3,4-Methylenedioxyamphetamine
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Routes of administration | Oral, sublingual, insufflation, intravenous |
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CYP extensively involved) | |
Excretion | Renal |
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3,4-Methylenedioxyamphetamine (also known as MDA and sass) is an
MDA is rarely sought as a recreational drug compared to other amphetamines; however, it remains widely used due to it being a primary metabolite,[2] the product of hepatic N-dealkylation,[3] of MDMA (ecstasy). It is also a common adulterant of illicitly produced MDMA.[4][5]
Uses
Medical
MDA currently has no accepted medical use.
Recreational
MDA is bought, sold, and used as a recreational 'love drug', due to its enhancement of mood and empathy.[6] A recreational dose of MDA is sometimes cited as being between 100 and 160 mg.[7]
Adverse effects
MDA can produce serotonergic neurotoxic effects in rodents,
Overdose
Symptoms of acute toxicity may include
]Pharmacology
Pharmacodynamics
MDA is a
The (S)-
In terms of the subjective and behavioral effects of MDA, it is thought that serotonin release is required for its empathogen-entactogen effects, release of dopamine and norepinephrine is responsible for its psychostimulant effects, dopamine release is necessary for its
Pharmacokinetics
The duration of the drug has been reported as about 6 to 8 hours.[7]
Chemistry
MDA is a
Synonyms
In addition to 3,4-methylenedioxyamphetamine, MDA is also known by other chemical synonyms such as the following:
- α-Methyl-3,4-methylenedioxy-β-phenylethylamine
- 1-(3,4-Methylenedioxyphenyl)-2-propanamine
- 1-(1,3-Benzodioxol-5-yl)-2-propanamine
Synthesis
MDA is typically synthesized from essential oils such as safrole or piperonal. Common approaches from these precursors include:
- Reaction of safrole's alkene functional group with a halogen containing mineral acid followed by amine alkylation.[17][18]
- Henry reaction of piperonal with nitroethane followed by nitro compound reduction.[18][21][22][23][24]
- MDP2P, which was then subjected to a Leuckart reaction.
- Two dogs or dopeboy clandestine method synthezized from helional as starting material. First creation of oxime using hydoxylamine. Then beckman reaction with nickel acetate to form the amide. Then hoffman rearrangement to form the freebase amine. Then an acid base extraction.[26]
Detection in body fluids
MDA may be quantitated in blood, plasma or urine to monitor for use, confirm a diagnosis of poisoning or assist in the forensic investigation of a traffic or other criminal violation or a sudden death. Some drug abuse screening programs rely on hair, saliva, or sweat as specimens. Most commercial amphetamine immunoassay screening tests cross-react significantly with MDA and major metabolites of MDMA, but chromatographic techniques can easily distinguish and separately measure each of these substances. The concentrations of MDA in the blood or urine of a person who has taken only MDMA are, in general, less than 10% those of the parent drug.[27][28][29]
Derivatives
MDA constitutes part of the core structure of the β-adrenergic receptor agonist protokylol.
History
MDA was first synthesized by
Society and culture
Name
When MDA was under development as a potential pharmaceutical drug, it was given the international nonproprietary name (INN) of tenamfetamine.
Legal status
Australia
MDA is schedule 9 prohibited substance under the Poisons Standards.[33] A schedule 9 substance is listed as a "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities."[33]
United States
MDA is a Schedule I controlled substance in the US.
Research
In 2010, the ability of MDA to invoke mystical experiences and alter vision in healthy volunteers was studied. The study concluded that MDA is a "potential tool to investigate mystical experiences and visual perception".[7]
A 2019 double-blind study administered both MDA and MDMA to healthy volunteers. The study found that MDA shared many properties with MDMA including entactogen and stimulant effects, but generally lasted longer and produced greater increases in psychedelic-like effects like complex imagery, synesthesia, and spiritual experiences.[34]
References
- ^ "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control]. Brazilian Health Regulatory Agency (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). 24 July 2023. Archived from the original on 27 August 2023. Retrieved 27 August 2023.
- PMID 16876329.
- ^ PMID 15228154.
- ^ "EcstasyData.org: Test Result Statistics: Substances by Year". EcstasyData.org. Retrieved 27 June 2017.
- ^ "Trans European Drug Information". idpc.net. Archived from the original on 4 November 2021. Retrieved 27 June 2017.
- PMID 8246240.
- ^ PMID 21152030.
- ^ PMID 24299738.
- PMID 11599334.
- ^ Diaz J (1996). How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall.
- PMID 22037049.
- PMID 17017961.
- ISBN 978-0-444-53235-0.
- PMID 19505264.
- S2CID 41352480.
- PMID 20126400.
- PMID 14477621.
- ^ ISBN 978-0-9630096-3-0.
- PMID 2875058.
- ^ .
- PMID 5412110.
- .
- . Retrieved 20 June 2014.
- ISBN 978-0-9630096-0-9.
- ISSN 0368-1769.
- SSRN 3973132. Retrieved 11 February 2024.
- ^ Kolbrich EA, Goodwin RS, Gorelick DA, Hayes RJ, Stein EA, Huestis MA. Plasma pharmacokinetics of 3,4-methyl
enedioxy methamphetamine after controlled oral administration to young adults. Ther. Drug Monit. 30: 320–332, 2008. - PMID 19168553.
- ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 9th edition, Biomedical Publications, Seal Beach, California, 2011, pp. 1078–1080.
- ^ "The First MDA trip and the measurement of 'mystical experience' after MDA, LSD, and Psilocybin". Psychedelic research. 18 July 2008. Archived from the original on 13 July 2012.
- PMID 5631047.
- S2CID 41155810.
- ^ a b Poisons Standard (October 2015) comlaw.gov.au
- S2CID 106410946.