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==External links==
==External links==
* [http://gmd.mpimp-golm.mpg.de/Spectrums/af2a22f3-4aa9-4e5c-9e61-bf278b87a7c4.aspx Phenethylamine MS Spectrum]
* [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
* [http://pihkal.info/read.php?domain=pk&id=142 Phenethylamine entry in PiHKAL • info]
* [http://pihkal.info/read.php?domain=pk&id=142 Phenethylamine entry in PiHKAL • info]

Revision as of 12:53, 21 February 2014

Not to be confused with 1-phenylethylamine.
Phenethylamine
Clinical data
Other names2-phenylethylamine, β-phenylethylamine, 1-amino-2-phenylethane
Routes of
administration		Oral
Legal status
Legal status
  • In general: uncontrolled
Pharmacokinetic data
MetabolismMAO-A, MAO-B, PNMT, ALDH, DBH, CYP2D6
Elimination half-life~5-10 minutes
Identifiers
  • 2-phenyl-2-ethanamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEBI
ChEMBL
NIAID ChemDB
CompTox Dashboard (EPA)
ECHA InfoCard100.000.523 Edit this at Wikidata
Chemical and physical data
FormulaC8H11N
Molar mass121.18 g/mol g·mol−1
3D model (JSmol)
Boiling point195 °C (383 °F)
  • c1ccc(cc1)CCN
  • InChI=1S/C8H11N/´´´´´´´´g5-8/h1-5H,6-7,9H2 ☒N
  • Key:BHHGXPLMPWCGHP-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Phenethylamine /fɛnˈɛθəlɒˈmiːn/ (PEA), β-phenethylamine, or phenylethylamine is an organic compound and a natural monoamine alkaloid, a trace amine, and also the name of a class of chemicals with many members well known for psychoactive drug and stimulant effects.[1] Phenylethylamine functions as a neuromodulator or neurotransmitter in the mammalian central nervous system.[2] It is biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate, especially after microbial fermentation. It is sold as a dietary supplement for purported mood and weight loss-related therapeutic benefits; however, orally ingested phenethylamine experiences extensive first-pass metabolism by monoamine oxidase B (MAO-B), which turns it into phenylacetic acid. This prevents significant concentrations from reaching the brain in low doses.[3][4]

The group of phenethylamine derivatives is referred to as the phenethylamines. Substituted phenethylamines, substituted amphetamines, and substituted methylenedioxyphenethylamines (MDxx) are a series of broad and diverse classes of compounds derived from phenethylamine that include stimulants, psychedelics, and entactogens, as well as anorectics, bronchodilators, decongestants, and antidepressants, among others.

Occurrence

Phenethylamine is widely distributed throughout the plant kingdom.[5]

Chemistry

Phenethylamine is a primary amine, the amino-group being attached to a benzene ring through a two-carbon, or ethyl group. It is a colorless liquid at room temperature. Phenethylamine is soluble in water, ethanol, and ether. 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, pKb = 4.17 (or pKa = 9.83), as measured using the HCl salt,[6] and forms a stable crystalline hydrochloride salt with a melting point of 217°C. Phenethylamine is also a skin irritant and possible sensitizer.[citation needed] Its density is 0.962 g/ml.

Synthesis

One method for preparing β-phenethylamine, set forth in J. C. Robinson's and H. R. Snyder's Organic Syntheses (published 1955), involves the reduction of benzyl cyanide with hydrogen in liquid ammonia, in the presence of a Raney-Nickel catalyst, at a temperature of 130°C and a pressure of 13.8 MPa. Alternative syntheses are outlined in the footnotes to this preparation.[7]

A much more convenient method for the synthesis of β-phenethylamine is the reduction of ω-nitrostyrene by lithium aluminum hydride in ether, whose successful execution was first reported by R. F. Nystrom and W. G. Brown in 1948.[8]

Pharmacology

Phenethylamine, similar to amphetamine in its action, releases norepinephrine and dopamine.[9][10][11] When taken orally, though, it is rapidly metabolized.[12]

Abnormally low concentrations of endogenous phenethylamine are found in those suffering from attention-deficit hyperactivity disorder (ADHD),[13] whereas abnormally high concentrations have been discovered to have a strong, positive correlation with the incidence of schizophrenia.[14]

Pharmacokinetics

Phenylethylamine's half-life is 5 to 10 minutes.[15] It is metabolized by phenylethanolamine N-methyltransferase,[16] MAOA,[4] MAOB,[3] aldehyde dehydrogenase, and dopamine-beta-hydroxylase.[15] N-methylphenethylamine, an isomer of amphetamine, is produced when phenethylamine is used as a substrate by phenylethanolamine N-methyltransferase.[16][17] When the initial phenylethylamine brain concentration is low, brain levels can be increased 1000-fold when taking an MAO inhibitor (MAOI), and by 3-4 times when the initial concentration is high.[18]

Toxicity

Acute toxicity studies on phenethylamine show an LD50 = 100 mg/kg, after intravenous administration to mice; substantial liver damage.[19]


See also

References

  1. ^ Glen R. Hanson, Peter J. Venturelli, Annette E. Fleckenstein (2005-11-03). Drugs and society (Ninth Edition). Jones and Bartlett Publishers. ISBN 978-0-7637-3732-0. Retrieved 2011-04-19.{{cite book}}: CS1 maint: multiple names: authors list (link)
  2. ^ Sabelli, HC; Mosnaim, AD; Vazquez, AJ; Giardina, WJ; Borison, RL; Pedemonte, WA (1976). "Biochemical plasticity of synaptic transmission: A critical review of Dale's Principle". Biological psychiatry. 11 (4): 481–524. PMID 9160.
  3. ^ a b Yang, HY; Neff, NH (1973). "Beta-phenylethylamine: A specific substrate for type B monoamine oxidase of brain". The Journal of pharmacology and experimental therapeutics. 187 (2): 365–71. PMID 4748552.
  4. ^ a b Suzuki, O.; Katsumata, Y.; Oya, M. (1981). "Oxidation of ?-Phenylethylamine by Both Types of Monoamine Oxidase: Examination of Enzymes in Brain and Liver Mitochondria of Eight Species". Journal of Neurochemistry. 36 (3): 1298–301. doi:10.1111/j.1471-4159.1981.tb01734.x. PMID 7205271.
  5. ^ Smith, Terence A. (1977). "Phenethylamine and related compounds in plants". Phytochemistry. 16 (1): 9–18. doi:10.1016/0031-9422(77)83004-5.
  6. ^ Leffler, Esther B.; Spencer, Hugh M.; Burger, Alfred (1951). "Dissociation Constants of Adrenergic Amines". Journal of the American Chemical Society. 73 (6): 2611–3. doi:10.1021/ja01150a055.
  7. ^ Robinson, J. C.; Snyder, H. R. (1955). "β-Phenylethylamine" (PDF). Organic Syntheses, Coll. 3: 720.
  8. ^ Nystrom, Robert F.; Brown, Weldon G. (1948). "Reduction of Organic Compounds by Lithium Aluminum Hydride. III. Halides, Quinones, Miscellaneous Nitrogen Compounds1". Journal of the American Chemical Society. 70 (11): 3738–40. doi:10.1021/ja01191a057. PMID 18102934.
  9. ^ Nakamura, Masato; Ishii, Akira; Nakahara, Daiichiro (1998). "Characterization of β-phenylethylamine-induced monoamine release in rat nucleus accumbens: A microdialysis study". European Journal of Pharmacology. 349 (2–3): 163–9. doi:10.1016/S0014-2999(98)00191-5. PMID 9671094.
  10. ^ EM Parker and LX Cubeddu (April 1988). "Comparative effects of amphetamine, phenylethylamine and related drugs on dopamine efflux, dopamine uptake and mazindol binding". Journal of Pharmacology and Experimental Therapeutics. 245 (1): 199–210. ISSN 0022-3565. PMID 3129549.
  11. ^ Paterson, I. A. (1993). "The potentiation of cortical neuron responses to noradrenaline by 2-phenylethylamine is independent of endogenous noradrenaline". Neurochemical Research. 18 (12): 1329–36. doi:10.1007/BF00975055. PMID 8272197.
  12. ^ Shulgin, Alexander; Ann Shulgin. "Erowid Online Books : "PIHKAL" - #142 PEA". Retrieved 2010-05-13.
  13. ^ Baker, G.B.; Bornstein, R.A.; Rouget, A.C.; Ashton, S.E.; Van Muyden, J.C.; Coutts, R.T. (1991). "Phenylethylaminergic mechanisms in attention-deficit disorder". Biological Psychiatry. 29 (1): 15–22. doi:10.1016/0006-3223(91)90207-3. PMID 2001444.
  14. ^ Potkin, S.; Karoum, F; Chuang, L.; Cannon-Spoor, H.; Phillips, I; Wyatt, R. (1979). "Phenylethylamine in paranoid chronic schizophrenia". Science. 206 (4417): 470–1. doi:10.1126/science.504988. PMID 504988.
  15. ^ a b Sabelli, Hector C.; J. I. Javaid (February 1, 1995). "Phenylethylamine modulation of affect: therapeutic and diagnostic implications". J Neuropsychiatry Clin Neurosci. 7 (1): 6–14. ISSN 0895-0172. PMID 7711493.
  16. ^ a b Pendleton, Robert G.; Gessner, George; Sawyer, John (1980). "Studies on lung N-methyltransferases, a pharmacological approach". Naunyn-Schmiedeberg's Archives of Pharmacology. 313 (3): 263–8. doi:10.1007/BF00505743. PMID 7432557.
  17. ^ Broadley, Kenneth J. (2010). "The vascular effects of trace amines and amphetamines". Pharmacology & Therapeutics. 125 (3): 363–75. doi:10.1016/j.pharmthera.2009.11.005. PMID 19948186.
  18. ^ Sabelli, Hector C.; Borison, Richard L.; Diamond, Bruce I.; Havdala, Henri S.; Narasimhachari, Nedathur (1978). "Phenylethylamine and brain function". Biochemical Pharmacology. 27 (13): 1707–11. doi:10.1016/0006-2952(78)90543-9. PMID 361043.
  19. ^ Lands, AM; Grant, JI (1952). "The vasopressor action and toxicity of cyclohexylethylamine derivatives". The Journal of pharmacology and experimental therapeutics. 106 (3): 341–5. PMID 13000630.

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