MMDA-2

MMDA-2
Clinical data
Routes of; administration	Oral,Insufflated,Rectal
ATC code	none;
Legal status
Legal status	CA:Schedule I; DE:NpSG(Industrial and scientific use only); UK:Class A; Uncontrolled(but may be covered under theFederal Analogue Actin theUnited Statesand under similar bills in other countries);
Identifiers
	IUPAC name 1-(6-Methoxy-1,3-benzodioxol-5-yl)propan-2-amine;
CAS Number	23693-18-7;
PubChemCID	90966;
ChemSpider	82147;
UNII	TG0B6ER184;
CompTox Dashboard(EPA)	DTXSID20903968;
Chemical and physical data
Formula	C11H15NO3
Molar mass	209.245g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O1c2cc(c(OC)cc2OC1)CC(N)C;

MMDA-2(2-methoxy-4,5-methylenedioxyamphetamine) is apsychedelic drugof theamphetamineclass.^[1]It is closely related toMMDAandMDA.^[1]

Alexander Shulginwas likely the first tosynthesizeMMDA-2.^[1]In his bookPiHKAL,the dose is listed as 25–50 mg, and the duration is listed as 8–12 hours.^[1]Shulgin reports that MMDA-2 produces effects such as enhancedawareness,empathy,andvisual facilitationanddistortion,as well as someside effectslikegastrointestinal upsetandappetite loss.^[1]He states that 30 mg is very similar to 80 mg of MDA, and also remarks that it would be impossible for anyone to have a bad experience on the drug at that dose.^[1]

Scientific research has shown that MMDA-2, unlike MMDA, but similarly to6-methyl-MDA,is only very weak at inducing the release ofserotoninordopamine,^[2]and accordingly, does not produceamphetamine-like responses in animals in drug discrimination studies.^[3]Instead, MMDA-2 is likely to act as a pure5-HT₂receptor agonistsimilarly to theDOxseries of compounds, with activation of the5-HT_2Areceptorconferring its psychedelic effects.^[4]

MMDA-2 has been sold as adesigner druginJapan.^[5]

References

^^a ^b ^c ^d ^e ^fShulgin A, Shulgin A (13 May 2016)."MMDA-2 (2-Methoxy-4,5-methylenedioxyamphetamine)".Pihkal: A Chemical Love Story.Transform Press.ISBN 978-0-9630096-0-9.
^McKenna DJ, Guan XM, Shulgin AT (March 1991)."3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine".Pharmacology, Biochemistry, and Behavior.38(3): 505–512.doi:10.1016/0091-3057(91)90005-M.PMID 1829838.S2CID 2740262.
^Glennon RA, Yousif M, Naiman N, Kalix P (March 1987). "Methcathinone: a new and potent amphetamine-like agent".Pharmacology, Biochemistry, and Behavior.26(3): 547–551.doi:10.1016/0091-3057(87)90164-X.PMID 3575369.S2CID 5890314.
^Clare BW (2002). "QSAR of benzene derivatives: comparison of classical descriptors, quantum theoretic parameters and flip regression, exemplified by phenylalkylamine hallucinogens".Journal of Computer-Aided Molecular Design.16(8–9): 611–633.Bibcode:2002JCAMD..16..611C.doi:10.1023/A:1021966231380.PMID 12602954.S2CID 9948738.
^Min JZ, Shimizu Y, Toyo'oka T, Inagaki S, Kikura-Hanajiri R, Goda Y (October 2008). "Simultaneous determination of 11 designated hallucinogenic phenethylamines by ultra-fast liquid chromatography with fluorescence detection".Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences.873(2): 187–194.doi:10.1016/j.jchromb.2008.08.020.PMID 18789774.

External links

[isbn0-9630096-0-5-1] Shulgin A, Shulgin A (13 May 2016)."MMDA-2 (2-Methoxy-4,5-methylenedioxyamphetamine)".Pihkal: A Chemical Love Story.Transform Press.ISBN 978-0-9630096-0-9.

[pmid1829838-2] McKenna DJ, Guan XM, Shulgin AT (March 1991)."3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine".Pharmacology, Biochemistry, and Behavior.38(3): 505–512.doi:10.1016/0091-3057(91)90005-M.PMID 1829838.S2CID 2740262.

[pmid3575369-3] Glennon RA, Yousif M, Naiman N, Kalix P (March 1987). "Methcathinone: a new and potent amphetamine-like agent".Pharmacology, Biochemistry, and Behavior.26(3): 547–551.doi:10.1016/0091-3057(87)90164-X.PMID 3575369.S2CID 5890314.

[pmid12602954-4] Clare BW (2002). "QSAR of benzene derivatives: comparison of classical descriptors, quantum theoretic parameters and flip regression, exemplified by phenylalkylamine hallucinogens".Journal of Computer-Aided Molecular Design.16(8–9): 611–633.Bibcode:2002JCAMD..16..611C.doi:10.1023/A:1021966231380.PMID 12602954.S2CID 9948738.

[pmid18789774-5] Min JZ, Shimizu Y, Toyo'oka T, Inagaki S, Kikura-Hanajiri R, Goda Y (October 2008). "Simultaneous determination of 11 designated hallucinogenic phenethylamines by ultra-fast liquid chromatography with fluorescence detection".Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences.873(2): 187–194.doi:10.1016/j.jchromb.2008.08.020.PMID 18789774.

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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) 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-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

v t e Phenethylamines
Phenethylamines	Psychedelics:25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 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-22 2C-T-22.5 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-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants:Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine(amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens:Lophophine MDPEA MDMPEA Others:BOH DMPEA
Amphetamines	Psychedelics:3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants:2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine(Dextroamphetamine,Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine(Dexfenfluramine,Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine(Dextromethamphetamine,Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N, Alpha -Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens:4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 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 TAP Others:3,4-DCA Amiflamine DiFMDA Selegiline(alsoD-Deprenyl)
Phentermines	Stimulants:Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens:MDPH MDMPH Others:Cericlamine
Cathinones	Stimulants: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 Radafaxine Entactogens:3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens:4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants:Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants:α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA(Dextrodopa) Dimetofrine Dopamine Epinephrine 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 Norfenefrine(m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol(Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

See also

References

External links