Phenethylamines

What are Phenthylamines?

Phenethylamines are a class of compounds with a core structure consisting of a phenyl ring linked to an amino group (NH2). This core structure gives rise to a wide range of variations in the chemical composition, each with its unique properties and effects. These compounds primarily affect the brain’s serotonin receptors, leading to altered states of consciousness characterized by vivid visual experiences, enhanced introspection, and perceptual changes.

 

PIHKAL: A Chemical Love Story

Alexander “Sasha” Shulgin, a pioneering figure in the field of psychedelic research, left an indelible mark on the exploration of psychoactive compounds. Born in 1925, Shulgin earned a Ph.D. in biochemistry and went on to work for Dow Chemical, where he became intrigued by the potential psychoactive effects of certain chemical compounds. In the 1960s, he began synthesizing and experimenting with various psychedelic substances, contributing to the discovery of novel compounds and their psychoactive properties. Shulgin’s groundbreaking work laid the foundation for a deeper understanding of the pharmacology and subjective effects of psychedelics.

In 1991, Shulgin, along with his wife Ann Shulgin, published “PiHKAL: A Chemical Love Story” (Phenethylamines I Have Known and Loved), a seminal work that documented over 160 phenethylamine compounds, including their chemical structures, synthesis methods, and detailed reports on subjective experiences. “PiHKAL” not only served as a comprehensive reference guide but also provided a unique blend of scientific rigor and personal narratives. Shulgin’s meticulous documentation of these substances, coupled with his experiential insights, significantly contributed to the collective knowledge about the diverse effects and potential applications of phenethylamines. His work has inspired subsequent generations of researchers, pharmacologists, and enthusiasts, shaping the discourse on psychedelic substances and their role in expanding our understanding of consciousness.

Following the success of “PiHKAL: A Chemical Love Story,” Alexander Shulgin continued his prolific contributions to the understanding of psychoactive substances by co-authoring another seminal work, “TiHKAL: The Continuation” (Tryptamines I Have Known and Loved), with his wife Ann Shulgin. Published in 1997, “TiHKAL” delves into the world of tryptamines, a class of compounds that, like phenethylamines, have significant psychoactive properties. The book follows a similar format to “PiHKAL,” providing detailed information on the synthesis, pharmacology, and subjective effects of numerous tryptamines.

 

Phenethylamine Substances

Phenethylamines constitute a diverse class of compounds, and they can be found in various natural sources as well as synthesized for medicinal or recreational purposes.

Here is a list of some notable phenethylamines:

  1. Mescaline: A naturally occurring psychedelic found in certain cacti, such as Peyote and San Pedro.
  2. MDMA (3,4-methylenedioxy-N-methylamphetamine): Known as Ecstasy or Molly, MDMA is a synthetic empathogen and stimulant with psychoactive effects.
  3. 2C-B (4-Bromo-2,5-dimethoxyphenethylamine): A synthetic psychedelic known for its hallucinogenic properties.
  4. DOM (2,5-dimethoxy-4-methylamphetamine): A psychedelic amphetamine with a long duration of action.
  5. DOB (4-bromo-2,5-dimethoxyamphetamine): Another synthetic psychedelic phenethylamine, similar to DOM.
  6. 2C-I (4-Iodo-2,5-dimethoxyphenethylamine): A synthetic psychedelic known for its hallucinogenic effects.
  7. 2C-E (4-ethyl-2,5-dimethoxyphenethylamine): Another member of the 2C family, producing psychedelic experiences.
  8. 2C-D (2,5-dimethoxy-4-methylphenethylamine): Known for its mild psychedelic effects.
  9. PEA (Phenethylamine): An endogenous compound found in the human body and certain foods, acting as a trace amine and neurotransmitter.
  10. Bromo-DragonFLY (4-bromo-2,5-dimethoxy-N-ethylphenethylamine): A potent psychedelic with a long duration of action.

 

Common Phenethylamine Subclasses

Phenethylamines can be divided into various subclasses, including amphetamines, substituted amphetamines, and psychedelics.  Amphetamines and psychedelic phenethylamines are very different from one another and are distinct classes of psychoactive substances, each with unique pharmacological effects and mechanisms of action. Amphetamines, such as methamphetamine and dextroamphetamine, primarily function as central nervous system stimulants by increasing the release and blocking the reuptake of neurotransmitters like dopamine and norepinephrine. This results in heightened alertness, improved focus, and increased energy levels. Amphetamines are commonly prescribed for conditions like attention deficit hyperactivity disorder (ADHD) and narcolepsy due to their stimulating effects on the brain.

While amphetamines are primarily recognized for their stimulant properties, certain substances within this class can also exhibit psychedelic effects under specific conditions. One notable example is Methylenedioxymethamphetamine (MDMA), which, despite being classified as an amphetamine, is renowned for its empathogenic and psychedelic qualities. MDMA acts as both a serotonin releaser and reuptake inhibitor, resulting in increased serotonin levels in the brain. This heightened serotonin activity contributes to the substance’s characteristic effects, which include not only euphoria and increased sociability but also sensory enhancement and altered perception. The psychedelic aspect of MDMA is particularly evident in the vivid sensory experiences and emotional introspection reported by users, showcasing the multifaceted nature of amphetamine compounds and their potential to elicit not only stimulant but also psychedelic responses.

On the other hand, psychedelic phenethylamines, exemplified by substances like mescaline and 2C-B, induce altered states of consciousness characterized by profound changes in perception, mood, and cognition. These substances primarily interact with serotonin receptors in the brain, particularly the 5-HT2A receptor subtype. The hallucinogenic effects of psychedelic phenethylamines are attributed to their ability to modulate serotonin levels, leading to visual distortions, enhanced sensory experiences, and altered thought patterns. Unlike amphetamines, psychedelic phenethylamines are not known for their stimulant properties and are instead associated with the exploration of altered states of consciousness and spiritual experiences. The dissimilarity in their effects highlights the diverse ways in which different classes of psychoactive substances interact with the brain’s neurotransmitter systems.  Psychedelic phenethylamines are famous for inducing sensory distortions, changes in thought patterns, and a profound sense of interconnectedness with the universe. These experiences can vary depending on the specific compound and dosage.

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