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MDM1EA - Wikipedia

From Wikipedia, the free encyclopedia

MDM1EA
Clinical data

Other names	N-Methyl-1-(3,4-methylenedioxyphenyl)-1-ethanamine; MDM1EA; α,N-Dimethyl-3,4-methylenedioxybenzylamine; α,N-DMMDBA; α,N-Dimethylpiperonylamine; α,N-Dimethyl-1,3-benzodioxole-5-methanamine
Identifiers
IUPAC name 1-(1,3-benzodioxol-5-yl)-N-methylethanamine
CAS Number	121734-65-4
PubChem CID	6424509
ChemSpider	4930000
Chemical and physical data
Formula	C₁₀H₁₃NO₂
Molar mass	179.219 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C1=CC2=C(C=C1)OCO2)NC
InChI InChI=1S/C10H13NO2/c1-7(11-2)8-3-4-9-10(5-8)13-6-12-9/h3-5,7,11H,6H2,1-2H3 Key:USAUUVXZKYYZIL-UHFFFAOYSA-N

N-Methyl-1-(3,4-methylenedioxyphenyl)-1-ethanamine (MDM1EA), also known as α,N-dimethyl-3,4-methylenedioxybenzylamine (α,N-DMMDBA) or as α,N-dimethylpiperonylamine, is an entactogen-like drug of the benzylamine family related to MDMA.^[1]^[2]^[3] It is the analogue of MDMA in which the side chain has been shortened by one carbon atom.^[1]^[2]^[3]

The drug has been found to be a weak serotonin reuptake inhibitor and partially substituted for MDMA in rodent drug discrimination tests at the highest assessed doses.^[1]^[2]^[4]^[3] The effects of α,N-DMMDBA in humans are unknown.^[1]

It is not a controlled substance in the United States as of 2011.^[1]

Homo-MDMA (HMDMA), an analogue of MDMA in which the side chain was extended by one carbon atom, has also been synthesized and studied.^[2]^[3] It partially substituted for MDMA similarly to MDM1EA.^[2]^[3]

References

^ ^a ^b ^c ^d ^e Shulgin A, Manning T, Daley PF (2011). "#45. α,N-DMMDBA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 80–81. ISBN 978-0-9630096-3-0. OCLC 709667010.
^ ^a ^b ^c ^d ^e Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German). Solothurn: Nachtschatten-Verlag. p. 594. ISBN 978-3-03788-700-4. OCLC 858805226. Retrieved 29 January 2025.
^ ^a ^b ^c ^d ^e Bronson ME, Barrios-Zambrano L, Jiang W, Clark CR, DeRuiter J, Newland MC (December 1994). "Behavioral and developmental effects of two 3,4-methylenedioxymethamphetamine (MDMA) derivatives". Drug and Alcohol Dependence. 36 (3): 161–166. doi:10.1016/0376-8716(94)90141-4. PMID 7889806.
^ Hashimoto K, Maeda H, Goromaru T (September 1992). "Antagonism of 3,4-methylenedioxymethamphetamine-induced neurotoxicity in rat brain by 1-piperonylpiperazine". European Journal of Pharmacology. 228 (2–3): 171–174. doi:10.1016/0926-6917(92)90027-a. PMID 1280228.

External links

α,N-DMMDBA - isomer design

Entactogens

Phenethylamines

Non-ring-extended	Amphetamines: 3-CMA 4-FA (PAL-303) 4-FMA 4-MA (PAL-313; Aptrol; normephedrine) 4-MMA (mephedrine) 4-MTA 4-MTMA (NMMTA; PAL-1063) MMA MMMA PMA PMEA PMMA Phenylisobutylamines: 4-CAB (AEPCA) Cathinones: 3-CMC (clophedrone; βk-3-CMA) 3-MMC (metaphedrone; βk-3-MMA) 4-EMC (βk-4-EMA) Brephedrone (4-BMC; βk-4-BMA) Flephedrone (4-FMC; βk-4-FMA) Mephedrone (4-MMC; 4-methylephedrone; βk-4-MMA) Methedrone (PMMC; βk-PMMA)
Benzodioxoles (methylenedioxy- or MDxx)	Phenethylamines: Lophophine (MMDPEA) Amphetamines: 2-Methyl-MDA 2,3-MDA (ORTHO-MDA) 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DFMDA DMMDA DMMDA-2 EIDA Lys-MDA Lys-MDMA MDEA (MDE) MDMA (midomafetamine; ecstasy) (R)-MDMA (EMP-01; MM-402) MDMA/citalopram MDMOH (FLEA; MDHMA) MDOH (MDH) MMDA (5-methoxy-MDA) MMDA-2 (6-methoxy-MDA) MMDMA (5-methoxy-MDMA) N-t-BOC-MDMA Phenylisobutylamines: BDB (J) EBDB (Ethyl-J) MBDB (Methyl-J) Phentermines: MDMP MDPH Cathinones: 5-Methoxymethylone (2-A1MP; βk-MMDMA) 5-Methylethylone (5-methyl-βk-MDEA) Butylone (βk-MBDB) Dimethylone (βk-MDDMA) Ethylone (MDEC; βk-MDEA) Eutylone (βk-EBDB) Methylenedioxycathinone (MDC; βk-MDA) Methylone (MDMC; βk-MDMA) Putylone (βk-PBDB)
Benzodioxines (ethylenedioxy-)	Amphetamines: EDA EDMA Cathinones: EDMC
Benzofurans	Amphetamines: 4-APB 5-APB 5-EAPB 5-MAPB 6-APB 6-EAPB 6-MAPB 7-APB Phenylisobutylamines: 5-MBPB (5-MABB) 6-MBPB (6-MABB) Cathinones: BK-5-MAPB BK-6-MAPB
Dihydrobenzofurans	Amphetamines: 5-APDB (EMA-4) 5-MAPDB 6-APDB (EMA-3) 6-MAPDB IBF5MAP (5-MAPP)
Benzothiophenes	Amphetamines: 4-APBT 5-APBT 5-MAPBT (MY400) 6-APBT 6-MAPBT (MY300) 7-APBT
Benzothiazoles	Amphetamines: 5-BZT-MDA 5-BZT-MDMA 6-BZT-MDA 6-BZT-MDMA
Benzoxathioles	Amphetamines: MY100 MY101 MY200
Indanes	Amphetamines: 5-APDI (IAP) 5-MAPDI (IMP)
Indoles	Amphetamines: 5-API (5-IT; PAL-571) 6-API (6-IT)
Naphthalenes	Amphetamines: Ethylnaphthylaminopropane (ENAP; PAL-1045) Methamnetamine (MNAP; PAL-1046; MY-10) Naphthylaminopropane (NAP; PAL-287)
Tetralins	Amphetamines: 6-APT (TAP) Cathinones: TH-PVP
Others	Amphetamines: ODMA SeDMA TDMA Unknown: MYCO-002 MYCO-006 MYCO-007

Cyclized
phenethylamines

Aminoindanes	5-IAI AMMI BFAI ETAI MDAI MDMAI MMAI MEAI (5-MeO-AI; CMND-100) TAI
Aminotetralins	6-CAT MDAT MDMAT
Aminorexes	4,4'-DMAR MDMAR

Tryptamines

α-Alkyltryptamines	4-Methyl-αET 5-Chloro-αMT (PAL-542) 5-Fluoro-αET (PAL-545) 5-Fluoro-αMT (PAL-212, PAL-544) αET (etryptamine; Monase; PAL-125) αMT (Indopan; PAL-17; 3-API; 3-IT) β-Ketotryptamines: BK-NM-AMT BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT

Others

Benzofurans	2-APB 2-MAPB 3-APB
Benzothiophenes	2-APBT 3-APBT (SKF-6678)
Indolizines	1Z2MAP1O
Isotryptamines	isoAMT (PAL-569; 1-API; 1-IT)
Others	Borax combo (Blue Bliss, Pink Star) MDM1EA (α,N-DMMDBA) Unknown TACT411 TACT833

Monoamine reuptake inhibitors

DAT
(DRIs)

Piperazines: DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 JJC8-088 Nefazodone Vanoxerine
Piperidines: 4-Fluoropethidine Benocyclidine (BTCP) Desoxypipradrol Dexmethylphenidate Difemetorex Ethylphenidate HDMP-28 Methylphenidate Pethidine (meperidine) Phencyclidine Pipradrol Serdexmethylphenidate Tenocyclidine
Pyrrolidines: Diphenylprolinol MDPV Naphyrone Prolintane Pyrovalerone
Tropanes: Altropane Benzatropine (benztropine) Brasofensine CFT Cocaine Dichloropane Difluoropine Etybenzatropine (ethybenztropine) FE-β-CPPIT FP-β-CPPIT Ioflupane (¹²³I) RTI-55 RTI-112 RTI-113 RTI-121 RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 Tesofensine Troparil Tropoxane WF-11 WF-23 WF-31 WF-33
Others: Adrafinil Amifitadine Armodafinil Amfonelic acid Amineptine Ansofaxine BTQ BTS 74,398 Bupropion Chaenomeles speciosa Ciclazindol Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) Dimethocaine Diphenylpyraline Dizocilpine (MK-801) DOV-102,677 DOV-216,303 Efavirenz Ephenidine Esketamine EXP-561 Fencamfamin Fezolamine Fluorenol GYKI-52895 Hydroxybupropion Indatraline Ketamine Lafadofensine Lefetamine Levophacetoperane Liafensine LR-5182 Manifaxine Mazindol Medifoxamine Mesocarb Metaphit MIN-117 (WF-516) Modafinil Nefopam Nomifensine NS-2359 O-2172 Oroxylin A Perafensine Pridefine Radafaxine Rimcazole Sertraline Sibutramine Solriamfetol Tametraline Tedatioxetine Threohydrobupropion Tripelennamine Venlafaxine

NET
(NRIs)

Selective norepinephrine reuptake inhibitors: Amedalin Alseroxylon Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Teniloxazine Viloxazine
Norepinephrine–dopamine reuptake inhibitors: Amineptine Bupropion Fencamine Fencamfamin Hydroxybupropion Lefetamine Levophacetoperane LR-5182 Manifaxine Methylphenidate Nomifensine O-2172 Radafaxine Serdexmethylphenidate Solriamfetol
Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) CP-39,332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA Nafenodone PPPA Tofenacin Venlafaxine
Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Lafadofensine Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g., cocaine)
Tricyclic antidepressants: Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Melitracen Nortriptyline Protriptyline Trimipramine
Tetracyclic antidepressants: Amoxapine Maprotiline Mianserin Oxaprotiline Setiptiline
Others: Antihistamines (e.g., brompheniramine, chlorphenamine, pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., ketamine, phencyclidine) Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol, methadone, pethidine (meperidine), tapentadol, tramadol, levorphanol)

SERT
(SRIs)

Selective serotonin reuptake inhibitors: 6-Nitroquipazine Alaproclate Centpropazine Cericlamine Citalopram Dapoxetine Desmethylcitalopram Didesmethylcitalopram Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Norfluoxetine Omiloxetine Panuramine Paroxetine PIM-35 Pirandamine RTI-353 Seproxetine Sertraline Zimelidine Selective serotonin reuptake inhibitors and serotonin receptor modulators: Etoperidone Litoxetine Lubazodone LY-393558 Quipazine SB-649915 TGBA01AD Trazodone Vilazodone Vortioxetine
Serotonin–norepinephrine reuptake inhibitors: Atomoxetine (tomoxetine) Bicifadine CP-39332 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN5652 Milnacipran N-Methyl-PPPA PPPA Tofenacin Venlafaxine
Serotonin–norepinephrine–dopamine reuptake inhibitors: 3,3-Diphenylcyclobutanamine Amifitadine Ansofaxine Bicifadine Brasofensine Centanafadine Cocaine Dasotraline Desmethylsertraline Desmethylsibutramine (BTS-54354) Diclofensine Didesmethylsibutramine (BTS-54505) DOV-102677 DOV-216303 EXP-561 Fezolamine HDMP-28 HP-505 Indatraline JNJ-7925476 JZ-IV-10 Lafadofensine Liafensine Mazindol Naphyrone Nefazodone Nefopam NS-2359 Perafensine PRC200 Pridefine SEP-228431 SEP-228432 Sibutramine Tedatioxetine Tesofensine Threohydrobupropion Tropanes (e.g., cocaine)
Tricyclic antidepressants: Amitriptyline Cianopramine Clomipramine Cyanodothiepin Desipramine Dosulepin (dothiepin) Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline
Others: A-80426 Amoxapine Antihistamines (e.g., brompheniramine, chlorphenamine, dimenhydrinate, diphenhydramine, mepyramine (pyrilamine), pheniramine, tripelennamine) Antipsychotics (e.g., loxapine, ziprasidone) Arylcyclohexylamines (e.g., 3-MeO-PCP, esketamine, ketamine, methoxetamine, phencyclidine) Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene, methadone, pethidine (meperidine), levorphanol, tapentadol, tramadol) Roxindole

VMATs

Amiodarone
Amphetamines (e.g., amphetamine, methamphetamine, MDMA)
APP
AZIK
Bietaserpine
Deserpidine
Deutetrabenazine
Dihydrotetrabenazine
Efavirenz
GBR-12935
GZ-793A
Ibogaine
Ketanserin
Lobeline
Methoxytetrabenazine
Reserpine
Rose bengal
Tetrabenazine
Valbenazine
Vanoxerine (GBR-12909)

Others

Unsorted: Cendifensine

DAT enhancers: Luteolin

DAT modulators: Agonist-like: SoRI-9804
SoRI-20040; Antagonist-like: SoRI-20041

See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

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