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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, June 21, 2012

Substituted Cathinones





Mephedrone 

Other Names:

4-MMC, Meow Meow, 4-methylmethcathinone, and 4-methylephedrone.

Basic:


Mephedrone is a centrally acting compound with psychostimulant and empathogen effects. It is an analogue of methcathinone and has in recent years appeared available as a research chemical and recreational drug. Prior to 2010 it was one of the more common ingredients contained in the highly publicized "bath salt" products, until political campaigns & media drove these novelty products, and the mephedrone they contained, further underground.

Chemistry:


Mephedrone is a synthetically produced propiophenone derivative, and a member of the substituted cathinone family. Structural relatives include cathinone, methcathinone, pyrovalerone, bupropion, and more distantly, methamphetamine and methylphenidate.

Mode of Action:


Like other cathinone & amphetamine homologues, mephedrone increases the tone of central monoamine pathways via its action at monoamine transporters. Its pharmacodynamic properties have not been investigated in depth, but mephedrone is believed to act similarly to the related drug methcathinone; stimulating the release of/blocking the reuptake of monoamine neurotransmitters (mainly dopamine and serotonin). 

In rat-studies, mephedrone was shown to increase accumbal dopamine levels up to 500% compared to baseline, and to increase 5HT levels by up to 950% compared to baseline; these increases are similar to those observed with both amphetamine and MDMA. In other words, mephedrone produces a massive increase of mesocorticolimbic serotonin and dopamine transmission followed by a rapid clearance.

Effects:


Mephedrone produces effects similar to amphetamine and MDMA. These effects include increased energy, increased wakefulness and alertness, euphoria, disinhibition, chattiness, enhanced perception of sensory input such as sight, smell and touch, along with increased appreciation for music.

Side effects are those typical of a sympathomimetic-type drugs; they likely include increased heart rate, hyperthermia, sweating, chest pressure, mydriasis (dilated pupils), tooth grinding, anorexia, palpitations, anxiety and paranoia. Stimulant psychosis has been reported with mephedrone. Overdose may lead to agitation, cardiovascular failure, serotonin syndrome, cardiac arrest and death. Persistent or long term use may be linked to severe depletions in 5HT function.

Use:

Mephedrone use has been reported by oral, intranasal, rectal, and intravenous routes. The typical dose ranges from 50 mg to 200 mg, and the effects generally last from 2 to 5 hours depending on dose and ROA.

4-MEC

Other Names:

4-methylethcathinone and "Meck".

Basic:

Chemically known as 4-methylethcathinone. 4 MEC is a psychoactive compound of the substituted
cathinone family. It produces stimulant and empathogen effects. Not long ago it appeared as a research chemical and designer drug. It was proposed as an alternative to mephedrone due to its similarity in structure and effects.

Chemistry:

small and large shards/chunks of  what appears to be 4-MEC 
4-MEC is a ring substituted cathinone closely related to mephedrone (i.e. 4-methylMETHcathinone), with the methylamino moiety of mephedrone being substituted with an ethylamino.

Use and Effects:

4-MEC seems to be extremely active in doses of 75 mg and up when taken by more direct routes of administration. Oral doses may require 100 mg or greater for this level of effects.

Its effects have been compared to MDA (methylenedioxyamphetamine). Its stimulant properties are accompanied by empathogen properties which are equally strong if not stronger. The 4MEC experience could be described as a tweaky "roll"-like experience, which lasts a few hours (typically not as long lasting as MDMA). 4-MEC produces an often overwhelming rush and an "instant roll" when administered by more direct routes. This is a very active chemical and should be handled/used with extra caution. Nausea is likely and may be intense, but generally subsides after vomiting.

Appearance:

High quality 4-MEC typically appears in the form of crystalline shards (small and large), which break into a sandy powder. This compound seems to dissolve fine in water, but not as readily or easily as the more powdery RC's (such as 2-FMA or 4-FA).

4-MEC has been sold as ecstasy and molly on the drug-scene. The web resource EcstasyData.org documented one such product which was distributed in a gel-capsule form and contained a 1.3 to 1 ratio of 4-MEC to methylone, respectively. Considering that this capsule contained 135 mg of material (and seemingly no dilutants), it would have to have contained roughly 70mg of 4MEC and 60mg of methylone; a strong dose even when taken orally.

4-EMC

Known chemically as 4-ethylmethcathinone. 4-EMC is a substituted cathinone related to 4-MMC (mephedrone) and 4-MEC. It produces psychostimulant effects which many users have compared to mephedrone.

4-EMC differs from mephedrone with an ethyl substitution rather than a methyl group on carbon 4 of the benzene ring; and it differs from 4-MEC with an N-methyl group and a 4-ethyl group (as opposed to an N-ethyl and a 4-methyl).

4-EMC has been sold as a research chemical. Anecdotal reports suggest that 4-EMC is more favorable as a mephedrone replacement than is 4-MEC. It may also be more potent than the latter.

Pentedrone

Pentedrone is a psychostimulant compound of the cathinone family. It has recently appeared as a grey market recreational drug and has been available by name as a research chemical, or as an active component in certain novelty powders.

Pentedrone is structurally similar to both methcathinone and a-PVP. Like a-PVP it features a pentyl substitution at the alpha position of the side chain (as opposed to the alpha-methyl group of methcathinone), however, the nitrogen substitution is non-cyclic and instead it features an amino-methyl chain.

Like other substituted cathinones such as methcathinone and buphedrone, pentedrone is a sympathomimetic agent, with a mode of action most likely involving the monoamine neurotransmitters dopamine and noradrenaline.

Pentedrone is generally active in the 10-20mg range; although it is crucial to note that different batches of the drug are known to be inconsistent in potency or purity, with the effective dose varying as much as 10-fold between individuals. This presents an obvious danger, requiring one to always start low and increase slowly.

Pentedrone produces effects which feel subjectively very similar to a-PVP, with a characteristic numbing throughout areas of the body (typically the upper or lower back, arms or legs). This numbing effect is particularly pronounced when the compound is administered intravenously.

Buphedrone

Buphedrone is a CNS stimulant of the substituted phenethylamine/cathinone families. It was first synthesized in the 1920's, but has more recently been sold as a research chemical and novelty product.

This is a chain shortened analogue of methcathinone and is, by extension, a close relative of pentedrone.

Buphedrone produces effects similar to methcathinone and pentedrone. Its mode of action involves arousal of the sympathetic nervous system (via potentiation of locus coeruleus noradrenaline pathways), and potentiation of ventral tegmental pathways comprising the brain's limbic "reward" system. Buphedrone presumably acts as a releasing agent and reuptake inhibitor of dopamine and norepinephrine.

NEB

N-ethylbuphedrone is a substituted cathinone with psychostimulant properties. It is the ethylamino analogue of buphedrone.

Brephedrone

Also known as 4-bromomethcathinone, brephedrone is an RC of the substituted cathinone family. It acts as a serotonin-noradrenaline reuptake inhibitor and is said to act as more of an antidepressant than a psychostimulant; one could speculate this to be due to its relatively mild dopaminergic action. Nonetheless, it has been marketed as a research chemical.

This compound is one of a number of cathinones and amphetamines containing a halogen substitution at the C4 position of the benzene ring. It is not currently known whether a 4-halogen substitution in the cathinone family causes toxicity to serotonergic neurons as it is believed to do in the amphetamine family.


Methylone:

Methylone goes by a few names and is an intriguiging drug by itself. Other names you may be familiar with include bk-MDMA (meaning beta-keto-MDMA), or MDMC (meaning methlenedioxymethcathinone).

This drug is very similar to MDMA in both the chemical sense and the pharmacological sense. In the simplest of terms, methylone is the beta-keto analog of MDMA (ecstasy). It is related to methcathinone in the same way MDMA is related to methamphetamine. It is best described as an analog of MDMA where the beta carbon contains a ketone group.

Methylone is believed to induce the release of the monoamine neurotransmitters while inhibiting their reuptake as well; leading to increased flow of monoamine transmission throughout the brain and CNS. Its affinity for the serotonin transporter is somewhat lesser than that of MDMA, while its affinity for dopamine and norepinephrine transporters is comparable to MDMA. This essentially means that it is likely to have moderate empathogenic effects and ecstasy-like euphorigenic and psychostimulant effects.

Butylone

Butylone is a compound of the substituted cathinone family. It is the chain lengthened homologue of methylone (bk-MDMA). It differs from methylone in that it contains an ethyl rather than a methyl group at the alpha carbon. Butylone is also the beta-keto homologue of MBDB.

Butylone produces stimulating enactogenic effects. Its mode of action involved potentiation of monoamine pathways, presumably through inhibition of 5HT, NE, and DA reuptake transporters and possibly through increased monoamine release.

Pentylone (bk-MBDP)

Pentylone is a centrally acting compound of the substituted cathinone family with psychostimulant and euphorigenic properties. It was originally synthesized in the 1960's and is/has been marketed as a research chemical and designer drug.

Pentylone is the 3,4-methylenedioxy analogue of pentedrone, and can be considered the methylamino analogue of MDPV.

The effects of pentylone are comparable to those of other cathinone-type stimulants. Pentylone is believed to act as a releasing agent and/or reuptake inhibitor of dopamine, norepinephrine, and possibly serotonin.

Ethylone (MDEC, bk-MDEA) 

Ethylone is a cathinone-based compound with stimulant, enactogen, and psychedelic properties. It is a relative of methylone and has been sold as a research chemical/designer drug. Ethylone has a very short history of human use and little is known regarding its toxicity or safety profile. 

Ethylone is the cathinone equivalent to MDEA ("Eve"), and differs only in containing a ketone at the bata side chain position. 

The pharmacological profile of this compound has not been studied, though it is likely to produce its effects via potentiation of monoamine + serotonin pathways.

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