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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, September 27, 2012

Pyrrolidinoalkylphenone Portal (Pyrovalerones) *New Section*

N-Pyrrolidinyl-Cathinones:

Compounds of this series are related to the stimulant drug pyrovalerone. They are chemically distinct from other substituted cathinones in that they contain a tertiary amino group rather than a secondary amino group, with the nitrogen atom being part of a pyrrolidinyl cyclic (i.e. ring) structure. The N-pyrrolidinyl cathinone analogues are speculated to be more potent than traditional substituted cathinones due to the aforementioned tertiary amino group, which may produce a more lipophilic molecule. Certain compounds of this series are active in doses as low as 5 mg (as opposed to other cathinone analogues such as mephedrone or 4-MEC, which are typically active at doses of 100 mg or more).

alpha-PVP

This compound is commonly referred to as APVP, or its chemical name alpha-pyrrolidinopentiophenone. a-PVP was first synthesized in the 1960's, though it was never marketed or used clinically. It has however recently surfaced as a grey market research chemical. It has gained popularity as an alternative to its recently banned methylenedioxy analogue MDPV, and has appeared as the active ingredient in certain novelty powders (sold as bath salts or glass cleaner).

a-PVP is a member of the substituted cathinone family, and therefore also a member of the much larger family of phenethylamine-type compounds. a-PVP is distinct from other cathinone analogues in that it features a pentyl group at the alpha position of the side chain and a pyrrolidinyl ring substitution in place of the usual non-cyclic amino-alkane group. It is one of a series of pyrrolidinyl substituted cathinones known as pyrrolidinylphenones. It is the demethylated derivative of pyrovalerone, a psychostimulant used clinically to promote weight loss.

Quality a-PVP typically appears as a snow white to off-white (slightly beige) powder with a very fine consistency similar to powdered sugar or talc. Powder a-PVP clumps together when compressed and falls apart into smaller flake-like chunks. Its odor is especially apparent when mixed into a solution with water; a pyrrolidine-like odor comparable to warm salty water. This has been likened by many to the smell of sweaty gym socks.

"Crystal "APVP chunk
Recently, solid form of a-PVP has appeared in the form of opaque, rock-like crystals. 

In terms of pharmacology, a-PVP is a potent psychostimulant. Although it doesn't produce an empathogen/enactogen effect on the same scale as ecstasy, a-PVP surely has empathy producing qualities. Its mode of action has not been studied in depth, but it presumably shares its pharmacology with other related compounds of the amphetamine-cathinone family. It is assumed to act by increasing synaptic concentrations of dopamine and norepinephrine, either by reversing the flow of the monoamine reuptake system or altogether blocking reuptake. 

Effects are apparent in the 5-10 mg range and are amphetamine-like in nature. Some users seem to be extremely sensitive to the compound and require doses of less than 10 mg, while others handle doses several times greater. This compound is taken by multiple routes of administration which include oral, intranasal, and intravenous. It has also been indirectly heated via flame and inhaled, in the same fashion cocaine or heroin hydrochloride powders are smoked.

APVP Precautions:

a-PVP toxicity typically presents similarly to an MDPV overdose; symptoms include severe hypertension, tachycardia, agitation, psychosis, visual and/or auditory hallucinations, and heart failure. MDPV toxicity is generally treated in the emergency department with benzodiazapines or antipsychotics.

Clonidine may be useful in reducing agitation.

Beta blockers for hypertension should be avoided due to the possibility of paradoxical increases in blood pressure.

Important to note is that a-PVP, like its relative MDPV, has a strong tendency to induce psychosis when used in excessive doses or when dosed too frequently.

Also important to note is that a-PVP and other pyrrolidinophenones like it seem to be particularly reinforcing (euphorigenic), especially when administered by the intravenous route. a-PVP can be extremely habit forming, therefore caution is advised. 

PV4 (i.e. Methyl-PHP, MPHP) 

This compound is known by the chemical name 4-methyl-alpha-pyrrolidinohexiophenone. It has appeared quite recently on the grey market research scene, likely deriving its name from the popular pyrovalerone compounds MDPV (PV-2) and a-PVP (PV-3). 

This compound is structurally similar to pyrovalerone, and only differs with an extension on the alpha-alkane chain; from a pentyl to a hexyl. By extension, it is an analogue of a-PVP.

PV-4 likely exhibits a mode of action similar to its relatives; targeting the monoamine transport/reuptake system and increasing dopaminergic and noradrenergic tone.

APBP (i.e. alpha-PBP) 

Known chemically as alpha-pyrrolidinobutiophenone. APBP is a CNS stimulant related to alpha-PVP and other pyrrolidinophenones. APBP is a somewhat rare research chemical with psychostimulant properties. It has been present as an active ingredient in certain novelty powders.

It is the chain shortened analogue of a-PVP, featuring a butyl rather than a pentyl chain at the alpha carbon. It is also the 4-demethylation product of MPBP.

Like its pyrovalerone based relatives, a-PBP is a sympathomimetic agent, with a mode of action most likely involving the monoamine neurotransmitters dopamine and noradrenaline.

MDPV 

MDPV is a centrally acting compound related to pyrovalerone. It is a potent psychostimulant with notable enactogenic and reinforcing qualities. It was easily available from 2010 until recently and had been one of the main constituents of the infamous "bath salt" products. It has also been known as the active component of NRG-1.

MDPV is known chemically as 3,4-methylenedioxy-pyrovalerone. It is an analogue of pyrovalerone containing the methylenedioxy group of MDMA, forming a dioxole ring off of the phenyl.

Despite its similarity to MDMA (i.e. ecstasy), MDPV primarily produces stimulant effects; its enactogenic properties are relatively mild. Its main mode of action involves increasing the available levels of synaptic catecholamines; specifically dopamine and norepinephrine. It acts mainly by blocking the reuptake of these two neurotransmitters. MDPV promotes sympathetic arousal and enhances the flow of ventral-tegmental dopamine to various "pleasure producing" structures. Its pharmacology, and its effects, are similar to other sympathomimetic amines such as amphetamine and methylphenidate. It reportedly has around 4 times the potency of the latter.

Side effects of this compound tend to include jitteriness, anxiety, agitation, hypertension, palpitations and arrhythmias, vasodilation, mydriasis (dilated pupils), bowel stimulation, and diuresis. Adverse effects could very well be serious. Overdose symptoms or extreme adverse events are likely to include irregular heartbeat, psychotic break, extreme confusion, slurred speech, aphasia (inability to speak), lazy eye or crossed-eyes, fear & panic, heart attack, stroke, cardiac arrest & death.

MDPV has typically been snorted, swallowed, or smoked. MDPV has been injected intravenously, which is known to be followed by an intense "rush" and a strong desire to re-dose. MDPV can be particularly habit forming when taken by the IV route, probably to at least the same extent as IV cocaine or methamphetamine.

IV and IM use of products labeled as "bath salts" has on occasion led to a serious, rapidly progressing, and untreatable infection known as necrotizing fasciitis; a rapid death of muscle and skin tissue leading to sepsis and death in a matter of hours if the affected area is not amputated right away. This condition has a 75% mortality rate; in other words, 3 out of 4 cases are fatal.

MDPV has a duration of 2 to 7 hours, depening on the dose and route of administration. Oral doses generally provide the longest duration.

MDPV Precautions:

There are numerous anecdotal reports of fatality attributed to MDPV toxicity.

An MDPV overdose presents similarly to amphetamine or methamphetamine overdose; symptoms include severe hypertension, tachycardia, agitation, psychosis, visual and/or auditory hallucinations, and heart failure. MDPV toxicity is generally treated in the emergency department with benzodiazapines or antipsychotics.

Some users report success with clonidine to combat agitation.

Beta blockers for hypertension should be avoided due to the possibility of paradoxical increases in blood pressure.

APVT

APVT Molecule
Known by its chemical name alpha-pyrrolidinopentiothiophenone, this compound has recently appeared for sale as an RC. APVT is an analogue of the stimulant compound APVP, where the benzene ring has been replaced with a thiophene ring. It has recently been available through some chemical vendors as an alternative to APVP and MDPV.

Little is known about its mode of action or its effects. There are anecdotal reports of stimulant effects resembling those of APVP (or its non beta-keto relative methiopropamine). Psychostimulant activity in the non beta-keto class of thiophenylalkylamines is believed to be relatively mild compared to the benzene substituted counterparts; though whether this applies to the beta-keto (cathinone) family of compounds is unclear.

Based on limited experience and other anecdotal reports, APVT produces short-lived stimulant effects in doses similar to, but slightly higher than, APVP.

The neurotoxic potential of this compound is unknown. And possible side effects include hypertension, agitation, and psychosis.



2 comments:

  1. This needs an update with info on PV8, and what the hell are PV's 5-7?

    ReplyDelete
  2. pv8 is a must to be looked into.

    ReplyDelete