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Methylone
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<h2 id="chemistry">Chemistry</h2> <p>Methylone is the substituted cathinone <a href="/facts/Structural_analog/3aysWSVG">analogue</a> of 3,4-methylenedioxymethamphetamine (MDMA) and the 3,4-<a href="/facts/Methylenedioxy/VltTYSFh">methylenedioxy</a> analog of <a href="/facts/Methcathinone/tF4VcbcI">methcathinone</a>. The only structural difference of methylone with respect to MDMA is the substitution of 2 hydrogen atoms by 1 oxygen atom in the β position of the <a href="/facts/Phenethylamine/XyjysSul">phenethylamine</a> core, forming a <a href="/facts/Ketone/BqQXpLo4">ketone</a> <a href="/facts/Functional_group/GXkSPsjM">group</a>.<a class="footnote-ref" id="fnref:38" href="#fn:38"><sup>38</sup></a> </p> <h2 id="effects">Effects</h2> <h3>Resemblance to MDMA</h3> <p class="note">See also: <a href="/facts/MDMA/WYDACxGN">MDMA</a></p> <p>Methylone substitutes for MDMA in <a href="/facts/Drug_discrimination/VGtKo2RY">drug discrimination</a> tests in rodents. Methylone does not substitute for the stimulant <a href="/facts/Amphetamine/yKIpLJ9E">amphetamine</a> or for the <a href="/facts/Hallucinogen/gn35weCu">hallucinogen</a> <a href="/facts/DOM_(drug)/YfQep4m0">DOM</a> in animal drug discrimination tests.<a class="footnote-ref" id="fnref:39" href="#fn:39"><sup>39</sup></a> Further, also in common with MDMA, methylone acts on monoaminergic systems. <i><a href="/facts/In_vitro/evp3hAX6">In vitro</a></i>, methylone has one third the potency of MDMA at inhibiting platelet serotonin accumulation and about the same in its inhibiting effects on the dopamine and noradrenaline transporters.<a class="footnote-ref" id="fnref:40" href="#fn:40"><sup>40</sup></a><a class="footnote-ref" id="fnref:41" href="#fn:41"><sup>41</sup></a><a class="footnote-ref" id="fnref:42" href="#fn:42"><sup>42</sup></a> </p><p>In spite of these behavioral and pharmacological similarities between methylone and MDMA, the observed subjective effects of both drugs are not completely identical. <a href="/facts/Alexander_Shulgin/DK7CAPtu">Alexander Shulgin</a> wrote of the former:<a class="footnote-ref" id="fnref:43" href="#fn:43"><sup>43</sup></a> </p> <blockquote><p>"[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."</p></blockquote> <p>In acute pharmacological studies of methylone (50–300 mg) in humans, the drug produced physiological and psychological effects including increased <a href="/facts/Blood_pressure/VtqqSM2J">blood pressure</a>, <a href="/facts/Heart_rate/YngB0bzg">heart rate</a>, <a href="/facts/Body_temperature/V692hIjw">body temperature</a>, <a href="/facts/Pupil_dilation/0wP5p5KL">pupil dilation</a>, <a href="/facts/Psychostimulant/nmBdAXM5">stimulation</a>, <a href="/facts/Euphoria/u4cnbWC4">euphoria</a>, feelings of <a href="/facts/Well-being/h1dsU4VU">well-being</a>, enhanced <a href="/facts/Empathy/Pak5Dvfh">empathy</a>, increased <a href="/facts/Sociability/RJtLfpfE">sociability</a>, and <a href="/facts/Altered_perception/97vjsHXF">altered perception</a>.<a class="footnote-ref" id="fnref:44" href="#fn:44"><sup>44</sup></a><a class="footnote-ref" id="fnref:45" href="#fn:45"><sup>45</sup></a> The studies found that the effects of methylone were similar to or milder than those of MDMA.<a class="footnote-ref" id="fnref:46" href="#fn:46"><sup>46</sup></a><a class="footnote-ref" id="fnref:47" href="#fn:47"><sup>47</sup></a> Methylone had a faster <a href="/facts/Onset_of_action/BTIWvLSY">onset of action</a> and its subjective effects wore off sooner than MDMA, which might lead to a redosing pattern of use.<a class="footnote-ref" id="fnref:48" href="#fn:48"><sup>48</sup></a> The <a href="/facts/Misuse_potential/e3jLXFsF">misuse potential</a> of methylone, as measured by for instance <a href="/facts/Drug_liking/6efVGoF8">drug liking</a> responses, appeared to be similar to that of MDMA.<a class="footnote-ref" id="fnref:49" href="#fn:49"><sup>49</sup></a> However it also has less off-target effects than MDMA which may be an advantage for medical applications.<a class="footnote-ref" id="fnref:50" href="#fn:50"><sup>50</sup></a><a class="footnote-ref" id="fnref:51" href="#fn:51"><sup>51</sup></a><a class="footnote-ref" id="fnref:52" href="#fn:52"><sup>52</sup></a> </p> <h2 id="pharmacology">Pharmacology</h2> <h3>Pharmacodynamics</h3> <p>Methylone acts as a mixed <a href="/facts/Releasing_agent/JwSvmyR8">releasing agent</a> and <a href="/facts/Reuptake_inhibitor/vsrPEUXF">reuptake inhibitor</a> of <a href="/facts/Serotonin/EzY58q4a">serotonin</a>, <a href="/facts/Norepinephrine/AjTIC9ox">norepinephrine</a>, and <a href="/facts/Dopamine/5gNy8Xkd">dopamine</a>.<a class="footnote-ref" id="fnref:53" href="#fn:53"><sup>53</sup></a><a class="footnote-ref" id="fnref:54" href="#fn:54"><sup>54</sup></a> In comparison to MDMA, it has approximately 3-fold lower <a href="/facts/Affinity_(pharmacology)/44QLL4eU">affinity</a> for the <a href="/facts/Serotonin_transporter/VPh5wtCy">serotonin transporter</a>, while its affinity for the <a href="/facts/Norepinephrine_transporter/532N8LIg">norepinephrine</a> and <a href="/facts/Dopamine_transporter/V9I2Uy1p">dopamine transporters</a> is similar.<a class="footnote-ref" id="fnref:55" href="#fn:55"><sup>55</sup></a><a class="footnote-ref" id="fnref:56" href="#fn:56"><sup>56</sup></a> Notably, methylone's affinity for the <a href="/facts/Vesicular_monoamine_transporter_2/SnQpq1zy">vesicular monoamine transporter 2</a> (VMAT2) is about 13-fold lower than that of MDMA.<a class="footnote-ref" id="fnref:57" href="#fn:57"><sup>57</sup></a> The results of these differences in pharmacology relative to MDMA are that methylone is less <a href="/facts/Potency_(pharmacology)/D38FDyPh">potent</a> in terms of <a href="/facts/Dose_(biochemistry)/Gez72mSn">dose</a>, has more balanced <a href="/facts/Catecholaminergic/5u1pUedP">catecholaminergic</a> effects relative to <a href="/facts/Serotonin/EzY58q4a">serotonergic</a>, and behaves more like a reuptake inhibitor like <a href="/facts/Methylphenidate/PHmG2R5p">methylphenidate</a> than a releaser like <a href="/facts/Amphetamine/yKIpLJ9E">amphetamine</a>; however, methylone still has relatively robust releasing capabilities.<a class="footnote-ref" id="fnref:58" href="#fn:58"><sup>58</sup></a> </p><p>In contrast to MDMA, methylone and its <a href="/facts/Metabolite/nAyywVtA">metabolites</a> lack significant affinity for the serotonin <a href="/facts/5-HT2A_receptor/YfTglQKQ">5-HT2A</a> and <a href="/facts/5-HT2C_receptor/RuyLstWf">5-HT2C receptors</a> and similarly do not activate the serotonin <a href="/facts/5-HT2B_receptor/Sy104fUR">5-HT2B receptor</a>.<a class="footnote-ref" id="fnref:59" href="#fn:59"><sup>59</sup></a><a class="footnote-ref" id="fnref:60" href="#fn:60"><sup>60</sup></a><a class="footnote-ref" id="fnref:61" href="#fn:61"><sup>61</sup></a> This may make methylone safer than MDMA, for instance in terms of long-term <a href="/facts/Cardiac_valvulopathy/V7lraqpM">cardiac valvulopathy</a> risk.<a class="footnote-ref" id="fnref:62" href="#fn:62"><sup>62</sup></a><a class="footnote-ref" id="fnref:63" href="#fn:63"><sup>63</sup></a><a class="footnote-ref" id="fnref:64" href="#fn:64"><sup>64</sup></a> Methylone is inactive at the mouse and rat <a href="/facts/Trace_amine-associated_receptor_1/Xf3Qpjtw">trace amine-associated receptor 1</a> (TAAR1).<a class="footnote-ref" id="fnref:65" href="#fn:65"><sup>65</sup></a><a class="footnote-ref" id="fnref:66" href="#fn:66"><sup>66</sup></a> </p><p>Methylone has been found to produce <a href="/facts/Psychoplastogen/bWuX1Kmo">psychoplastogenic</a> effects in <a href="/facts/Preclinical_research/WSI14rnq">preclinical research</a> and showed greater effects than MDMA.<a class="footnote-ref" id="fnref:67" href="#fn:67"><sup>67</sup></a> </p><p>Similarly to MDMA, methylone has been found to be a <a href="/facts/Monoaminergic_neurotoxin/c4S00WQj">monoaminergic neurotoxin</a> in animals.<a class="footnote-ref" id="fnref:68" href="#fn:68"><sup>68</sup></a> It has specifically been found to produce <a href="/facts/Serotonergic_neurotoxin/c4S00WQj">serotonergic</a> and <a href="/facts/Dopaminergic_neurotoxin/c4S00WQj">dopaminergic neurotoxicity</a> in rodents.<a class="footnote-ref" id="fnref:69" href="#fn:69"><sup>69</sup></a> However, in one study, moderate doses of MDMA produced serotonergic neurotoxicity in rodents whereas methylone and mephedrone did not do so, suggesting that cathinones like methylone may be less neurotoxic than their corresponding amphetamine counterparts like MDMA.<a class="footnote-ref" id="fnref:70" href="#fn:70"><sup>70</sup></a><a class="footnote-ref" id="fnref:71" href="#fn:71"><sup>71</sup></a> </p> <a href="/facts/Monoamine_releasing_agent/JwSvmyR8">Monoamine release</a> of methylone and related agents (<a href="/facts/Half_maximal_effective_concentration/x7oD7ITx">EC50</a>Tooltip Half maximal effective concentration, nM)<table><tbody><tr><th>Compound</th><th><a href="/facts/Serotonin/EzY58q4a">5-HT</a>Tooltip Serotonin</th><th><a href="/facts/Norepinephrine/AjTIC9ox">NE</a>Tooltip Norepinephrine</th><th><a href="/facts/Dopamine/5gNy8Xkd">DA</a>Tooltip Dopamine</th><th>Ref</th></tr><tr><td><a href="/facts/Dextroamphetamine/SoVP3mKN">Dextroamphetamine</a></td><td>698–1,765</td><td>6.6–7.2</td><td>5.8–24.8</td><td><a class="footnote-ref" id="fnref:72" href="#fn:72"><sup>72</sup></a><a class="footnote-ref" id="fnref:73" href="#fn:73"><sup>73</sup></a></td></tr><tr><td><a href="/facts/Dextromethamphetamine/vS1jloMe">Dextromethamphetamine</a></td><td>736–1,292</td><td>12.3–13.8</td><td>8.5–24.5</td><td><a class="footnote-ref" id="fnref:74" href="#fn:74"><sup>74</sup></a><a class="footnote-ref" id="fnref:75" href="#fn:75"><sup>75</sup></a></td></tr><tr><td><a href="/facts/Methylenedioxyamphetamine/VY3nE55f">MDA</a>Tooltip Methylenedioxyamphetamine</td><td>160–162</td><td>47–108</td><td>106–190</td><td><a class="footnote-ref" id="fnref:76" href="#fn:76"><sup>76</sup></a><a class="footnote-ref" id="fnref:77" href="#fn:77"><sup>77</sup></a><a class="footnote-ref" id="fnref:78" href="#fn:78"><sup>78</sup></a></td></tr><tr><td><a href="/facts/Methylenedioxymethamphetamine/WYDACxGN">MDMA</a>Tooltip Methylenedioxymethamphetamine</td><td>49.6–72</td><td>54.1–110</td><td>51.2–278</td><td><a class="footnote-ref" id="fnref:79" href="#fn:79"><sup>79</sup></a><a class="footnote-ref" id="fnref:80" href="#fn:80"><sup>80</sup></a><a class="footnote-ref" id="fnref:81" href="#fn:81"><sup>81</sup></a><a class="footnote-ref" id="fnref:82" href="#fn:82"><sup>82</sup></a><a class="footnote-ref" id="fnref:83" href="#fn:83"><sup>83</sup></a></td></tr><tr><td><a href="/facts/Cathinone/wDASEcYS">Cathinone</a></td><td>6,100–7,595</td><td>23.6–25.6</td><td>34.8–83.1</td><td><a class="footnote-ref" id="fnref:84" href="#fn:84"><sup>84</sup></a><a class="footnote-ref" id="fnref:85" href="#fn:85"><sup>85</sup></a><a class="footnote-ref" id="fnref:86" href="#fn:86"><sup>86</sup></a></td></tr><tr><td><a href="/facts/Methcathinone/tF4VcbcI">Methcathinone</a></td><td>2,592–5,853</td><td>22–26.1</td><td>12.5–49.9</td><td><a class="footnote-ref" id="fnref:87" href="#fn:87"><sup>87</sup></a><a class="footnote-ref" id="fnref:88" href="#fn:88"><sup>88</sup></a><a class="footnote-ref" id="fnref:89" href="#fn:89"><sup>89</sup></a><a class="footnote-ref" id="fnref:90" href="#fn:90"><sup>90</sup></a><a class="footnote-ref" id="fnref:91" href="#fn:91"><sup>91</sup></a></td></tr><tr><td><a href="/facts/Methylenedioxycathinone/RKT74FQI">MDC</a>Tooltip Methylenedioxycathinone</td><td>966</td><td>394</td><td>370</td><td><a class="footnote-ref" id="fnref:92" href="#fn:92"><sup>92</sup></a></td></tr><tr><td>Methylone (MDMC)</td><td>234–708</td><td>140–270</td><td>117–220</td><td><a class="footnote-ref" id="fnref:93" href="#fn:93"><sup>93</sup></a><a class="footnote-ref" id="fnref:94" href="#fn:94"><sup>94</sup></a><a class="footnote-ref" id="fnref:95" href="#fn:95"><sup>95</sup></a><a class="footnote-ref" id="fnref:96" href="#fn:96"><sup>96</sup></a><a class="footnote-ref" id="fnref:97" href="#fn:97"><sup>97</sup></a></td></tr><tr><td><a href="/facts/Mephedrone/ffV6RrUr">Mephedrone</a></td><td>118.3–122</td><td>58–62.7</td><td>49.1–51</td><td><a class="footnote-ref" id="fnref:98" href="#fn:98"><sup>98</sup></a><a class="footnote-ref" id="fnref:99" href="#fn:99"><sup>99</sup></a><a class="footnote-ref" id="fnref:100" href="#fn:100"><sup>100</sup></a><a class="footnote-ref" id="fnref:101" href="#fn:101"><sup>101</sup></a><a class="footnote-ref" id="fnref:102" href="#fn:102"><sup>102</sup></a></td></tr><tr><td colspan="5">Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The <a href="/facts/Bioassay/hRM3LIJn">assays</a> were done in rat brain <a href="/facts/Synaptosome/VTwyaNB1">synaptosomes</a> and human <a href="/facts/Potency_(pharmacology)/D38FDyPh">potencies</a> may be different. See also <a href="/facts/Monoamine_releasing_agent/JwSvmyR8">Monoamine releasing agent § Activity profiles</a> for a larger table with more compounds. Refs: <a class="footnote-ref" id="fnref:103" href="#fn:103"><sup>103</sup></a><a class="footnote-ref" id="fnref:104" href="#fn:104"><sup>104</sup></a></td></tr></tbody></table> <h3>Pharmacokinetics</h3> <p>The two major <a href="/facts/Metabolic_pathway/8Py8HKJd">metabolic pathways</a> in <a href="/facts/Mammal/phSwTzBo">mammals</a> for methylone are <i>N</i>-<a href="/facts/Demethylation/AvM5BLjD">demethylation</a> to <a href="/facts/Methylenedioxycathinone/RKT74FQI">methylenedioxycathinone</a> (MDC), and <a href="/facts/Demethylation/AvM5BLjD">demethylation</a> followed by <i>O</i>-<a href="/facts/Methylation/EvDMWVW5">methylation</a> of the 3- or 4-<a href="/facts/Hydroxyl/1Hs2QAEv">hydroxy</a> <a href="/facts/Functional_group/GXkSPsjM">group</a> to <a href="/facts/4-hydroxy-3-methoxymethcathinone/JhTmdgqK">4-hydroxy-3-methoxymethcathinone</a> (HMMC) or 3-hydroxy-4-methoxymethcathinone (3-OH-4-MeO-MC). Another <a href="/facts/Metabolite/nAyywVtA">metabolite</a> is <a href="/facts/3,4-dihydroxymethcathinone/zdWGqxQp">3,4-dihydroxymethcathinone</a> (HHMC).<a class="footnote-ref" id="fnref:105" href="#fn:105"><sup>105</sup></a><a class="footnote-ref" id="fnref:106" href="#fn:106"><sup>106</sup></a> 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).<a class="footnote-ref" id="fnref:107" href="#fn:107"><sup>107</sup></a> The mean <a href="/facts/Elimination_half-life/7nB2JtMr">elimination half-lives</a> of methylone in humans following <a href="/facts/Oral_administration/vNQcvLVx">oral administration</a> of doses of 50 to 200 mg ranged from 5.8 to 6.9 hours.<a class="footnote-ref" id="fnref:108" href="#fn:108"><sup>108</sup></a> The <a href="/facts/Onset_of_action/BTIWvLSY">onset of action</a> and <a href="/facts/Duration_of_action/zdvfFshl">duration of action</a> of methylone in humans are 0.5 hours and 2.5 to 3.0 hours, respectively.<a class="footnote-ref" id="fnref:109" href="#fn:109"><sup>109</sup></a> </p> <h2 id="history">History</h2> <p>Methylone was first <a href="/facts/Chemical_synthesis/3KXsVVwC">synthesized</a> by <a href="/facts/Peyton_Jacob_III/Jwn3w1eQ">Peyton Jacob III</a> and <a href="/facts/Alexander_Shulgin/DK7CAPtu">Alexander Shulgin</a> in the mid-1990s.<a class="footnote-ref" id="fnref:110" href="#fn:110"><sup>110</sup></a><a class="footnote-ref" id="fnref:111" href="#fn:111"><sup>111</sup></a><a class="footnote-ref" id="fnref:112" href="#fn:112"><sup>112</sup></a> This was after the publication of Shulgin's <a href="/facts/PiHKAL/sAR8owwC">PiHKAL</a> (1991), and so methylone is not included in this book.<a class="footnote-ref" id="fnref:113" href="#fn:113"><sup>113</sup></a> However, it was subsequently included in <i><a href="/facts/The_Shulgin_Index/bevcka9e">The Shulgin Index</a></i> (2011).<a class="footnote-ref" id="fnref:114" href="#fn:114"><sup>114</sup></a> The drug was <a href="/facts/Patent/LjT2bG3A">patented</a> by Jacob and Shulgin as a potential <a href="/facts/Antidepressant/N62ND3Fa">antidepressant</a> and <a href="/facts/Antiparkinsonian_agent/ESoJ5bf5">antiparkinsonian agent</a>, but was never developed or marketed.<a class="footnote-ref" id="fnref:115" href="#fn:115"><sup>115</sup></a><a class="footnote-ref" id="fnref:116" href="#fn:116"><sup>116</sup></a> This was the first time that methylone was described in the literature.<a class="footnote-ref" id="fnref:117" href="#fn:117"><sup>117</sup></a> The drug was first described in the <a href="/facts/Scientific_literature/nJh0Bx22">scientific literature</a> by 1997.<a class="footnote-ref" id="fnref:118" href="#fn:118"><sup>118</sup></a> Methylone was encountered as a <a href="/facts/Designer_drug/QWFd3KV4">designer</a> and <a href="/facts/Recreational_drug/eoBD3vKn">recreational drug</a> by 2004.<a class="footnote-ref" id="fnref:119" href="#fn:119"><sup>119</sup></a><a class="footnote-ref" id="fnref:120" href="#fn:120"><sup>120</sup></a> It has become a <a href="/facts/Controlled_substance/Hx9cKG4f">controlled substance</a> in many countries.<a class="footnote-ref" id="fnref:121" href="#fn:121"><sup>121</sup></a> </p> <h2 id="society-and-culture">Society and culture</h2> <h3>Names and etymology</h3> <p>"Methylone" is also a trademarked brand name for an injectable form of <a href="/facts/Methylprednisolone/wzGSj2jQ">methylprednisolone</a>, a corticosteroid hormone used to treat arthritis and severe allergic reactions; hence, methylone may be confused with it. Aside from context, they can be distinguished by the fact that the name will usually be capitalized when referring to the prescription drug. </p><p>A proposed alternate name is βk-MDMA, or beta-keto-MDMA. While this nomenclature has not caught on because the name "methylone" became widely used before the conflicting Methylone trademark was noticed, the analogous names for related chemicals <a href="/facts/Bk-MDEA/QM75ckRE">βk-MDEA</a> and <a href="/facts/Bk-MBDB/WWfsRRex">βk-MBDB</a> have become the established names for those substances. </p> <h3>Commercial distribution</h3> <p>Analysis of "Explosion" has confirmed that the active ingredient is methylone.<a class="footnote-ref" id="fnref:122" href="#fn:122"><sup>122</sup></a>[<i>unreliable source?</i>] Many other formulations marketed as household chemicals, as well as the pure powder, have been sold. </p> <h3>Legal status</h3> <h4>Netherlands</h4> <p>In the Netherlands, methylone is not yet listed under the <a href="/facts/Opium_Law/tR5wLQmF">Opium Law</a>, but is covered under the medicine act. Because methylone is not registered officially, 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.<a class="footnote-ref" id="fnref:123" href="#fn:123"><sup>123</sup></a> Until now, no research has been conducted on the toxicity of methylone, so nothing is known about the harmfulness of this new drug. </p> <h4>New Zealand</h4> <p>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 was sold in New Zealand for around 6 months from November 2005 to April 2006 as an MDMA substitute, under the name "Ease". The product was withdrawn after legal disputes with the government.<a class="footnote-ref" id="fnref:124" href="#fn:124"><sup>124</sup></a><a class="footnote-ref" id="fnref:125" href="#fn:125"><sup>125</sup></a> </p> <h4>United Kingdom</h4> <p>In the United Kingdom, methylone is illegal since the 16/04/2010 revision of the misuse of drugs act. Before this it was not specifically mentioned in United Kingdom (U.K.) law as the β-ketone was not covered under the <a href="/facts/Misuse_of_Drugs_Act_1971/nKQyQ4c5">Misuse of Drugs Act</a>. In March 2010, plans were announced to make methylone and other cathinones, Class B drugs, "within weeks". While delayed by dissatisfaction in the <a href="/facts/Advisory_Council_on_the_Misuse_of_Drugs/xsYwYbmH">Advisory Council on the Misuse of Drugs</a>, the revision was rushed through by the government with little regard for the views of the council. The importation of the compound was banned immediately.<a class="footnote-ref" id="fnref:126" href="#fn:126"><sup>126</sup></a> </p> <h4>Sweden</h4> <p><a href="/facts/Riksdag/uarwUozH"><i>Sveriges riksdag</i></a> added methylone to schedule I (<i>"substances, plant materials and fungi which normally do not have medical use"</i>) as narcotics in Sweden as of Oct 1, 2010, published by <a href="/facts/Medical_Products_Agency_(Sweden)/TAAAhvnH"><i>Medical Products Agency</i></a> in their regulation LVFS 2010:23 listed as Metylon, 2-metylamino-1-(3,4-metylendioxifenyl)propan-1-on.<a class="footnote-ref" id="fnref:127" href="#fn:127"><sup>127</sup></a> Methylone was first classified by <a href="/facts/Riksdag/uarwUozH"><i>Sveriges riksdags</i></a> health ministry Statens folkhälsoinstitut [sv] as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor [sv] (translated <i>Act on the Prohibition of Certain Goods Dangerous to Health</i>) as of Nov 1, 2005, in their regulation SFS 2005:733 listed as 3,4-metylendioximetkatinon (Metylon).<a class="footnote-ref" id="fnref:128" href="#fn:128"><sup>128</sup></a> </p> <h4>Canada</h4> <p>Although not listed as a <a href="/facts/Controlled_Substances_Act/8laeNsgD">Schedule 1</a><a class="footnote-ref" id="fnref:129" href="#fn:129"><sup>129</sup></a> substance, Health Canada reports that methylone falls under the scheduling as an analogue of amphetamine. However, Methylone bears the exact chemical difference between amphetamine and <a href="/facts/Cathinone/wDASEcYS">cathinone</a> – and cathinone is listed as not being an analogue of amphetamine, possibly implying that methylone is unscheduled in Canada.<a class="footnote-ref" id="fnref:130" href="#fn:130"><sup>130</sup></a> The CDSA was updated as a result of the Safe Streets Act changing amphetamines from <a href="/facts/Controlled_Substances_Act/8laeNsgD">Schedule 3</a> to <a href="/facts/Controlled_Substances_Act/8laeNsgD">Schedule 1</a>; however, methylone was not added.<a class="footnote-ref" id="fnref:131" href="#fn:131"><sup>131</sup></a> </p> <h4>United States</h4> <p>In October 2011, the <a href="/facts/Drug_Enforcement_Administration/qGQpHNB8">DEA</a> issued an emergency ban on methylone. It was made illegal to possess and distribute.<a class="footnote-ref" id="fnref:132" href="#fn:132"><sup>132</sup></a><a class="footnote-ref" id="fnref:133" href="#fn:133"><sup>133</sup></a> On April 4, 2013, the DEA placed methylone as a Schedule 1 substance under the CSA.<a class="footnote-ref" id="fnref:134" href="#fn:134"><sup>134</sup></a> </p> <ul><li>Arizona:</li></ul> Effective February 16, 2012, methylenedioxymethcathinone (methylone) was classified as a dangerous drug, making it a felony to knowingly possess, use, possess for sale, manufacture, administer, transport for sale, import into the state, or offer to transport for sale or import into this state, sell, transfer or offer to sell or transfer. A.R.S. 13-3401(6)(c)(xliii), 2012 Ariz. Legis. Serv. Ch. 1 (H.B. 2356). <ul><li>Florida:</li></ul> In January 2011, it was reported that Florida Attorney General Pam Bondi issued an emergency ban on MDPV, Methylone, Mephedrone, 3-methoxymethcathinone, 3-fluoromethcathinone, and 4-fluoromethcathinone as media attention on products labeled as "bath salts" grew. These chemicals are now Schedule I under Florida law.<a class="footnote-ref" id="fnref:135" href="#fn:135"><sup>135</sup></a> <ul><li>Louisiana:</li></ul> In January 2011, Louisiana Governor Bobby Jindal emergency scheduled 3,4-methylenedioxymethcathinone (methylone), 3,4-methyenedioxypyrovalerone (<a href="/facts/MDPV/jJzoqd5M">MDPV</a>), 4-methylmethcathinone (<a href="/facts/Mephedrone/ffV6RrUr">mephedrone</a>), 4-methoxymethcathinone (<a href="/facts/Methedrone/S0gYTRxU">methedrone</a>), 4-fluoromethcathinone (<a href="/facts/Flephedrone/xJ89aoQu">flephedrone</a>), and 3-fluoromethcathinone (<a href="/facts/3-FMC/pU5Sn7Xl">3-FMC</a>). <ul><li>Tennessee:</li></ul> On May 5, 2011, Tennessee Governor <a href="/facts/Bill_Haslam/bfwgJEMx">Bill Haslam</a> signed a law making it a crime to knowingly produce, manufacture, distribute, sell, offer for sale or possess with intent produce, manufacture, distribute, sell, or offer for sale any product containing 3,4-methylenedioxymethcathinone (methylone), 3,4-methyenedioxypyrovalerone (<a href="/facts/MDPV/jJzoqd5M">MDPV</a>), 4-methylmethcathinone (<a href="/facts/Mephedrone/ffV6RrUr">mephedrone</a>), 4-methoxymethcathinone (<a href="/facts/Methedrone/S0gYTRxU">methedrone</a>), 4-fluoromethcathinone (<a href="/facts/Flephedrone/xJ89aoQu">flephedrone</a>), and 3-fluoromethcathinone (<a href="/facts/3-FMC/pU5Sn7Xl">3-FMC</a>).<a class="footnote-ref" id="fnref:136" href="#fn:136"><sup>136</sup></a> <ul><li>Texas:</li></ul> In September 2011, Texas added 3,4-methylenedioxy-<i>N</i>-methylcathinone to the Penalty Group 2 listing of the Health and Safety Code. Possession of a substance in penalty group 2 is a minimum of a state jail felony. <ul><li>Michigan:</li></ul> Schedule 1 controlled substance in 2012. <h2 id="research">Research</h2> <h3>Post-traumatic stress disorder</h3> <p>Under the developmental code TSND-201, methylone is under <a href="/facts/Drug_development/k34jgV4B">development</a> by Transcend Therapeutics for the treatment of <a href="/facts/Post-traumatic_stress_disorder/9etKu7bX">post-traumatic stress disorder</a> (PTSD).<a class="footnote-ref" id="fnref:137" href="#fn:137"><sup>137</sup></a><a class="footnote-ref" id="fnref:138" href="#fn:138"><sup>138</sup></a><a class="footnote-ref" id="fnref:139" href="#fn:139"><sup>139</sup></a> As of July 2024, it is in <a href="/facts/Phases_of_clinical_research/o8hEodVu">phase 2</a> <a href="/facts/Clinical_trial/q8LMr832">clinical trials</a> for this indication.<a class="footnote-ref" id="fnref:140" href="#fn:140"><sup>140</sup></a><a class="footnote-ref" id="fnref:141" href="#fn:141"><sup>141</sup></a> </p> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Oeri HE (May 2021). 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Retrieved 2010-01-17. <a href="https://web.archive.org/web/20100413235500/http://www.cognitiveliberty.org/shulgin/adsarchive/cathinone.htm" target="_blank">https://web.archive.org/web/20100413235500/http://www.cognitiveliberty.org/shulgin/adsarchive/cathinone.htm</a> <a href="#fnref:23" class="footnote-back-ref">↩</a></p></li> <li id="fn:24"><p>Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". J Psychopharmacol. 35 (5): 512–536. doi:10.1177/0269881120920420. PMC 8155739. PMID 32909493. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8155739" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8155739</a> <a href="#fnref:24" class="footnote-back-ref">↩</a></p></li> <li id="fn:25"><p>Oeri HE (May 2021). "Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy". 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