Methylone

Methylone
Clinical data
Other names	3,4-Methylenedioxy-N-methylcathinone; Methylenedioxymethcathinone; MDMC; β-Keto-MDMA; βk-MDMA; M1; TSND-201; TSND201
Routes of; administration	Common: oral, insufflation; Uncommon: IV or IM injection, rectal
ATC code	None;
Legal status
Legal status	AU: Unscheduled; BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I; UN: Schedule II [1]; PL: I-P;
Pharmacokinetic data
Onset of action	0.5 hours
Elimination half-life	5.8–6.9 hours
Duration of action	2.5–3.0 hours
Identifiers
	IUPAC name 1-(1,3-Benzodioxol-5-yl)-2-(methylamino)propan-1-one;
CAS Number	186028-79-5 (racemic); 191916-41-3 (+);
PubChem CID	27281606;
ChemSpider	21106350 ;
UNII	L4I4B1R01F;
KEGG	C20126 ;
CompTox Dashboard (EPA)	DTXSID80870167 ;
Chemical and physical data
Formula	C11H13NO3
Molar mass	207.229 g·mol−1
3D model (JSmol)	Interactive image;
Solubility in water	357 mg/mL (20 °C)
	SMILES CC(NC)C(=O)C1=CC=C(OCO2)C2=C1;
	InChI InChI=1S/C11H13NO3/c1-7(12-2)11(13)8-3-4-9-10(5-8)15-6-14-9/h3-5,7,12H,6H2,1-2H3 ; Key:VKEQBMCRQDSRET-UHFFFAOYSA-N ;
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Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an empathogen and stimulant psychoactive drug. It is a member of the amphetamine, cathinone and methylenedioxyphenethylamine classes.

Methylone is a slight modification of 3,4-methylenedioxymethamphetamine (MDMA, also known as ecstasy). It was first synthesized by the chemists Peyton Jacob III and Alexander Shulgin in 1996 for potential use as an antidepressant.^[4] Methylone has been sold for recreational use, taking advantage of the absence of legal prohibition of this compound in many countries.^{[citation needed]}

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved 17 June 2011.
^ ^a ^b ^c Poyatos L, Lo Faro AF, Berardinelli D, Sprega G, Malaca S, Pichini S, et al. (November 2022). "Methylone and MDMA Pharmacokinetics Following Controlled Administration in Humans". International Journal of Molecular Sciences. 23 (23): 14636. doi:10.3390/ijms232314636. PMC 9736016. PMID 36498963.
^ WO 9639133, Jacob III P, Shulgin AT, "Novel N-Substituted-2-Amino-3',4'-Methylene-dioxypropiophenones", published 1996-12-12, assigned to Neurobiological Technologies Inc.

[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[2] "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. Retrieved 17 June 2011.

[pmid36498963-3] Poyatos L, Lo Faro AF, Berardinelli D, Sprega G, Malaca S, Pichini S, et al. (November 2022). "Methylone and MDMA Pharmacokinetics Following Controlled Administration in Humans". International Journal of Molecular Sciences. 23 (23): 14636. doi:10.3390/ijms232314636. PMC 9736016. PMID 36498963.

[4] WO 9639133, Jacob III P, Shulgin AT, "Novel N-Substituted-2-Amino-3',4'-Methylene-dioxypropiophenones", published 1996-12-12, assigned to Neurobiological Technologies Inc.

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Clinical data


Other names	3,4-Methylenedioxy-N-methylcathinone; Methylenedioxymethcathinone; MDMC; β-Keto-MDMA; βk-MDMA; M1; TSND-201; TSND201
Routes of administration	Common: oral, insufflation Uncommon: IV or IM injection, rectal
ATC code	None
Legal status
Legal status	AU: Unscheduled BR: Class F2 (Prohibited psychotropics)^[1] CA: Schedule I DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I UN: Schedule II [1] PL: I-P^[2]
Pharmacokinetic data
Onset of action	0.5 hours^[3]
Elimination half-life	5.8–6.9 hours^[3]
Duration of action	2.5–3.0 hours^[3]
Identifiers
IUPAC name 1-(1,3-Benzodioxol-5-yl)-2-(methylamino)propan-1-one
CAS Number	186028-79-5^N (racemic) 191916-41-3 (+)
PubChem CID	27281606
ChemSpider	21106350^Y
UNII	L4I4B1R01F
KEGG	C20126^N
CompTox Dashboard (EPA)	DTXSID80870167
Chemical and physical data
Formula	C₁₁H₁₃NO₃
Molar mass	207.229 g·mol⁻¹
3D model (JSmol)	Interactive image
Solubility in water	357 mg/mL (20 °C)
SMILES CC(NC)C(=O)C1=CC=C(OCO2)C2=C1
InChI InChI=1S/C11H13NO3/c1-7(12-2)11(13)8-3-4-9-10(5-8)15-6-14-9/h3-5,7,12H,6H2,1-2H3^Y Key:VKEQBMCRQDSRET-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

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Methylone

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