# Dimethylamphetamine

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Chemical compound

Pharmaceutical compound

Dimethylamphetamine INN: Dimetamfetamine Clinical data Routes of administration Oral ATC code none Legal status Legal status AU: S9 (Prohibited substance) US: Schedule I Identifiers IUPAC name N,N-dimethyl-1-phenylpropan-2-amine CAS Number 4075-96-1 Y PubChem CID 20006 ChemSpider 18847 N UNII IYE3F3MHCU KEGG C22825 Y CompTox Dashboard (EPA) DTXSID40860201 Chemical and physical data Formula C11H17N Molar mass 163.264 g·mol−1 3D model (JSmol) Interactive image SMILES CC(N(C)C)CC1=CC=CC=C1 InChI InChI=1S/C11H17N/c1-10(12(2)3)9-11-7-5-4-6-8-11/h4-8,10H,9H2,1-3H3 Y Key:OBDSVYOSYSKVMX-UHFFFAOYSA-N Y NY (what is this?) (verify)

**Dimethylamphetamine** (**Metrotonin**), also known as **dimetamfetamine** ([INN](/source/International_Nonproprietary_Name)), **dimephenopan** and ***N*,*N*-dimethylamphetamine**, is a [stimulant](/source/Stimulant) [drug](/source/Drug) of the [phenethylamine](/source/Substituted_phenethylamine) and [amphetamine](/source/Substituted_amphetamine) [chemical classes](/source/Chemical_class). Dimethylamphetamine has weaker stimulant effects than [amphetamine](/source/Amphetamine) or [methamphetamine](/source/Methamphetamine) and is considerably less addictive[1] and less [neurotoxic](/source/Neurotoxicity) compared to methamphetamine.[2][3] However, it still retains some mild stimulant effects and abuse potential,[4] and is illegal in both the United States and Australia.

Dimethylamphetamine has occasionally been found in illicit [methamphetamine laboratories](/source/Meth_lab), but is usually an [impurity](/source/Chemical_impurity) rather than the desired product. It may be produced by accident when methamphetamine is [synthesised](/source/Chemical_synthesis) by N-[methylation](/source/Methylation) of [dextroamphetamine](/source/Dextroamphetamine) if the reaction temperature is too high or an excess of [methylating agent](/source/Methylation) is used.[5][6]

It is said to be a [prodrug](/source/Prodrug) of methamphetamine and amphetamine, which are minor [metabolites](/source/Metabolite).[7][8][9]

## See also

- [Substituted amphetamine](/source/Substituted_amphetamine)

## References

1. **[^](#cite_ref-pmid2338643_1-0)** Witkin JM, Ricaurte GA, Katz JL (May 1990). "Behavioral effects of N-methylamphetamine and N,N-dimethylamphetamine in rats and squirrel monkeys". *The Journal of Pharmacology and Experimental Therapeutics*. **253** (2): 466–74. [PMID](/source/PMID_(identifier)) [2338643](https://pubmed.ncbi.nlm.nih.gov/2338643).

1. **[^](#cite_ref-pmid2765865_2-0)** Ricaurte GA, DeLanney LE, Irwin I, Witkin JM, Katz JL, Langston JW (June 1989). "Evaluation of the neurotoxic potential of N,N-dimethylamphetamine: an illicit analog of methamphetamine". *Brain Research*. **490** (2): 301–6. [doi](/source/Doi_(identifier)):[10.1016/0006-8993(89)90247-3](https://doi.org/10.1016%2F0006-8993%2889%2990247-3). [PMID](/source/PMID_(identifier)) [2765865](https://pubmed.ncbi.nlm.nih.gov/2765865). [S2CID](/source/S2CID_(identifier)) [20682993](https://api.semanticscholar.org/CorpusID:20682993).

1. **[^](#cite_ref-pmid9383014_3-0)** Fasciano J, Hatzidimitriou G, Yuan J, Katz JL, Ricaurte GA (October 1997). ["N-methylation dissociates methamphetamine's neurotoxic and behavioral pharmacologic effects"](https://doi.org/10.1016%2Fs0006-8993%2897%2900801-9). *Brain Research*. **771** (1): 115–20. [doi](/source/Doi_(identifier)):[10.1016/s0006-8993(97)00801-9](https://doi.org/10.1016%2Fs0006-8993%2897%2900801-9). [PMID](/source/PMID_(identifier)) [9383014](https://pubmed.ncbi.nlm.nih.gov/9383014). [S2CID](/source/S2CID_(identifier)) [8456534](https://api.semanticscholar.org/CorpusID:8456534).

1. **[^](#cite_ref-pmid1615131_4-0)** Katz JL, Ricaurte GA, Witkin JM (1992). "Reinforcing effects of enantiomers of N,N-dimethylamphetamine in squirrel monkeys". *Psychopharmacology*. **107** (2–3): 315–8. [doi](/source/Doi_(identifier)):[10.1007/BF02245154](https://doi.org/10.1007%2FBF02245154). [PMID](/source/PMID_(identifier)) [1615131](https://pubmed.ncbi.nlm.nih.gov/1615131). [S2CID](/source/S2CID_(identifier)) [24707878](https://api.semanticscholar.org/CorpusID:24707878).

1. **[^](#cite_ref-5)** ["Microgram Bulletin"](https://web.archive.org/web/20130414122936/http://www.justice.gov/dea/pr/micrograms/2005/mg0205.pdf) (PDF). US Drug Enforcement Administration. Archived from [the original](https://www.justice.gov/dea/pr/micrograms/2005/mg0205.pdf) (PDF) on 2013-04-14. Retrieved 2013-08-06.

1. **[^](#cite_ref-6)** ["The Identification of d-N,N-Dimethylamphetamine (DMA) in an Exhibit in Malaysia"](https://www.erowid.org/library/periodicals/microgram/microgram_journal_2003-2.pdf) (PDF). US Drug Enforcement Administration.

1. **[^](#cite_ref-DettmeyerVerhoff2013_7-0)** Dettmeyer R, Verhoff MA, Schütz HF (9 October 2013). [*Forensic Medicine: Fundamentals and Perspectives*](https://books.google.com/books?id=yHHABAAAQBAJ&pg=PA519). Springer Science & Business Media. p. 519. [ISBN](/source/ISBN_(identifier)) [978-3-642-38818-7](https://en.wikipedia.org/wiki/Special:BookSources/978-3-642-38818-7). Table 30.13: Amphetamine Data [...] *Note:* So-called prodrugs, such as amphetaminil (psychoanaleptic), benzphetamine, clobenzorex, dimethylamphetamine, ethylamphetamine, famprofazone, fencamine, fenethylline, fenproporex, furfenorex, mefenorex, mesocarb, prenylamine, and selegiline (antiparkinson agent), can result in the production of methamphetamine or amphetamine in the organism

1. **[^](#cite_ref-Cody2002_8-0)** Cody JT (May 2002). "Precursor medications as a source of methamphetamine and/or amphetamine positive drug testing results". *J Occup Environ Med*. **44** (5): 435–450. [doi](/source/Doi_(identifier)):[10.1097/00043764-200205000-00012](https://doi.org/10.1097%2F00043764-200205000-00012). [PMID](/source/PMID_(identifier)) [12024689](https://pubmed.ncbi.nlm.nih.gov/12024689).

1. **[^](#cite_ref-InoueSuzuki1987_9-0)** Inoue T, Suzuki S (August 1987). "The metabolism of dimethylamphetamine in rat and man". *Xenobiotica*. **17** (8): 965–971. [doi](/source/Doi_(identifier)):[10.3109/00498258709044195](https://doi.org/10.3109%2F00498258709044195). [PMID](/source/PMID_(identifier)) [3673111](https://pubmed.ncbi.nlm.nih.gov/3673111).

## External links

- [NNDMA (*N*,*N*-Dimethylamphetamine) - Isomer Design](https://isomerdesign.com/pihkal/explore/2007)

v t e Stimulants Adamantanes Adapromine Amantadine Bromantane Memantine Rimantadine Adenosine antagonists 8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline Alkylamines Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane Ampakines CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram Arylcyclohexylamines Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine Benzazepines 6-Br-APB SKF-77434 SKF-81297 SKF-82958 Cathinones 3-FMC 3-MMC 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone Cholinergics A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538 Convulsants Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone Eugeroics Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil Oxazolines 4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone Phenethylamines 1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-ME 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine FDE Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lomardexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Pyr-AI Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine Phenylmorpholines 3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine Piperazines 2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine Piperidines 1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472 Phenethylpyrrolidines 2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPEP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone Racetams Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide Psychedelics 2,5-DMA (DOH) 2C-B 2C-D 2C-G-N 5-MeO-DiPT 5-MeO-MiPT Ariadne (4C-DOM; BL-3912; Dimoxamine) ASR-2001 (2CB-5PrO) DOET DOM DON DOPR LSD MTFEM Tropanes 4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (123I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33 Tryptamines 4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT Others 2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine ATC code: N06B

v t e Monoamine releasing agents DRAsTooltip Dopamine releasing agents Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA 5-APB 5-APBT 5-MAPB 6-APB 6-APBT 6-MAPB Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine (Dextroamphetamine Levoamphetamine) Amphetaminil β-Me-PEA BDB BOH Benzphetamine Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine D-Deprenyl DMA DMMA Dimethylamphetamine Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex 4-Fluorodeprenyl Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lomardexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine SDA (3T-MDA) SDMA (3T-MDMA) Tiflorex Tyramine Xylopropamine Zylofuramine Piperazines: 2C-B-BZP BZP MBZP MDBZP MeOPP oMPP Others: 2-ADN 2-AI 2-AT 4-BP 5-APDI 5-IAI Amineptine Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine NRAsTooltip Norepinephrine releasing agents Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA 4-ME 5-APB 5-APBT 5-MAPB 6-APB 6-APBT 6-MAPB Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil β-Me-PEA BDB Benzphetamine BOH Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine Deprenyl Dimethylamphetamine DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex 4-Fluorodeprenyl Furfenorex Hordenine 4-Hydroxyamphetamine 5-APDI (IAP) Iofetamine (123I) Lisdexamfetamine Lomardexamfetamine Lophophine MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) Metamfepramone MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone Methylone Morforex Naphthylaminopropane Ortetamine pBA pCA Pentorex Phenethylamine Pholedrine Phenpromethamine Phentermine Phenylpropanolamine pIA Prenylamine Propylamphetamine Pseudoephedrine SDA (3T-MDA) SDMA (3T-MDMA) Selegiline (also D-Deprenyl) Tiflorex Tyramine Xylopropamine Zylofuramine Piperazines: 2C-B-BZP BZP MBZP mCPP MDBZP MeOPP oMPP pFPP Others: 2-ADN 2-AI 2-AT 2-BP 4-BP 5-IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine Tuaminoheptane SRAsTooltip Serotonin releasing agents Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI TAI Aminotetralins: 6-CAT 8-OH-DPAT MDAT MDMAT Oxazolines: 4-Methylaminorex Aminorex Clominorex Fluminorex Phenethylamines: 2-Methyl-MDA pCPE 4-CAB 4-FA 4-FMA 4-HA 4-MTA 4-ME 5-APB 5-APBT 5-APDB 5-MAPB 5-Methyl-MDA 6-APB 6-APBT 6-APDB 6-MAPB 6-Methyl-MDA AEMMA Amiflamine BDB BOH Brephedrone Butylone Chlorphentermine Cloforex Amfepramone Metamfepramone DCA Dexfenfluramine DFMDA DMA DMMA EBDB EDMA Ethylone Etolorex Fenfluramine Flephedrone Flucetorex IAP Iofetamine Levofenfluramine Lophophine MBDB MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDMPEA MDOH MDPEA Mephedrone Methedrone Methylone MMA MMDA MMDA-3b MMDMA MMMA NAP Norfenfluramine 4-TFMA pBA pCA pIA PMA PMEA PMMA SDA (3T-MDA) SDMA (3T-MDMA) TAP Piperazines: 2C-B-BZP 3-MeOPP BZP DCPP MBZP mCPP MDBZP MeOPP Mepiprazole oMPP pCPP pFPP pTFMPP TFMPP Tryptamines: 4-Methyl-αET 4-Methyl-αMT 5-CT 5-MeO-αET 5-MeO-αMT 5-MT αET αMT DMT Tryptamine Others/unsorted: Indeloxazine PAL-335 Viqualine Others DAT modulators: Agonist-like: SoRI-9804 SoRI-20040; Antagonist-like: SoRI-20041 Adrenergic release blockers: Bethanidine Bretylium Guanadrel Guanazodine Guanethidine Guanoxan See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

v t e Phenethylamines Phenethylamines Psychedelics: 3,4-DMPEA-NDEPA 24H-NBOMe 25B-NBOMe 25C-NBOMe 25D-NBOMe 25D-NM-NDEAOP 25H-NBOMe 25I-NBOMe 25N-NBOMe 25O-NBOMe 2C-B 2C-B-AN 2C-B-OH 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-DB 2C-E 2C-EF 2C-F 2C-G 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-NH2 2C-O 2C-O-2 2C-O-4 2C-P 2C-Ph 2C-Se 2C-Se-TFM 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-21.5 2C-T-22 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-tBu 2C-Te 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline BOH-2C-B CT-5172 DESOXY N,N-Diformylmescaline Escaline N-Formylmescaline Isoproscaline 3-Methoxy-4,5-dihydroxyphenethylamine M-NDEPA Macromerine MEPEA Mescaline Metaescaline Methallylescaline N-DEAOP-NMPEA N-Methylmescaline Proscaline Psi-2C-T-4 Trichocereine (N,N-dimethylmescaline) Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Phenacylamine (β-ketophenethylamine) Solriamfetol Entactogens: Lophophine MDPEA MDMPEA Others: N-Acetylmescaline Amidephrine ASR-2001 Biscaline BOH Buscaline Denopamine Desvenlafaxine DMPEA F-17475 Mescaloruvic acid Mescaloxylic acid Phenibut 4-PhPr-PEA pCPE Pronethalol Salbutamol Levosalbutamol Venlafaxine Amphetamines Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY DMA DMMDA DOB DOB-NDEPA DOC DODB DOEF DOET DOI DOI-NDEPA DOM DOM-NDEPA DON DOPR DOTFM DOTFM-NDEPA DOTMA Ganesha MMDA MMDA-2 MMDA-3a MMDA-3b N-Hydroxy-DOM Psi-DOM TMA TMA-2 TMA-2-NDEPA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA β-Phenylmethamphetamine Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Deprenyl D-Deprenyl Dimethylamphetamine Ephedrine FDE Ephenidine Etafedrine Etilamfetamine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine Dexfenfluramine Levofenfluramine Fenproporex Flucetorex Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine 4-ME Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Lomardexamfetamine Mefenorex Metaraminol Methamphetamine Dextromethamphetamine Levomethamphetamine Methoxamine Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine α,N-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PBMA PCA PCMA PFA PFMA PIA PIMA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APBT 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-APBT 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane ODMA SDA (3T-MDA) SDMA (3T-MDMA) SeDMA TAP TDMA Others: 3,4-DCA DOOH Amiflamine Cafedrine Deprenyl D-Deprenyl Selegiline (L-deprenyl) DiFMDA 4-Fluorodeprenyl 4-Fluoroselegiline Thiamphenicol UWA-101 (α-cPr-MDMA) Phentermines Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine Cathinones Stimulants: 3-BMC 3-CMC 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone Propylone Phenylisobutylamines (and further-extended) Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: α-Propylphenethylamine Hexapradol Phenylisobutylamine (α-ethylphenethylamine) Catecholamines (and close relatives) 6-FNE 6-OHDA α-Me-DA α-Me-TRA A-69024 Adrenochrome Arbutamine Ciladopa D-DOPA (dextrodopa) Dimetofrine Dipropyldopamine (DPDA) Dobutamine Dopamine Dopexamine Epinephrine (adrenaline) Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (levodopa) L-DOPS (droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin Levonordefrin Norepinephrine (noradrenaline) Norfenefrine (m-octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine Theodrenaline Cyclized phenethylamines Phenylalkylpyrrolidines α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP Fluorolintane MOPPP MOPVP MPBP MPEP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone 2-Benzylpiperidines (phenidates) 2-Benzylpiperidine 3-Bromomethylphenidate 3-Chloromethylphenidate 3-Methylmethylphenidate 3,4-Dichloro-2-benzylpiperidine 3,4-Dichloroethylphenidate 3,4-Dichloromethylphenidate 4-Bromoethylphenidate 4-Bromomethylphenidate 4-Chloromethylphenidate 4-Fluoroethylphenidate 4-Fluoroisopropylphenidate 4-Fluoromethylphenidate 4-Methyl-2-benzylpiperidine 4-Methylisopropylphenidate 4-Methylmethylphenidate 4-Nitromethylphenidate α-Acetyl-2-benzylpiperidine α-Keto-2-benzylpiperidine CPMBP DMBMPP Desoxypipradrol (2-DPMP) Difemetorex Ethylnaphthidate (HDEP-28) Ethylphenidate Isopropylnaphthidate Isopropylphenidate MDMPH Methylnaphthidate (HDMP-28) Methylphenidate Phacetoperane Pipradrol Propylphenidate Rimiterol Ritalinamide Ritalinic acid SCH-5472 Serdexmethylphenidate Phenylmorpholines (phenmetrazines) (2R,3R)-Hydroxybupropion 2-(2,5-Dimethoxy-4-bromophenyl)morpholine 2-Fluorophenmetrazine 2-Methylphenmetrazine 2-Phenylmorpholine 2-Phenyl-3,6-dimethylmorpholine 3-Chlorophenmetrazine (PAL-594) 3-Fluorophenetrazine 3-Fluorophenmetrazine (PAL-593) 3-Methoxyphenmetrazine 3-Methylphenmetrazine (PAL-773) 4-Fluorophenmetrazine (PAL-748) 4-Methylphendimetrazine 4-Methylphenmetrazine (PAL-747) 2C-B-morpholine Fenbutrazate Fenmetramide Flumexadol G-130 Isophenmetrazine Manifaxine Methylenedioxyphenmetrazine Morazone N-Ethylphenmetrazol Naphthylmetrazine (PAL-704) Naphthylmorpholine (PAL-678) Oxaflozane PDM-35 PF-219,061) Phendimetrazine Phenetrazine Phenmetetrazine Phenmetrazine Phenmetrazol Pseudophenmetrazine Radafaxine ((2S,3S)-hydroxybupropion) Phenyloxazolamines (aminorexes) 3-Methylaminorex 4-Ethylaminorex (4-EAR) 4'-Fluoroaminorex 4-Methylaminorex (4-MAR) 4,4'-Dimethylaminorex (4,4'-DMAR) 2C-B-aminorex 2F-MAR 4B-MAR 4C-MAR 4F-MAR Aminorex Clominorex Cyclazodone Ephedroxane Fenozolone Fluminorex MDMAR Methylenedioxyaminorex (MDAR) N-Methylcyclazodone N,N-Dimethylaminorex Pemoline Thozalinone Isoquinolines and tetrahydroisoquinolines A-69024 Anhalamine Anhalidine Anhalinine Anhalonidine Anhalonine Anhalotine Arizonine Calycotomine Carnegine (pectenine) Corypalline Debrisoquine Deglucopterocereine Deutetrabenazine Diclofensine DOB-CR DOM-CR Esproquin Gigantine Hedycarine Heliamine Hydrastinine Hydrocotarnine Hydrohydrastinine (MDMTHIQ; MDMA-CR) Isoanhalamine Isoanhalidine Isoanhalonidine Isocorypalline Isopellotine Isosalsoline Lemaireocereine Longimammamine Longimammatine Longimammidine Longimammosine Lophocerine Lophophorine Lophotine MDMA-CR Mescalotam N-Methylanhalinine N-Methylheliamine N-Methylisosalsoline N-Methyl-DOM-CR (Beatrice-CR) N-Methyl-THIQ (METH-CR) Nomifensine Norsalsolinol Nortehaunine Norweberine O-Methylanhalonidine O-Methylpellotine Pachycereine Pellotine Perafensine Peyoglutam Peyophorine Peyotine PMMA-CR Quinisocaine Reticuline Salsolidine Salsoline Salsolinol TDIQ (MDTHIQ, MDA-CR) Tehaunine Tehaunine N-oxide Tepenine Tetrabenazine Tetrahydroisoquinoline (THIQ; AMPH-CR) Tetrahydropapaveroline Tilisolol Tretoquinol Uberine Valbenazine Weberidine Weberine Zelandopam 2-Aminoindanes 2-Aminoindane (2-AI) 5-IAI Aprindine BFAI BFMAI DHAI DOM-AI ETAI Indantadol MDAI MDMAI MEAI (5-MeO-AI) MMAI NM-2-AI PNU-99,194 Pyr-AI TAI 2-Aminotetralins 2-Aminotetralin (2-AT) 5-OH-DPAT 6-CAT 7-OH-DPAT 8-OH-DPAT AS-19 CHF-1024 DOM-AT MDAT MDMAT Nolomirole UH-232 Others / unsorted 1-Aminomethylindanes (e.g., 2CB-Ind, AMMI, bromojimscaline, jimscaline) 2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Aminochromans (e.g., CT-5126, 5-MeO-DPAC, robalzotan, ebalzotan) 3-Benzazepines (e.g., fenoldopam, lorcaserin, 7-chlorolorcaserin, SCHEMBL5334361) 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g., 3-phenylpiperidine, 3-PPP, OSU-6162 (PNU-96391), LPH-5, LPH-48, 2C-B-3PIP, 2C-B-3PIP-NBOMe, 2C-B-3PIP-POMe, Z3517967757 (Z7757)) 6-AB AL-1095 Aminochromes (e.g., adrenochrome, adrenolutin) AMMT Benzocyclobutenes (e.g., 2CBCB-NBOMe, bromotomscaline, S33005, TCB-2, tomscaline) Benzoxepins (e.g., BBOX, IBOX, TFMBOX) Butyltolylquinuclidine Camfetamine Clausenamide Cypenamine (trans-2-phenylcyclopentylamine) Diphenidine Diphenylprolinol Ergolines (e.g., LSD) Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g., NDTDI, RU-27849, DEIMDHPCA, DEMPDHPCA, DEMPDHPCA-2C-D, RU-27251) PF-592,379 Phenanthrenes (e.g., atherosperminine (atherospermine)) Phenylcyclopropylamines (e.g., DMCPA, TMT, tranylcypromine) Phenylmethylpyrrolidines (e.g., APA-01) Phenylpiracetams (e.g., phenylpiracetam, MRZ-9547, RGPU-95) Pyridopyrroloquinoxalines (e.g., lumateperone, deulumateperone, IHCH-7079, IHCH-7086, IHCH-7113, ITI-1549) Thienopyridines (e.g., SKF-89145, SKF-89615, SKF-89626) Tolazoline Tricyclics (e.g., AMDA, AMDH, benzoctamine, dizocilpine, SpAMDA) ZC-B Related compounds 2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g., 1,3-DMBATooltip 1,3-dimethylbutylamine, 1,4-DMAATooltip 1,4-dimethylamylamine, heptaminol, iproheptine, isometheptene, methylhexanamine/1,3-DMAA, octodrine, oenethyl, tuaminoheptane) Benzylamines (e.g., benzylamine, α-methylbenzylamine, MDM1EA, ALPHA, M-ALPHA, pargyline) Benzylpiperazines (e.g., benzylpiperazine, MDBZP, fipexide) Cyclohexylaminopropanes (e.g., propylhexedrine, norpropylhexedrine) Cyclopentylaminopropanes (e.g., isocyclamine, cyclopentamine) Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine, CT-4719, ORG-37684) Phenylalkenylamines (e.g., phenylbutenamine) Phenylalkynylamines (e.g., phenylbutynamine) Phenylpiperazines (e.g., 1-phenylpiperazine, mCPPTooltip meta-chlorophenylpiperazine, TFMPPTooltip trifluoromethylphenylpiperazine, oMPPTooltip ortho-methylphenylpiperazine, pFPPTooltip para-fluorophenylpiperazine, pMeOPPTooltip para-methoxyphenylpiperazine) Phenylpropylamines (e.g., phenylpropylamine, homo-MDA, homo-MDMA) Thienylaminopropanes (thiopropamines) (e.g., thiopropamine, methiopropamine, thiothinone) Phenylbutylamines (e.g., 4-Phenylbutylamine, 4-Phenylpentan-1-amine) See also: Tryptamines Ergolines and lysergamides Stimulants Entactogens Psychedelics

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Adapted from the Wikipedia article [Dimethylamphetamine](https://en.wikipedia.org/wiki/Dimethylamphetamine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Dimethylamphetamine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.