2,5-DMA
| Summary sheet: 2,5-DMA |
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| Chemical Nomenclature | |||||||||||||||||||||||
| Common names | 2,5-DMA, DOH | ||||||||||||||||||||||
| Substitutive name | 2,5-Dimethoxyamphetamine | ||||||||||||||||||||||
| Systematic name | 1-(2,5-dimethoxyphenyl)propan-2-amine | ||||||||||||||||||||||
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| Psychoactive class | Stimulant / Psychedelic | ||||||||||||||||||||||
| Chemical class | Amphetamine | ||||||||||||||||||||||
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| Tramadol | |||||||||||||||||||||||
| Lithium | |||||||||||||||||||||||
2,5-Dimethoxyamphetamine (also known as 2,5-DMA, unformally as simply DMA, and unofficially as DOH) is a lesser-known psychoactive substance of the amphetamine class. 2,5-DMA belongs to the DOx family of substituted amphetamines.
However, it reportedly does not have noteable psychedelic properties and is primarily used as a precursor in the synthesis of other psychedelic amphetamines such as DOB, DOI and DON.
2,5-DMA was first synthesized in Tuckahoe, New York by Richard Baltzly and Johannes S. Buck in 1939.[1] Its effects in humans were explored in the by Alexander Shulgin, who published his findings in the book PiHKAL (Phenethylamines I Have Known and Loved).
In PiHKAL, Shulgin commented that 2,5-DMA "appeared to be totally a physical trip with tremors and some cardiovascular push and nothing of a sensory nature", while other reports note pleasant intoxication along with enhanced interest in one’s surroundings, no perceptual changes, no overt stimulation, and no major gross physiological effects. High dosages were reported to be considerably stimulating albeit with no sensory effects.
It may or may not be more active when taken sublingually.[citation needed]. However, it is unknown whether this would result in typical psychedelic effects. Unlike its phenethylamine counterpart, 2C-H, it does not appear to be inactive. It should therefore not be tried in combination with a MAOI.
Very little data exists about the pharmacological properties, metabolism, and toxicity of 2,5-DMA. It is highly advised to use harm reduction practices when using this substance.
Chemistry
2,5-DMA, or 2,5-dimethoxyamphetamine, is a substituted phenethylamine and amphetamine featuring a phenyl ring bound to an amino (NH2) group through an ethyl chain along with a methyl group at the alpha carbon. 2,5-DMA contains methoxy functional groups CH3O- attached to carbons R2 and R5 as well as a hydrogen atom attached to carbon R4 of the phenyl ring.
2,5-DMA belongs to the DOx family of amphetamines, which contain methoxy groups on the 2 and 5 positions of the benzene ring, and is also their simplest member. It is commonly used as a precursor to other compounds of the DOx family, including DOB, DOI and DON.
Pharmacology
There is no record of 2,5-DMA trials in humans and very little data exists about the pharmacological properties, metabolism, and toxicity of 2,5-DMA.
Subjective effects
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This subjective effects section is a stub. As such, it is still in progress and may contain incomplete or wrong information. You can help by expanding or correcting it. |
2,5-DMA appears to be primarily stimulating in its effects rather than being a psychedelic. It does not seem to have noteable sensory enhancement effects.
Physical effects 
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- Stimulation - 2,5-DMA can occasionally produce notable stimulation proportional to its dosage. However, some reports suggest little stimulation at the same dosages.
- Spontaneous physical sensations 2,5-DMA has been reported to produce a mild to moderate body load
- Increased heart rate
- Increased blood pressure
- Muscle tension
- Temperature regulation suppression
- Pupil dilation
- Increased perspiration
Visual effects 
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- Color enhancement - This effect is debated.
Experience reports
There are currently no anecdotal reports which describe the effects of this compound within our experience index.
Toxicity and harm potential
The toxicity and long-term health effects of recreational 2,5-DMA use do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because 2,5-DMA is a research chemical with very little history of human usage.
Anecdotal reports from those who have tried 2,5-DMA suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.
It is strongly recommended that one use harm reduction practices, such as volumetric dosing, when using this substance so as to ensure the accurate administration of the intended dose.
Tolerance and addiction potential
Although no formal studies have been conducted, it is not unreasonable to assume that as is the case with psychedelics in general, 2,5-DMA is not habit-forming and that the desire to use it can actually decrease with use. However, it's stimulating properties do provide a possible risk of addiction which would be associated with other stimulants.
Tolerance to the effects of 2,5-DMA is built after ingestion over the couse of multiple days. After that, it takes about 3-5 days for the tolerance to be reduced to half and 7-10 days to be back at baseline (in the absence of further consumption). 2,5-DMA may present cross-tolerance, although unlikely, with all psychedelics, meaning that after the consumption of 2,5-DMA all psychedelics will have a reduced effect. It may also produce tolerance to stimulants as well.
Dangerous interactions
Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
- Lithium - Lithium is commonly prescribed for the treatment of bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.
- Cannabis - Cannabis may have an unexpectedly strong and unpredictable synergy with the effects of 2,5-DMA. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid unintentional overdose.
- Stimulants - Stimulants like amphetamine, cocaine or methylphenidate affect many parts of the brain and alter dopaminergic function. This combination can increase the risk of anxiety, paranoia, panic attacks, and thought loops. This interaction may also result in an elevated risk of mania and psychosis.[citation needed]
- Tramadol - Tramadol is well-documented to lower the seizure threshold[2] and psychedelics may act to trigger seizures in susceptible individuals.[citation needed]
Legal status
- Germany: 2,5-DMA is controlled under the NpSG[citation needed] (New Psychoactive Substances Act) as of November 26, 2016.[3] Production and import with the aim to place it on the market, administration to another person, placing it on the market and trading is punishable. Possession is illegal but not punishable.[4][5] The legislator considers it possible that orders of 2C-H are punishable as an incitement to place it on the market.[6]
- Switzerland: 2,5-DMA can be considered a controlled substance as a defined derivative of Phenethylamine under Verzeichnis E point 130. It is legal when used for scientific or industrial use.[7]
- United Kingdom: 2,5-DMA is a Class A drug in the United Kingdom as a result of the phenethylamine catch-all clause.[8]
- United States: 2,5-DMA could be considered an analog of 2C-H or amphetamine, which could make it illegal under the Federal Analog Act.[citation needed]
See also
External links
- Dimethoxyamphetamine (including 2,5-DMA) (Wikipedia)
- 2,5-DMA (PiHKAL)
- 2,5-DMA (PiHKAL / Isomer Design)
References
- ↑ Baltzly, R., Buck, J. S. (January 1940). "Amines Related to 2,5-Dimethoxyphenethylamine. 1 I". Journal of the American Chemical Society. 62 (1): 161–164. doi:10.1021/ja01858a046. ISSN 0002-7863.
- ↑ Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. doi:10.1007/BF03161089. ISSN 1556-9039.
- ↑ "Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF). Bundesgesetzblatt Jahrgang 2016 Teil I Nr. 55 (in German). Bundesanzeiger Verlag (published November 25, 2016). November 21, 2016. pp. 2615–2622. ISSN 0341-1095. OCLC 1004462279.
- ↑ "§ 4 NpSG" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019.
- ↑ "§ 3 NpSG" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019.
- ↑ "Gesetzentwurf der Bundesregierung: Entwurf eines Gesetzes zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF) (in German). Deutscher Bundestag. May 30, 2016. p. 20. Drucksache 18/8579.
- ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.
- ↑ "Schedule 2: Part I: Class A Drugs". "Misuse of Drugs Act 1971". UK Government. Retrieved August 20, 2020.