980s, researcher Michael Liebowitz

Michael Liebowitz

Dr. Michael R. Liebowitz is a Columbia University psychiatrist and wiktionary:Founder of the Anxiety Disorders Clinic, the first of its kind, at the New York State Psychiatric Institute....
, author of the popular 1983 book The Chemistry of Love, remarked to reporters that "chocolate

Chocolate

Chocolate comprises a number of raw and processed foods that are produced from the seed of the tropical cacao tree.Chocolate has become one of the most popular flavors in the world....
is loaded with PEA." This became the focus for an article in The New York Times, which was then taken up by the wire services, then by magazine free-lancers, and evolved into the now-eponymous "chocolate theory of love." However, as noted earlier, phenethylamine is rapidly metabolized by the enzyme

Enzyme

Substituted phenethylamines

Substituted phenethylamines carry additional chemical modifications at the phenyl ring, the sidechain, or the amino group:

Substituted Amphetamines
Substituted amphetamines

The substituted amphetamines are a family of amphetamine-based stimulants, hallucinogens, and other recreational drugs. They each have a methyl group on the alpha carbon, often have Methoxy on the 2 and 5 carbons, and have variant groups on the 3, 4, and 5 carbons....
are homologue
Homologous series

In chemistry, a homologous series is a series of organic compounds with a similar general formula, possessing similar chemical properties due to the presence of the same functional group, and shows a gradation in physical properties as a result of increase in molecular size and mass ....
s of phenethylamines carrying an alpha-methyl (a-CH₃) group at the sidechain carbon
Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
atom next to the amino group.
Catecholamine
Catecholamine

Catecholamines are chemical compounds derived from the amino acid tyrosine. Their name is derived from the fact that they contain catechol and amine moieties....
s are phenethylamines carrying two hydroxy
Hydroxyl

Hydroxyl in chemistry stands for a molecule consisting of an oxygen atom and a hydrogen atom connected by a covalent bond. The neutral form is a hydroxyl Radical and the hydroxyl anion is called a hydroxide....
groups in positions 3 and 4 of the phenyl ring. Examples are the hormones and neurotransmitters dopamine
Dopamine

Dopamine is a neurotransmitter occurring in a wide variety of animals, including both vertebrates and invertebrates. In the human brain, this phenethylamine functions as a neurotransmitter, activating the five types of dopamine receptors ? D1, D2, D3, D4 and D5, and their variants....
, epinephrine
Epinephrine

Epinephrine is a hormone and neurotransmitter.Epinephrine increases the "fight or flight" response of the Sympathetic nervous system of the autonomic nervous system....
(adrenaline), and norepinephrine
Norepinephrine

Norepinephrine or noradrenaline is a catecholamine with dual roles as a hormone and a neurotransmitter.As a stress hormone, norepinephrine affects parts of the brain where attention and responding actions are controlled....
(noradrenaline).
The aromatic amino acids phenylalanine
Phenylalanine

Phenylalanine is an a-amino acid with the chemical formula HO2CCHCH2C6H5, which is found naturally in the breast milk of mammals and manufactured for food and drink products and are also sold as nutritional supplements for their reputed analgesic and antidepressant effects....
and tyrosine
Tyrosine

Tyrosine or 4-hydroxyphenylalanine, is one of the 20 amino acids that are used by cell to protein biosynthesis proteins. This is a non-essential amino acid and it is found in casein....
are phenethylamines carrying a carboxyl group (COOH) in alpha position.
2Cs are phenethylamines with methoxy groups
Methoxy

In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. It has the formula:The word is used in organic nomenclature usually to describe an ether....
attached to the 2 and 5 carbons and no alpha-methyl group.

Pharmacology

Phenylethylamine's half life is 5-10 minutes. Phenylethylamine is metabolized by MAO-A , MAO-B , aldehyde dehydrogenase

Aldehyde dehydrogenase

Aldehyde dehydrogenases, E.C. 1.2.1.3, are a group of enzymes that catalyse the oxidation of aldehydes.Mitochondrial Aldehyde Dehydrogenase is a polymorphic enzyme #Crabb2004 responsible for the oxidation of aldehydes to carboxylic acids, which leave the liver and are metabolized by the body?s muscle and heart #Crabb2004....
and dopamine-beta-hydroxylase. Phenylethylamine brain levels can be increased by a 1000 fold when taking an MAO Inhibitor and 3-4 times when taken by itself. Alcohol and THC increase phenylethylamine levels by a 4 fold.

Many substituted phenethylamines are pharmacologically

Pharmacology

Pharmacology is the study of drug action. More specifically it is the study of the interactions that occur between a living organism and exogenous chemicals that alter normal biochemical function....
active drugs due to their similarity to the monoamine neurotransmitters:

Stimulant
Stimulant

Stimulant drugs are drugs that temporarily increase alertness and awareness. They usually have increased side-effects with increased effectiveness, and the more powerful variants are therefore often prescription medicines or illegal drugs....
s like the plant alkaloids ephedrine
Ephedrine

Ephedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia....
and cathinone
Cathinone

Cathinone is a monoamine alkaloid found in the shrub Catha edulis and is chemically similar to ephedrine, cathine and other amphetamines. Amphetamine induces the release of dopamine from striatal preparations that are prelabelled either with dopamine or its precursors, and it has been shown that cathinone also does this....
and the synthetic drug dextroamphetamine
Dextroamphetamine

Dextroamphetamine is a psychostimulant which is known to produce increased wakefulness and focus in association with decreased fatigue and appetite....
and methylphenidate
Methylphenidate

Methylphenidate is the most commonly medical prescription psychostimulant and is indicated in the treatment of attention-deficit hyperactivity disorder and narcolepsy, although off-label uses include treating lethargy, depression, neural insult and obesity....
Hallucinogens like the plant alkaloid mescaline
Mescaline

Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally-occurring psychedelic alkaloid of the phenethylamine class. It is mainly used as a recreational drug, an entheogen, and a tool to supplement various practices for transcendence , including in meditation, psychonautics, art projects, and psychedelic psychotherapy....
and the synthetic drug 2C-B
2C-B

2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a Psychedelics, dissociatives and deliriants of the 2C's, an Empathogen-entactogen. It was first synthesized by Alexander Shulgin in 1974....
Empathogen-entactogen
Empathogen-entactogen

The terms empathogen and entactogen are different terms used to describe a class of psychoactive drugs that produce distinctive emotional and social effects similar to those of methylenedioxymethamphetamine ....
s like MDMA (ecstasy) and MDA
3,4-Methylenedioxyamphetamine

3,4-Methylenedioxyamphetamine is a psychedelic psychedelics, dissociatives and deliriants and empathogen-entactogen of the phenethylamine family....
Anorectic
Anorectic

Anorexics, anorexigenics or appetite suppressants are substances that reduce the appetite and cause a person to eat less....
s like phentermine
Phentermine

Phentermine, a contraction for "phenyl-Butyl#Nomenclatureamine", is an appetite suppressant of the amphetamine and phenethylamine class.It is approved as an appetite suppressant to help reduce weight in obese patients when used short-term and combined with exercise, diet, and behavioral modification....
, fenfluramine
Fenfluramine

Fenfluramine is a drug that was part of the Fen-Phen anti-obesity medication . Also known as Pondimin, fenfluramine was introduced on the U.S....
, and amphetamine
Amphetamine

Amphetamine and related drugs such as methamphetamine are a group of drugs that act by increasing levels of norepinephrine, serotonin, and dopamine in the brain....
Bronchodilator
Bronchodilator

A bronchodilator is a substance that Wiktionary:dilate#Verb the Bronchus and bronchioles, decreasing airway resistance and thereby facilitating airflow....
s like salbutamol
Salbutamol

Salbutamol or albuterol is a short-acting beta2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and chronic obstructive pulmonary disease....
and ephedrine
Ephedrine

Ephedrine is a sympathomimetic amine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia....
Antidepressant
Antidepressant

An antidepressant is a psychiatric medication used for alleviating major depressive disorder or dysthymia. Drug groups known as MAOIs, tricyclics, and second-generation antidepressants such as SSRIs, and serotonin-norepinephrine reuptake inhibitors are particularly associated with the term....
s like venlafaxine
Venlafaxine

Venlafaxine is an antidepressant of the serotonin-norepinephrine reuptake inhibitor class first introduced by Wyeth in 1993. It is prescribed for the treatment of major depressive disorder and anxiety disorders, among other uses....
, bupropion
Bupropion

Bupropion is an atypical antidepressant that acts as a norepinephrine reuptake inhibitor and dopamine reuptake inhibitor, and nicotinic antagonist....
and the monoamine oxidase inhibitor
Monoamine oxidase inhibitor

Monoamine oxidase inhibitors are a class of powerful Antidepressants prescribed for the treatment of clinical depression. They are particularly effective in treating atypical depression, and have also shown efficacy in smoking cessation....
s phenelzine
Phenelzine

Phenelzine is a monoamine oxidase inhibitor used as an antidepressant Medication....
and tranylcypromine
Tranylcypromine

Tranylcypromine is a monoamine oxidase inhibitor used as an antidepressant medication. It is marketed by GlaxoSmithKline....
.

Substitution table

Some of the more important phenethylamines are tabulated below. For simplicity, the stereochemistry

Stereochemistry

Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms within molecules. An important branch of stereochemistry is the study of chirality molecules ....
of the sidechain is not covered in the table. Hundreds of other simple synthetic phenethylamines are known. This is due in large part to the pioneering work of Alexander Shulgin

Alexander Shulgin

Alexander "Sasha" Shulgin is a Russian-American pharmacologist, chemist and psychoactive drug developer.Shulgin is credited with the popularization of Methylenedioxymethamphetamine in the late 1970s and early 1980s, especially for psychopharmacology use and the treatment of depression and post-traumatic stress disorder....
, much of which is described in the book PiHKAL (Phenethylamines i Have Known And Loved)
PiHKAL

PiHKAL is a 1991 book by Dr. Alexander Shulgin and Ann Shulgin about psychedelic phenethylamines. The full title of the book is Phenethylamines i Have Known And Loved: A Chemical Love Story....
.

Selected Phenethylamines
Short Name	R^N	R^a	R^ß	R²	R³	R⁴	R⁵	Full Name
Tyramine Tyramine In organic chemistry chemistry tyramine is a monoamine Chemical compound derived from the amino acid tyrosine. Tyramine can cause the release of stored monoamines, such as dopamine, norepinephrine, and epinephrine....						OH Hydroxyl Hydroxyl in chemistry stands for a molecule consisting of an oxygen atom and a hydrogen atom connected by a covalent bond. The neutral form is a hydroxyl Radical and the hydroxyl anion is called a hydroxide....		4-hydroxy-phenethylamine
Dopamine Dopamine Dopamine is a neurotransmitter occurring in a wide variety of animals, including both vertebrates and invertebrates. In the human brain, this phenethylamine functions as a neurotransmitter, activating the five types of dopamine receptors ? D1, D2, D3, D4 and D5, and their variants....					OH	OH		3,4-dihydroxy-phenethylamine
Epinephrine Epinephrine Epinephrine is a hormone and neurotransmitter.Epinephrine increases the "fight or flight" response of the Sympathetic nervous system of the autonomic nervous system.... (Adrenaline)	CH₃ Methyl group In chemistry, a methyl group is a hydrophobic alkyl functional group named after methane . It has the chemical formula -3 and is often abbreviated -Me....		OH		OH	OH		ß,3,4-trihydroxy-N-methyl Methyl group In chemistry, a methyl group is a hydrophobic alkyl functional group named after methane . It has the chemical formula -3 and is often abbreviated -Me.... phenethylamine
Norepinephrine Norepinephrine Norepinephrine or noradrenaline is a catecholamine with dual roles as a hormone and a neurotransmitter.As a stress hormone, norepinephrine affects parts of the brain where attention and responding actions are controlled.... (Noradrenaline)			OH		OH	OH		ß,3,4-trihydroxyphenethylamine
Phenylephrine Phenylephrine Phenylephrine or Neo-Synephrine is an Alpha-1_adrenergic_receptor agonist used primarily as a decongestant, as an agent to dilate the pupil and to increase blood pressure....	CH₃		OH		OH			ß,3-dihydroxy-N-methylphenethylamine
6-Hydroxydopamine 6-Hydroxydopamine 6-Hydroxydopamine, or 6-OHDA, is a neurotoxin used by neurobiologists to selectively kill dopaminergic and noradrenergic neurons. 6-OHDA enters the neurons via the dopamine and noradrenaline reuptake transporters....				OH		OH	OH	2,4,5-trihydroxyphenethylamine
Salbutamol Salbutamol Salbutamol or albuterol is a short-acting beta2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and chronic obstructive pulmonary disease....	C(CH₃)₃		OH			OH	CH₂OH Hydroxymethyl Hydroxymethyl in the field of chemistry, particularly in organic chemistry, is the name for a functional group with the structural formula -CH2-OH....	ß,4-dihydroxy-3-hydroxymethyl Hydroxymethyl Hydroxymethyl in the field of chemistry, particularly in organic chemistry, is the name for a functional group with the structural formula -CH2-OH.... -N-tert-butyl-phenethylamine
Beta-methyl-phenethylamine Beta-methyl-phenethylamine ?-Methylphenethylamine is a drug related to amphetamine. It is found in many Acacia species. It has stimulant effects in man as the beta-methyl group slows metabolism by monoamine oxidase enzymes....			CH₃					ß-methylphenethylamine
Amphetamine Amphetamine Amphetamine and related drugs such as methamphetamine are a group of drugs that act by increasing levels of norepinephrine, serotonin, and dopamine in the brain....		CH₃						a-methylphenethylamine
Methamphetamine Methamphetamine is a stimulant and sympathomimetics psychoactive drug. It is a member of the family of phenylethylamines. The levorotary levomethamphetamine is an over-the-counter drug and used in Vicks Inhalers for nasal decongestion and does not possess the Central nervous system activity of dextro or racemic methamphetamine....	CH₃	CH₃						N-methylamphetamine
Methylphenidate Methylphenidate Methylphenidate is the most commonly medical prescription psychostimulant and is indicated in the treatment of attention-deficit hyperactivity disorder and narcolepsy, although off-label uses include treating lethargy, depression, neural insult and obesity....	-CH₂-CH₂-CH₂-CH₂-		C(OCH₃)=O					N,a-butylene-ß-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 amine amine commonly used as a decongestant. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many Over-the-counter drug preparations either as single-ingredient preparations, or more commonly in combination with antihistamines, paracetamol and/or ibuprofen....	CH₃	CH₃	OH					N-methyl-ß-hydroxyamphetamine
Acetylamphetamine		CH₃			COCH₃			a-methyl-3-acetylphenethylamine
Cathine Cathine Cathine is a monoamine alkaloid found in the shrub Catha edulis ....		CH₃	OH					ß-hydroxy-amphetamine
Cathinone Cathinone Cathinone is a monoamine alkaloid found in the shrub Catha edulis and is chemically similar to ephedrine, cathine and other amphetamines. Amphetamine induces the release of dopamine from striatal preparations that are prelabelled either with dopamine or its precursors, and it has been shown that cathinone also does this....		CH₃	=O Ketone In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....					ß-keto Ketone In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen .... amphetamine
Methcathinone Methcathinone Methcathinone is a psychoactive stimulant. It is sometimes used as a recreational drug and is considered to be addictive. It is usually snorted, but can be smoked, injected, or taken orally....	CH₃	CH₃	=O					N-methyl-ß-ketoamphetamine
Bupropion Bupropion Bupropion is an atypical antidepressant that acts as a norepinephrine reuptake inhibitor and dopamine reuptake inhibitor, and nicotinic antagonist....	C(CH₃)₃	CH₃	=O		Cl Chlorine Chlorine...			3-chloro-N-tert-butyl-ß-ketoamphetamine
Fenfluramine Fenfluramine Fenfluramine is a drug that was part of the Fen-Phen anti-obesity medication . Also known as Pondimin, fenfluramine was introduced on the U.S....	CH₂CH₃ Ethyl group In chemistry, an ethyl group is an alkyl functional group derived from ethane . It has the chemical formula -Carbon2Hydrogen5 and is very often abbreviated -Et....	CH₃			CF₃ Trifluoromethyl Trifluoromethyl is a functional group in organofluorines that has the chemical formula -CF3. The naming of is group is derived from the methyl group , by replacing each hydrogen atom by a fluorine atom....			3-trifluoromethyl Trifluoromethyl Trifluoromethyl is a functional group in organofluorines that has the chemical formula -CF3. The naming of is group is derived from the methyl group , by replacing each hydrogen atom by a fluorine atom.... -N-ethyl Ethyl group In chemistry, an ethyl group is an alkyl functional group derived from ethane . It has the chemical formula -Carbon2Hydrogen5 and is very often abbreviated -Et.... -amphetamine
Phentermine Phentermine Phentermine, a contraction for "phenyl-Butyl#Nomenclatureamine", is an appetite suppressant of the amphetamine and phenethylamine class.It is approved as an appetite suppressant to help reduce weight in obese patients when used short-term and combined with exercise, diet, and behavioral modification....		2CH₃						a,a-dimethylphenethylamine
Mescaline Mescaline Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally-occurring psychedelic alkaloid of the phenethylamine class. It is mainly used as a recreational drug, an entheogen, and a tool to supplement various practices for transcendence , including in meditation, psychonautics, art projects, and psychedelic psychotherapy....					OCH₃ Methoxy In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. It has the formula: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. It has the formula:The word is used in organic nomenclature usually to describe an ether.... phenethylamine
MDA 3,4-Methylenedioxyamphetamine 3,4-Methylenedioxyamphetamine is a psychedelic psychedelics, dissociatives and deliriants and empathogen-entactogen of the phenethylamine family....		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 -O-CH2-O- which is connected to the rest of a molecule by two chemical bonds.... amphetamine
MDMA	CH₃	CH₃			-O-CH₂-O-			3,4-methylenedioxy-N-methylamphetamine
MDMC	CH₃	CH₃	=O		-O-CH₂-O-			3,4-methylenedioxy-N-methyl-ß-ketoamphetamine
DOM 2,5-Dimethoxy-4-methylamphetamine DOM is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, sometimes used as an entheogen....		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 Psychedelics, dissociatives and deliriants and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen....		CH₃		OCH₃		Br Bromine Bromine , , meaning "stench " ), is a chemical element with the symbol Br and atomic number 35. A halogen element, bromine is a reddish-brown Volatility liquid at Standard conditions for temperature and pressure that is intermediate in reactivity between chlorine and iodine....	OCH₃	2,5-dimethoxy-4-bromoamphetamine
DON 2,5-Dimethoxy-4-nitroamphetamine 2,5-Dimethoxy-4-nitroamphetamine is an analog of 2,5-dimethoxy-4-methylamphetamine and 2,5-Dimethoxy-4-bromoamphetamine. It is also closely related to 2C-N, and produces Psychedelics, dissociatives and deliriants, psychedelic, and entheogenic effects....		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....	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.... amphetamine
2C-B 2C-B 2C-B or 4-bromo-2,5-dimethoxyphenethylamine is a Psychedelics, dissociatives and deliriants of the 2C's, an Empathogen-entactogen. It was first synthesized by Alexander Shulgin in 1974....				OCH₃		Br	OCH₃	2,5-dimethoxy-4-bromophenethylamine
2C-C 2C-C 2C-C is a Psychedelics, dissociatives and deliriants of the 2C . It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. The full name of the chemical is 4-chloro-2,5-dimethoxyphenethylamine....				OCH₃		Cl	OCH₃	2,5-dimethoxy-4-chlorophenethylamine
DOI 2,5-Dimethoxy-4-iodoamphetamine DOI or 2,5-dimethoxy-4-iodoamphetamine is a psychedelic drug and a substituted amphetamine of the phenethylamine family. Despite being a Substitution amphetamine it is not a stimulant....		CH₃		OCH₃		I Iodine Iodine , is a chemical element that has the symbol I and atomic number 53. Naturally-occurring iodine is a single isotope with 74 neutrons....	OCH₃	2,5-dimethoxy-4-iodo Iodo Iodo may refer to;Socotra RockIodo , South Korean film directed by Kim Ki-young*Iodine, chemical element... amphetamine
2C-I 2C-I 2C-I is a Psychedelics, Dissociatives and Deliriants and phenethylamine of the 2C . It was developed and popularized by Alexander Shulgin. It was described in Shulgin?s book PiHKAL....				OCH₃		I	OCH₃	2,5-dimethoxy-4-iodophenethylamine
2C-D 2C-D 2C-D is a Psychedelics, dissociatives and deliriants of the 2C . It was first synthesized by Alexander Shulgin, sometimes used as an entheogen....				OCH₃		CH₃	OCH₃	2,5-dimethoxy-4-methylphenethylamine
2C-E 2C-E 2C-E is a Psychedelics, dissociatives and deliriants and phenethylamines of the 2C . It was first synthesized by Alexander Shulgin, sometimes used as an entheogen....				OCH₃		CH₂-CH₃	OCH₃	2,5-dimethoxy-4-ethylphenethylamine
2C-F 2C-F 2C-F, or 4-fluoro-2,5-dimethoxyphenethylamine, is a lesser-known Psychedelics, dissociatives and deliriants of the 2C's. It was first synthesized by Alexander Shulgin....				OCH₃		F Fluorine Fluorine is the chemical element with the symbol F and atomic number 9. Fluorine forms a single bond with itself in elemental form, resulting in the diatomic F2 molecule....	OCH₃	2,5-dimethoxy-4-fluorophenethylamine
2C-N 2C-N 2C-N, or 2,5-Dimethoxy-4-nitrophenethylamine, is a psychedelic phenethylamine of the 2C . It was first synthesized by Alexander Shulgin and is sometimes used as an entheogen....				OCH₃		NO₂	OCH₃	2,5-dimethoxy-4-nitrophenethylamine
2C-T-2 2C-T-2 2C-T-2, or 2,5-dimethoxy-4-ethyl groupthiophenethylamine, is a psychedelic and entheogenic phenethylamine of the 2C . It was first synthesized in 1981 by Alexander Shulgin....				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.... -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.... -phenethylamine
2C-T-4 2C-T-4 2C-T-4 or 2,5-dimethoxy-4-isopropylthiophenethylamine is a psychedelic phenethylamine of the 2C's. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen....				OCH₃		S-CH(CH₃)₂ Isopropyl In organic chemistry, isopropyl is a substituent form of propane, the three-carbon alkyl functional group. As an isomer of propyl, bonding to an R group occurs at the secondary carbon....	OCH₃	2,5-dimethoxy-4-isopropyl Isopropyl In organic chemistry, isopropyl is a substituent form of propane, the three-carbon alkyl functional group. As an isomer of propyl, bonding to an R group occurs at the secondary carbon.... thio-phenethylamine
2C-T-7 2C-T-7 2C-T-7 is a hallucinogenic phenethylamine of the 2C . In his book PiHKAL, Alexander Shulgin lists the dosage range as 10 to 30 milligram. 2C-T-7 is generally taken Mouth, and produces psychedelic and entheogenic 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 . It was first synthesized by Alexander Shulgin, sometimes used as an entheogen....				OCH₃		S-CH₂-C₃H₅	OCH₃	2,5-dimethoxy-4-cyclopropylmethylthio-phenethylamine
2C-T-9 2C-T-9 2C-T-9 is a psychedelic phenethylamine of the 2C . It was first synthesized by Alexander Shulgin, sometimes used as an entheogen....				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's. 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....				OCH₃		S-CH₂-CH₂-F	OCH₃	2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine
Short Name	R^N	R^a	R^ß	R²	R³	R⁴	R⁵	Full Name

Relation to amphetamine

Despite the negative stigma tagged to amphetamine

Amphetamine

Amphetamine and related drugs such as methamphetamine are a group of drugs that act by increasing levels of norepinephrine, serotonin, and dopamine in the brain....
(alpha-methylphenethylamine) ("speed", "amp", "uppers") and methylamphetamine (N-methyl-alpha-methylphenethylamine) ("speed", "meth", "ice", "crystal") and its recreational compounds, the phenylethylamines comprise amphetamine and methamphetamine, and make up many drugs with important uses including the bronchodilator

Bronchodilator

A bronchodilator is a substance that Wiktionary:dilate#Verb the Bronchus and bronchioles, decreasing airway resistance and thereby facilitating airflow....
s. These are used for dilating or "opening" the bronchi and bronchioles, which is of benefit to, and can save the life of, an asthmatic (with salbutamol or albuterol

Salbutamol

Salbutamol or albuterol is a short-acting beta2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and chronic obstructive pulmonary disease....
or adrenaline for someone with life-threatening allergic reactions).

The phenethylamines also include some medically used stimulants like amphetamine (Adderall

Adderall

Adderall is a brand-name pharmaceutical psychostimulant composed of mixed amphetamine Salt , which is thought to work by increasing the amount of norepinephrine and dopamine in the brain....
, Dexedrine), methylamphetamine (Desoxyn

Desoxyn

Desoxyn is a brand of methamphetamine hydrochloride , indicated for treatment of Attention Deficit/Hyperactivity Disorder , narcolepsy, and exogenous obesity....
), methylphenidate

Methylphenidate

Methylphenidate is the most commonly medical prescription psychostimulant and is indicated in the treatment of attention-deficit hyperactivity disorder and narcolepsy, although off-label uses include treating lethargy, depression, neural insult and obesity....
(Ritalin, Concerta and others), which benefit people with ADHD and ADD

ADD

ADD is a three-letter acronym that may refer to:* Attention-Deficit Hyperactivity Disorder, previously known as Attention-Deficit Disorder.* Adult_attention-deficit_disorder, adult form of ADHD....
(attention and behavioral disorders affecting many children and some adults), narcolepsy

Narcolepsy

Narcolepsy is a chronic sleep disorder characterized by overwhelming daytime drowsiness and sudden attacks of sleep. The condition is most characterized by excessive daytime sleepiness , in which a person experiences extreme tiredness and possibly falls asleep during the day at inappropriate times, such as at work or school....
(the sudden, irresistable urge to fall asleep at any time regardless of how much sleep you have had the night before) and chronic fatigue syndrome (CFS)

Chronic fatigue syndrome

Chronic fatigue syndrome is the most common name given to a poorly understood, variably debilitating disorder or disorders of uncertain etiology....
.

The majority of phenylethylamines used by many have some or all of the actions of the stigmatized amphetamine and methamphetamine (though sometimes they lack the recreational abuse) and also share great structural similarity to methamphetamine and amphetamine.

Graphical overview

External links

online
Review and summary of PiHKAL, including table of 300+ phenethylamines:

Phenethylamine

Chemistry

Neurochemistry

Chocolate theory of love

Substituted phenethylamines

Pharmacology

Substitution table

Relation to amphetamine

Graphical overview

See also

External links