Chemistry: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 the Federal Analogue Act in the United States and 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;
PubChem CID	90966;
ChemSpider	82147;
UNII	TG0B6ER184;
Chemical and physical data
Formula	C11H15NO3
Molar mass	209.245 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O1c2cc(c(OC)cc2OC1)CC(N)C;

Short description: Psychedelic drug

MMDA-2 (2-methoxy-4,5-methylenedioxyamphetamine) is a psychedelic drug of the amphetamine class.^[1] It is closely related to MMDA and MDA.^[1]

Alexander Shulgin was likely the first to synthesize MMDA-2.^[1] In his book PiHKAL, 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 enhanced awareness, empathy, and visual facilitation and distortion, as well as some side effects like gastrointestinal upset and appetite 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 to 6-methyl-MDA, is only very weak at inducing the release of serotonin or dopamine,^[2] and accordingly, does not produce amphetamine-like responses in animals in drug discrimination studies.^[3] Instead, MMDA-2 is likely to act as a pure 5-HT₂ receptor agonist similarly to the DOx series of compounds, with activation of the 5-HT_2A receptor conferring its psychedelic effects.^[4]

MMDA-2 has been sold as a designer drug in Japan .^[5]

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 "MMDA-2 (2-Methoxy-4,5-methylenedioxyamphetamine)". Pihkal: A Chemical Love Story. Transform Press. 13 May 2016. ISBN 978-0-9630096-0-9. http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=133.
↑ "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. March 1991. doi:10.1016/0091-3057(91)90005-M. PMID 1829838.
↑ "Methcathinone: a new and potent amphetamine-like agent". Pharmacology, Biochemistry, and Behavior 26 (3): 547–551. March 1987. doi:10.1016/0091-3057(87)90164-X. PMID 3575369.
↑ "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. 2002. doi:10.1023/A:1021966231380. PMID 12602954. Bibcode: 2002JCAMD..16..611C.
↑ "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. October 2008. doi:10.1016/j.jchromb.2008.08.020. PMID 18789774.

External links

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/MMDA-2. Read more

[isbn0-9630096-0-5-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 "MMDA-2 (2-Methoxy-4,5-methylenedioxyamphetamine)". Pihkal: A Chemical Love Story. Transform Press. 13 May 2016. ISBN 978-0-9630096-0-9. http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=133.

[pmid1829838-2] "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. March 1991. doi:10.1016/0091-3057(91)90005-M. PMID 1829838.

[pmid3575369-3] "Methcathinone: a new and potent amphetamine-like agent". Pharmacology, Biochemistry, and Behavior 26 (3): 547–551. March 1987. doi:10.1016/0091-3057(87)90164-X. PMID 3575369.

[pmid12602954-4] "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. 2002. doi:10.1023/A:1021966231380. PMID 12602954. Bibcode: 2002JCAMD..16..611C.

[pmid18789774-5] "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. October 2008. doi:10.1016/j.jchromb.2008.08.020. PMID 18789774.

[1]

[2]

[3]

[4]

[5]

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 DiFMDA DMMDA DMMDA-2 EIDA MDEA MDMA (midomafetamine) MDMOH MDOH MMDA MMDA-2 MMDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans and dihydrobenzofurans: 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 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 ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-MMC 4-EMC Brephedrone Butylone 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 α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 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 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 Phenpromethamine 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 (also D -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

Anonymous

Search

Chemistry:MMDA-2

Namespaces

More

Page actions

See also

References

External links

Navigation

Navigation

Help

Translate

Wiki tools

Wiki tools

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 the Federal Analogue Act in the United States and 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
PubChem CID	90966
ChemSpider	82147
UNII	TG0B6ER184
Chemical and physical data
Formula	C₁₁H₁₅NO₃
Molar mass	209.245 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O1c2cc(c(OC)cc2OC1)CC(N)C

Anonymous

Search

Chemistry:MMDA-2

See also

References

External links

Navigation

Wiki tools

Page tools

Other projects

Categories