From Wikipedia, the free encyclopedia
3,4-Methylenedioxyamphetamine
(MDA) is a psychedelic, stimulant, and empathogen-entactogen of the phenethylamine
and amphetamine chemical classes. It is mainly used as a recreational drug, an entheogen, and a tool in use to supplement various types of
practices for transcendence, including in meditation, psychonautics, and illegal psychedelic psychotherapy, whether self
administered or not. It was first synthesized by G. Mannish and W.
Jacobson in 1910. There are about 20 different synthetic routes
described in the literature for its preparation.
Medical
use
There are no currently accepted medical uses for MDA. However,
researchers have investigated many possible uses in the past. It
was first ingested in July of 1930 by Gordon Alles who then
licensed the drug to Smith Kline and French.[1]. MDA
was first used in animal tests in 1939, and human trials began in 1941 in the
exploration of possible therapies for Parkinson's disease. From 1949 to
1957, more than 500 human subjects were given MDA in an
investigation of its potential use as an antidepressant and/or anorectic by Smith, Kline & French.
The United
States Army also experimented with the drug, code named
EA-1298, while working to develop a truth drug or incapacitating agent. One
human subject [2]died in
January 1953 after being intravenously injected with 450mg of the
drug. MDA was patented as a cough suppressant by H. D. Brown in
1958, as an ataractic by Smith, Kline & French in
1960, and as an anorectic under the trade name
“Amphedoxamine” in 1961. Several researchers, including Claudio Naranjo
and Richard Yensen, have explored MDA in the field of psychotherapy.
Synthesis
One method of MDA synthesis is to turn safrole into isosafrole via isomerization. The
isosafrole is then oxidized, using a peroxyacid, to produce
MDP2P (methylenedioxyphenylacetone). Finally, it is converted
to MDA via reductive amination with ammonia. This synthesis is very
similar to that of MDMA
(Ecstasy) and of MDEA. The most
common route is by starting from piperonal, and condensing it with
nitroethane. The resulting nitro-isosafrole can then be reduced to
MDA with a suitable reducing agent.
Recreational
use
MDA began to appear on the recreational drug scene around
1963 to 1964. It was then inexpensive and readily available as a research chemical from several scientific
supply houses. Although now illegal, MDA continues to be bought,
sold, and used for recreational purposes, often in the form of tablets purporting to contain MDMA (Ecstasy).
Effects
A recreational dose of MDA is commonly between 100 and 160mg.
The “S” optical isomer of MDA is more potent than
the “R” optical isomer as a psychostimulant,
possessing greater affinity for the three monoamine transporter proteins
(SERT, NET and DAT).
Although there is some debate, the duration of the drug is now
generally believed to be roughly 6 to 10 hours; but most
individuals report the duration of the drug's effects to be around
5-6 hours, slightly longer than that of MDMA. (In the late 90s, Alexander
Shulgin changed his opinion of the duration to 3-6 hours).
MDA is thought to be similar in pharmacological mechanism of
action and phenomenological effects to its more widely used
N-methyl analogue MDMA (Ecstasy). Like MDMA, MDA causes serotonin
and dopamine release by acting as a substrate at the SERT and DAT,
respectively. This may explain the similar euphoric and empathogenic effects of the two
compounds. However, (R)-MDA has a higher efficacy in stimulating
the 5-HT2A
receptor than (R)-MDMA; thus MDA tends to cause more
psychedelic-like effects, such as visual hallucinations. MDMA can also produce
psychedelic-like visual effects, though these are generally less
pronounced than those of MDA, or require a heavier dose to become
apparent.
MDA is said to share the empathogen/entactogenic effects
of MDMA. While it is generally similar to MDMA, users report that
MDA has more stimulant, or psychedelic hallucinogenic
qualities and slightly less intense empathogen/entactogenic effects
than MDMA. MDA is also considered less predictable than MDMA, with
effects varying greatly from person to person. However, no properly
controlled experiments have compared these drugs in humans.
MDA also differs from its methylated cousin MDMA in its acute
toxicity--it is clearly more toxic, with toxicity indicative of
overstimulation of the central nervous system and the
cardiovascular system.[3]
Symptoms of acute toxicity may include agitation, sweating,
increased blood pressure and heart rate, dramatic increase in body
temperature, convulsions, and death. Death is usually caused by
cardiac effects and subsequent hemorrhaging in the brain
(stroke).[3]
The website erowid.org lists
the fatality rate at roughly 2 in 100,000 users, assuming it has
similar rates as MDMA.[4] The LD50
in mice has been reported as 92mg/kg by intraperitoneal
injection.
Legality
In 1970, the Controlled Substances Act was
enacted in the United States, placing MDA into Schedule I. It is similarly
controlled in other nations. In Canada MDA is a Schedule III drug.
Internationally, MDA is a Schedule I drug under the Convention on
Psychotropic Substances. The US has also essentially banned any
drug with (methylenedioxy) in its structure, as well as several
other phenethylamine-based compounds. This means that all
unscheduled MDXX chemicals can be prosecuted under the Federal
Analog Act. [5]
See also
External
links
References
- Lee, M.A. and Shlain, B., Acid Dreams: The CIA, LSD, and
the Sixties Rebellion. Grove, 1985.
- Stafford, P. Psychedelics Encyclopedia. Ronin,
1992.
- Pihkal: A Chemical Love Story, Transform Press, Alexander
Shulgin, Ann Shulgin.
| Entactogens |
|
| Oxytocics |
|
|
| Serotonergics |
|
|
|
|
|
|
|
|
|
|
Methylenedioxy-substituted: MDMPEA • MMDPEA (Lophophine,
Homomyristicylamine) • MDPEA
(Homopiperonylamine)
|
|
|
|
Methylenedioxy-substituted: MDMP (MDMPH) • MDPH (MDPHP)
|
|
|
|
4-substituted: 4-BMC
• 4-FMC (Flephedrone) • 4-MMC (Mephedrone) • 4-MeOMC (Methedrone);
Methylenedioxy-substituted: bk-MDEA (MDEC, MDECAT;
Ethylone) • bk-MDMA
(MDMC, MDMCAT; Methylone)
|
|
|
|
|
4-substituted: α-Et-DOM (Ariadne);
Methylenedioxy-substituted: BDB (J) • DMBDB (Dimethyl-J) •
EBDB (Ethyl-J) • HBDB (BOH; Hydroxy-J) •
MBDB (Methyl-J;
"Eden")
|
|
Methylenedioxy-substituted: bk-MBDB (Butylone) •
bk-EBDB (Eutylone)
|
|
|
|
|
Methylenedioxy-substituted: BDP (K) • EBDP (Ethyl-K) • MBDP (Methyl-K) •
bk-Methyl-K
|
|
|
|
|
|
|
|
| Stimulants |
|
| Adamantanes |
|
|
| Arylcyclohexylamines |
|
|
| Benzazepines |
|
|
| Cholinergics |
|
|
| Convulsants |
|
|
| Eugeroics |
|
|
| Oxazolines |
|
|
| Phenethylamines |
2-Fluoroamphetamine • 2-OH-PEA •
2-Phenyl-3-aminobutane • 2-Phenyl-3-methylaminobutane • 2,3-MDA • 3-Fluoroamphetamine • 3-Methoxyamphetamine • 3-Methylamphetamine • 4-BMC
• 4-Ethylamphetamine • 4-FA •
4-FMA • 4-MA •
4-MMA • 4-MTA • Alfetamine • α-Ethylphenethylamine • Amfecloral • Amfepentorex • Amidephrine • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Arbutamine • Atomoxetine
(Tomoxetine) • β-Methylphenethylamine • Benfluorex • Benzphetamine • BDB (J) • BOH (Hydroxy-J) • BPAP • Buphedrone • Bupropion (Amfebutamone) •
Butylone • Cathine • Cathinone • Chlorphentermine • Clenbuterol • Clobenzorex • Clortermine • D-Deprenyl • Denopamine • Diethylcathinone (Diethylpropion,
Amfepramone) • Dimethoxyamphetamine • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion,
Metamfepramone) • Dobutamine • DOPA (Dextrodopa, Levodopa) • Dopamine • Dopexamine • Droxidopa • EBDB (Ethyl-J) • Ephedrine • Epinephrine
(Adrenaline) • Epinine (Deoxyepinephrine) • Etafedrine • Ethcathinone
(Ethylpropion) • Ethylamphetamine (Etilamfetamine) • Ethylone • Etilefrine • Fenbutrazate
• Fencamine • Fencamfamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Flephedrone • Fludorex • Furfenorex • Gepefrine • HMMA • Hordenine • Ibopamine • Indanorex • IMP • Indanylamphetamine • Isoetarine • Isoprenaline (Isoproterenol) • L-Deprenyl (Selegiline) • Lefetamine • Lisdexamfetamine • Lophophine (Homomyristicylamine) • Manifaxine • MBDB (Methyl-J; "Eden") •
MDA
(Tenamfetamine) • MDBU • MDEA ("Eve") • MDMA
("Ecstasy", "Adam") • MDMPEA
(Homarylamine) • MDOH • MDPR • MDPEA (Homopiperonylamine)
• Medifoxamine •
Mefenorex • Mephedrone • Mephentermine • Metanephrine • Metaraminol • Methamphetamine
(Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methoxamine • Methoxyphenamine • MMA • Methcathinone (Methylpropion) • Methedrone • Methoxyphenamine • Methylone • MMDA • MMDMA • MMMA • Naphthylamphetamine • Nisoxetine • Norepinephrine (Noradrenaline) • Norfenefrine • Norfenfluramine
• Normetanephrine • Octopamine • Orciprenaline • Ortetamine • Oxilofrine • Paredrine (Norpholedrine, Oxamphetamine,
Mycadrine) • PBA • PCA • PHA • Pargyline • Phendimetrazine
• Phenmetrazine
• Phenpentermine • Phenpromethamine • Phentermine • Phenylalanine • Phenylephrine
(Neosynephrine) • Phenylpropanolamine • Pholedrine • PIA • PMA • PMEA • PMMA • PPAP • Prenylamine • Propylamphetamine • Pseudoephedrine
• Radafaxine • Ropinirole • Salbutamol (Albuterol; Levosalbutamol) •
Sibutramine • Synephrine (Oxedrine) •
Theodrenaline •
Tiflorex (Flutiorex) • Tranylcypromine
• Tyramine • Tyrosine • Xamoterol • Xylopropamine • Zylofuramine
|
|
| Piperazines |
|
|
| Piperidines |
|
|
| Pyrrolidines |
|
|
| Tropanes |
|
|
| Xanthines |
|
|
| Others |
|
|
| See also Sympathomimetic amines |
|
| Dopaminergics |
|
Receptor
Ligands |
|
|
Benzazepines: 6-Br-APB • Fenoldopam • SKF-38,393 • SKF-77,434 • SKF-81,297 • SKF-82,958 • SKF-83,959; Ergot-derivatives: Bromocriptine • Cabergoline • Dihydroergocryptine • Lisuride • LSD • Pergolide;
Dihydrexidine-derivatives: 2-OH-NPA • A-86,929 • Dihydrexidine • Dinapsoline • Dinoxyline • Doxanthrine;
Morphine-derivatives: Apomorphine • Propylnorapomorphine;
Piperazines: ABT-724 • Aripiprazole • Piribedil • WAY-100,635; Others: 7-OH-DPAT • 8-OH-PBZI • A-68,930
• A-77,636 • A-412,997 •
ABT-670 • Amantadine • Aplindore • CY-208,243 • Etilevodopa • Melevodopa • Memantine • PD-128,907 • PF-219,061 • Pramipexole • Pukateine • Quinpirole • RDS-127 • Rimantadine • Ropinirole • Rotigotine • SKF-89145 •
SKF-89626
|
|
|
|
|
|
|
Reuptake
Inhibitors |
|
|
Releasing
Agents |
Morpholines: Phendimetrazine
• Phenmetrazine;
Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone;
Phenethylamines (also Amphetamines,
Cathinones, Phentermines, etc): 2-Hydroxyphenethylamine
(2-OH-PEA) • 4-Methylamphetamine (4-MA) • 4-Methylmethamphetamine (4-MMA)
• Alfetamine • Amfecloral • Amfepentorex • Amphetamine ( Dextroamphetamine, Levoamphetamine) • Amphetaminil • β-Methylphenethylamine
(β-Me-PEA) • Benzodioxolylbutanamine (BDB) •
Benzodioxolylhydroxybutanamine
(BOH) • Benzphetamine • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex • Clortermine • D-Deprenyl • Diethylcathinone (Diethylpropion,
Amfepramone) • Dimethoxyamphetamine (DMA) • Dimethoxymethamphetamine
(DMMA) • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion,
Metamfepramone) • Ethcathinone (Ethylpropion) • Ethylamphetamine • Ethylbenzodioxolylbutanamine
(EBDB) • Ethylone • Fenethylline • Fenproporex • Flephedrone • Fludorex • Furfenorex • Hordenine • Indanorex • Lophophine (Homomyristicylamine) • Mefenorex • Mephedrone • Methamphetamine
(Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methcathinone
(Methylpropion) • Methedrone • Methoxymethylenedioxyamphetamine
(MMDA) • Methoxymethylenedioxymethamphetamine
(MMDMA) • Methylbenzodioxolylbutanamine
(MBDB) • Methylenedioxyamphetamine (MDA;
Tenamfetamine) • Methylenedioxyethylamphetamine
(MDEA) • Methylenedioxyhydroxyamphetamine
(MDOH) • Methylenedioxymethamphetamine (MDMA) • Methylenedioxymethylphenethylamine
(MDMPEA; Homarylamine) • Methylenedioxyphenethylamine
(MDPEA; Homopiperonylamine) • Methylone • Ortetamine • Parabromoamphetamine (PBA) • Parachloroamphetamine (PCA) • Parafluoroamphetamine (PFA) • Parafluoromethamphetamine
(PFMA) • Parahydroxyamphetamine (PHA) • Paraiodoamphetamine (PIA) • Paramethoxyamphetamine (PMA) • Paramethoxyethylamphetamine
(PMEA) • Paramethoxymethamphetamine
(PMMA) • Paredrine (Norpholedrine, Oxamphetamine) •
Phenethylamine
(PEA) • Pholedrine •
Phenpromethamine • Prenylamine • Propylamphetamine • Tiflorex (Flutiorex) • Tyramine (TRA) • Xylopropamine • Zylofuramine;
Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine
(2C-B-BZP) • Benzylpiperazine (BZP) • Methoxyphenylpiperazine (MeOPP;
Paraperazine) • Methylbenzylpiperazine (MBZP) •
Methylenedioxybenzylpiperazine
(MDBZP; Piperonylpiperazine); Others: 2-Amino-1,2-dihydronaphthalene
(2-ADN) • 2-Aminoindane (2-AI) • 2-Aminotetralin
(2-AT) • 4-Benzylpiperidine (4-BP) • Clofenciclan • Cyclopentamine •
Cypenamine • Cyprodenate • Feprosidnine • Gilutensin • Heptaminol • Hexacyclonate • Indanylaminopropane (IAP) • Isometheptene • Methylhexanamine • Naphthylaminopropane (NAP) • Octodrine • Phthalimidopropiophenone • Propylhexedrine
(PHX) • Tuaminoheptane (Tuamine)
|
|
Enzyme
Inhibitors |
|
|
|
Others |
|
|
| Serotonergics |
|
Receptor
ligands |
|
|
|
|
|
|
|
|
|
|
|
|
Agonists:
Lysergamides: Dihydroergotamine • Methysergide;
Triptans: Almotriptan • Avitriptan • Eletriptan • Frovatriptan • Naratriptan • Rizatriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT;
Others: CP-135,807 • CP-286,601 • GR-46611 • L-694,247 •
L-772,405 • PNU-109,291 • PNU-142,633
Antagonists: Lysergamides: Metergoline;
Others: Alniditan BRL-15572 • GR-127,935 • Ketanserin • LY-310,762 • LY-367,642 •
LY-456,219 • LY-456,220 • Metitepine/Methiothepin • Ritanserin • Yohimbine • Ziprasidone
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
Agonists:
Phenethylamines: 2C-B •
2C-E • 2C-I • 2C-T-2
• 2C-T-7 • 2C-T-21 • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline • Myristicin; Piperazines: Aripiprazole • mCPP •
TFMPP;
Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin;
Others: A-372,159 • AL-38022A • CP-809,101 • Lorcaserin• Medifoxamine • MK-212 •
N-Dealkyloxaflozane • ORG-37,684 • Oxaflozane • PNU-22394 • Ro60-0175 • Vabicaserin • WAY-629 •
WAY-161,503 • YM-348
Antagonists: Atypical Antipsychotics: Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical
Antipsychotics: Chlorpromazine • Loxapine • Pipamperone; Antidepressants: Agomelatine • Amitriptyline • Amoxapine • Etoperidone • Fluoxetine • Mianserin • Mirtazapine • Nefazodone • Nortriptyline • Trazodone; Others:
Cinanserin • Cyproheptadine •
Deramciclane • Dimebolin • Dotarizine • Eltoprazine •
FR-260,010 • Ketanserin • Ketotifen • Metitepine/Methiothepin • Methysergide • Pizotifen • Ritanserin • RS-102,221 • SB-200,646 •
SB-206,553 • SB-221,284 • SB-228,357 • SB-242,084 • SB-243,213 • SDZ SER-082 • Xylamidine
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
|
Reuptake
inhibitors |
|
|
Releasing
agents |
|
|
Enzyme
inhibitors |
|
|
|
Others |
|
|
| Hallucinogens |
|
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|LSB • Lysergic Acid
2,4-Dimethylazetidide • Methylergometrine • Methylisopropyllysergamide •
Methysergide • MLD-41 • PARGY-LAD • PRO-LAD;
Phenethylamines: Aleph •
2C-B • 2C-B-FLY • 2CBFly-NBOMe • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-O • 2C-O-4 • 2C-P • 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 • 2CBCB-NBOMe • 25B-NBOMe • 25I-NBMD • 25I-NBOH • 25I-NBOMe • 3C-E • 3C-P • Br-DFLY • DESOXY • DMMDA-2 • DOB • DOC • DOEF • DOET • DOF • DOI
• DOM • DON • DOPR • DOTFM • Escaline • Ganesha • HOT-2 • HOT-7
• HOT-17 • Isoproscaline • Jimscaline • Lophophine • MDA •
MDEA • MDMA
• MMDA • MMDA-2 • MMDA-3a • MMDMA • Macromerine • Mescaline • Methallylescaline • Proscaline • TCB-2 • TFMFly • TMA;
Piperazines: pFPP •
TMFPP;
Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine
• 2,N,N-TMT •
4,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-Hydroxy-N-Methyl-(a,N-trimethylene)tryptamine •
5-Me-MIPT • 5-N,N-TMT
• 5-AcO-DMT • 5-MeO-2,N,N-TMT •
5-MeO-4,N,N-TMT • 5-MeO-a,N,N-TMT • 5-MeO-a-ET • 5-MeO-a-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-Methoxy-N-methyl-(a,N-trimethylene)tryptamine •
7,N,N-TMT • a,N,N-TMT • a-ET • a-MT • AL-37350A • Baeocystin • Bufotenin • DBT • 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 |
|
|
Miscellaneous
Atypicals |
|
|
| MDxx |
|
| Phenethylamines |
bk-MDMPEA • bk-MDPEA • MDMPEA • MMDPEA (Lophophine,
Homomyristicylamine) • MDPEA
(Homopiperonylamine) |
|
| Amphetamines |
2-Methyl-MDA • 3-Desoxy-MDA •
5-Methyl-MDA •
DMMDA • DMMDA-2 •
MADAM-6 • MDA (Tenamfetamine; "Hug Drug", "Love
Drug", "Mellow Drug of America") • MDAL (MDAA) • MDBU (MDBA) • MDBZ (MDBZA) • MDCPM
(MDCPMA, MDCA) • MDDM (MDDMA) • MDEA (MDE; "Eve") • MDIP (MDIPR, MDIPA)
• MDMA
(MDM; "Ecstasy", "Adam", "Empathy", "Molly", "E", "X", "XTC") • MDOH (MDH) • MDHOET (MDHET,
MDHEA) • MDMEO (MDMEOA) • MDMEOET (MDMEOET,
MDMEOEA, MDMEA) • MDMOH (MDMHO, MDMHA, MDMH; FLEA) • MDPR (MDPA) • MDPL (MDPLA) • MMDA • MMDMA |
|
| Cathinones |
bk-MDA (MDC, MDCAT) • bk-MDEA (MDEC, MDECAT; Ethylone) • bk-MDMA
(MDMC, MDMCAT; Methylone; "Explosion", "Ease") |
|
| Phentermines |
|
|
| Butanamines |
BDB (J) • bk-BDB (bk-J) •
bk-EDBD (Eutylone) • bk-MBDB (Butylone) • BOH (Hydroxy-J) • DMBDB
(Dimethyl-J) • EBDB (Ethyl-J) • MBDB (Methyl-J;
"Eden")
|
|
| Pentylamines |
|
|
| Miscellaneous |
|
|
Wikis
Search
