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Phenethylamine[1]
Chemical structure of Phenethylamine
IUPAC name 2-Phenylethylamine
Other names Phenethylamine
β-Phenylethylamine
2-Phenyl-1-aminoethane
β-Aminoethylamine
2-Phenylethanamine
Identifiers
CAS number [64-04-0]
SMILES c1ccccc1CCN
Properties
Molecular formula C8H11N
Molar mass 121. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 18 g/mol
Density 0. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 964 g/cm3
Melting point

-60 °C
Boiling point

194. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 5-195 °C
Hazards
MSDS MSDS for phenethylamine
NFPA 704
2
2
2
 
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Phenethylamine, or β-Phenylethylamine (2-Phenylethylamine), is an alkaloid and monoamine. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly This article is about the chemical compounds alkaloids For the Pharmaceutical company in the Republic of Macedonia see Alkaloid (company. Monoamine neurotransmitters are Neurotransmitters and Neuromodulators that contain one Amino group that is connected to an aromatic ring by a Phenethylamine also has a constitutional isomer α-Phenylethylamine (1-Phenylethylamine), which has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine. Stereoisomers are isomeric molecules that have the same molecular formula and sequence of bonded atoms (constitution but which differ in the three dimensional orientations In the human brain, 2-phenethylamine is believed to function as a neuromodulator or neurotransmitter (trace amine). In neuroscience neuromodulation is the process in which several classes of Neurotransmitters in the nervous system regulate diverse populations of Neurons (one See Chemical synapse for an introduction to concepts and terminology used in this article Trace amines are Endogenous compounds structurally related to classical Biogenic amines, such as Catecholamines, Serotonin and Histamine Phenethylamine is a natural compound biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. In Chemistry, an amino acid is a Molecule containing both Amine and Carboxyl Functional groups In Biochemistry, this Phe redirects here For the BitTorrent feature see PHE. For the constellation see Phoenix (constellation. Decarboxylation is any Chemical reaction in which a Carboxyl group (-COOH is split off from a compound as Carbon dioxide (CO2 It is also found in many foods such as chocolate, especially after microbial fermentation. Chocolate ( pronounced or /-ˈələt/ comprises a number of raw and processed foods that are produced from the seed of the tropical Cacao tree A microorganism (also spelled micro organism or micro-organism and also called a microbe) is an Organism that is Microscopic (usually Fermentation in Food processing typically refers to the conversion of Sugar to Alcohol using Yeast under Anaerobic conditions 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. Enzymes are Biomolecules that catalyze ( ie increase the rates of Chemical reactions Almost all enzymes are Proteins

Substituted phenethylamines are a broad and diverse class of compounds that include neurotransmitters, hormones, stimulants, hallucinogens, entactogens, anorectics, bronchodilators, and antidepressants. See Chemical synapse for an introduction to concepts and terminology used in this article Hormones (from Greek ὁρμή - "impetus" are chemicals released by cells that affect cells in other parts of the body Stimulant drugs are Drugs that temporarily increase alertness and awareness The general group of pharmacological agents commonly known as hallucinogens can be divided into three broad categories Psychedelics, Dissociatives The terms empathogen and entactogen are different terms used to describe a class of Psychoactive drugs that produce distinctive emotional and social effects similar Note "Anorectic" is also a term for an anorexic person a person suffering from Anorexia nervosa Anorectics, anorexigenics A bronchodilator is a substance that dilates the bronchi and Bronchioles decreasing airway resistance and thereby facilitating airflow An antidepressant is a Psychiatric medication used for alleviating major depression or Dysthymia ('milder' depression

Contents

Chemistry

Phenethylamine (PEA) is an aromatic amine, which is a colorless liquid at room temperature. It is soluble in water, ethanol, and ether. Diethyl ether, also known as ether and ethoxyethane, is a clear colorless and highly Flammable liquid with a low Boiling point and a [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. In Chemistry, a carbonate is a salt or Ester of Carbonic acid. Salt is a Dietary mineral composed primarily of Sodium chloride that is essential for Animal life but toxic to most land plants Carbon dioxide ( Chemical formula:) is a Chemical compound composed of two Oxygen Atoms covalently bonded to a single Phenethylamine is strongly basic and forms a stable crystalline hydrochloride salt with a melting point of 217 °C. In Chemistry, a base is most commonly thought of as an aqueous substance that can accept Protons This refers to the Brønsted-Lowry theory of acids and In chemistry hydrochlorides are salts resulting or regarded as resulting from the reaction of Hydrochloric acid with an organic base (mostly Amines Phenethylamine is also a skin irritant and possible sensitizer.

Neurochemistry

Infusion of PEA increased extracellular levels of dopamine[2] while at the same time inhibiting DA neuron firings. [3][4] It also modulates noradrenergic transmission. [5] It has GABAergic antagonism. [6]

Low levels are found in ADHD[7] and often in depression, while levels are elevated in schizophrenia. [8] 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, author of the popular 1983 book The Chemistry of Love, remarked to reporters that "chocolate is loaded with PEA. Dr Michael R Liebowitz is a Columbia University Psychiatrist and founder of the Anxiety Disorders Clinic, the first of its kind at the Chocolate ( pronounced or /-ˈələt/ comprises a number of raw and processed foods that are produced from the seed of the tropical Cacao tree " 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. "[9] However, as noted earlier, phenethylamine is rapidly metabolized by the enzyme MAO-B, preventing significant concentrations from reaching the brain, thus contributing no perceptible psychoactive effect. Enzymes are Biomolecules that catalyze ( ie increase the rates of Chemical reactions Almost all enzymes are Proteins

Substituted phenethylamines

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

Pharmacology

Many substituted phenethylamines are pharmacologically active drugs due to their similarity to the monoamine neurotransmitters:

Substitution table

Some of the more important phenethylamines are tabulated below. For simplicity, the stereochemistry of the sidechain is not covered in the table. Stereochemistry, a subdiscipline of Chemistry, involves the study of the relative spatial arrangement of Atoms within Molecules An important branch Hundreds of other simple synthetic phenethylamines are known. This is due in large part to the pioneering work of Alexander Shulgin, much of which is described in the book PiHKAL (Phenethylamines i Have Known And Loved). Alexander "Sasha" Shulgin (born June 17 1925 in Berkeley, California) is a Russian-American Pharmacologist, Chemist and PiHKAL is a 1991 book by Dr Alexander Shulgin and Ann Shulgin about Psychedelic Phenethylamines The full title of the book

Substituted phenethylamines, tabulated by structure
Short Name Rα Rβ R2 R3 R4 R5 RN Full Name
Tyramine OH 4-hydroxy-phenethylamine
Dopamine OH OH 3,4-dihydroxy-phenethylamine
Epinephrine (Adrenaline) OH OH OH CH3 β,3,4-trihydroxy-N-methylphenethylamine
Norepinephrine (Noradrenaline) OH OH OH β,3,4-trihydroxyphenethylamine
Phenylephrine OH OH CH3 β,3-dihydroxy-N-methylphenethylamine
6-Hydroxydopamine OH OH OH 2,4,5-trihydroxyphenethylamine
Salbutamol OH OH CH2OH C(CH3)3 β,4-dihydroxy-3-hydroxymethyl-N-tert-butyl-phenethylamine
Beta-methyl-phenethylamine CH3 β-methylphenethylamine
Amphetamine CH3 α-methylphenethylamine
Methamphetamine CH3 CH3 N-methylamphetamine
Methylphenidate N,α-butylene-β-methoxycarbonylphenethylamine
Ephedrine,
pseudoephedrine		 CH3 OH CH3 N-methyl-β-hydroxyamphetamine
Acetylamphetamine CH3 COCH3 α-methyl-3-acetylphenethylamine
Cathine CH3 OH β-hydroxy-amphetamine
Cathinone CH3 =O β-ketoamphetamine
Methcathinone CH3 =O CH3 N-methyl-β-ketoamphetamine
Bupropion CH3 =O Cl C(CH3)3 3-chloro-N-tert-butyl-β-ketoamphetamine
Fenfluramine CH3 CF3 CH2CH3 3-trifluoromethyl-N-ethyl-amphetamine
Phentermine 2CH3 α,α-dimethylphenethylamine
Mescaline OCH3 OCH3 OCH3 3,4,5-trimethoxyphenethylamine
MDA CH3 -O-CH2-O- 3,4-methylenedioxyamphetamine
MDMA CH3 -O-CH2-O- CH3 3,4-methylenedioxy-N-methylamphetamine
MDMC CH3 =O -O-CH2-O- CH3 3,4-methylenedioxy-N-methyl-β-ketoamphetamine
DOM CH3 OCH3 CH3 OCH3 2,5-dimethoxy-4-methylamphetamine
DOB CH3 OCH3 Br OCH3 2,5-dimethoxy-4-bromoamphetamine
DON CH3 OCH3 NO2 OCH3 2,5-dimethoxy-4-nitroamphetamine
2C-B OCH3 Br OCH3 2,5-dimethoxy-4-bromophenethylamine
2C-C OCH3 Cl OCH3 2,5-dimethoxy-4-chlorophenethylamine
DOI CH3 OCH3 I OCH3 2,5-dimethoxy-4-iodoamphetamine
2C-I OCH3 I OCH3 2,5-dimethoxy-4-iodophenethylamine
2C-D OCH3 CH3 OCH3 2,5-dimethoxy-4-methylphenethylamine
2C-E OCH3 CH2-CH3 OCH3 2,5-dimethoxy-4-ethylphenethylamine
2C-F OCH3 F OCH3 2,5-dimethoxy-4-fluorophenethylamine
2C-N OCH3 NO2 OCH3 2,5-dimethoxy-4-nitrophenethylamine
2C-T-2 OCH3 S-CH2CH3 OCH3 2,5-dimethoxy-4-ethylthio-phenethylamine
2C-T-4 OCH3 S-CH(CH3)2 OCH3 2,5-dimethoxy-4-isopropylthio-phenethylamine
2C-T-7 OCH3 S-CH2CH2CH3 OCH3 2,5-dimethoxy-4-propylthio-phenethylamine
2C-T-8 OCH3 S-CH2-C3H5 OCH3 2,5-dimethoxy-4-cyclopropylmethylthio-phenethylamine
2C-T-9 OCH3 S-C(CH3)3 OCH3 2,5-dimethoxy-4-tert-butylthio-phenethylamine
2C-T-21 OCH3 S-CH2-CH2-F OCH3 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine

Graphical overview

See also

PiHKAL (Phenethylamines i Have Known And Loved)

References

  1. ^ a b Merck Index, 12th Edition, 7371. In organic Chemistry tyramine (4-hydroxy- Phenethylamine, para-tyramine p-tyramine is a Monoamine compound derived from the Hydroxyl in Chemistry stands for a molecule consisting of an Oxygen atom and a Hydrogen atom connected by a Covalent bond. Dopamine is a Hormone and Neurotransmitter occurring in a wide variety of animals including both vertebrates and invertebrates In Chemistry, a methyl group is a Hydrophobic Alkyl Functional group named after Methane (4 In Chemistry, a methyl group is a Hydrophobic Alkyl Functional group named after Methane (4 Norepinephrine ( INN) (abbreviated norepi or NE) or noradrenaline ( BAN) (abbreviated NA or NAd) is a Phenylephrine or Neo-Synephrine is an α1-adrenergic receptor Agonist used primarily as a Decongestant, as an agent to dilate the 6-Hydroxydopamine, or 6-OHDA is a neurotoxin used by neurobiologists to selectively kill Dopaminergic and Noradrenergic neurons Salbutamol ( INN) or albuterol ( USAN) is a short-acting β2-adrenergic receptor agonist used for the relief of Bronchospasm Hydroxymethyl in the field of Chemistry, particularly in Organic chemistry, is the name for a Functional group with the Structural formula -CH2-OH In Organic chemistry, butyl is a four- Carbon Alkyl substituent with Chemical formula -C4H9. Hydroxymethyl in the field of Chemistry, particularly in Organic chemistry, is the name for a Functional group with the Structural formula -CH2-OH In Organic chemistry, butyl is a four- Carbon Alkyl substituent with Chemical formula -C4H9. Beta-methyl-phenethylamine is a drug related to Amphetamine. The chemical is also known under the name diamondina. Amphetamine, and related drugs such as Methamphetamine are a group of drugs that act by increasing levels of Norepinephrine, Serotonin, and Dopamine Ephedrine (EPH is a Sympathomimetic Amine commonly used as a Stimulant, appetite suppressant concentration aid Decongestant, and to treat Pseudoephedrine (commonly abbreviated as PSE is a sympathomimetic Amine commonly used as a Decongestant. Cathine (D- norpseudoephedrine) is a Monoamine Alkaloid found in the Shrub Catha edulis (khat Cathinone ( β - keto[[amphetamine]] is a Monoamine Alkaloid found in the Shrub Catha edulis ( Khat A ketone (pronounced as key tone) is either the Functional group characterized by a Carbonyl group (O=C linked to two other Carbon atoms or A ketone (pronounced as key tone) is either the Functional group characterized by a Carbonyl group (O=C linked to two other Carbon atoms or Methcathinone ( 2-(methylamino-propiophenone, α-methylamino-propiophenone) is a Psychoactive Stimulant. Bupropion ( INN, previously known as amfebutamone; sold as Wellbutrin, Zyban, and several other Trade names is an atypical Antidepressant Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and Fenfluramine is a drug that was part of the Fen/Phen anti- Obesity medication (the other drug being Phentermine) Trifluoromethyl is a Functional group in Chemistry that has the formula -CF3 In Chemistry, an ethyl group is an Alkyl Functional group derived from Ethane ( C 2 H 6 Trifluoromethyl is a Functional group in Chemistry that has the formula -CF3 In Chemistry, an ethyl group is an Alkyl Functional group derived from Ethane ( C 2 H 6 Phentermine, a contraction for " '''phen'''yl - '''ter'''tiary-butyl[[amine a' mine' ]]" is an Appetite suppressant of the Amphetamine Mescaline or 345-trimethoxyphenethylamine is a naturally-occurring Psychedelic Alkaloid of the Phenethylamine class In Chemistry (particularly Organic chemistry) methoxy refers to the Functional group consisting of a Methyl group bound to Oxygen In Chemistry (particularly Organic chemistry) methoxy refers to the Functional group consisting of a Methyl group bound to Oxygen 34-Methylenedioxyamphetamine ( MDA or Tenamfetamine) is a Psychedelic hallucinogenic drug and empathogen/entactogen of the Methylenedioxy in the field of Chemistry, particularly in Organic chemistry, is the name for a Functional group with the Structural formula -O-CH2-O- MDMA ( 34-methylenedioxy- N -methylamphetamine) most commonly known today by the street name Ecstasy (often abbreviated E, X, Explosion At the end of 2004, a new designer drug called ‘Explosion’ appeared in the Netherlands. DOM (or STP, allegedly standing for Serenity Tranquility and Peace but based on the motor oil company STP as named by Owsley Stanley) is a Psychedelic DOB, also known as Brolamfetamine and Bromo-DMA, is a Psychedelic hallucinogenic drug and a Substituted amphetamine of the 25-Dimethoxy-4-nitroamphetamine ( DON) is an analogue of DOM and DOB. Nitro compounds are Organic compounds that contain one or more nitro Functional groups (-2 Nitro compounds are Organic compounds that contain one or more nitro Functional groups (-2 2C-B or 4-bromo-25-dimethoxyphenethylamine is a psychedelic drug of the 2C family, an entactogen. 2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an Entheogen. DOI or 25-dimethoxy-4-iodoamphetamine is a Psychedelic drug and a Substituted amphetamine of the Phenethylamine family Iodine (ˈaɪədaɪn ˈaɪədɪn or /ˈaɪədiːn/ from ιώδης iodes "violet" is a Chemical element that has the symbol I and Atomic Iodine (ˈaɪədaɪn ˈaɪədɪn or /ˈaɪədiːn/ from ιώδης iodes "violet" is a Chemical element that has the symbol I and Atomic 2C-I is a psychedelic drug and Phenethylamine of the 2C family. 2C-D is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an Entheogen. 2C-E (25-dimethoxy-4-ethylphenethylamine is a psychedelic drug and phenethylamine of the 2C family. 2C-F, or 4-fluoro-25-dimethoxy Phenethylamine, is a lesser-known psychedelic drug of the 2C family. Fluorine, fluorum meaning "to flow" is the Chemical element with the symbol F and Atomic number 9 Fluorine, fluorum meaning "to flow" is the Chemical element with the symbol F and Atomic number 9 2C-N, or 25-Dimethoxy-4-nitrophenethylamine is a Psychedelic Phenethylamine of the 2C family. 2C-T-2, or 25-di Methoxy -4- Ethyl[[thio]][[phenethylamine]], is a Psychedelic and Entheogenic Phenethylamine of the The prefix thio-, when applied to a chemical such as an Ion, denotes that there is at least one extra Sulfur Atom added to the chemical named The prefix thio-, when applied to a chemical such as an Ion, denotes that there is at least one extra Sulfur Atom added to the chemical named 2C-T-4 or 25-dimethoxy-4-isopropylthiophenethylamine is a Psychedelic Phenethylamine of the 2C family. In Organic chemistry, isopropyl is a substituent form of Propane, the three- Carbon Alkyl Functional group. In Organic chemistry, isopropyl is a substituent form of Propane, the three- Carbon Alkyl Functional group. 2C-T-7 is a Hallucinogenic Phenethylamine of the 2C family. In his book PiHKAL (Phenethylamines i Have Known And Loved, 2C-T-8 is a Psychedelic Phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an Entheogen Cyclopropane is a Cycloalkane Molecule with the molecular formula C3H6 consisting of three Carbon Atoms linked to Cyclopropane is a Cycloalkane Molecule with the molecular formula C3H6 consisting of three Carbon Atoms linked to 2C-T-9 is a Psychedelic Phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an Entheogen 2C-T-21 is a Psychedelic Phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an Entheogen Alexander "Sasha" Shulgin (born June 17 1925 in Berkeley, California) is a Russian-American Pharmacologist, Chemist and PiHKAL is a 1991 book by Dr Alexander Shulgin and Ann Shulgin about Psychedelic Phenethylamines The full title of the book Phenethyl alcohol, or 2-phenylethanol, is the Organic compound with the formula C6H5CH2CH2OH 2C is a general name for the family of Psychedelic Phenethylamines containing methoxy groups on the 2 and 5 positions of the Benzene
  2. ^ Nakamura, Ishii, Nakahara. "Characterization of β-phenylethylamine-induced monoamine release in rat nucleus accumbens : a microdialysis study". European journal of pharmacology.  
  3. ^ Kota Ishida, Mikio Murata et al. (2005). "Effects of -Phenylethylamine on Dopaminergic Neurons of the Ventral Tegmental Area in the Rat: A Combined Electrophysiological and Microdialysis Study". Journal of Pharmacology And Experimental Therapeutics Fast Forward 314: 916. doi:10.1124/jpet.105.084764. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 15879004.  
  4. ^ EM Parker and LX Cubeddu. "Comparative effects of amphetamine, phenylethylamine and related drugs on dopamine efflux, dopamine uptake and mazindol binding" (abstract). PMID 3129549.  
  5. ^ I. A. Paterson (1993). "The potentiation of cortical neuron responses to noradrenaline by 2-phenylethylamine is independent of endogenous noradrenaline". Neurochemical Resarch 18: 1329. doi:10.1007/BF00975055. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
  6. ^ M Federici et al. . "Citation is missing a {{{title}}}. Either specify one, or click here and a bot will complete the citation details for you. {{{title}}}" (abstract).  
  7. ^ Baker GB et al. . "Phenylethylaminergic mechanisms in attention-deficit disorder".  
  8. ^ SG Potkin et al (1979). "Phenylethylamine in paranoid chronic schizophrenia". Science 206: 470. doi:10.1126/science.504988. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
  9. ^ Liebowitz, Michael, R. (1983). The Chemistry of Love. Boston: Little, Brown, & Co.

External links

Dictionary

phenethylamine

-noun

  1. (uncountable, organic chemistry) An aromatic amine which is a colorless liquid at room temperature.
  2. (countable, organic chemistry) One of a group of compounds derived from phenethylamine.
  3. (biochemistry) A monoamine neurotransmitter and neuromodulator found in the brain.
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