Dimethylone

Dimethylone
Clinical data
ATC code	None;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name 1-(1,3-benzodioxol-5-yl)-2-(dimethylamino)propan-1-one;
CAS Number	765231-58-1 ; 109367-07-9 (HCl);
PubChem CID	9794472;
ChemSpider	7970239;
UNII	4G26NSP297;
CompTox Dashboard (EPA)	DTXSID801016917 ;
Chemical and physical data
Formula	C12H15NO3
Molar mass	221.256 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C(=O)C1=CC2=C(C=C1)OCO2)N(C)C;
	InChI InChI=1S/C12H15NO3/c1-8(13(2)3)12(14)9-4-5-10-11(6-9)16-7-15-10/h4-6,8H,7H2,1-3H3; Key:OSNIIMCBVLBNGS-UHFFFAOYSA-N;

Dimethylone (βk-MDDMA) is a substituted cathinone derivative with stimulant and empathogenic effects. Unlike the corresponding amphetamine derivative MDDM which is thought to be practically inactive, dimethylone substitutes for methamphetamine and MDMA in animal studies and has been sold as a designer drug.^[2]^[3]^[4]^[5]

Legal Status

In the United States, dimethylone is considered a Schedule I controlled substance as a positional isomer of butylone.^[6]

References

^ 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.
^ Zaitsu K, Katagi M, Kamata HT, Miki A, Tsuchihashi H (2008). "Discrimination and identification of regioisomeric β-keto analogues of 3,4-methylenedioxyamphetamines by gas chromatography-mass spectrometry". Forensic Toxicol. 26 (2): 45–51. doi:10.1007/s11419-008-0050-1. S2CID 2871089.
^ Kikura-Hanajiri R, Uchiyama N, Goda Y (May 2011). "Survey of current trends in the abuse of psychotropic substances and plants in Japan". Legal Medicine. 13 (3): 109–15. doi:10.1016/j.legalmed.2011.02.003. PMID 21377397.
^ Krotulski AJ, Mohr AL, Fogarty MF, Logan BK (October 2018). "The Detection of Novel Stimulants in Oral Fluid from Users Reporting Ecstasy, Molly and MDMA Ingestion". Journal of Analytical Toxicology. 42 (8): 544–553. doi:10.1093/jat/bky051. PMID 30371847.
^ Gatch MB, Dolan SB, Forster MJ (June 2019). "Locomotor activity and discriminative stimulus effects of five novel synthetic cathinone analogs in mice and rats". Drug and Alcohol Dependence. 199: 50–58. doi:10.1016/j.drugalcdep.2019.02.016. PMC 6534427. PMID 30986635.
^ https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf ^{[bare URL PDF]}

[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] Zaitsu K, Katagi M, Kamata HT, Miki A, Tsuchihashi H (2008). "Discrimination and identification of regioisomeric β-keto analogues of 3,4-methylenedioxyamphetamines by gas chromatography-mass spectrometry". Forensic Toxicol. 26 (2): 45–51. doi:10.1007/s11419-008-0050-1. S2CID 2871089.

[3] Kikura-Hanajiri R, Uchiyama N, Goda Y (May 2011). "Survey of current trends in the abuse of psychotropic substances and plants in Japan". Legal Medicine. 13 (3): 109–15. doi:10.1016/j.legalmed.2011.02.003. PMID 21377397.

[4] Krotulski AJ, Mohr AL, Fogarty MF, Logan BK (October 2018). "The Detection of Novel Stimulants in Oral Fluid from Users Reporting Ecstasy, Molly and MDMA Ingestion". Journal of Analytical Toxicology. 42 (8): 544–553. doi:10.1093/jat/bky051. PMID 30371847.

[pmid30986635-5] Gatch MB, Dolan SB, Forster MJ (June 2019). "Locomotor activity and discriminative stimulus effects of five novel synthetic cathinone analogs in mice and rats". Drug and Alcohol Dependence. 199: 50–58. doi:10.1016/j.drugalcdep.2019.02.016. PMC 6534427. PMID 30986635.

[6] ttps://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf ^{[bare URL PDF]}

[1]

v t e Empathogens/entactogens
Phenylalkyl- amines (other than cathinones)	Unfused benzene ring: 3-CMA 4-CAB 4-FA 4-MA 4-MMA 4-FMA 4-MTA 4,4'-DMAR Ariadne Metaescaline MMA PMA PMEA PMMA mMMA Benzodioxine: EDMA Benzodioxoles: Phenethylamine: { Lophophine } Amphetamines: { 2-Methyl-MDA 2,3-MDA 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DFMDA DMMDA DMMDA-2 EIDA Lys-MDA MDEA MDMA (midomafetamine) (R)-MDMA MDMOH MDOH MMDA MMDA-2 MMDMA N-t-BOC-MDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans, dihydrobenzofurans and benzothiophenes: 2-MAPB 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 5-MAPBT 5-MBPB 6-APB 6-APDB 6-EAPB 6-MAPB 6-MAPDB IBF5MAP Indanes: 5-APDI 5-MAPDI Indoles: 5-IT 6-API Naphthalenes: Methamnetamine Naphthylaminopropane Tetralin: 6-APT
Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI BFAI ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-CMC 3-MMC 4-EMC BK-5-MAPB Brephedrone Butylone Dimethylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone TH-PVP
Tryptamines	4-Methyl-αET αET αMT
Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine

Legal Status

See also

References