3,4-Methylenedioxyamphetamine Explained

Verifiedfields:verified
Watchedfields:verified
Verifiedrevid:646873547
Image Class:skin-invert-image
Inn:Tenamfetamine
Class:Entactogen
Stimulant; Psychedelic; Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist
Legal Au:S9
Legal Br:F2
Legal Br Comment:[1]
Legal Ca:Schedule I
Legal De:Anlage I
Legal Uk:Class A
Legal Us:Schedule I
Legal Un:Psychotropic Schedule I
Routes Of Administration:By mouth, sublingual, insufflation, intravenous
Metabolism:Hepatic (CYP extensively involved)
Elimination Half-Life:10.9hours
Duration Of Action:6–8hours
Excretion:Renal
Cas Number:4764-17-4
Unii:XJZ28FJ27W
Atc Prefix:None
Pubchem:1614
Drugbank:DB01509
Chemspiderid:1555
Chembl:6731
Chebi:166520
Kegg:D12715
Synonyms:MDA; Tenamfetamine; Amphedoxamine; Sally; Sassafras; Sass-a-frass; Sass; Mellow Drug of America; Hug drug; Love; 3,4-Methylenedioxy-α-methylphenethylamine; 5-(2-Aminopropyl)-1,3-benzodioxole; EA-1298; NSC-9978; NSC-27106; SKF-5
Iupac Name:1-(2H-1,3-Benzodioxol-5-yl)propan-2-amine
C:10
H:13
N:1
O:2
Smiles:NC(C)CC1=CC2=C(C=C1)OCO2
Inchi:1/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
Inchikey:NGBBVGZWCFBOGO-UHFFFAOYAO-->
Stdinchi:1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3
Stdinchikey:NGBBVGZWCFBOGO-UHFFFAOYSA-N

3,4-Methylenedioxyamphetamine (MDA), sometimes referred to as sass, is an empathogen-entactogen, stimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

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. 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 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. It produces MDMA-like effects, including entactogen and psychedelic effects.[7]

Side effects

Side effects of MDA include sympathomimetic effects like increased heart rate and blood pressure as well as increased cortisol and prolactin levels.

Overdose

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).[8]

Pharmacology

Pharmacodynamics

Affinity (Ki, nM)
5,600–>10,000 (Ki)
478–4,900
160–162 (rat)
13,000 (Ki)
150–420
47–108 (rat)
>26,000 (Ki)
890–20,500
106–190 (rat)
3,762–>10,000
>10,000
>10,000
>10,000
3,200–>10,000 (Ki)
630–1,767
57–99%
91–100 (Ki)
190–850
51–80%
3,000–6,418 (Ki)
98–4,800
79–118%
>10,000
>10,000
>10,000
3,548
8,700–>10,000
>10,000
1,100–2,600
690
229
>10,000
>10,000–>20,000
>10,000–>13,000
220–250 (Ki) (rat)
740 (rat)
86% (rat)
160–180 (Ki) (mouse)
580 (mouse)
102% (rat)
3,600 (human)
11% (human)
>10,000
Notes: The smaller the value, the more avidly the drug binds to the site. Proteins are human unless otherwise specified. Refs: [9] [10] [11] [12] [13] [14] [15] [16] [17] [18]

MDA is a substrate of the serotonin, norepinephrine, dopamine, and vesicular monoamine transporters, and in relation to this, acts as a reuptake inhibitor and releasing agent of serotonin, norepinephrine, and dopamine (that is, it is an).[19] It is also an agonist of the serotonin 5-HT2A,[20] 5-HT2B,[21] and 5-HT2C receptors[22] and shows affinity for the α2A-, α2B-, and α2C-adrenergic receptors and serotonin 5-HT1A and 5-HT7 receptors.[23]

The (S)-optical isomer of MDA is more potent than the (R)-optical isomer as a psychostimulant, possessing greater affinity for the three monoamine transporters.

In terms of the subjective and behavioral effects of MDA, it is thought that serotonin release is required for its empathogenic effects, dopamine release is required for its euphoriant (rewarding and addictive) effects, dopamine and norepinephrine release is required for its psychostimulant effects, and direct agonism of the serotonin 5-HT2A receptor is required for its mild psychedelic effects.

In addition to its actions as a monoamine releasing agent, MDA is a potent high-efficacy partial agonist or full agonist of the rodent TAAR1. Conversely, MDA is much weaker in terms of potency as an agonist of the human TAAR1.[24] Moreover, MDA acts as a very weak partial agonist or antagonist of the human TAAR1 rather than as an efficacious agonist. TAAR1 activation is thought to auto-inhibit and constrain the effects of amphetamines that act as TAAR1 agonists, for instance MDMA in rodents.[25] [26] [27] [28]

Activities of MDMA, its enantiomers, and related compounds
Compound Monoamine release (nM)
Dopamine
(S)-Amphetamine (d) 698–1,765 6.6–7.2 5.8–24.8
(R)-Amphetamine (l) 9.5 27.7
(S)-Methamphetamine (d) 736–1,292 12.3–13.8 8.5–24.5
(R)-Methamphetamine (l) 4,640 28.5 416
MDA 160 108 190
(S)-MDA (d) 100 50 98
(R)-MDA (l) 310 290 900
49.6–72 54.1–110 51.2–278
(S)-MDMA (d) 74 136 142
(R)-MDMA (l) 340 560 3,700
47 2,608 622
540 3,300 >100,000
114 117 1,334
Notes: The smaller the value, the more strongly the compound produces the effect. Refs: [29] [30] [31] [32] [33] [34] [35]

Pharmacokinetics

The pharmacokinetics of MDA have been studied.[36] Its duration of action has been reported to be about 6 to 8hours.[37] The duration of MDA is longer than that of MDMA, about 8hours for MDA versus 6hours for MDMA. The elimination half-life of MDA is 10.9hours. Differences in the duration of MDA versus MDMA may be due pharmacodynamics rather than pharmacokinetics.

Chemistry

MDA is a substituted methylenedioxylated phenethylamine and amphetamine derivative. In relation to other phenethylamines and amphetamines, it is the 3,4-methylenedioxy, α-methyl derivative of β-phenylethylamine, the 3,4-methylenedioxy derivative of amphetamine, and the N-desmethyl derivative of MDMA.

Synonyms

In addition to 3,4-methylenedioxyamphetamine, MDA is also known by other chemical synonyms such as the following:

Synthesis

MDA is typically synthesized from essential oils such as safrole or piperonal. Common approaches from these precursors include:

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.[48] [49] [50]

Derivatives

MDA constitutes part of the core structure of the β-adrenergic receptor agonist protokylol.

History

MDA was first synthesized by Carl Mannich and W. Jacobsohn in 1910. It was first ingested in July 1930 by Gordon Alles who later licensed the drug to Smith, Kline & French.[51] 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 five hundred 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. Harold Blauer died in January 1953 after being intravenously injected, without his knowledge or consent, with 450 mg of the drug as part of Project MKUltra. MDA was patented as an ataractic by Smith, Kline & French in 1960, and as an anorectic under the trade name "Amphedoxamine" in 1961. 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. Several researchers, including Claudio Naranjo and Richard Yensen, have explored MDA in the field of psychotherapy.[52] [53]

The International Nonproprietary Name (INN) tenamfetamine was recommended by the World Health Organization (WHO) in 1986.[54] It was recommended in the same published list in which the INN of 2,5-dimethoxy-4-bromoamphetamine (DOB), brolamfetamine, was recommended. These events suggest that MDA and DOB were under development as potential pharmaceutical drugs at the time.

Society and culture

Name

When MDA was under development as a potential pharmaceutical drug, it was given the International Nonproprietary Name (INN) of tenamfetamine.[55]

Legal status

Australia

MDA is schedule 9 prohibited substance under the Poisons Standards.[56] 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."

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".

A 2019 double-blind study administered both MDA and MDMA to healthy volunteers. The study found that MDA shared many properties with MDMA including entactogenic and stimulant effects, but generally lasted longer and produced greater increases in psychedelic-like effects like complex imagery, synesthesia, and spiritual experiences.[57]

Adverse effects

MDA can produce serotonergic neurotoxic effects in rodents,[58] [59] which might in part be due to transformation into MDA followed by subsequent metabolism. In addition, MDA activates a response of the neuroglia, though this subsides after use.

See also

External links

Notes and References

  1. Web site: Brazilian Health Regulatory Agency . 2023-07-24 . 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. live . https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 . 2023-08-27 . 2023-08-27 . . pt-BR . 2023-07-25.
  2. Crean RD, Davis SA, Von Huben SN, Lay CC, Katner SN, Taffe MA . Effects of (+/-)3,4-methylenedioxymethamphetamine, (+/-)3,4-methylenedioxyamphetamine and methamphetamine on temperature and activity in rhesus macaques . Neuroscience . 142 . 2 . 515–525 . October 2006 . 16876329 . 1853374 . 10.1016/j.neuroscience.2006.06.033 .
  3. de la Torre R, Farré M, Roset PN, Pizarro N, Abanades S, Segura M, Segura J, Camí J . 6 . Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition . Therapeutic Drug Monitoring . 26 . 2 . 137–144 . April 2004 . 15228154 . 10.1097/00007691-200404000-00009 .
  4. Web site: EcstasyData.org: Test Result Statistics: Substances by Year. EcstasyData.org . 2017-06-27.
  5. Web site: Trans European Drug Information. idpc.net. en. 2017-06-27. 4 November 2021. https://web.archive.org/web/20211104230649/https://idpc.net/profile/Trans-european-drug-information. dead.
  6. Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE . Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine . Journal of Medicinal Chemistry . 36 . 23 . 3700–3706 . November 1993 . 8246240 . 10.1021/jm00075a027 .
  7. Baggott MJ, Siegrist J, Coyle JR, Flower K, Galloway G, Mendelson J . Poster Session III (PIII 1-84): PIII-09 Pharmacodynamic Effects of 3,4-Methylenedioxyamphetamine (MDA) . Clinical Pharmacology & Therapeutics . 87 . Suppl 1 . 2010 . 0009-9236 . 10.1038/clpt.2009.277 . S68–S95 (S70) . In a placebo-controlled, double-blind, within-subjects study, 12 individuals received a single 98 mg/70 kg bw dose of MDA. This is the molar equivalent of 105 mg/ 70 kg bw MDMA, a well-studied dose. [...] MDA increased cortisol by 16.39 ug/dL (95%CI: 13.03-19.74, P < 1e-3) and prolactin by 18.37 ng/mL (95%CI: 7.39-29.35, P < 1e-3). These hormonal changes are comparable to those seen after MDMA. Heart rate increased by 9.05 bpm (95%CI: 6.10-11.99, P < 1e-5) and blood pressure increased by 18.98 / 12.73 mm Hg (Systolic 95%CI: 16.47 - 21.49, P < 1e-7; Diastolic 95%CI: 10.82 - 14.63, P < 1e-4). [...] There were robust self-report VAS changes in both MDMA-like (e.g., “closeness to others”) and hallucinogen-like (e.g., “familiar things seem unfamiliar”, time distortions, closed-eye visuals) effects that were generally similar to those seen after MDMA. [...] MDA is a psychoactive sympathomimetic phenethylamine with effects similar to MDMA. Although differences may exist in the magnitude of physiological effects, the overall profiles appear remarkably similar. .
  8. Book: Diaz J. How Drugs Influence Behavior . Englewood Cliffs . Prentice Hall . 1996 .
  9. Web site: PDSP Database . UNC . zu . 13 December 2024.
  10. Web site: Liu T . BindingDB BDBM50005247 (+/-)2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine::(-)2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine::(R)-(-)-2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine::(S)-(+)-2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine::2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine::2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine((R)-(-)-MDA)::3,4-methylenedioxyamphetamine::CHEMBL6731::MDA::MDA, (R,S)::MDA,R(-)::Tenamfetamine::methylenedioxyamphetamine ]. BindingDB . 13 December 2024.
  11. Ray TS . Psychedelics and the human receptorome . PLOS ONE . 5 . 2 . e9019 . February 2010 . 20126400 . 2814854 . 10.1371/journal.pone.0009019 . free . 2010PLoSO...5.9019R .
  12. Luethi D, Kolaczynska KE, Walter M, Suzuki M, Rice KC, Blough BE, Hoener MC, Baumann MH, Liechti ME . Metabolites of the ring-substituted stimulants MDMA, methylone and MDPV differentially affect human monoaminergic systems . J Psychopharmacol . 33 . 7 . 831–841 . July 2019 . 31038382 . 8269116 . 10.1177/0269881119844185 .
  13. Kolaczynska KE, Ducret P, Trachsel D, Hoener MC, Liechti ME, Luethi D . Pharmacological characterization of 3,4-methylenedioxyamphetamine (MDA) analogs and two amphetamine-based compounds: N,α-DEPEA and DPIA . Eur Neuropsychopharmacol . 59 . 9–22 . June 2022 . 35378384 . 10.1016/j.euroneuro.2022.03.006 . free .
  14. Rickli A, Kopf S, Hoener MC, Liechti ME . Pharmacological profile of novel psychoactive benzofurans . Br J Pharmacol . 172 . 13 . 3412–3425 . July 2015 . 25765500 . 4500375 . 10.1111/bph.13128 .
  15. Setola V, Hufeisen SJ, Grande-Allen KJ, Vesely I, Glennon RA, Blough B, Rothman RB, Roth BL . 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") induces fenfluramine-like proliferative actions on human cardiac valvular interstitial cells in vitro . Mol Pharmacol . 63 . 6 . 1223–1229 . June 2003 . 12761331 . 10.1124/mol.63.6.1223 .
  16. Brandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH . The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats . Psychopharmacology (Berl) . 237 . 12 . 3703–3714 . December 2020 . 32875347 . 7686291 . 10.1007/s00213-020-05648-z .
  17. Gainetdinov RR, Hoener MC, Berry MD . Trace Amines and Their Receptors . Pharmacol Rev . 70 . 3 . 549–620 . July 2018 . 29941461 . 10.1124/pr.117.015305 . free .
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  24. Lewin AH, Miller GM, Gilmour B . Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class . Bioorganic & Medicinal Chemistry . 19 . 23 . 7044–7048 . December 2011 . 22037049 . 3236098 . 10.1016/j.bmc.2011.10.007 .
  25. Book: Espinoza S, Gainetdinov RR . Taste and Smell . Neuronal Functions and Emerging Pharmacology of TAAR1 . Springer International Publishing . Cham . 23 . 2014 . 978-3-319-48925-4 . 10.1007/7355_2014_78 . 175–194 . Interestingly, the concentrations of amphetamine found to be necessary to activate TAAR1 are in line with what was found in drug abusers [3, 51, 52]. Thus, it is likely that some of the effects produced by amphetamines could be mediated by TAAR1. Indeed, in a study in mice, MDMA effects were found to be mediated in part by TAAR1, in a sense that MDMA auto-inhibits its neurochemical and functional actions [46]. Based on this and other studies (see other section), it has been suggested that TAAR1 could play a role in reward mechanisms and that amphetamine activity on TAAR1 counteracts their known behavioral and neurochemical effects mediated via dopamine neurotransmission. .
  26. Kuropka P, Zawadzki M, Szpot P . A narrative review of the neuropharmacology of synthetic cathinones-Popular alternatives to classical drugs of abuse . Hum Psychopharmacol . 38 . 3 . e2866 . May 2023 . 36866677 . 10.1002/hup.2866 . Another feature that distinguishes [synthetic cathinones (SCs)] from amphetamines is their negligible interaction with the trace amine associated receptor 1 (TAAR1). Activation of this receptor reduces the activity of dopaminergic neurones, thereby reducing psychostimulatory effects and addictive potential (Miller, 2011; Simmler et al., 2016). Amphetamines are potent agonists of this receptor, making them likely to self‐inhibit their stimulating effects. In contrast, SCs show negligible activity towards TAAR1 (Kolaczynska et al., 2021; Rickli et al., 2015; Simmler et al., 2014, 2016). [...] It is worth noting, however, that for TAAR1 there is considerable species variability in its interaction with ligands, and it is possible that the in vitro activity of [rodent TAAR1 agonists] may not translate into activity in the human body (Simmler et al., 2016). The lack of self‐regulation by TAAR1 may partly explain the higher addictive potential of SCs compared to amphetamines (Miller, 2011; Simmler et al., 2013). .
  27. Simmler LD, Buser TA, Donzelli M, Schramm Y, Dieu LH, Huwyler J, Chaboz S, Hoener MC, Liechti ME . Pharmacological characterization of designer cathinones in vitro . Br J Pharmacol . 168 . 2 . 458–470 . January 2013 . 22897747 . 3572571 . 10.1111/j.1476-5381.2012.02145.x . β-Keto-analogue cathinones also exhibited approximately 10-fold lower affinity for the TA1 receptor compared with their respective non-β-keto amphetamines. [...] Activation of TA1 receptors negatively modulates dopaminergic neurotransmission. Importantly, methamphetamine decreased DAT surface expression via a TA1 receptor-mediated mechanism and thereby reduced the presence of its own pharmacological target (Xie and Miller, 2009). MDMA and amphetamine have been shown to produce enhanced DA and 5-HT release and locomotor activity in TA1 receptor knockout mice compared with wild-type mice (Lindemann et al., 2008; Di Cara et al., 2011). Because methamphetamine and MDMA auto-inhibit their neurochemical and functional effects via TA1 receptors, low affinity for these receptors may result in stronger effects on monoamine systems by cathinones compared with the classic amphetamines. .
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  32. Marusich JA, Antonazzo KR, Blough BE, Brandt SD, Kavanagh PV, Partilla JS, Baumann MH . The new psychoactive substances 5-(2-aminopropyl)indole (5-IT) and 6-(2-aminopropyl)indole (6-IT) interact with monoamine transporters in brain tissue . Neuropharmacology . 101 . 68–75 . February 2016 . 26362361 . 4681602 . 10.1016/j.neuropharm.2015.09.004 .
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  36. Baggott MJ, Li L, Galloway GP, Scheidweiler KB, Barnes AJ, Huestis MA, Mendelson J . Poster Session III (PIII 1-110): PIII-110: Pharmacokinetics of Oral 3,4-Methylenedioxyamphetamine in Humans . Clinical Pharmacology & Therapeutics . 91 . Suppl 1 . 2012 . 0009-9236 . 10.1038/clpt.2011.363 . S96–S135 . Knowledge of MDA and HMA kinetics in humans is limited to data from MDMA administration studies where minimal formation of these compounds likely leads to inaccurate parameter estimation. We administered a single [98 mg/70 kg body weight] oral dose of MDA to participants in a controlled setting to characterize plasma MDA pharmacokinetics for the first time. [...] Cmax and AUC0-∞ for MDA were 229 ± 39 ng/mL (mean ± SD) and 3636 ± 958 for MDA and 92 ± 61 ng/mL and 1544 ± 741 for the metabolite HMA. Total MDA clearance was 30267 ± 8214 mL/min. There was considerable between-subject variation in metabolite exposure: HMA Cmax and AUC varied over 7-fold and 4-fold, respectively, between the highest and lowest individuals. [...] Pharmacokinetics of MDA resemble those of an iso-molar dose of MDMA, suggesting differences in duration of acute effects between MDA and MDMA are not due to kinetic differences. .
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