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Methylenedioxymethcathinone

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Bottle with methylone aka explosion

Explosion

methylenedioxymethcathinone or Methylone is a designer drug that is a beta-ketone analogue of MDMA (Ecstasy). It is also known as bk-MDMA, M1, MDMDog or MDMCat. MDMCat is related to methcathinone as MDMA is related to methamphetamine and MDA is to amphetamine. [1] Methylone is an empathogen and a mild stimulant, producing effects similar to, yet less intense than MDMA.

At the end of 2004, a new designer drug called ‘Explosion’ appeared in the Netherlands. This new drug is sold as a liquid via the internet and in Dutch ‘smartshops’, stores selling non-scheduled psychoactive substances. The product is advertised as a ‘room odorizer’ and is sold in plastic tubes containing 5 ml of liquid. The tubes cost between €10 and €15 ($13–$20) and do not present any information about the composition of Explosion; they contain only a label saying ‘Room odorizer Vanilla. Do not ingest’ and ‘Keep away from children. Never use more than one bottle’. In spite of this label, users mention that they ingest the liquid to reach the intended psychoactive effect.[How to reference and link to summary or text] The text was probably put onto the label to circumvent Dutch regulations for illicit drugs and psychoactive substances. Analyses of Explosion have demonstrated that the main ingredient of the liquid is the compound methylone (3,4-methylenedioxymethcathinone or 2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one). 3,4-Methylenedioxymethcathinone (MDMCAT) is the benzylic ketone analogue of 3,4-methylenedioxymethamphetamine (MDMA): it contains an additional oxygen atom at the benzylic position of the molecule ( Figure 1) (Cozzi et al., 1999). 3,4-Methylenedioxymethcathinone was first synthesized by Alexander Shulgin. Because of the similarity of effects between methamphetamine and its benzylic ketone methcathinone, he examined whether there was a comparable connection between MDMA and its benzylic analogue. He called the new substance methylone. [2] Methylone resembles MDMA in its behavioural profile, as methylone substitutes for MDMA in rats trained to discriminate MDMA from saline. Methylone does not substitute for amphetamine or for the hallucinogenic DOM in animals trained to discriminate between these drugs and saline (Dal Cason et al., 1997). Further, also in common with MDMA, methylone acts on monoaminergic systems. In vitro, methylone is threefold less potent than MDMA at inhibiting platelet serotonin accumulation and as potent as MDMA in its inhibiting effects on the dopamine and noradrenaline transporters (Cozzi et al., 1999). [1]

Effects Edit

Reported dosages in clinical essays range from 100 to 500 mg orally and from 50–150 mg intravenously (though it's extremely unsafe to use "Explosion" or any "cut" powdered methylone intravenously).

The effects of methylone may include the following:

Cognitive
Peripheral

Most of these effects are similar to those of other psychostimulants.


Pharmacology Edit

Pharmacodynamics Edit

Methylone acts as a mixed reuptake inhibitor/releasing agent of serotonin, norepinephrine, and dopamine.[2][3] In comparison to MDMA, it has approximately 3x lower affinity for the serotonin transporter, while its affinity for the norepinephrine and dopamine transporters is similar.[2][3] Notably, methylone's affinity for the vesicular monoamine transporter 2 (VMAT2) is about 13x lower than that of MDMA.[2] The results of these differences in pharmacology relative to MDMA are that methylone is less potent in terms of dose, has more balanced catecholaminergic effects relative to serotonergic, and behaves more like a reuptake inhibitor like methylphenidate than a releaser like amphetamine; though, it should be noted that methylone still has relatively robust releasing capabilities.[3]

Pharmacokinetics Edit

Little is currently known about the pharmacokinetics of methylone, aside from metabolism.

Metabolism Edit

The two major metabolic pathways in mammals for methylone are N-demethylation to methylenedioxycathinone (MDC), and demethylation followed by O-methylation of the 3- or 4-hydroxy group to 4-hydroxy-3-methoxymethcathinone (HMMC) or 3-hydroxy-4-methoxymethcathinone (3-OH-4-MeO-MC). When 5 mg/kg of methylone was administered to rats, it was found that around 26% was excreted as HMMC within the first 48 hours (less than 3% excreted unchanged).[4]

See alsoEdit

ReferencesEdit

  1. Xenobioica. H. T. Kamata, N. Shima, K. Zaitsu, T. Kamata, A. Miki, M. Nishikawa, M. Katagi, H. Tsuchihashi. (2006). Metabolism of methylone in humans and rats. Volume 36, Number 8 / August 2006.
  2. 2.0 2.1 2.2 Cozzi NV, Sievert MK, Shulgin AT, Jacob P, Ruoho AE (September 1999). Inhibition of plasma membrane monoamine transporters by beta-ketoamphetamines. European Journal of Pharmacology 381 (1): 63–9.
  3. 3.0 3.1 3.2 Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain. European Journal of Pharmacology 559 (2–3): 132–7.
  4. Xenobioica. HT Kamata, N Shima, K Zaitsu, T Kamata, A Miki, M Nishikawa, M Katagi, H Tsuchihashi. (2006). Metabolism of methylone in humans and rats. Volume 36, Number 8 / August 2006.

External linksEdit



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MDMC
MDMC-3d-sticks Methylenedioxymethcathinone

IUPAC name:
2-methylamino-1-(3,4-methylenedioxyphenyl)propan-1-one
CAS number
Racemic Methylone: 186028-79-5; (S)-Methylone: 191916-41-3
ATC code
��?
Chemical formula C

11H13NO3

Molecular weight 207.23
Elimination half life ��?
Legal status Unscheduled (USA)
Unscheduled (UK)
Unscheduled (CA)
Delivery 150-200mg orally </br> 50-150mg intravenously
Recreational uses:
:*euphoria:*bonding
Other uses:
:*Marriage counseling:*Anxiety
Contraindications:
:*Not for use in combination with stimulants (amphetamines, large doses of caffeine, etc).:*Not for use in combination with diuretics (alcohol).
  • Not for use in individuals with high blood pressure, hypertension, or blood clotting disorders.
  • Not for use in individuals who have displayed allergies to amphetamine drugs.
  • Must never be used in combination with MAOI (Monoamine Oxidase Inhibitor) drugs.
Side effects:
Endocrine:
:*hyponatremia
Eye:
:*mydriasis
Psychological:
:*euphoria:*strong sense of empathy
  • serotonin deficiency
Skin:
:*sweaty palms:*heavy sweating
Miscellaneous:
:*restlessness:*chattering teeth

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