The Full Wiki

Phenethylamine: Wikis

  

Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.

Encyclopedia

From Wikipedia, the free encyclopedia

Phenethylamine
Systematic (IUPAC) name
phenylethan-2-amine
Identifiers
CAS number 64-04-0
ATC code  ?
PubChem 1001
ChemSpider 13856352
Chemical data
Formula C8H11N 
Mol. mass 121.18 g/mol
SMILES eMolecules & PubChem
Synonyms 2-phenylethylamine, β-phenylethylamine, 1-amino-2-phenylethane
Pharmacokinetic data
Metabolism MAO-A, MAO-B, ALDH, DBH, CYP2D6
Half life ~5-10 minutes
Therapeutic considerations
Pregnancy cat.  ?
Legal status Uncontrolled
Routes Oral

Phenethylamine (PEA) is a natural monoamine alkaloid, trace amine, and psychoactive drug with stimulant effects. In the mammalian central nervous system, phenethylamine is believed to function as a neuromodulator or neurotransmitter. It is biosynthesized from the amino acid phenylalanine by enzymatic decarboxylation. Besides 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 is usually inactive on account of extensive first-pass metabolism by monoamine oxidase (MAO) into phenylacetic acid, preventing significant concentrations from reaching the brain.[1][2]

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.

Contents

Chemistry

Phenethylamine is an aromatic amine, which is a colorless liquid at room temperature. It 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 and forms a stable crystalline hydrochloride salt with a melting point of 217 °C. Phenethylamine is also a skin irritant and possible sensitizer.

Phenethylamine has an inactive constitutional isomer 1-phenylethylamine, which itself has two stereoisomers: (R)-(+)-1-phenylethylamine and (S)-(-)-1-phenylethylamine.

Pharmacology

Phenethylamine, similarly to amphetamine, acts as a releasing agent of norepinephrine and dopamine.[3][4][5] For this reason, it has been called the "body's endogenous amphetamine".

Low concentrations of endogenous phenethylamine are found in those suffering from attention-deficit hyperactivity disorder (ADHD)[6] and often in clinical depression, while levels are elevated in schizophrenia.[7]

Pharmacokinetics

Phenylethylamine's half life is 5–10 minutes.[8] Phenylethylamine is metabolized by MAO-A [2], MAO-B [1], aldehyde dehydrogenase and dopamine-beta-hydroxylase.[8] Phenylethylamine brain levels can be increased by a 1000 fold when taking a MAO Inhibitor and 3-4 times when taken by itself.[9] Alcohol and THC increase phenylethylamine levels by a 4 fold.[9]

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." 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."[10] 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 without the use of an monoamine oxidase inhibitor (MAOI).

See also

External links

References

  1. ^ a b Yang HY, Neff NH. (November 1973). "Beta-phenylethylamine: a specific substrate for type B monoamine oxidase of brain". The Journal of Pharmacology and Experimental Therapeutics 187 (2): 365–71. ISSN 0022-3565. PMID 4748552. 
  2. ^ a b Suzuki O, Katsumata Y, Oya M. (March 1981). "Oxidation of beta-phenylethylamine by both types of monoamine oxidase: examination of enzymes in brain and liver mitochondria of eight species". The Journal of Neurochemistry 36 (3): 1298–301. doi:10.1111/j.1471-4159.1981.tb01734.x. ISSN 0022-3042. PMID 7205271. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+64-04-0. 
  3. ^ Nakamura, Ishii, Nakahara (1998). "Characterization of β-phenylethylamine-induced monoamine release in rat nucleus accumbens : a microdialysis study". European journal of pharmacology 349 (2-3): 163. doi:10.1016/S0014-2999(98)00191-5. PMID 9671094. http://cat.inist.fr/?aModele=afficheN&cpsidt=2350263. 
  4. ^ EM Parker and LX Cubeddu (04/01/1988). "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. ISSN 0022-3565. PMID 3129549. http://jpet.aspetjournals.org/cgi/content/abstract/245/1/199. 
  5. ^ I. A. Paterson (1993). "The potentiation of cortical neuron responses to noradrenaline by 2-phenylethylamine is independent of endogenous noradrenaline". Neurochemical Research 18 (12): 1329. doi:10.1007/BF00975055. PMID 8272197. http://www.springerlink.com/content/l221368846768g16/. 
  6. ^ Baker GB et al. (1991). "Phenylethylaminergic mechanisms in attention-deficit disorder". Biological psychiatry 29 (1): 15–22. PMID 2001444. 
  7. ^ SG Potkin et al. (October 1979). "Phenylethylamine in paranoid chronic schizophrenia". Science 206 (4417): 470. doi:10.1126/science.504988. ISSN 0036-8075. PMID 504988. 
  8. ^ a b Sabelli, Hector C.; J. I. Javaid (02/01/1995). "Phenylethylamine modulation of affect: therapeutic and diagnostic implications". J Neuropsychiatry Clin Neurosci 7 (1): 6–14. ISSN 0895-0172. PMID 7711493. http://neuro.psychiatryonline.org/cgi/content/abstract/7/1/6. 
  9. ^ a b Sabelli, Hector C.; et al. (1978). "Phenylethylamine and brain function". Biochem Pharmacol. 27 (13): 1707–1711. doi:10.1016/0006-2952(78)90543-9. ISSN 0006-2952. PMID 361043. 
  10. ^ Liebowitz, Michael, R. (1983). The Chemistry of Love. Boston: Little, Brown, & Co.







Got something to say? Make a comment.
Your name
Your email address
Message