About

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").

Thursday, February 28, 2013

Tryptamines Portal

DMT

Known also as dimethyltryptamine. DMT is a naturally occuring psychedelic of the tryptamine family. It is present in many plants & mammals, and is available for recreational use. Chemically known as dimethyltryptamine, it is structurally related to the neurotransmitter serotonin, the hormone melatonin, and the psychedelic compound psilocybin. 

DMT products are consumed primarily for their psychedelic, hallucinogenic, or entheogenic properties. When combined with an MAOI to facilitate oral absorbtion, DMT is the main constituent in ayahuasca; a beverage consumed in Amazonian circles for entheogenic purposes.

DMT produces intense and short acting effects when smoked. Dosages commonly range from 2-60 milligrams (smoked).

Its mode of action is complex. DMT is known to act as a non selective agonist at multiple serotonergic receptors. It also interacts with dopaminergic, adrenergic, sigma, and trace amine associated (TAAR) receptors, with varying profiles of efficacy.

AMT

Also known as alpha-methyltryptamine. AMT is a synthetically produced psychedelic of the tryptamine family, also related to DMT. Its effects are relatively long lasting, and recommended dosages are slightly higher than those for DMT.

AMT produces both psychedelic and stimulant effects. In addition to its action as a non-selective 5HT receptor agonist, AMT acts as a monoamine releasing agent (that is, it induces synaptic release of dopamine, noradrenaline, and serotonin).

AMT is chemically related to tryptamine in the same way amphetamine is related to phenethylamine; with the addition of an alpha methyl group on the alkyl chain. AMT differs chemically from DMT in two ways; a) a secondary amine rather than a tertiary amine, and b) the aforementioned CH3 group at the alpha carbon.

AMT is commonly smoked or consumed orally. Its effects can take up to 2 hours to become fully apparent, and may last 12 hours or more when high doses are consumed. Nausea and vomiting has been commonly reported.

Psilocybin:

Psilocybin is a naturally occurring psychedelic compound which is present in 200 or more species of mushrooms. Psilocybin containing mushrooms are popularly known as "magic mushrooms". Magic mushrooms grow naturally in the US and elsewhere, or, may be artificially cultivated indoors.

Psilocybin is a drug of the tryptamine family, chemically related to DMT as well as the endogenous neurotransmitter, serotonin.

Psilocybin is rapidly metabolized to psilocin via dephosphorylation, with psilocin being mainly responsible for its effects. Psilocin targets the brain's serotonergic pathways, acting as an agonist at the 5HT2A receptor, as well as other subtypes, to a lesser extent.

MiPT 

Known chemically as methylisopropyltryptamine, MiPT is a psychoactive compound related to other tryptamines such as DMT and DiPT. 

It was mentioned in Alexander Shulgin's book TIHKAL.

MiPT is reported to affect auditory perception and cognition more so than visual perception.

Analogues of MiPT have been marketed as research chemicals in recent years.

DiPT

Known chemically as diisopropyltryptamine, DiPY is a psychedelic tryptamine related to both DMT and MiPT.

Users have reported marked changes in auditory perception with the experience.

Numerous analogues of DiPT have been marketed as research chemicals.

DALT

Known chemically as N,N-diallyltryptamine. DALT is a psychedelic tryptamine related to DMT, MiPT, and DiPT.

It was mentioned in Shulgin's book TIHKAL, and numerous analogues of this compound have appeared for sale as research chemicals.

4-ACO-DMT

Also known as O-acetylpsilocin. 4-ACO-DMT is a psychoactive compound of the tryptamine family. It is a ring substituted homologue of DMT, related to psilocybin and psilocin (the magic mushroom alkaloids). 4-ACO-DMT is an RC and is usually prepared synthetically, but like psilocybin, it acts as a prodrug for psilocin.

Realities of Current Drug Policy (A Revision)

I recently revised this piece. Thought I would share it again for those who've not yet read it....

"We have failed to cultivate the self-reliance and self-discipline we must possess as competent adults surrounded by the fruits of our pharmacological-technological age" (Thomas Szasz)

Project Narco: Realities of Current Drug Policy

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.



And More Links of Interest

Pyrovalerone Analogues: A Promising Class of Monoamine Uptake Inhibitors

Patent Info: Pyrovalerone Analogues and Uses Thereof

A Report on MDPV by the Psychonaut Web-Mapping Research Project

Studies on the Metabolism and Toxicological Analysis of a-PVP in Rats






Interesting Reading on Ketamine & Methoxetamine Related Toxicity

The first link describes the incidence of urinary tract symptoms and renal toxicity associated with chronic ketamine use: An Abstract/Summary

Next is an interesting read on methoxetamine (or MXE, the popular RC); a letter sent to the Home Office of the UK recommending that MXE be permanently listed as a Class B drug under the UK's Misuse of Drugs Act. Below the letter itself the author describes pharmacology of the drug itself as well as some documented cases of methoxetamine-related toxicity, including cerebellar toxicity, hyper-arousal ("sympathomimetic toxicity"), and renal/urinary tract symptoms: Full Text Here

DXM Related Deaths (A Case Study)

The full text can be seen HERE

Excerpt: "The blood dextromethorphan concentrations were all in excess of 950 µg/L, which suggests a lower threshold for lethality than previously reported cases. The principal findings in each case were of heavy congested lungs, a common finding in drug overdose deaths. None of the deaths was witnessed, so the symptomology necessary to diagnose serotonin syndrome was not documented; however, that, and generalized CNS depression, are the most likely mechanisms of death."


Monday, February 18, 2013

Substituted Amphetamines

4-FA

Basic:
 
Also known as 4-fluoroamphetamine or para-fluoroamphetamine. 4-FA is a psychoactive compound and RC of the amphetamine family. It produces stimulant and enactogen effects, and has been sold as a research chemical or designer drug.

Chemistry:


4-FA is a halogen-substituted derivative of amphetamine, differing only by a fluoride substituent on the benzene ring.

Mode of Action:


4-FA is a triple reuptake inhibitor (or TRI); meaning it binds to the reuptake transporters for serotonin,
norepinephrine, and dopamine, leading to a net increase in monoaminergic tone. It also acts as a releasing agent for these three neurotransmitters.

Unlike other closely related 4-halogenated amphetamines such as para-chloroamphetamine and para-iodoamphetamine, 4-FA has not been shown to cause neurotoxicity via depletion of brain serotonin.

Use:

4-FA has never been produced as a pharmaceutical or used in the clinical setting. Most of the available
Source: Erowid.org
supply of this compound has been manufactured overseas, often in a clandestine setting, and distributed specifically for use as a research chemical.

4-FA is typically purchased in its nearly-pure form and taken recreationally or as a study aid. A typical dose could range 75-150mg orally.

4-FA can be taken by mouth, insufflation, or injection. It may or may not be suited for vaporization/smoking.

Effects:

The experience in its entirety can last around 4-10 hours, and typical oral dosages range from 50-150mg by the oral route.

Effects have been described as mild and amphetamine-like, with a delayed onset and a relatively soft comedown. Social disinhibition and chattiness are common, and 4-FA is often used for just this purpose. 4-FA is commonly reported to have an MDMA-like empathogenic component to its effects.

Most common effects of 4-FA include increased energy, appetite suppression, chattiness, wakefulness, insomnia, along with physiological effects such as increased heart rate, perspiration, and pupil dilation. Major effects last a few hours.
Side effects may include increased heart rate or blood pressure, dilated pupils, increased perspiration, nausea and vomiting, dizziness, agitation, anxiety or fear, paranoia, amphetamine-induced psychosis, seizures, cardiac arrhythmias, cardiac arrest, and death.

2-FMA

Basic:

Also known as 2-fluoromethamphetamine. 2-FMA is a psychoactive compound of the amphetamine family.It has been sold as a research chemical and designer drug.

Chemistry:

2-FMA is a halogenated analogue of methamphetamine. It differs from its parent drug in that it contains a fluoride atom attached to carbon 2 of the benzene ring. It is one of a series of halogenated amphetamines, some of which have also been sold and used as designer drugs.

Mode of Action:

2-FMA a psychostimulant with amphetamine-type effects, likely mediated via potentiation of the monoamine system (i.e. the dopamine, norepinephrine, serotonin neurotransmission system).

Use:

2-FMA is sold/used as a research chemical and designer drug. Some suggest that 2-FMA is an ideal replacement for stimulant medications such as Adderall (dextroamphetamine/amphetamine mixture) and Vyvanse (lisdexamphetamine). Others claim it is a cleaner and more functional replacement for traditional methamphetamine.

2-FMA is usually taken orally or by the intranasal route. 50 to 100 mg seems to be typical for the oral dose range. 2-FMA may also be injected by the IV route. It has also been heated and smoked.

Effects:

Most users report 2-FMA is a functional, "clean", or "clear headed" stimulant; that it has most of the positive attributes that are desired in a stimulant and fewer of the negatives/downsides such  as anxiety or agitation, paranoia, or severe crashing. Users have reported a mild anxiolytic effect, seemingly uncommon in other stimulants. Some report being able to fall asleep during the course of a 2-FMA experience. Many find it easy to work, study, maintain hygeine, and otherwise function properly while regularly using this compound. 

Effects are characterized by an increase in mood, increased energy, increased focus and alertness, improved cognition, enhanced creativity, social disinhibition, mild anxiolysis, and increased motivation. Major effects last for 3 to 5 hours.

Side effects may include increased heart rate or blood pressure, dilated pupils, increased perspiration, dizziness, agitation, anxiety or fear, paranoia, amphetamine-induced psychosis, seizures, cardiac arrhythmias, cardiac arrest, and death.

Methiopropamine:

Methiopropamine (or MPA) is a psychostimulant compound discovered in the 1940's, which has been marketed as a research chemical. It is a ring substituted analogue of methamphetamine, where the benzene ring has been replaced with a thiophene ring.

Chemically speaking, substitution of the phenyl moeity in the amphetamine class with a thienyl moeity reduces but does not abolish stimulant activity.

MPA is believed to act as a norepinephrine/dopamine reptake inhibitor and/or releasing agent, similar to methamphetamine.

It is most often consumed by the oral or intranasal routes, and has also been smoked. Dosages are similar to those for amphetamine.

Saturday, February 16, 2013

Aminoindane Family (Benzocyclopentylamines, Cyclopentyl-amphetamines)

2-aminoindane

2-AI

Known chemically as 2-aminoindane, 2AI is a structural analogue of amphetamine, where the alpha section of the propane chain has been attatched to the benzene ring to form a cyclopentyl moiety. It has psychostimulant properties similar to amphetamine and has been marketed as an RC.

5-IAI

Known chemically as 5-iodoaminoindane, 5IAI is a halogenated analogue of 2-AI. It produces stimulant and enactogenic effects. Its mode of action involves potentiation of monoamine pathways, due to an increased synaptic release of serotonin, noradrenaline, and dopamine.