Methylone

Structural formula
( R ) -form (top) and ( S ) -form (bottom) 1: 1 mixture ( racemate )
General
Surname	Methylone
other names	( RS ) -1- (1,3-Benzodioxol-5-yl) -2- (methylamino) propan-1-one ( IUPAC ) 2-methylamino-1- (3,4-methylenedioxyphenyl) propan-1-one 3,4-methylenedioxy- N -methylcathinone βk-MDMA MDMC Mina (scene name)
Molecular formula	C 11 H 13 NO 3
External identifiers / databases
CAS number 186028-79-5 ( racemate ) 191916-41-3 [(+) - methylone] 186028-80-8 (hydrochloride) PubChem 45789647 Wikidata Q4046265
Drug information
Drug class	Psychoactive amphetamine derivative , entactogen , stimulant
properties
Molar mass	207.23 g · mol -1
Physical state	firmly
density	1.19 g cm −3 [( S ) -methylone]
Melting point	225 ° C ( hydrochloride )
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Methylon ( explosion , Ease , neocor ), also known as MDMC (3,4 M ethylene d ioxy- N - m ethyl c Athinon) (scene name "Mina") is a psycho-active substance , is within the group of amphetamines to the cathinone - derivatives . It is the β- ketone - analogue ( βk-MDMA ) of 3,4-methylenedioxy N -methylamphetamins (MDMA), the most common active ingredient in ecstasy tablets. Methylone gained general fame through its use as a so-called designer drug .

"Explosion"

explosion

At the end of 2004, the new designer drug "Explosion" became famous in the Netherlands . Methylone is sold in liquid form on the Internet and in so-called “smart shops” that offer psychoactive substances or legal highs that are not regulated by law in the Netherlands. The product is officially declared as an air freshener and sold as a solution in tubes of 250 mg of active ingredient each. The cost per tube is between € 10 and € 15. The composition of "explosion" is not given; the label only recommends use as a vanilla room air freshener and warns against ingesting the substance. If it is taken in spite of the warning, a state of intoxication can be reached. Chemical analyzes of the contents of "Explosion" showed that the main component of the liquid is methylone.

Effects

According to various experience reports, the usual dose for an intoxicating effect for oral consumption is between 100 mg and 250 mg; with pernasal consumption, the dose is slightly lower. Effects intended by consumption are euphoria, increased feeling of empathy and connectedness, increased need for communication, increased stamina, decreased need for sleep and changed visual, auditory, haptic perception and time perception. Possible side effects are hyponatremia ( sodium level too low in the blood), dilation of the pupils, depletion of the serotonin reserves , increased sweating and as a result dehydration (lack of water), mental restlessness up to restlessness and paranoia , confusion, jaw tremors (so-called "bite" or "chew") ), Increase in body temperature and heart rate, and sleep disorders. Physical exhaustion, lethargy, apathy, and depression may occur after consumption. The spectrum of activity is very similar to that of the chemically related MDMA, which is why methylone can also be a component of ecstasy tablets. Since the mechanisms of action and the toxicity have hardly been researched, the consumption of methylone harbors a particularly high risk due to the still unknown long-term side effects.

Similarity to MDMA

Methylone is very similar to MDMA. Rats conditioned to distinguish MDMA from MDMC were able to distinguish the substances from one another even after the MDMA was replaced by methylone. Methylone is not a suitable substitute for amphetamine and the hallucinogenic 2,5-dimethoxy-4-methylamphetamine (DOM) in this experiment. Furthermore, like MDMA, methylone works in the monoaminergic systems. Despite the pharmacological similarity and the similarity of the spectrum of effects of both substances, there are differences in the subjective effects.

use

Because of the stimulating and empathogenic effect of methylone, it is consumed as an intoxicant. Furthermore, the possible uses of methylone in couples therapy, as an antidepressant and sedative , in the therapy of post-traumatic stress disorder and in palliative medicine were investigated. Methylone contraindications:

• Use of other psychostimulants such as amphetamines, high doses of caffeine, cocaine
• Taking MAO inhibitors (can lead to life-threatening serotonin syndrome )
• Consumption of diuretics such as alcohol, as severe dehydration is possible
• High blood pressure and / or bleeding disorders
• Allergic reactions to amphetamines

Metabolism

The two important metabolic pathways in mammals are N-demethylation to methylenedioxycathinone (MDC) and demethylation, to 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) follows. Application of 5 mg / kg methylone to rats showed that within 48 hours 26% are excreted as HMMC and less than 3% unchanged.

etymology

The name methylone can be traced back to Alexander Shulgin . It is problematic in that “methylone” already refers to a trademarked injectable form of methylprednisolone that is used in arthritis and severe allergic reactions. There is also a phenolic resin with the brand name “Methylon”. This results in a possible mix-up of the substances.

Legal position

• Germany : With the “twenty-sixth ordinance amending narcotics regulations” of May 25, 2012, methylone was made subject to the BtMG in Annex II as a marketable, but not prescribable substance.
• Denmark: Methylone may only be used for medical or scientific purposes. Since February 2008, import and export are only permitted with approval from the Danish Ministry of Health.
• Netherlands : Although methylone is not yet legally classified as a drug, it is classified as a psychoactive drug. Since it is not registered and authorized as such, trading is illegal.
• USA : Methylone was temporarily added to the “Schedule I” list in autumn 2011 by means of “emergency scheduling” ; Trade and possession are therefore punishable.
• United Kingdom : Methylone was included in the Misuse of Drugs Act on April 16, 2010, along with many other beta-ketones. This makes possession and trade illegal.
• Sweden : Methylone has been classified as a hazardous substance since 2007, which results in a restriction on sales and trade.
• Switzerland : Methylone was made subject to the Narcotics Act by Swissmedic when the revised Narcotics Ordinance came into force on December 1, 2010 and has been illegal since then. Importation, possession, distribution etc. are punished according to the Narcotics Act.

literature

• Terry A Dal Cason, Richard Young, Richard A Glennon: Cathinone: An Investigation of Several N-Alkyl and Methylenedioxy-Substituted Analogs. (PDF; 96 kB) In: Pharmacology, Biochemistry and Behavior , Volume 58, Issue 4, December 1997, pp. 1109-1116 doi: 10.1016 / S0091-3057 (97) 00323-7 PMID 9408221
• Chiharu Sogawa, Norio Sogawa, Kazumi Ohyama, et al .: Methylone and Monoamine Transporters: Correlation with Toxicity In: Curr Neuropharmacol. 2011 March; 9 (1): 58-62. doi: 10.2174 / 157015911795017425 PMID 21886563
• Michael H Baumann, Mario A Ayestas, John S Partilla, Jacqueline R Sink, Alexander T Shulgin, Paul F Daley, Simon D Brandt, Richard B Rothman, Arnold E Ruoho, Nicholas V Cozzi: The Designer Methcathinone Analogs, Mephedrone and Methylone, are Substrates for Monoamine Transporters in Brain Tissue. In: Neuropsychopharmacology . 37, 2011, pp. 1192-1203, doi: 10.1038 / npp.2011.304 .

Web links

• Methylones . In: Erowid . (English)

See also

• Methcathinone
• Cathinone
• MDMA

Individual evidence

1. ↑ Entry on methylone at ChemBlink , accessed on February 25, 2011.
2. ↑ Terry A Dal Cason, Richard Young, Richard A Glennon: Cathinone: An Investigation of Several N-Alkyl and Methylenedioxy-Substituted Analogs. (PDF; 96 kB) In: Pharmacology Biochemistry and Behavior , Volume 58, Issue 4, December 1997, pp. 1109-1116 doi: 10.1016 / S0091-3057 (97) 00323-7 , PMID 9408221 .
3. ^ Royal Pharmaceutical Society (Ed.): Clarke's Analysis of Drugs and Poisons FOURTH EDITION . Pharmaceutical Press, London / Chicago 2011, ISBN 978-0-85369-711-4 .
4. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
5. ↑ Accompanied Neocor trip for 100 euros , taz.de, March 17, 2010.
6. ^ NV Cozzi, MK Sievert, AT Shulgin, P. Jacob III, AE Ruoho: Inhibition of plasma membrane monoamine transporters by β-ketoamphetamines. Eur. J. Pharmacol., 381, 63-69 (1999), doi: 10.1016 / S0014-2999 (99) 00538-5 .
7. ↑ Follows from the designation bk-MDMA for beta-ketone-MDMA.
8. ^ Methylone sold under "Explosion" and "Inpact" brand names in the Netherlands and Japan . In: Erowid . (English) April 2005.
9. ↑ Methylone Dosage . In: Erowid . (English)
10. ^ Methylone Effects . In: Erowid . (English)
11. ^ NV Cozzi, MK Sievert, AT Shulgin, P. Jacob III, AE Ruoho: Methcathinone and 2 methylamino-1- (3,4-methylenedioxyphenyl) propan-1-one (methylone) selectively inhibit plasma membrane catecholamine reuptake transporters . Soc. Neurosci. Abs., 24, 341.8 (1998).
12. ^ NV Cozzi, AT Shulgin, AE Ruoho: Methcathinone (MCAT) and 2-methylamino-1- (3,4 methylenedioxyphenyl) propan-1-one (MDMCAT) inhibit [ ³ H] serotonin uptake into human platelets. Amer. Chem. Soc. Div. Med. Chem. Abs., 215, 152 (1998).
13. ↑ HT Kamata, N. Shima, K. Zaitsu, T. Kamata, A. Miki, M. Nishikawa, M. Katagi, H. Tsuchihashi: Metabolism of the recently encountered designer drug, methylone, in humans and rats. In: Xenobioica, Volume 36, Number 8, pp. 709-723, August 2006. doi: 10.1080 / 00498250600780191 .
14. ↑ Irene Ash: Chemical Tradename Dictionary. John Wiley and Sons, 1997, ISBN 978-0-471-18857-5 , p. 230.
15. ↑ Twenty-sixth ordinance amending narcotics law, Federal Law Gazette 2012 I p. 1639 .
16. ↑ European Legal Database on Drugs (ELDD) - Methylone .
17. ↑ DENMARK: Ketamine, methylone under control. In: European Legal Database on Drugs. EMCDDA , February 7, 2008, accessed May 30, 2017 . 
18. ^ DEA Announces Emergency Ban on 'Bath Salts' , abcnews.go.com.
19. ↑ Swissmedic Narcotics Ordinance, which came into force on December 1, 2010 (PDF; 590 kB) .
20. ↑ Swiss Narcotics Act: (PDF; 190 kB) . Relevant criminal provisions: Art. 19 and following.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !