Phenethylamine [1]
Chemical name	2-Phenylethylamine
Other names	Phenethylamine β-Phenylethylamine 2-Phenyl-1-aminoethane β-Aminoethylamine 2-Phenylethanamine
Chemical formula	C8H11N
Molecular mass	121.18 g/mol
CAS number	[64-04-0]
Density	0.964 g/cm3
Melting point	-60 °C
Boiling point	194.5-195 °C
SMILES	c1ccccc1CCN
NFPA 704	Chemical structure of phenethylamine Selfmade by cacycle File links The following pages link to this file: Phenethylamine Categories: GFDL images ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, Density is defined as mass m per unit volume V. Mathematically, it is expressed as where, in SI units: ρ (rho) is the density of the substance, measured in kg m-3 m is the mass of the substance, measured in kg v is the volume of the substance... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... 2 2 2
Disclaimer and references

Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. In the human brain, it is believed to function as a neuromodulator or neurotransmitter (trace amine). Phenethylamine is a natural compound biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. It is also found in many foods such as chocolate, especially after microbial fermentation. It has been suggested that phenethylamine from food may have psychoactive effects in sufficient quantities. However, it is quickly metabolized by the enzyme MAO-B, preventing significant concentrations from reaching the brain. Diagram of Ephedrine An alkaloid, strictly speaking, is a naturally-occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... In biochemistry, monoamines are a group of organic compounds containing only one amino group. ... A neuromodulator is a substance other than a neurotransmitter, released by a neuron at a synapse and conveying information to adjacent or distant neurons, either enhancing or damping their activities. ... Chemical structure of D-Aspartic Acid, a common Amino Acid neurotransmitter. ... Trace amines are endogenous compounds structurally related to classical biogenic amines, such as catecholamines, serotonin and histamine. ... Phenylalanine is one of the standard amino acids. ... Phe redirects here. ... A Decarboxylation is any chemical reaction in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide (CO2). ... CHOCOLATE IS VERY NICE! Chocolate most commonly comes in dark, milk, and white varieties, with cocoa solids contributing to the brown coloration. ... A cluster of Escherichia coli bacteria magnified 10,000 times. ... Beer fermenting at a brewery. ... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... MAO-B is an abbreviation for monoamine oxidase B. There are 2 varieties of monoamine oxidase, which are MAO-A and MAO-B. MAO-A mainly breaks down the neurochemicals serotonin and norepinephrine, whereas MAO-B mainly breaks down the neurochemicals dopamine and phenylethylamine. ...

Substituted phenethylamines are a broad and diverse class of compounds that include neurotransmitters, hormones, stimulants, hallucinogens, entactogens, anorectics, bronchodilators, and antidepressants. The phenethylamine structure can also be found as part of more complex ring systems such as the ergoline system of LSD or the morphinan system of morphine. Chemical structure of D-Aspartic Acid, a common Amino Acid neurotransmitter. ... Norepinephrine A hormone (from Greek όρμή - to set in motion) is a chemical messenger from one cell (or group of cells) to another. ... Stimulants are drugs that increase alertness and wakefulness. ... The general group of pharmacological agents commonly known as hallucinogens can be divided into three broad categories: psychedelics, dissociatives, and deliriants. ... The terms empathogen and entactogen are different terms used to describe one class of hallucinogens that function as serotonin releasers; most of these are phenethylamines. ... Anorectics, anorexigenics or appetite suppressants are drugs that reduce the desire to eat (anorectic, from the Greek an- = not and oreg- = extend, reach). (Anorectic is also a term for an anorexic person, a person suffering from Anorexia nervosa. ... A bronchodilator is a medication intended to improve bronchial airflow. ... A recent form of antidepressant medication - Prozac Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant, in the most common usage, is a medication taken to alleviate clinical depression or dysthymia (milder depression). ... Chemical structure of ergoline Ergoline is a chemical compound whose structure serves as the skeleton for a diverse range of alkaloids and synthetic drugs. ... Lysergic acid diethylamide, commonly called LSD, LSD-25, or acid. ... Morphinan is the base chemical structures of a subgroup of opioids. ... Morphine (INN) (IPA: ) is a highly potent opiate analgesic drug and is the principal active agent in opium and the prototypical opiate. ...

Chemistry

Phenethylamine is an aromatic amine which is a colorless liquid at room temperature. It is soluble in water, ethanol, and ether.^[1] Similar to other low molecular weight amines, it has a fishy odor. Upon exposure to air, it forms a solid carbonate salt with carbon dioxide. Phenethylamine is strongly basic and forms a stable crystalline hydrochloride salt with a melting point of 217 °C. Phenethylamine is also a skin irritant and possible sensitizer. In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless, slightly toxic chemical compound with a distinctive perfume-like odor, and is the alcohol found in alcoholic beverages. ... Diethyl ether, also known as ether and ethoxyethane, is a clear, colorless, and highly flammable liquid with a low boiling point and a characteristic smell. ... In organic chemistry, a carbonate is a salt of carbonic acid. ... A magnified crystal of a salt (halite/sodium chloride) Salt covering the floor of Bad Water in Death Valley, CA, the lowest point in the US. A salt, in chemistry, is any ionic compound composed of cations (positively charged ions) and anions (negative ions) so that the product is neutral... Carbon dioxide is a chemical compound composed of one carbon and two oxygen atoms. ... A base in chemistry is a chemical substance which has a free pair of electrons to bind a hydrogen ion commonly referred to as a proton (IUPAC definition). ... In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (mostly amines). ...

Substituted phenethylamines

General structure of phenethylamines and amphetamines (see the table below).

Substituted phenethylamines carry additional chemical modifications at the phenyl ring, the sidechain, or the amino group: Chemical structure of phenethylamine with rests Selfmade by cacycle File links The following pages link to this file: Phenethylamine Categories: GFDL images ... Substitution in the context of organic chemistry has the general meaning of replacing an atom, a functional group, or a substituent in a molecule. ... In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 Picture where the six carbon atoms are arranged in a cyclic manner. ... ... In chemistry, especially in organic chemistry and biochemistry, an amino group is an ammonia-like functional group. ...

• Amphetamines are homologues of phenethylamines carrying an alpha-methyl (α-CH₃) group at the sidechain carbon atom next to the amino group.
• Catecholamines are phenethylamines carrying two hydroxy groups in positions 3 and 4 of the phenyl ring. Examples are the hormones and neurotransmitters dopamine, epinephrine (adrenaline), and norepinephrine (noradrenaline).
• The aromatic amino acids phenylalanine and tyrosine are phenethylamines carrying a carboxyl group (COOH) in alpha position.
• 2C's are phenethylamines with methoxy groups attached to the 2 and 5 carbons and no alpha-methyl group.

Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... 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 (see relative molecular mass). ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... tyrosine epinephrine norepinephrine dopamine Synthesis This article or section does not cite its references or sources. ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... This article or section is in need of attention from an expert on the subject. ... Adrenaline redirects here. ... Norepinephrine (INN) or noradrenaline (BAN) is a catecholamine and a phenethylamine with chemical formula C8H11NO3. ... In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... Phe redirects here. ... Tyrosine (from the Greek tyros, meaning cheese, as it was first discovered in 1846 by German chemist Justus von Liebig in cheese[1][2]), 4-hydroxyphenylalanine, or 2-amino-3(4-hydroxyphenyl)-propanoic acid, is one of the 20 amino acids that are used by cells to synthesize proteins. ... A carboxyl or carboxylic group is a functional group consisting of a carbon atom and an oxygen atom doubly bonded to each other. ... 2C is a general name for the family of psychedelic and entheogenic phenethylamines containing methoxy groups on the 2 and 5 positions of the benzene ring. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ...

Pharmacology

Many substituted phenethylamines are pharmacologically active drugs due to their similarity to the monoamine neurotransmitters: Pharmacology (in Greek: pharmacon (φάρμακον) meaning drug, and logos (λόγος) meaning science) is the study of how substances interact with living organisms to produce a change in function. ...

• Stimulants like the plant alkaloids ephedrine and cathinone and the synthetic drug dextroamphetamine and methylphenidate.
• Hallucinogens like the plant alkaloid mescaline and the synthetic drug 2C-B.
• Empathogen-entactogens like MDMA (ecstasy) and MDA.
• Anorectics like phentermine, fenfluramine, and amphetamine.
• Bronchodilators like salbutamol and ephedrine.
• Antidepressants like bupropion and the monoamine oxidase inhibitors phenelzine and tranylcypromine.

Stimulants are drugs that increase alertness and wakefulness. ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). ... Dextroamphetamine (also known as dextroamphetamine sulfate, dexamphetamine sulphate, d-amphetamine, dexamphetamine, Dexedrine, Dextrostat, Dexampex, Ferndex, Oxydess II, Robese, Spancap #1, and, informally, Dex), a stereoisomer of amphetamine, is a potent central nervous system stimulant that induces the release of the neurotransmitters dopamine and norepinephrine into nerve synapses in certain areas... Methylphenidate (MPH) is an amphetamine-like prescription stimulant commonly used to treat Attention Deficit Hyperactivity Disorder (ADHD) in children and adults. ... The general group of pharmacological agents commonly known as hallucinogens can be divided into three broad categories: psychedelics, dissociatives, and deliriants. ... Mescaline (3,4,5-trimethoxyphenethylamine) is a hallucinogenic alkaloid of the phenethylamine class. ... 2C-B, or 4-bromo-2,5-dimethoxyphenethylamine, is a lesser known psychedelic drug that was first synthesized by Alexander Shulgin in 1974. ... The terms empathogen and entactogen are different terms used to describe one class of hallucinogens that function as serotonin releasers; most of these are phenethylamines. ... ecstasy and religious ecstasy MDMA, most commonly known today by the street name ecstasy, is a synthetic entactogen of the phenethylamine family whose primary effect is to stimulate the brain to rapidly secrete large amounts of serotonin, causing a general sense of openness, empathy, energy, euphoria, and well-being. ... 3,4-Methylenedioxyamphetamine, or MDA, is a psychedelic hallucinogenic drug and empathogen/entactogen of the phenethylamine family. ... Anorectics, anorexigenics or appetite suppressants are drugs that reduce the desire to eat (anorectic, from the Greek an- = not and oreg- = extend, reach). (Anorectic is also a term for an anorexic person, a person suffering from Anorexia nervosa. ... Phentermine is a drug primarily used as an appetite suppressant. ... Fenfluramine is a drug that was part of the Fen-Phen anti-obesity (the other drug being phentermine). ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... A bronchodilator is a medication intended to improve bronchial airflow. ... Salbutamol (INN) or albuterol (USAN) is a short-acting β2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and COPD. Salbutamol sulfate is usually given by the inhaled route for direct effect on bronchial smooth muscle. ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... A recent form of antidepressant medication - Prozac Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant, in the most common usage, is a medication taken to alleviate clinical depression or dysthymia (milder depression). ... Bupropion (INN; also amfebutamone,[1] brand names Wellbutrin and Zyban) is an antidepressant of the aminoketone class, chemically unrelated to tricyclics or selective serotonin reuptake inhibitors (SSRIs). ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... Phenelzine (brand name Nardil) is an antidepressant drug that belongs to the monoamine oxidase inhibitor (MAOI) class of drugs. ... Tranylcypromine (sold under the brand name Parnate®) is a monoamine oxidase inhibitor (MAOI) used as an antidepressant drug. ...

Substitution table

Some of the more important phenethylamines are tabulated below. For simplicity, the stereochemistry of the sidechain is not covered in the table. Hundreds of other simple synthetic phenethylamines are known. This is due in part to the pioneering work of Alexander Shulgin, much of which is described in the book PiHKAL. The different types of isomers. ... Alexander and Ann Shulgin, in a photo from their book TiHKAL, c. ... PiHKAL is a 1991 book by Dr. Alexander Shulgin and Ann Shulgin about psychedelic phenethylamines. ...

Tyramine (4-hydroxy-phenethylamine) is a monoamine compound derived from the amino acid tyrosine. ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... This article or section is in need of attention from an expert on the subject. ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... Adrenaline redirects here. ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Norepinephrine (INN) or noradrenaline (BAN) is a catecholamine and a phenethylamine with chemical formula C8H11NO3. ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... Salbutamol (INN) or albuterol (USAN) is a short-acting β2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and COPD. Salbutamol sulfate is usually given by the inhaled route for direct effect on bronchial smooth muscle. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... Dextroamphetamine (also known as dextroamphetamine sulfate, dexamphetamine sulphate, d-amphetamine, dexamphetamine, Dexedrine, Dextrostat, Dexampex, Ferndex, Oxydess II, Robese, Spancap #1, and, informally, Dex), a stereoisomer of amphetamine, is a potent central nervous system stimulant that induces the release of the neurotransmitters dopamine and norepinephrine into nerve synapses in certain areas... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Dextromethamphetamine (dextro-N-α-dimethyl-phenethylamine is an N-methylated analog of dextroamphetamine. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... Levmetamfetamine (other names: l-desoxyephedrine, l-methamphetamine, levo-methamphetamine) is the l- stereoisomer of methamphetamine, a sympathomimetic vasoconstrictor which may be used in over-the-counter nasal decongestants. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... Ephedrine (EPH) is a sympathomimetic amine similar in structure to the synthetic derivatives amphetamine and methamphetamine. ... Pseudoephedrine (commonly abbreviated as PSE) is a sympathomimetic amine commonly used as a decongestant. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... Cathine (β-hydroxyamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (khat). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... To meet Wikipedias quality standards, this article or section may require cleanup. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... Bupropion (INN; also amfebutamone,[1] brand names Wellbutrin and Zyban) is an antidepressant of the aminoketone class, chemically unrelated to tricyclics or selective serotonin reuptake inhibitors (SSRIs). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... General Name, Symbol, Number chlorine, Cl, 17 Series halogens Group, Period, Block 17 (VIIA), 3, p Density, Hardness 3. ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... Fenfluramine is a drug that was part of the Fen-Phen anti-obesity (the other drug being phentermine). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number fluorine, F, 9 Chemical series halogens Group, Period, Block 17, 2, p Appearance Yellowish brown gas Atomic mass 18. ... Ethyl is a two-carbon substituent in organic chemistry. ... General Name, Symbol, Number Fluorine, F, 9 Series Halogens Group, Period, Block 17 (VIIA), 2 , p Density, Hardness 1. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Ethyl is a two-carbon substituent in organic chemistry. ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... Phentermine is a drug primarily used as an appetite suppressant. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Mescaline (3,4,5-trimethoxyphenethylamine) is a hallucinogenic alkaloid of the phenethylamine class. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... 3,4-Methylenedioxyamphetamine, or MDA, is a psychedelic hallucinogenic drug and empathogen/entactogen of the phenethylamine family. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry, methylene is a divalent functional group CH2 derived formally from methane. ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... ecstasy and religious ecstasy MDMA, most commonly known today by the street name ecstasy, is a synthetic entactogen of the phenethylamine family whose primary effect is to stimulate the brain to rapidly secrete large amounts of serotonin, causing a general sense of openness, empathy, energy, euphoria, and well-being. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry, methylene is a divalent functional group CH2 derived formally from methane. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... Methylone is a designer drug that is an analogue of MDMA (Ecstasy). ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry, methylene is a divalent functional group CH2 derived formally from methane. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... DOM (or STP, allegedly standing for Serenity, Tranquillity and Peace) is a psychedelic hallucinogenic drug of the phenethylamine class of compounds, sometimes used as an entheogen. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... DOB (or Bromo-DMA) is a psychedelic hallucinogenic drug of the phenethylamine class of compounds, sometimes used as an entheogen. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number bromine, Br, 35 Chemical series halogens Group, Period, Block 17, 4, p Appearance gas/liquid: red-brown solid: metallic luster Atomic mass 79. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number bromine, Br, 35 Series halogens Group, Period, Block 17 (VIIA), 4, p Density, Hardness 3119 kg/m3 (300 K), NA Appearance Gas: red-brown solid: metallic luster Atomic properties Atomic weight 79. ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... DON 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. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... Nitro may refer to: Nitroglycerin, an extremely explosive chemical compound Nitrous, a type of fuel additive for race cars Nitromethane, another type of fuel additive for race cars Glyceryl trinitrate (pharmacology), a medical compound used for the treatment of angina pectoris Nitrogen, especially when used in draught beer Nitrocellulose, an... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... Nitro may refer to: Nitroglycerin, an extremely explosive chemical compound Nitrous, a type of fuel additive for race cars Nitromethane, another type of fuel additive for race cars Glyceryl trinitrate (pharmacology), a medical compound used for the treatment of angina pectoris Nitrogen, especially when used in draught beer Nitrocellulose, an... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... 2C-B, or 4-bromo-2,5-dimethoxyphenethylamine, is a lesser known psychedelic drug that was first synthesized by Alexander Shulgin in 1974. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number bromine, Br, 35 Chemical series halogens Group, Period, Block 17, 4, p Appearance gas/liquid: red-brown solid: metallic luster Atomic mass 79. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number bromine, Br, 35 Series halogens Group, Period, Block 17 (VIIA), 4, p Density, Hardness 3119 kg/m3 (300 K), NA Appearance Gas: red-brown solid: metallic luster Atomic properties Atomic weight 79. ... 2C-C is a psychedelic hallucinogenic drug first synthesized by Alexander Shulgin, sometimes used as an entheogen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number chlorine, Cl, 17 Series halogens Group, Period, Block 17 (VIIA), 3, p Density, Hardness 3. ... DOI or 2,5-dimethoxy-4-iodoamphetamine is a psychedelic hallucinogenic drug of the phenethylamine family. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number iodine, I, 53 Chemical series halogens Group, Period, Block 17, 5, p Appearance violet-dark gray, lustrous Atomic mass 126. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number iodine, I, 53 Series halogens Group, Period, Block 17 (VIIA), 5 , p Density, Hardness 4940 kg/m3, no data Appearance violet-dark grey, lustrous Atomic properties Atomic weight 126. ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... 2C-I is a psychedelic drug and phenethylamine that was developed and popularized by Alexander Shulgin. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number iodine, I, 53 Chemical series halogens Group, Period, Block 17, 5, p Appearance violet-dark gray, lustrous Atomic mass 126. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number iodine, I, 53 Series halogens Group, Period, Block 17 (VIIA), 5 , p Density, Hardness 4940 kg/m3, no data Appearance violet-dark grey, lustrous Atomic properties Atomic weight 126. ... 2C-D is a psychedelic hallucinogenic drug first synthesized by Alexander Shulgin, sometimes used as an entheogen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... 2C-E (2,5-dimethoxy-4-ethylphenethylamine) is a psychedelic drug and phenethylamine first synthesized by Alexander Shulgin, sometimes used as an entheogen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... Ethyl is a two-carbon substituent in organic chemistry. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... Ethyl is a two-carbon substituent in organic chemistry. ... 2C-F, or 4-fluoro-2,5-dimethoxyphenethylamine, is a lesser-known psychedelic drug of the 2C family. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number fluorine, F, 9 Chemical series halogens Group, Period, Block 17, 2, p Appearance Yellowish brown gas Atomic mass 18. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number Fluorine, F, 9 Series Halogens Group, Period, Block 17 (VIIA), 2 , p Density, Hardness 1. ... 2C-N is a psychedelic entheogen first synthesized by Alexander Shulgin. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... Nitro may refer to: Nitroglycerin, an extremely explosive chemical compound Nitrous, a type of fuel additive for race cars Nitromethane, another type of fuel additive for race cars Glyceryl trinitrate (pharmacology), a medical compound used for the treatment of angina pectoris Nitrogen, especially when used in draught beer Nitrocellulose, an... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... Nitro may refer to: Nitroglycerin, an extremely explosive chemical compound Nitrous, a type of fuel additive for race cars Nitromethane, another type of fuel additive for race cars Glyceryl trinitrate (pharmacology), a medical compound used for the treatment of angina pectoris Nitrogen, especially when used in draught beer Nitrocellulose, an... 2C-T-2 is a psychedelic phenethylamine presumably first synthesized in 1981 by Alexander Shulgin, sometimes used as an entheogen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... Ethyl is a two-carbon substituent in organic chemistry. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... Ethyl is a two-carbon substituent in organic chemistry. ... For the related sulfur-containing chemical compound, see Thiol. ... 2C-T-4 or 2,5-dimethoxy-4-(i)-propylthiophenethylamine is a psychedelic phenethylamine presumably first synthesized by Alexander Shulgin, sometimes used as an entheogen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... Isopropyl is a term in organic chemistry to refer to a three carbon structure. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula -C3H7. ... For the related sulfur-containing chemical compound, see Thiol. ... 2C-T-7 is a psychedelic phenethylamine and is sometimes used as an entheogen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula -C3H7. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula -C3H7. ... For the related sulfur-containing chemical compound, see Thiol. ... 2C-T-8 is a psychedelic phenethylamine first synthesized by Alexander Shulgin, sometimes used as an entheogen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Molecule structure formula of cyclopropane Cyclopropane is a cycloalkane molecule with the molecular formula C3H6 consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... Molecule structure formula of cyclopropane Cyclopropane is a cycloalkane molecule with the molecular formula C3H6 consisting of three carbon atoms linked to each other to form a ring, with each carbon atom bearing two hydrogen atoms. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... For the related sulfur-containing chemical compound, see Thiol. ... 2C-T-9 is a relatively unexciting psychedelic phenethylamine first synthesized by Alexander Shulgin, sometimes used as an entheogen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... For the related sulfur-containing chemical compound, see Thiol. ... 2C-T-21 is a psychedelic phenethylamine first synthesized by Alexander Shulgin, sometimes used as an entheogen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... General Name, Symbol, Number fluorine, F, 9 Chemical series halogens Group, Period, Block 17, 2, p Appearance Yellowish brown gas Atomic mass 18. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... In chemistry, the methoxy prefix indicates the function group consisting of the methyl group and oxygen. ... General Name, Symbol, Number Fluorine, F, 9 Series Halogens Group, Period, Block 17 (VIIA), 2 , p Density, Hardness 1. ... Ethyl is a two-carbon substituent in organic chemistry. ... For the related sulfur-containing chemical compound, see Thiol. ... Image File history File links Download high resolution version (1877x970, 53 KB) Overview Phenethylamines Autor: User:C.Löser Lizenz: CC by sa 2. ...

See also

• Catecholamines
• PiHKAL
• Alexander Shulgin
• Venom (comics) An alien in the Fictional Spider Man comic series relies on this chemical.
• Phenethyl alcohol
• 2C's

tyrosine epinephrine norepinephrine dopamine Synthesis This article or section does not cite its references or sources. ... PiHKAL is a 1991 book by Dr. Alexander Shulgin and Ann Shulgin about psychedelic phenethylamines. ... Alexander and Ann Shulgin, in a photo from their book TiHKAL, c. ... Venom is a moniker used of several characters in the Marvel Comics fictional Marvel Universe. ... Peter Parker redirects here. ... Phenethyl alcohol, or 2-phenylethanol, is a natural organic compound that is found in a variety of essential oils, such as rose, carnation, hyacinth, Aleppo pine, orange blossom, geranium, neroli, and champaca. ... 2C is a general name for the family of psychedelic and entheogenic phenethylamines containing methoxy groups on the 2 and 5 positions of the benzene ring. ...

References

1. ^ ^{a b} Merck Index, 12th Edition, 7371.

External links

• MSDS for phenethylamine
• Book II of PiHKAL online
• Review and summary of PiHKAL, including table of 300+ phenethylamines: ascii postscript
• A Structural Tour of PiHKAL
• Links to external chemical sources