User:Mark PEA/Phenethylamine

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Phenethylamine[1]
Chemical structure of Phenethylamine
Names
IUPAC name
2-Phenylethylamine
Other names
Phenethylamine
β-Phenylethylamine
2-Phenyl-1-aminoethane
β-Aminoethylamine
2-Phenylethanamine
Identifiers
3D model (
JSmol
)
UNII
  • c1ccccc1CCN
Properties
C8H11N
Molar mass 121.18 g/mol
Density 0.964 g/cm3
Melting point -60 °C
Boiling point 194.5-195 °C
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
2
2
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phenethylamine, or β-Phenylethylamine (2-Phenylethylamine), is an

fermentation. It has been shown that phenylethylamine as a supplement in doses of roughly 1-2 grams has psychoactive effects.[2]

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

entactogens, anorectics, bronchodilators, and antidepressants
.

Chemistry

Phenethylamine (PEA) 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.

Neurochemistry

Infusion of PEA increased extracellular levels of dopamine[3] while at the same time inhibiting DA neuron firings.[4][5] It also modulates noradrenergic transmission.[6] It has GABAergic antagonism.[7]

Low levels are found in ADHD[8] and often in depression, while levels are elevated in schizophrenia.[9] This is associated with low dopamine in ADHD and depression and high dopamine in schizophrenia.

Chocolate theory of love

In the early 1980s, researcher

MAO-B
, preventing significant concentrations from reaching the brain, thus contributing no perceptible psychoactive effect.

Substituted phenethylamines

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

amino
group:

Pharmacology

Phenylethylamine's half life is 5-10 minutes.[2] Phenylethylamine is metabolized by

dopamine-beta-hydroxylase.[2]
Phenylethylamine brain levels can be increased by a 1000 fold when taking an MAO Inhibitor and 3-4 times when taken by itself.[11] Alcohol and THC increase PEA levels by a 4 fold.[11]

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 large part to the pioneering work of Alexander Shulgin, much of which is described in the book PiHKAL (Phenethylamines i Have Known And Loved).

Selected Phenethylamines
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-
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-tri
methoxy
phenethylamine
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-
fluoro
phenethylamine
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-
isopropyl
thio-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-
cyclopropyl
methylthio-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
Short Name Rα Rβ R2 R3 R4 R5 RN Full Name

Relation to amphetamine

Despite the negative stigma tagged to

gastrointestinal problems like IBS and other negative symptoms, and can be used for traumatic brain injury (TBS)
. The majority of phenylethylamines used by many have some or all of the actions of the stigmatized amphetamine and methamphetamine (though sometimes they lack the recreational abuse) and also share great structural similarity to methamphetamine and amphetamine.

Graphical overview

See also

PiHKAL (Phenethylamines i Have Known And Loved)

References

  1. ^ a b Merck Index, 12th Edition, 7371.
  2. ^
    PMID 7711493. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help
    )
  3. ^ Nakamura, Ishii, Nakahara. "Characterization of β-phenylethylamine-induced monoamine release in rat nucleus accumbens : a microdialysis study". European journal of pharmacology.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. PMID 15879004. {{cite journal}}: Explicit use of et al. in: |author= (help
    )
  5. PMID 3129549. {{cite journal}}: Cite journal requires |journal= (help
    )
  6. doi:10.1007/BF00975055
    .
  7. PMID 15644497. {{cite journal}}: Explicit use of et al. in: |author= (help
    )
  8. ^ Baker GB; et al. "Phenylethylaminergic mechanisms in attention-deficit disorder". {{cite journal}}: Cite journal requires |journal= (help); Explicit use of et al. in: |author= (help)
  9. PMID 504988. {{cite journal}}: Explicit use of et al. in: |author= (help
    )
  10. ^ Liebowitz, Michael, R. (1983). The Chemistry of Love. Boston: Little, Brown, & Co.
  11. ^
    PMID 361043. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help
    )

External links

{{PiHKAL}} [[Category:Phenethylamines]] [[ca:Fenetilamina]] [[cs:Fenylethylamin]] [[de:Phenethylamin]] [[es:Feniletilamina]] [[fr:Phényléthylamine]] [[hr:Feniletilamin]] [[it:Feniletilamina]] [[he:פנתילאמין]] [[nl:Fenylethylamine]] [[ja:フェネチルアミン]] [[pl:Fenyloetyloamina]] [[ru:Фенилэтиламин]] [[sk:Fenyletylamín]] [[fi:Fenetyyliamiini]] [[sv:Fenetylamin]] [[zh:苯乙胺]]

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