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{{BioPsy}}
 
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{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
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<table border="1" cellpadding="2" cellspacing="0" align="right" style="margin-left:1em">
  
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! {{chembox header}}| '''{{{name|Phenethylamine}}}''' <ref name ="Merck">''Merck Index'', 12th Edition, '''7371'''.</ref>
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|-
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<tr><th colspan="2" align=center bgcolor="#cccccc">'''Phenethylamine'''</th></tr>
  
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| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Phenethylamine structure.png|Chemical structure of Phenethylamine]] <br>[[Image:Phenethylamine-3d.png|150px]]
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|-
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<tr><td>[[IUPAC nomenclature|Chemical name]]</td><td>2-Phenyl-ethylamine or<br>2-phenylethanamine</td></tr>
  
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| [[IUPAC nomenclature|Chemical name]]
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| {{{IUPAC|2-Phenylethylamine}}}
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<tr><td>[[Chemical formula]]</td><td>C<sub>8</sub>H<sub>11</sub>N</td></tr>
  
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|-
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| Other names
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<tr><td>[[Molecular mass]]</td><td>121.18 g/mol</td></tr>
  
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| Phenethylamine<br>β-Phenylethylamine<br>2-Phenyl-1-aminoethane<br>β-Aminoethylamine<br>2-Phenylethanamine
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|-
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<tr><td>[[Density]]</td><td>0.965 g/ml</td></tr>
  
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| [[Chemical formula]]
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| {{{formula|C<sub>8</sub>H<sub>11</sub>N}}}
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<tr><td>[[Melting point]]</td><td>-60 °C</td></tr>
  
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|-
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| [[Molecular mass]]
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<tr><td>[[Boiling point]]</td><td>200 °C</td></tr>
  
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| {{{mol_mass|121.18}}} g/mol
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|-
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<tr><td>[[CAS registry number|CAS number]]</td><td>64-04-0</td></tr>
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| [[CAS registry number|CAS number]]
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| [{{{CAS|64-04-0}}}]
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<tr><td>[[Simplified molecular input line entry specification|SMILES]]</td>
  
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|-
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<td>c1ccccc1CCN</td></tr>
  
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| [[Density]]
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| {{{density|0.964}}} g/cm<sup>3</sup>
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<tr><td colspan="2" align="center">[[Image:Phenethylamine_structure.png|Chemical structure of Phenethylamine]]</td></tr>
  
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|-
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| [[Melting point]]
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| {{{melting_point|-60}}} °C
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|-
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| [[Boiling point]]
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| {{{boiling_point|194.5-195}}} °C
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|-
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| [[Simplified molecular input line entry specification|SMILES]]
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| {{{SMILES|c1ccccc1CCN}}}
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|-
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| [[NFPA 704]]
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| {{NFPA 704 | Health=2 | Flammability=2 |Reactivity=2}}
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|-
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| {{chembox header}} | <small>[[wikipedia:Chemical infobox|Disclaimer and references]]</small>
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|-
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|}
   
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'''Phenethylamine''' ('''PEA'''), 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 [[Microorganism|microbial]] [[fermentation (food)|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.
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</table>
  
   
  ⚫
'''Substituted phenethylamines''' are a broad and diverse class of compounds that include [[neurotransmitter]]s, [[hormone]]s, [[stimulant]]s, [[Psychedelics, dissociatives and deliriants|hallucinogens]], [[empathogen-entactogen|entactogen]]s, [[anorectic]]s, [[bronchodilator]]s, and [[antidepressant]]s. 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]].
⚫
'''Phenethylamine''' (''&beta;''-Phenylethylamine) is an [[alkaloid]] and [[monoamine]]. In the human brain, it is believed to function as a [[neuromodulator]] or [[neurotransmitter]] ([[trace amine]]). A colorless liquid that forms a solid [[carbonate]] [[salt]] with [[carbon dioxide]] (CO<sub>2</sub>) upon exposure to air, phenethylamine in nature is synthesized from the [[amino acid]] [[phenylalanine]] by enzymatic [[decarboxylation]]. It is also found in many foods, especially after [[Microorganism|microbial]] [[fermentation]], e.g., in [[chocolate]].
  
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It has been suggested that phenethylamine from food (e.g., chocolate) may have psychoactive effects in sufficient quantities. However, it is quickly metabolized by the [[enzyme]] [[MAO-B]], preventing significant concentrations from reaching the brain.
 
   
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== Chemistry ==
⚫
'''Substituted phenethylamines''' are a broad and diverse class of compounds that include [[neurotransmitter]]s, [[hormone]]s, [[stimulant]]s, [[Psychedelics, dissociatives and deliriants|hallucinogens]], [[empathogen-entactogen|entactogen]]s, [[anorectic]]s, [[bronchodilator]]s, and [[antidepressant]]s.
  
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Phenethylamine is an [[aromatic]] amine which is a colorless liquid at room temperature. It is soluble in water, [[ethanol]], and [[diethyl ether|ether]].<ref name ="Merck"/> 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 [[base (chemistry)|basic]] and forms a stable crystalline [[hydrochloride]] salt with a melting point of 217 °C. Phenethylamine is also a skin irritant and possible sensitizer.
   
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==Chocolate theory of love==
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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]].
 
  +
In the early 1980s, [[chemistry of love]] researcher [[Michael Libowitz]], author of the popular 1983 book ''The Chemistry of Love'', remarked to reporters that “chocolate was 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”.<ref>Liebowitz, Michael, R. (1983). ''The Chemistry of Love''. Boston: Little, Brown, & Co.</ref>
   
 
== Substituted phenethylamines ==
  
== Substituted phenethylamines ==
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[[Image:Phenethylamine rests.png|frame|right|General structure of phenethylamines and amphetamines (see the table below).]]
  
[[Image:Phenethylamine rests.png|frame|right|General structure of phenethylamines and amphetamines (see the table below).]]
   
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[[Substitution|Substituted]] phenethylamines carry additional chemical modifications at the [[phenyl]] ring, the [[sidechain]], or the [[amino]] group:
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[[Substitution (chemistry)|Substituted]] phenethylamines carry additional chemical modifications at the [[phenyl]] ring, the [[sidechain]], or the [[amino]] group:
   
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* [[Amphetamine]]s are [[homologous series|homologue]]s of phenethylamines carrying an alpha-methyl (''&alpha;''-CH<sub>3</sub>) group at the sidechain [[carbon]] atom next to the amino group.
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* [[Substituted Amphetamines]] are [[homologous series|homologue]]s of phenethylamines carrying an alpha-methyl (''α''-CH<sub>3</sub>) group at the sidechain [[carbon]] atom next to the amino group.
 
* [[Catecholamine]]s 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).
  
* [[Catecholamine]]s 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.
  
* The [[aromatic]] amino acids [[phenylalanine]] and [[tyrosine]] are phenethylamines carrying a [[carboxyl]] group (COOH) in alpha position.
  +
* [[2C's]] are phenethylamines with [[Methoxy|methoxy groups]] attached to the 2 and 5 carbons and no alpha-methyl group.
   
 
== Pharmacology ==
  
== Pharmacology ==
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Many substituted phenethylamines are [[Pharmacology|pharmacologically]] active drugs due to their similarity to the monoamine neurotransmitters:
  
Many substituted phenethylamines are [[Pharmacology|pharmacologically]] active drugs due to their similarity to the monoamine neurotransmitters:
   
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* [[Stimulant]]s like the plant alkaloids [[ephedrine]] and [[cathinone]] and the synthetic drugs [[amphetamine]] (''speed'', ''benzedrine'') and [[methylphenidate]]
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* [[Stimulant]]s like the plant alkaloids [[ephedrine]] and [[cathinone]] and the synthetic drug [[dextroamphetamine]] and [[methylphenidate]].
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* [[Psychedelics, dissociatives and deliriants|Hallucinogens]] like the plant alkaloid [[mescaline]] and the synthetic drug [[2C-B]]
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* [[Psychedelics, dissociatives and deliriants|Hallucinogens]] like the plant alkaloid [[mescaline]] and the synthetic drug [[2C-B]].
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* [[Empathogen-entactogen]]s like [[MDMA]] (''ecstasy'') and [[3,4-methylenedioxyamphetamine|MDA]]
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* [[Empathogen-entactogen]]s like [[MDMA]] (''ecstasy'') and [[3,4-methylenedioxyamphetamine|MDA]].
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* [[Anorectic]]s like [[phentermine]], [[fenfluramine]], and [[amphetamine]]
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* [[Anorectic]]s like [[phentermine]], [[fenfluramine]], and [[amphetamine]].
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* [[Bronchodilator]]s like [[salbutamol]] and [[ephedrine]]
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* [[Bronchodilator]]s like [[salbutamol]] and [[ephedrine]].
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* [[Antidepressant]]s like [[bupropion]] and the [[monoamine oxidase inhibitor]]s [[phenelzine]] and [[tranylcypromine]].
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* [[Antidepressant]]s like [[venlafaxine]], [[bupropion]] and the [[monoamine oxidase inhibitor]]s [[phenelzine]] and [[tranylcypromine]].
   
 
== Substitution table ==
  
== Substitution table ==
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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]].
  
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]].
   
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{| border="1" cellspacing="0"
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{| class="wikitable"
 
|+ '''Substituted phenethylamines''', tabulated by structure
  
|+ '''Substituted phenethylamines''', tabulated by structure
 
! Short Name
  
! Short Name
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! ''R<sub>&alpha;</sub>''
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! ''R<sub>α</sub>''
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! ''R<sub>&beta;</sub>''
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! ''R<sub>β</sub>''
 
! ''R<sub>2</sub>''
  
! ''R<sub>2</sub>''
 
! ''R<sub>3</sub>''
 
! ''R<sub>3</sub>''
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|[[Dopamine]] || || || || [[Hydroxy|OH]] || [[Hydroxy|OH]] || || || 3,4-di[[hydroxy]]-<nowiki>phenethylamine</nowiki>
 
|[[Dopamine]] || || || || [[Hydroxy|OH]] || [[Hydroxy|OH]] || || || 3,4-di[[hydroxy]]-<nowiki>phenethylamine</nowiki>
 
|-
  
|-
−
|[[Epinephrine]] (Adrenaline) || || [[Hydroxy|OH]]|| || [[Hydroxy|OH]] || [[Hydroxy|OH]] || || [[Methyl|CH<sub>3</sub>]]|| &beta;,3,4-tri[[hydroxy]]-''N''-[[methyl]]-<nowiki>phenethylamine</nowiki>
+
|[[Epinephrine]] (Adrenaline) || || [[Hydroxy|OH]]|| || [[Hydroxy|OH]] || [[Hydroxy|OH]] || || [[Methyl|CH<sub>3</sub>]]|| β,3,4-tri[[hydroxy]]-''N''-[[methyl]]-<nowiki>phenethylamine</nowiki>
 
|-
  
|-
−
|[[Norepinephrine]] (Noradrenaline) || || [[Hydroxy|OH]]|| || [[Hydroxy|OH]] || [[Hydroxy|OH]] || || || &beta;,3,4-tri[[hydroxy]]<nowiki>phenethylamine</nowiki>
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|[[Norepinephrine]] (Noradrenaline) || || [[Hydroxy|OH]]|| || [[Hydroxy|OH]] || [[Hydroxy|OH]] || || || β,3,4-tri[[hydroxy]]<nowiki>phenethylamine</nowiki>
 
|-
  
|-
−
|[[Salbutamol]] || || [[hydroxyl|OH]] || || || [[hydroxyl|OH]] || CH<sub>2</sub>CH<sub>2</sub>OH || C(CH<sub>3</sub>)<sub>3</sub> || 4-(2-(''tert''-Butylamino)-1-hydroxyethyl)-2-(hydroxymethyl)phenol
 +
|[[Salbutamol]] || || [[hydroxyl|OH]] || || || [[hydroxyl|OH]] || CH<sub>2</sub>OH || [[Butyl|C(CH<sub>3</sub>)<sub>3</sub>]] || β,4-di[[hydroxy]]-3-[[hydroxy]][[methyl]]-''N''-(''t'')-[[butyl]]-phenethylamine
 
|-
  
|-
−
|[[Amphetamine]] || [[Methyl|CH<sub>3</sub>]] || || || || || || || &alpha;-[[methyl]]-<nowiki>phenethylamine</nowiki>
+
|[[Beta-Methyl-phenethylamine]] || || [[Methyl|CH<sub>3</sub>]] || || || || || || β-[[methyl]]-<nowiki>phenethylamine</nowiki>
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|-
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|[[Amphetamine]] || [[Methyl|CH<sub>3</sub>]] || || || || || || || α-[[methyl]]-<nowiki>phenethylamine</nowiki>
 
|-
  
|-
 
|[[Methamphetamine]]|| [[Methyl|CH<sub>3</sub>]] || || || || || || [[Methyl|CH<sub>3</sub>]] || ''N''-[[methyl]]-[[amphetamine]]
 
|[[Methamphetamine]]|| [[Methyl|CH<sub>3</sub>]] || || || || || || [[Methyl|CH<sub>3</sub>]] || ''N''-[[methyl]]-[[amphetamine]]
 
|-
  
|-
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|[[Levmetamfetamine]]|| [[Methyl|CH<sub>3</sub>]] || || || || || || [[Methyl|CH<sub>3</sub>]]
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|[[Methylphenidate]] || || || || || || || || ''N'',α-[[butylene]]-β-[[methoxy]][[carbonyl]]-phenethylamine
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|| ''N''-[[methyl]]-[[amphetamine]]
  
 
|-
  
|-
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|[[Ephedrine]],<br>[[pseudoephedrine]]|| [[Methyl|CH<sub>3</sub>]] || [[Hydroxy|OH]] || || || || || [[Methyl|CH<sub>3</sub>]] || ''N''-[[methyl]]-&beta;-[[hydroxy]]-[[amphetamine]]
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|[[Ephedrine]],<br>[[pseudoephedrine]]|| [[Methyl|CH<sub>3</sub>]] || [[Hydroxy|OH]] || || || || || [[Methyl|CH<sub>3</sub>]] || ''N''-[[methyl]]-β-[[hydroxy]]-[[amphetamine]]
 
|-
  
|-
−
|[[Cathine]] || [[Methyl|CH<sub>3</sub>]] || [[hydroxy|OH]] || || || || || || &beta;-[[hydroxy]]-[[amphetamine]]
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|[[Cathine]] || [[Methyl|CH<sub>3</sub>]] || [[hydroxy|OH]] || || || || || || β-[[hydroxy]]-[[amphetamine]]
 
|-
  
|-
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|[[Cathinone]] || [[Methyl|CH<sub>3</sub>]] || [[ketone|=O]] || || || || || || &beta;-[[ketone|keto]]-[[amphetamine]]
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|[[Cathinone]] || [[Methyl|CH<sub>3</sub>]] || [[ketone|=O]] || || || || || || β-[[ketone|keto]]-[[amphetamine]]
 
|-
  
|-
−
|[[Methcathinone]] || [[Methyl|CH<sub>3</sub>]] || [[ketone|=O]] || || || || ||[[Methyl|CH<sub>3</sub>]] || ''N''-[[methyl]]-&beta;-[[ketone|keto]]-[[amphetamine]]
 +
|[[Methcathinone]] || [[Methyl|CH<sub>3</sub>]] || [[ketone|=O]] || || || || ||[[Methyl|CH<sub>3</sub>]] || ''N''-[[methyl]]-β-[[ketone|keto]]-[[amphetamine]]
 
|-
  
|-
−
|[[Bupropion]] || [[Methyl|CH<sub>3</sub>]] || [[ketone|=O]] || || [[chlorine|Cl]] || || ||C(CH<sub>3</sub>)<sub>3</sub> || 3-[[chloro]]-''N''-''tert''-butyl-&beta;-[[ketone|keto]]-[[amphetamine]]
 +
|[[Bupropion]] || [[Methyl|CH<sub>3</sub>]] || [[ketone|=O]] || || [[chlorine|Cl]] || || || [[Butyl|C(CH<sub>3</sub>)<sub>3</sub>]] || 3-[[chloro]]-''N''-(''t'')-[[butyl]]-β-[[ketone|keto]]-[[amphetamine]]
 
|-
  
|-
 
|[[Fenfluramine]]|| [[Methyl|CH<sub>3</sub>]] || || || [[Carbon|C]][[Fluorine|F]]<sub>3</sub> || || || [[Ethyl|CH<sub>2</sub>CH<sub>3</sub>]] || 3-tri[[fluoro]][[methyl]]-''N''-[[ethyl]]-[[amphetamine]]
 
|[[Fenfluramine]]|| [[Methyl|CH<sub>3</sub>]] || || || [[Carbon|C]][[Fluorine|F]]<sub>3</sub> || || || [[Ethyl|CH<sub>2</sub>CH<sub>3</sub>]] || 3-tri[[fluoro]][[methyl]]-''N''-[[ethyl]]-[[amphetamine]]
 
|-
  
|-
−
|[[Phentermine]] || [[Methyl|CH<sub>3</sub>]],[[Methyl|CH<sub>3</sub>]] || || || || || || || &alpha;,&alpha;-di[[methyl]]-<nowiki>phenethylamine</nowiki>
+
|[[Phentermine]] || [[Methyl|CH<sub>3</sub>]],[[Methyl|CH<sub>3</sub>]] || || || || || || || α,α-di[[methyl]]-<nowiki>phenethylamine</nowiki>
 
|-
  
|-
 
|[[Mescaline]] || || || || [[Methoxy|OCH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || || 3,4,5-tri[[methoxy]]-<nowiki>phenethylamine</nowiki>
  
|[[Mescaline]] || || || || [[Methoxy|OCH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || || 3,4,5-tri[[methoxy]]-<nowiki>phenethylamine</nowiki>
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|-
  
|-
 
|[[MDMA]] || [[Methyl|CH<sub>3</sub>]] || || ||colspan=2| -O-CH<sub>2</sub>-O- || || [[Methyl|CH<sub>3</sub>]] || 3,4-[[methylene]]dioxy-''N''-[[methyl]]-[[amphetamine]]
  
|[[MDMA]] || [[Methyl|CH<sub>3</sub>]] || || ||colspan=2| -O-CH<sub>2</sub>-O- || || [[Methyl|CH<sub>3</sub>]] || 3,4-[[methylene]]dioxy-''N''-[[methyl]]-[[amphetamine]]
  +
|-
  +
|[[MDMC]] || [[Methyl|CH<sub>3</sub>]] || [[ketone|=O]] || ||colspan=2| -O-CH<sub>2</sub>-O- || || [[Methyl|CH<sub>3</sub>]] || 3,4-[[methylene]]dioxy-''N''-[[methyl]]-β-[[ketone|keto]]-[[amphetamine]]
 
|-
  
|-
 
|[[2,5-dimethoxy-4-methylamphetamine|DOM]] || [[Methyl|CH<sub>3</sub>]] || || [[Methoxy|OCH<sub>3</sub>]] || || [[Methyl|CH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[methyl]]-[[amphetamine]]
  
|[[2,5-dimethoxy-4-methylamphetamine|DOM]] || [[Methyl|CH<sub>3</sub>]] || || [[Methoxy|OCH<sub>3</sub>]] || || [[Methyl|CH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[methyl]]-[[amphetamine]]
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|-
  
|-
 
|[[2C-E]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[Ethyl|CH<sub>2</sub>CH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[ethyl]]-<nowiki>phenethylamine</nowiki>
  
|[[2C-E]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[Ethyl|CH<sub>2</sub>CH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[ethyl]]-<nowiki>phenethylamine</nowiki>
  +
|-
  +
|[[2C-F]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[fluorine|F]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[Fluoro]]-<nowiki>phenethylamine</nowiki>
 
|-
  
|-
 
|[[2C-N]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[Nitro|NO<sub>2</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[Nitro]]-<nowiki>phenethylamine</nowiki>
  
|[[2C-N]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[Nitro|NO<sub>2</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[Nitro]]-<nowiki>phenethylamine</nowiki>
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|[[2C-T-2]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]][[Ethyl|CH<sub>2</sub>CH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[ethyl]][[thio]]-<nowiki>phenethylamine</nowiki>
  
|[[2C-T-2]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]][[Ethyl|CH<sub>2</sub>CH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[ethyl]][[thio]]-<nowiki>phenethylamine</nowiki>
 
|-
  
|-
−
|[[2C-T-4]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]][[Isopropyl|CHCH<sub>3</sub>CH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-(i)-[[propyl]][[thio]]-<nowiki>phenethylamine</nowiki>
 +
|[[2C-T-4]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]][[Isopropyl|CHCH<sub>3</sub>CH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-(''i'')-[[propyl]][[thio]]-<nowiki>phenethylamine</nowiki>
 
|-
  
|-
 
|[[2C-T-7]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]][[Propyl|CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[propyl]][[thio]]-<nowiki>phenethylamine</nowiki>
  
|[[2C-T-7]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]][[Propyl|CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[propyl]][[thio]]-<nowiki>phenethylamine</nowiki>
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|[[2C-T-8]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]][[Methyl|CH<sub>2</sub>]][[Cyclopropyl|CHCH<sub>2</sub>CH<sub>2</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[cyclopropyl]][[methyl]][[thio]]-<nowiki>phenethylamine</nowiki>
  
|[[2C-T-8]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]][[Methyl|CH<sub>2</sub>]][[Cyclopropyl|CHCH<sub>2</sub>CH<sub>2</sub>]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[cyclopropyl]][[methyl]][[thio]]-<nowiki>phenethylamine</nowiki>
 
|-
  
|-
−
|[[2C-T-9]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]]-[[(t)-Butyl|(CH<sub>3</sub>)<sub>3</sub>C]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-[[(t)-Butyl]][[thio]]-<nowiki>phenethylamine</nowiki>
 +
|[[2C-T-9]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]]-[[Butyl|(CH<sub>3</sub>)<sub>3</sub>C]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-(''t'')-[[Butyl]][[thio]]-<nowiki>phenethylamine</nowiki>
 
|-
  
|-
 
|[[2C-T-21]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]]CH<sub>2</sub>CH<sub>2</sub>[[fluorine|F]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-(2-[[fluoro]][[ethyl]][[thio]])-<nowiki>phenethylamine</nowiki>
  
|[[2C-T-21]]|| || || [[Methoxy|OCH<sub>3</sub>]] || || [[sulfur|S]]CH<sub>2</sub>CH<sub>2</sub>[[fluorine|F]] || [[Methoxy|OCH<sub>3</sub>]] || ||2,5-di[[methoxy]]-4-(2-[[fluoro]][[ethyl]][[thio]])-<nowiki>phenethylamine</nowiki>
 
|}
  
|}
   
  +
== Graphical overview ==
−
[[Image:Overview Phenethylamines.png|500px]]
 +
[[Image:Overview Phenethylamines.png|600px]]
   
 
== See also ==
 
== See also ==
  +
* [[Amphetamines]]
−  
 
* [[Catecholamine]]s
  
* [[Catecholamine]]s
 
* [[PiHKAL]]
  
* [[PiHKAL]]
 
* [[Alexander Shulgin]]
  
* [[Alexander Shulgin]]
  +
* [[Phenethyl alcohol]]
−
* [[Venom (comics)]] The alien symbiote relies on this chemical.
  
  +
* [[2C (psychedelics)|2C's]]
−
* [[chocolate]] This substance is found in chocolate.
  
   
  +
==References==
⚫
== External links ==
  
  +
<references/>
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  +
  ⚫
== External links ==
  +
* [http://www.sciencelab.com/xMSDS-Phenethylamine-9927690 MSDS for phenethylamine]
 
* [http://www.erowid.org/library/books_online/pihkal/pihkal.shtml Book II of PiHKAL] online
  
* [http://www.erowid.org/library/books_online/pihkal/pihkal.shtml Book II of PiHKAL] online
 
* Review and summary of PiHKAL, including table of 300+ phenethylamines: [http://www.erowid.org/archive/hyperreal/drugs/psychedelics/phenethylamines/pihkal.review ascii] [http://www.erowid.org/archive/hyperreal/drugs/psychedelics/phenethylamines/pihkal.review.ps postscript]
  
* Review and summary of PiHKAL, including table of 300+ phenethylamines: [http://www.erowid.org/archive/hyperreal/drugs/psychedelics/phenethylamines/pihkal.review ascii] [http://www.erowid.org/archive/hyperreal/drugs/psychedelics/phenethylamines/pihkal.review.ps postscript]
 
* [http://www.erowid.org/archive/rhodium/chemistry/pihkaltour/ A Structural Tour of PiHKAL]
  
* [http://www.erowid.org/archive/rhodium/chemistry/pihkaltour/ A Structural Tour of PiHKAL]
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== Categorization ==
  
   
 
{{Phenethylamines}}
  
{{Phenethylamines}}
 
{{Hallucinogenic phenethylamines}}
  
{{Hallucinogenic phenethylamines}}
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{{PiHKAL}}
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[[Category:Amines]]
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[[Category:Phenethylamines| ]]
   
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[[fi:Fenetyyliamiini]][http://www.batbat.batcave.net/phentermine phentermine]
  
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Latest revision as of 00:52, 25 April 2008

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Phenethylamine [1]
Chemical structure of Phenethylamine
Phenethylamine-3d
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
NFPA 704
2
2
2
 


Disclaimer and references

Phenethylamine (PEA), 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.

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.

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.

Chocolate theory of love

In the early 1980s, chemistry of love researcher Michael Libowitz, author of the popular 1983 book The Chemistry of Love, remarked to reporters that “chocolate was 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”.[2]

Substituted phenethylamines

Phenethylamine rests

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. 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.

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-methyl-phenethylamine
Norepinephrine (Noradrenaline) OH OH OH β,3,4-trihydroxyphenethylamine
Salbutamol OH OH CH2OH C(CH3)3 β,4-dihydroxy-3-hydroxymethyl-N-(t)-butyl-phenethylamine
Beta-Methyl-phenethylamine CH3 β-methyl-phenethylamine
Amphetamine CH3 α-methyl-phenethylamine
Methamphetamine CH3 CH3 N-methyl-amphetamine
Methylphenidate N,α-butylene-β-methoxycarbonyl-phenethylamine
Ephedrine,
pseudoephedrine		 CH3 OH CH3 N-methyl-β-hydroxy-amphetamine
Cathine CH3 OH β-hydroxy-amphetamine
Cathinone CH3 =O β-keto-amphetamine
Methcathinone CH3 =O CH3 N-methyl-β-keto-amphetamine
Bupropion CH3 =O Cl C(CH3)3 3-chloro-N-(t)-butyl-β-keto-amphetamine
Fenfluramine CH3 CF3 CH2CH3 3-trifluoromethyl-N-ethyl-amphetamine
Phentermine CH3,CH3 α,α-dimethyl-phenethylamine
Mescaline OCH3 OCH3 OCH3 3,4,5-trimethoxy-phenethylamine
MDA CH3 -O-CH2-O- 3,4-methylenedioxy-amphetamine
MDMA CH3 -O-CH2-O- CH3 3,4-methylenedioxy-N-methyl-amphetamine
MDMC CH3 =O -O-CH2-O- CH3 3,4-methylenedioxy-N-methyl-β-keto-amphetamine
DOM CH3 OCH3 CH3 OCH3 2,5-dimethoxy-4-methyl-amphetamine
DOB CH3 OCH3 Br OCH3 2,5-dimethoxy-4-bromo-amphetamine
DON CH3 OCH3 NO2 OCH3 2,5-dimethoxy-4-nitro-amphetamine
2C-B OCH3 Br OCH3 2,5-dimethoxy-4-bromo-phenethylamine
2C-C OCH3 Cl OCH3 2,5-dimethoxy-4-chloro-phenethylamine
DOI CH3 OCH3 I OCH3 2,5-dimethoxy-4-iodo-amphetamine
2C-I OCH3 I OCH3 2,5-dimethoxy-4-iodo-phenethylamine
2C-D OCH3 CH3 OCH3 2,5-dimethoxy-4-methyl-phenethylamine
2C-E OCH3 CH2CH3 OCH3 2,5-dimethoxy-4-ethyl-phenethylamine
2C-F OCH3 F OCH3 2,5-dimethoxy-4-Fluoro-phenethylamine
2C-N OCH3 NO2 OCH3 2,5-dimethoxy-4-Nitro-phenethylamine
2C-T-2 OCH3 SCH2CH3 OCH3 2,5-dimethoxy-4-ethylthio-phenethylamine
2C-T-4 OCH3 SCHCH3CH3 OCH3 2,5-dimethoxy-4-(i)-propylthio-phenethylamine
2C-T-7 OCH3 SCH2CH2CH3 OCH3 2,5-dimethoxy-4-propylthio-phenethylamine
2C-T-8 OCH3 SCH2CHCH2CH2 OCH3 2,5-dimethoxy-4-cyclopropylmethylthio-phenethylamine
2C-T-9 OCH3 S-(CH3)3C OCH3 2,5-dimethoxy-4-(t)-Butylthio-phenethylamine
2C-T-21 OCH3 SCH2CH2F OCH3 2,5-dimethoxy-4-(2-fluoroethylthio)-phenethylamine

Graphical overview

Overview Phenethylamines

See also

References

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Phenethylamines

{2C-B} {2C-C} {2C-D} {2C-E} {2C-I} {2C-N} {2C-T-2} {2C-T-21} {2C-T-4} {2C-T-7} {2C-T-8} {3C-E} {4-FMP} {Bupropion} {Cathine} {Cathinone} {DESOXY} {Dextroamphetamine} {Methamphetamine} {Diethylcathinone} {Dimethylcathinone} {DOC} {DOB} {DOI} {DOM} {bk-MBDB} {Dopamine} {Br-DFLY} {Ephedrine} {Epinephrine} {Escaline} {Fenfluramine} {Levalbuterol} {Levmetamfetamine} {MBDB} {MDA} {MDMA} {bk-MDMA/MDMC/MDMCat/Methylone} {MDEA} (MDPV) {Mescaline} {Methcathinone} {Methylphenidate} {Norepinephrine} {Phentermine} {Salbutamol} {Tyramine} {Venlafaxine}

Psychedelic phenethylamines

Aleph • 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-O • 2C-O-4 • 2C-P • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 3C-E • 3C-P • Br-DFLY • DESOXY • DMMDA-2 • DOB • DOC • DOET • DOI • DOM • DON • Escaline • Ganesha • HOT-2 • HOT-7 • HOT-17 • Isoproscaline • Lophophine • MDA • MMDA • MMDA-2 • MMDA-3a • MMDMA • Macromerine • Mescaline • Proscaline • TMA

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