Phenethylamine

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Generic structure of a phenethylamine molecule

Phenethylamine (also called PEA, β-phenylethylamine, β-phenethylamine, or benzeneethanamine) is a trace amine and influencer of many neurotransmitters, such as dopamine and serotonin. Phenethylamine is an important molecule in the brain, but is not often used as a supplement because it is rapidly broken down into inactive components before it is able to reach and cross the blood-brain barrier.[1]

Phenylethylamine functions as a monoaminergic neuromodulator and, to a lesser extent, a neurotransmitter in the human central nervous system. In addition to its presence in mammals, phenethylamine is found in many other organisms and foods, such as chocolate.[2] It is also plays a role in feelings of affection, and this mechanism is perhaps partially responsible for its ability to enhance empathy, affection, and sociability.[3]

When taken in combination with an MAOI such as hordenine, it can produce profound entactogenic effects similar to that of MDMA. However, the effects are notably shorter-lived and accompanied by more severe side effects.

Chemistry

Phenethylamine is comprised of a benzene ring attached to a mono-amine group via an ethyl side-chain. Orally ingested without a MAOI, phenethylamine goes through extensive first-pass metabolism by monoamine oxidase B (MAO-B) and then aldehyde dehydrogenase (ALDH), which metabolize it into phenylacetic acid. This prevents significant concentrations from reaching the brain in low doses.[4]

In the body, it is biosynthesized from the amino acid L-phenylalanine by enzymatic decarboxylation via the enzyme aromatic L-amino acid decarboxylase.[5]

Hydrogen atoms around the structure can be substituted for other functional groups to produce drugs of varying potency, affinity, efficacy, and half-life.

Pharmacology

Further information: Serotonergic psychedelic

The psychedelic effects of phenethylamines are believed to come from their efficacy at the 5-HT2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

Several neurotransmitters are derived from phenethylamine such as:

Subjective effects

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The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects should be taken with a grain of salt and will rarely (if ever) occur all at once, but heavier doses will increase the chances and are more likely to induce a full range of effects. Likewise, adverse effects become much more likely on higher doses and may include injury or death.

The effects described are most often associated with combining phenethylamine with a MAOI such as hordenine, but may be present by itself in high doses.

Physical effects
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Visual effects
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Cognitive effects
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Toxicity and harm potential

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This toxicity and harm potential section is a stub.

As such, it may contain incomplete or even dangerously wrong information. You can help by expanding upon or correcting it.
We also recommend that you practice diligent independent research and the most thorough harm reduction practices when using this substance.

Legal status

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As such, it may contain incomplete or wrong information. You can help by expanding it.

In most countries, phenethylamine is easily accessible. It is sold as a dietary supplement for purported mood- and weight loss-related therapeutic benefits.

See also

References

  1. http://www.hmdb.ca/metabolites/HMDB12275
  2. http://onlinelibrary.wiley.com/doi/10.1111/j.1471-4159.2004.02501.x/pdf
  3. http://xray.bmc.uu.se/Courses/Bke1/1998/Projects/Lovechem/projekt.html
  4. http://www.hmdb.ca/metabolites/HMDB12275
  5. https://www.ncbi.nlm.nih.gov/pubmed/15228583