Providing straightforward information pertaining to drugs, drug use & drug policy. The Grey Pages promotes drug-related literacy and advocates a system of viable and tolerant drug policies. This is my personal collection of commentaries, essays, tid-bits, and other such writings on everything ranging from drug use, drug policy and drug-myths, to drug-science, addiction, human behavior, and the workings of the human brain. I started this blog with a particular focus on opioids, and over the past year have found my interest gravitate toward the intriguing, ever-changing world of designer intoxicants (i.e. "research chemicals" or "designer drugs").

Friday, February 22, 2013

Tryptamines: Introduction

Tryptamine itself is a naturally occurring monoamine alkaloid. Chemically, it features an indole ring attatched to an ethylamine group. It can be found in plants, mammals, and certain fungi. It is structurally similar to the amino acid tryptophan. Tryptamine, along with tryptamine derivatives such as 5-hydroxytryptamine (serotonin) function as natural neurotransmitters in the human brain. 

The tryptamine molecule is also the structural prototype from which a laundry list of psychoactive compounds, both naturally occurring and synthetic, are derived. Most of these compounds are psychedelic or hallucinogenic drugs. Most of these drugs produce their psychedelic effect through the serotonin system, which runs throughout the cerebral cortex and is implicated in mood, memory, sleep/wake cycle and various higher-cognitive processes.

Naturally occurring tryptamines include psilocybin (the active constituent in magic mushrooms) and psilocin (the main metabolite of psilocybin), DMT (found in numerous plants and mammals), and 5-OH-DMT (i.e. bufotenin - found in the skin of certain toads).  

Alexander Shulgin in 2011
Synthetically produced tryptamines include aMT (alpha-methyltryptamine) and 4-ACO-DMT (4-acetoxy-DMT) and MiPT (methyl-isopropytryptamine). Certain naturally occurring tryptamines may also be prepared synthetically.

The compound LSD, though not a tryptamine in the proper sense, can be considered a relative of the tryptamine family, as it contains the indole moeity within its structure. 

The American author, pharmacologist, and clandestine chemist Alexander Shulgin, in his book TIHKAL (tryptamine that I have known and loved) investigated dozens of tryptamine-based hallucinogens, detailing their synthesis and their psychoactive effects. Shulgin prepared and sampled many of these compounds himself. Shulgin's work has been a valuable asset to clandestine chemists and recreational drug manufacturers around the world, who continue producing new and exciting analogues of DMT, psilocybin, LSD, and more.

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