MDA
1-(1,3-benzodioxol-5-yl)propan-2-amine
Overview
MDA belongs to Entactogens/Empathogens / Phenethylamines.
Effects
- Euphoria, emotional warmth, empathy and closeness, increased introspection and self-acceptance, and stimulation/increased energy. MDA tends to feel more introspective and emotionally intense, and more psychedelic, than the more social, extroverted MDMA.
- At higher doses perceptual changes are common: brightened colours, closed-eye imagery, occasional mild visuals and, rarely, mild hallucinations, without the full sensory disruption of a classical psychedelic.
- Unwanted effects include jaw clenching and teeth grinding, dilated pupils, raised heart rate and temperature, anxiety or fear, insomnia, and a multi-day 'comedown' of low mood, irritability and fatigue as serotonin recovers.
Dosing & duration
Oral (the common route). The values below are for oral use. These are commonly cited recreational reference ranges (PsychonautWiki), not a safe dose. MDA is longer-acting and more stimulating and psychedelic than MDMA, and redosing worsens the neurotoxic and comedown burden: avoid it. Do not combine with MAOIs or other serotonergic drugs (serotonin-syndrome risk). Keep cool and take breaks to avoid overheating. Sip rather than gulp water, and remember that powders sold as 'MDA'/'sass' are often mis-sold or adulterated, so test the substance.
Dose ranges
20 mg
40–60 mg
60–100 mg
100–145 mg
145 mg +
Duration
30–90 min
5–8 h
4–48 h comedown (low mood, fatigue, anxiety)
Chemical & Physical Properties
| Formula | C10H13NO2 |
| Molar mass | 179.22 g/mol |
| State | Liquid |
| Melting point | Not reported |
| Boiling point | 157 °C at 22 mmHg, 80–90 °C at 0.2 mmHg |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | 9.67 (25 °C) |
| LogP | 1.64 |
| Solubility | Not reported |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 4764-17-4 |
| CAS (enantiomer) | |
| PubChem CID | 1614 |
| InChIKey | NGBBVGZWCFBOGO-UHFFFAOYSA-N |
| InChI | InChI=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 |
| SMILES | CC(CC1=CC2=C(C=C1)OCO2)N |
Synonyms
- 3,4-Methylenedioxyamphetamine
- Tenamfetamine
- Sass
- Love drug
- Sally
- Sassafras
Pharmacodynamics & Biochemistry
MDA (3,4-methylenedioxyamphetamine) is an entactogen with mixed stimulant and psychedelic character, and is also the primary active metabolite of MDMA (MDMA is its N-methyl homologue). Like MDMA it acts mainly as a monoamine releaser: it is carried into the nerve terminal as a substrate by the serotonin (SERT), noradrenaline (NET) and dopamine (DAT) transporters, where it disrupts vesicular storage via VMAT2 and reverses transporter flow, driving serotonin, noradrenaline and dopamine out into the synapse rather than merely blocking their reuptake. Reported release potencies are fairly balanced across the three transporters (EC50 on the order of ~110–190 nM), so it produces both serotonergic entactogenic and catecholaminergic stimulant effects. It also has direct agonist activity at 5-HT2A (and 5-HT2B/2C) receptors, more so than MDMA, and this stronger direct serotonergic-receptor action is thought to give MDA its greater psychedelic/hallucinogenic quality (brightened colours, imagery, occasional mild visuals) layered on top of the empathogenic effects. The two enantiomers differ: R-(−)-MDA carries most of the psychedelic, LSD-like character, whereas S-(+)-MDA is the more potent transporter substrate and drives the stimulant and entactogenic effects. MDA is normally used as the racemate.
Biological targets
- SERT
- DAT
- NET
- 5-HT2A
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| Dopamine transporter | EC50 106 ± 7.0 nM Emax 104% | Rat |
| Noradrenaline transporter | EC50 47 ± 7.0 nM Emax 91% | Rat |
| Serotonin transporter | EC50 162 ± 28 nM Emax 109% | Rat |
Pharmacokinetics
| Bioavailability | Oral, well absorbed |
| Tmax | ≈1–2 h |
| Half-life | ≈6–8 h |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Hepatic CYP2D6 demethylenation. Also a metabolite of MDMA |
| Excretion | Renal |
Toxicology & Safety
140 mg/kg (mouse, i.p.)
MDA carries the same core risks as MDMA, generally at a longer duration and with a more dopaminergic, more hallucinogenic character. The main acute dangers are serotonergic and thermal: dangerous overheating (hyperthermia), especially when dancing in a hot, crowded space, and serotonin syndrome when combined with other serotonergic drugs: MAOIs are especially dangerous and the combination can be fatal. It raises heart rate, blood pressure and body temperature and strains the cardiovascular system. Deaths are usually from cardiovascular collapse or hyperthermia and its complications. As with MDMA, high or repeated doses are linked to serotonergic neurotoxicity in animals, and heavy use is followed by a serotonin-depletion 'comedown' of low mood, anxiety and fatigue lasting days. MDA tends to produce more anxiety, fear and stimulation than MDMA. Drinking too much water while unable to excrete it can cause dangerous hyponatraemia (low blood sodium). It should not be combined with MAOIs, other stimulants, or other serotonergic drugs, and material sold as 'MDA' or 'sass' is frequently mis-sold or adulterated.[5][2]
Legal Status
US: Schedule I. UK: Class A. DE: BtMG Anlage I
Interactions & Contraindications
Drug interactions
Contraindications
No interactions or contraindications listed.
Usage & Context
- A recreational entactogen/psychedelic ('Sass', 'Sally', and sometimes sold as or alongside 'sassafras'), used for euphoria, empathy, emotional openness and mild psychedelic effects: mainly in dance, festival and psychonaut settings.
- It is also the primary active metabolite of MDMA, so part of MDMA's effect and harm profile reflects MDA exposure.
- It has no accepted medical use and is a Schedule I / Class A / Anlage I controlled substance. It was studied in mid-20th-century research (including unethical secret experiments) before being prohibited.
Sources & Evidence
- PubChem: 3,4-MDA (CID 1614) — identifiers & computed properties
- de la Torre R, Farré M, Navarro M, et al. (2004). Clinical pharmacokinetics of amfetamine and related substances: monitoring in conventional and non-conventional matrices. Clin Pharmacokinet 43:157-85.
PMID 14871155 · doi:10.2165/00003088-200443030-00002
- Johnson MP, Hoffman AJ, Nichols DE (1986). Effects of the enantiomers of MDA, MDMA and related analogues on [3H]serotonin and [3H]dopamine release from superfused rat brain slices. Eur J Pharmacol 132:269-76.
PMID 2880735 · doi:10.1016/0014-2999(86)90615-1
- Nash JF, Roth BL, Brodkin JD, et al. (1994). Effect of the R(-) and S(+) isomers of MDA and MDMA on phosphatidyl inositol turnover in cultured cells expressing 5-HT2A or 5-HT2C receptors. Neurosci Lett 177:111-5.
PMID 7824160 · doi:10.1016/0304-3940(94)90057-4
- Wikipedia: 3,4-Methylenedioxyamphetamine (MDA) — pharmacology (monoamine release & 5-HT2 agonism), enantiomers, effects & legal status CC BY-SA 4.0
- PsychonautWiki: MDA — recreational dosage, duration & subjective effects CC BY-SA 4.0
- DEA Diversion Control Division: Controlled Substance Schedules (MDA is Schedule I)
- GOV.UK: Controlled drugs list — MDA is Class A (Misuse of Drugs Act 1971) OGL v3.0
- Anlage I BtMG — Betäubungsmittelgesetz (Gesetze im Internet): MDA (Tenamfetamin) ist nicht verkehrsfähig
- Brandt SD, Walters HM, Partilla JS, et al. (2020). 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) 237:3703-3714.
PMID 32875347 · doi:10.1007/s00213-020-05648-z