MMDA (drug)

MMDA (drug)
MMDA (drug)
Clinical data
Pregnancy cat.  ?
Legal status Schedule I (US)
Routes Oral, Insufflation, Rectal
Identifiers
CAS number 13674-05-0
ATC code None
PubChem CID 26175
ChemSpider 24386
Chemical data
Formula C11H15NO3 
Mol. mass 209.24 g/mol
SMILES eMolecules & PubChem

3-Methoxy-4,5-methylenedioxyamphetamine (MMDA; 3-Methoxy-MDA) is a psychedelic and entactogen drug of the amphetamine class. It is an analogue of lophophine, MDA, and MDMA, and also bears resemblance to the essential oil myristicin found in nutmeg.

MMDA was described by Alexander Shulgin in his book PiHKAL. Shulgin lists the dosage range of MMDA as 100–250 mg. The first symptoms appear within 30–60 minutes following oral administration. MMDA produces euphoria and loving warmth, and attenuates feelings such as anxiety and loneliness. MMDA also produces eyes-closed visuals, a state of drowsiness, muscle relaxation, and time dilation. Side effects include moderate mydriasis, dizziness, sensations of heat or cold, and trembling. The imagery is generally realistic, and often related to everyday perception of people, landscapes, or objects. The effects of MMDA usually reach a peak after the first hour following the initial symptoms, and begin to wane during the second hour, and usually completely disappear by the end of the fifth hour.

Contents

Psychotherapeutic actions

In his 1973 book, "The Healing Journey", Claudio Naranjo explored the psychotherapeutic potential of MMDA. Like MDA, he found that MMDA facilitates communication and suggested it has potential applications in psychotherapy. Worldwide as of 2005, MMDA has not been approved for any human applications.

Pharmacology

MMDA has been shown to act as a non-neurotoxic serotonin releasing agent with no effects on dopamine release and probably norepinephrine release as well,[1] and as a 5-HT2A receptor agonist.[2] The latter property is responsible for its psychedelic effects, whereas the former mediates its mood-lifting and empathogenic effects.

Legality

MMDA is classified as a Schedule 1 substance in the United States, and is similarly controlled in other parts of the world. Internationally, MMDA is a Schedule I drug under the Convention on Psychotropic Substances[1].

See also

References

  1. ^ 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): 505–12. doi:10.1016/0091-3057(91)90005-M. PMID 1829838. http://linkinghub.elsevier.com/retrieve/pii/0091-3057(91)90005-M. 
  2. ^ Zhang Z, An L, Hu W, Xiang Y (April 2007). "3D-QSAR study of hallucinogenic phenylalkylamines by using CoMFA approach". Journal of Computer-aided Molecular Design 21 (4): 145–53. doi:10.1007/s10822-006-9090-y. PMID 17203365. 

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v · d · eEntactogens
Aminoindanes
5-IAI • ETAI • TAI
Aminotetralins
6-CAT
Phenethylamines
(and amphetamines,
cathinones, etc)
4-CAB • 4-FA • 4-FMA • 4-MTA • 4-FPP • 5-APDB • 6-APDB • Ariadne • BDB • Brephedrone • Eutylone • Flephedrone • IAP • IMP • Metaescaline • Mephedrone • Methedrone • MMA • NAP • Norfenfluramine • Pentylone • PMA • PMEA • PMMA • TAP
MDxx
2-Methyl-MDA • 5-Methyl-MDA • 6-Methyl-MDA • bk-MBDB (butylone) • bk-MDEA (ethylone) • bk-MDMA (methylone) • DMMDA • DMMDA-2 • EBDB • EBDP • EDMA • MDAI • MDMAI • MMAI • MDAT • MDMAT • MDA • MDDM • MDEA • MDIP • MDMA • MDMOH • MDMP • MDMPEA • MDOH • MDPEA • MDPH • MDPR • MMDPEA (Lophophine) • MBDB • MBDP • MMDA • MMDA-2 • MMDMA
Tryptamines
4-Methyl-αET • αET
v · d · eHallucinogens
Psychedelics
5-HT2AR agonists
Lysergamides: AL-LAD • ALD-52 • BU-LAD • CYP-LAD • DAM-57 • Diallyllysergamide • Ergometrine (Ergonovine, Ergobasine) • ETH-LAD • LAE-32 • LSA (Ergine, Lysergamide) • LSD • LSH • LPD-824 • LSM-775 • Lysergic Acid 2-Butyl Amide • Lysergic Acid 2,4-Dimethylazetidide • Lysergic Acid 3-Pentyl Amide • Methylergometrine • Methylisopropyllysergamide • Methysergide • MLD-41 • PARGY-LAD • PRO-LAD;
Phenethylamines: Aleph • 2C-B • 2C-B-Dragonfly · 2C-B-FLY • 2C-C-FLY • 2C-D-FLY • 2C-E-FLY • 2C-I-FLY • 2CBFly-NBOMe • 2C-T-7-FLY • 2C-C • 2C-C-NBOMe • 2C-CN-NBOMe • 2C-D • 2CD-5EtO • 2C-D-NBOMe • 2C-E • 2C-EF • 2C-E-NBOMe • 2C-F • 2C-F-NBOMe • 2C-G • 2C-G-NBOMe • 2C-H-NBOMe • 2C-I • 2C-N • 2C-N-NBOMe • 2C-O • 2C-O-4 • 2C-P • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-4-NBOMe • 2C-T-7 • 2C-T-7-NBOH • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-TFM-NBOMe • 2C-YN • 2CBCB-NBOMe • 25B-NBOMe • 25I-NBMD • 25I-NBOH • 25I-NBOMe • 3C-E • 3C-P • 5-APB • 5-APDB • 6-APB • 6-APDB • Br-DFLY • DESOXY • DMMDA • DMMDA-2 • DOB • DOB-FLY • DOM-FLY • DOC • DOEF • DOET • DOF • DOI • DOM • DON • DOPR • DOTFM • Escaline • Ganesha • HOT-2 • HOT-7 • HOT-17 • IAP • Isoproscaline • Jimscaline • Lophophine • MDA • MDEA • MDMA • MMA • MMDA • MMDA-2 • MMDA-3a • MMDMA • Macromerine • Mescaline • Methallylescaline • NBOMe-mescaline • Proscaline • TCB-2 • TFMFly • TMA;
Piperazines: pFPP • TMFPP;
Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine • 2,N,N-TMT • 4-HO-5-MeO-DMT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-Acetoxy-DPT • 4-Acetoxy-MiPT • 4-HO-DPT • 4-HO-MET • 4-Propionyloxy-DMT • 4-HO-MPMI • 5-Me-MIPT • 5-N,N-TMT • 5-AcO-DMT • 5-MeO-2,N,N-TMT • 5-MeO-α,N,N-TMT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-EiPT • 5-MeO-MET • 5-MeO-MIPT • 5-MeO-MPMI • 7,N,N-TMT • α,N,N-TMT • α-ET • α-MT • AL-37350A • Baeocystin • Bufotenin • DALT • DBT • DCPT • DET • DIPT • DMT • DPT • EiPT • Ethocin • Ethocybin • Iprocin • MET • Miprocin • MIPT • Norbaeocystin • PiPT • Psilocin • Psilocybin;
Others: AL-38022A • Ibogaine • Noribogaine • Voacangine
Dissociatives
NMDAR antagonists
Deliriants
mAChR antagonists
3-Quinuclidinyl benzilate • Atropine • Benactyzine • Benzatropine • Benzydamine • Biperiden • Brompheniramine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • Chlorpheniramine • Chloropyramine • Clemastine • CS-27349 • Cyclizine • Cyproheptadine • Dicyclomine (Dicycloverine) • Dimenhydrinate • Diphenhydramine • Ditran • Doxylamine • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Flavoxate • Hydroxyzine • Hyoscyamine • Meclizine • Myristicin • N-Ethyl-3-piperidyl benzilate • N-Methyl-3-piperidyl benzilate • Pyrilamine • Orphenadrine • Oxybutynin • Pheniramine • Phenyltoloxamine • Procyclidine • Promethazine • Scopolamine (Hyoscine) • Tolterodine • Trihexyphenidyl • Tripelennamine • Triprolidine • WIN-2299
Miscellaneous
Cannabinoids
CB1R agonists
Cannabinol • CP-47,497 • CP-55,244 • CP-55,940 • DMHP • HU-210 • JWH-018 • JWH-030 • JWH-073 • JWH-081 • JWH-200 • JWH-250 • Nabilone • Nabitan • Nantradol • Parahexyl • THC (Dronabinol) • WIN-55,212-2
Butane • Chloroform • Diethyl Ether (Ether) • Enflurane • Freon • Gasoline (Petrol) • Kerosene (Paraffin) • Propane
2-EMSB • 2-MMSB • Alazocine • Bremazocine • Butorphanol • Cyclazocine • Cyprenorphine • Dextrallorphan • Dezocine • Enadoline • Herkinorin • HZ-2 • Ibogaine • Ketazocine • Metazocine • Nalbuphine • Nalorphine • Noribogaine • Pentazocine • Phenazocine • Salvinorin A • Spiradoline • Tifluadom • U-50,488 • U-69,593
Others
v · d · ePhenethylamines
Phenethylamines
Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2
Stimulants: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA)
Entactogens: Lophophine • MDPEA • MDMPEA
Others: BOH • DMPEA
Amphetamines
Phenylisopropylamines
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: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Norfenfluramine • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine
Entactogens: 5-APDB • 6-APB • 6-APDB • EDA • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP
Others: Amiflamine • DFMDA • D-Deprenyl • L-Deprenyl (Selegiline)
Phentermines
Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine
Entactogens: MDPH • MDMPH
Cathinones
Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone
Entactogens: Ethylone • Methylone
Phenylisobutylamines
Entactogens: 4-CAB • 4-MAB • Ariadne (α-Et-DOM) • BDB (J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • Eutylone (bk-EBDB) • MBDB (Methyl-J)
Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines
Stimulants: α-PBP • α-PPP • α-PVP • MDPBP • MDPPP • MDPV • MOPPP • MPBP • MPHP • MPPP • Naphyrone • PEP • Prolintane • Pyrovalerone
Catecholamines
(and relatives..)
6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine
Miscellaneous
Amidephrine • Arbutamine • Cafedrine • Denopamine • Dobutamine • Dopexamine • Etafedrine • Ethylnorepinephrine • Etilefrine • Famprofazone • Gepefrine • Isoprenaline (Isoproterenol) • Isoetarine • Metaraminol • Metaterol • Methoxamine • Norfenefrine • Orciprenaline • Phenylephrine (Neosynephrine) • Phenoxybenzamine • Prenalterol • Pronethalol • Propranolol • Salbutamol (Albuterol; Levosalbutamol) • Synephrine (Oxedrine) • Theodrenaline • Xamoterol
v · d · eDrugs from PiHKAL

AEM • AL • Aleph • Aleph-2 • Aleph-4 • Aleph-6 • Aleph-7 • Ariadne • Asymbescaline • Buscaline • Beatrice • Bis-TOM • BOB • BOD • BOH • BOHD • BOM • 4-Bromo-3,5-dimethoxyamphetamine • 2-Bromo-4,5-methylenedioxyamphetamine • 2C-B • 3C-BZ • 2C-C • 2C-D • 2C-E • 3C-E • 2C-F • 2C-G • 2C-G-3 • 2C-G-4 • 2C-G-5 • 2C-G-N • 2C-H • 2C-I • 2C-N • 2C-O • 2C-O-4 • 2C-P • CPM • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • psi-2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 4-D • beta-D • DESOXY • 2,4-DMA • 2,5-DMA • 3,4-DMA • DMCPA • DME • DMMDA • DMMDA-2 • DMPEA • DOAM • DOB • DOBU • DOC • DOEF • DOET • DOI • DOM • psi-DOM • DON • DOPR • Escaline • EEE • EEM • EME • EMM • Ethyl-J (EBDB) • Ethyl-K • F-2 • F-22 • Flea • G-3 • G-4 • G-5 • G-N • Ganesha • HOT-2 • HOT-7 • HOT-17 • IDNNA • Isomescaline • Isoproscaline • Iris • J (BDB) • Lophophine • PMA • Mescaline • Madam-6 • Methallylescaline • MDA • MDAL • MDBU • MDBZ • MDCPM • MDDM • MDE • MDHOET • MDIP • MDMA • MDMC (EDMA) • MDMEO • MDMEOET • MDMP • MDOH • MDPEA • MDPH • MDPL • MDPR • Metaescaline • MEDA • MEE • MEM • MEPEA • Meta-DOB • Meta-DOT • Methyl-DMA • Methyl-DOB • Methyl-J (MBDB) • Methyl-K • Methyl-MA (PMMA) • Methyl-MMDA-2 • MMDA • MMDA-2 • MMDA-3a • MMDA-3b • MME • Metaproscaline • MPM • Ortho-DOT • Proscaline • Phenescaline • Phenethylamine • Propynyl • Symbescaline • 2,3,4,5-Tetramethoxyamphetamine • 3-TASB • 4-TASB • 5-TASB • Thiobuscaline • 3-TE • 4-TE • 3-TIM • 4-TIM • 5-TIM • 3-TM • 4-TM • TMA • TMA-2 • TMA-3 • TMA-4 • TMA-5 • TMA-6 • 3-TME • 4-TME • 5-TME • 2T-MMDA-3a • 4T-MMDA-2 • 2-TOET • 5-TOET • 2-TOM • 5-TOM • TOMSO • Thioproscaline • Trisescaline • 3-TSB • 4-TSB • 3-T-Trisescaline • 4-T-Trisescaline

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