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20-September-2008 09:55:56 - Methylenedioxymethcathinone Redirected from Methylone MDMC chemical structure Methylenedioxymethcathinone IUPAC name: 2-methylamino-1-3,4-methylenedioxyphenylpropan-1-one CAS number Racemic Methylone: 186028-79-5; S-Methylone: 191916-41-3 ATC code ? Chemical formula C11H13NO3 Molecular weight 207.23 Elimination half life ? Legal status Unscheduled USA Unscheduled UK Unscheduled CA Delivery 150-200mg orally 50-150mg intravenously Recreational uses: euphoria bonding Other uses: Marriage counseling Anxiety PTSD End of Life Care 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 Explosion Explosion Methylone, or properly 3,4-methylenedioxymethcathinone, is a beta-ketone analogue of MDMA. Also known as bk-MDMA, M1, or MDMCat, the abbreviation MDMC is not used as this designation was already given to another chemical by Alexander Shulgin. In spite of some substantial pharmacokinetic differences its dopaminergic activity is far more pronounced relative to its serotonergic activity, methylone is an empathogen-like drug and a mild stimulant, producing effects similar to, yet less intense than MDMA.citation needed Contents 1 Explosion 2 MDMA resemblance 3 Legal Status 4 Metabolites 5 Combination with MBDB 6 Naming problem 7 References 8 See also 9 External links Explosion 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.citation needed 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-methylenedioxyphenylpropan-1-one. 3,4-Methylenedioxymethcathinone MDMCat or methylone is the benzylic ketone analogue of 3,4-methylenedioxymethamphetamine MDMA: it contains an additional oxygen atom at the benzylic position of the molecule Figure 1.1 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 MDMA resemblance 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.3 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.456 In spite of these behavioural and pharmacological similarities between methylone and MDMA, the observed subjective effects of both drugs are not completely identical. Alexander Shulgin wrote of the former: 'methylone has almost the same potency of MDMA, but it does not produce the same effects. It has an almost antidepressant action, pleasant and positive, but not the unique magic of MDMA'. Legal Status In the Netherlands, methylone is not yet scheduled as a drug of abuse, but is considered to be a psychoactive medicine. Because methylone is not registered officially, as such, it is forbidden to trade in methylone. The Minister of Health has asked the Coordination point Assessment and Monitoring new drugs group CAM to gather information about this substance, resulting possibly in an official risk assessment van Amsterdam et al., 2004. Until now, no research has been conducted on the toxicity of methylone, so nothing is known about the harmfulness of this new drug. Methylone is not explicitly scheduled in the United States, but possession may still result in prosecution under the Federal Analog Act as an MDMA analogue. In New Zealand, although methylone is not explicitly scheduled and falls outside the strict definitions of an amphetamine analogue in the Misuse of Drugs Act, it is considered to be substantially similar to methcathinone and is thus considered by law enforcement authorities to be a Class C illegal drug. Methylone is currently not specifically mentioned in UK law as the beta-ketone is not covered under the Misuse of Phenethylamines Law. Methylone was sold in New Zealand for around 6 months from November 2005 to April 2006 as an Ecstasy substitute, under the brand name Ease. The product was withdrawn after legal disputes with the government. Metabolites The two major metabolic pathways in humans and rats are N-demethylation to methylenedioxycathinone MDC, and demethylation followed by O-methylation of the 3- or 4-OH group to 4-hydroxy-3-methoxymethcathinone HMMC or 3-hydroxy-4-methoxymethcathinone 3-OH-4-MeO-MC. When 5mg/kg of methylone HCl was administered to rats, it was found that around 26% was excreted as HMMC within the first 48 hours less than 3% excreated unchanged. 7 Combination with MBDB This section does not cite any references or sources. Please help improve this section by adding citations to reliable sources. August 2008 MDMA has both serotonergic and dopaminergic actions. Methylone does as well, but the dopaminergic activity is much more pronounced. MBDB is another closely related chemical, but its activity is mostly serotonergic. Some people have interpreted this situation as meaning that methylone and MBDB are split halves of the effects of MDMA, and have taken the two chemicals together in an attempt to recreate the pharmacology of MDMA. Whether or not the pharmacology of this mixture is comparable to MDMA is unknown, as is the safety of such mixtures. Naming problem While Shulgin assigned the name Methylone to this chemical, and that name has become the standard nomenclature, it is a problematic name. The problem is that Methylone is a trademarked brand name for an injectible form of methylprednisolone, a corticosteroid hormone used to treat arthritis and severe allergic reactions. Aside from context, they can be distinguished by the fact that the name will always be capitalized when referring to the prescription drug. References ^ 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 ^ Cathinone. ^ TA Dal Cason, R Young, RA Glennon. Cathinone: an investigation of several N-alkyl and methylenedioxy-substituted analogs. Pharmacol. Biochem. Behav. 58, 1109-1116 1997 ^ NV Cozzi, MK Sievert, AT Shulgin, P Jacob III, AE Ruoho. Methcathinone and 2 methylamino-1-3,4-methylenedioxyphenylpropan-1-one methylone selectively inhibit plasma membrane catecholamine reuptake transporters. Soc. Neurosci. Abs., 24, 341.8 1998 ^ NV Cozzi, AT Shulgin, AE Ruoho. Methcathinone MCAT and 2-methylamino-1-3,4 methylenedioxyphenylpropan-1-one MDMCAT inhibit 3Hserotonin uptake into human platelets. Amer. Chem. Soc. Div. Med. Chem. Abs., 215, 152 1998 ^ 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 ^ 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. See also Methcathinone Cathinone MDMA MBDB Phenethylamine External links Erowid Methylone Vault Difference between Methylone and MDMA - 2d molecules v d e Empathogen-entactogens 4-Fluoroamphetamine 5-APDB 5-MeO-DALT 5-Me-MDA α-ET bk-MBDB bk-MDEA bk-MDMA DMMDA-2 IAP MBDB MDA MDAI MDEA MDMA MMDA v d e Phenethylamines 2C-B 2C-C 2C-D 2C-E 2C-I 2C-N 2C-T-2 2C-T-21 2C-T-4 2C-T-7 2C-T-8 3C-E 4-FMP Bupropion Cathine Cathinone Clenbuterol DESOXY Dextroamphetamine Methamphetamine Diethylcathinone Dimethylcathinone DOC DOB DOI DOM bk-MBDB Dopamine Br-DFLY Ephedrine Epinephrine Escaline Etafedrine Fenfluramine Levosalbutamol Levmetamfetamine MBDB MDA MDMA MDMC MDEA MDPV Mescaline Methcathinone Norepinephrine Phentermine Salbutamol Tyramine Venlafaxine Retrieved from http://en..org/wiki/Methylenedioxymethcathinone Categories: Alkaloids | Amphetamines | Entactogens and Empathogens | Psychedelic phenethylaminesHidden categories: All articles with statements | Articles with statements since August 2008 | Articles with statements since February 2007 | Articles needing additional references from August 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Français Nederlands This page was last modified on 14 August 2008, at 14:38
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