Phenethylamine (compound)

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. A thorough investigation of 179 phenethylamine compounds was published by Ann and Alexander Shulgin under the title PiHKAL.

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.^[2]

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

Pharmacology

Several neurotransmitters are derived from phenethylamine such as adrenaline, dopamine, norepinephrine.

Phenethylamine, being similar to Amphetamine in its action at their common biomolecular targets, releases Norepinephrine and Dopamine.^[5]^[6]^[7] Phenethylamine also appears to induce Acetylcholine release via a glutamate-mediated mechanism.^[8]

Phenethylamine has been shown to bind to human trace amine-associated receptor 1 (hTAAR1) as an Agonist.^[9] Phenethylamine is also an odorant binding TAAR4 in mice thought to mediate predator avoidance.^[10]

Subjective effects

This subjective effects section is a stub.

As such, it is still in progress and may contain incomplete or wrong information.

You can help by expanding or correcting it.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe 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

- Physical euphoria
- Tactile enhancement
- Sedation
- Respiratory depression
- Teeth grinding
- Motor controll loss
- Spontaneous physical sensations - The "body high" of phenethylamine can be described as a moderate to extreme euphoric, soft, fuzzy, and warm tingling sensation that encompasses the entire body. It is capable of becoming overwhelmingly pleasurable at higher doses. This sensation maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached.
- Increased perspiration
- Perception of bodily lightness
- Temporary erectile dysfunction
- Increased heart rate^{[citation needed]}
- Increased blood pressure^{[citation needed]}

Visual effects

The visual effects of phenethylamine only occur at higher doses and are subtly psychedelic. These generally include:
- Visual acuity enhancement
- Colour enhancement
- Visual haze

Cognitive effects

The cognitive effects of phenethylamine can be broken down into several components which progressively intensify proportional to dosage. The general head space of phenethylamine is described by many as one of euphoria and feelings of love or empathy. It contains a number of typical entactogenic cognitive effects. The most prominent of these cognitive effects generally include:
- Anxiety or Anxiety suppression
- Cognitive euphoria - Strong emotional euphoria and feelings of happiness are present within phenethylamine and are a direct result of serotonin and dopamine release.
- Disinhibition
- Empathy, affection, and sociability enhancement
- Thought acceleration
- Mindfulness
- Immersion enhancement
- Novelty enhancement
- Focus enhancement
- Increased libido

Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include:

Additional experience reports can be found here:

Erowid Experience Vaults: Phenethylamine

Toxicity and harm potential

This toxicity and harm potential section is a stub.

As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it.
Note: Always conduct independent research and use harm reduction practices if using this substance.

There are some cases of users experiencing extremely dangerous brain bleeds caused by the increase in blood pressure in high doses. Even normal high dose use that doesn't cause a brain bleed, causes a rapid and dangerous increases in blood pressure and could result in many acute medical issues. Extreme caution should be used when taking this substance, especially with an MAOI.

Legal status

This legality section is a stub.

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.

External links

References

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0x270 ~ > vim phenethylamine 0x270 ~ > cat phenethylamine

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.^[11]

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.^[12]

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. A thorough investigation of 179 phenethylamine compounds was published by Ann and Alexander Shulgin under the title PiHKAL.

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.^[13]

In the body, it is biosynthesized from the amino acid L-phenylalanine by enzymatic decarboxylation via the enzyme aromatic L-amino acid decarboxylase.^[2]

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

Pharmacology

Several neurotransmitters are derived from phenethylamine such as adrenaline, dopamine, norepinephrine.

Phenethylamine, being similar to Amphetamine in its action at their common biomolecular targets, releases Norepinephrine and Dopamine.^[14]^[15]^[16] Phenethylamine also appears to induce Acetylcholine release via a glutamate-mediated mechanism.^[17]

Phenethylamine has been shown to bind to human trace amine-associated receptor 1 (hTAAR1) as an Agonist.^[18] Phenethylamine is also an odorant binding TAAR4 in mice thought to mediate predator avoidance.^[19]

Subjective effects

This subjective effects section is a stub.

As such, it is still in progress and may contain incomplete or wrong information.

You can help by expanding or correcting it.

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe 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.