2,5-Dimethoxyamphetamine (2,5-DMA), also known as DMA-4 or as DOH, is a

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

of the

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace ami ...

and

amphetamine Amphetamine (contracted from Alpha and beta carbon, alpha-methylphenethylamine, methylphenethylamine) is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, an ...

families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers. The drug is notable in being the parent compound of the DOx (4-substituted-2,5-dimethoxyamphetamine) series of drugs.

Use and effects

2,5-DMA is said to be inactive as a psychedelic, at least at the doses that have been assessed. However, it has been reported to produce some

stimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, ...

-like effects, as well as sympathomimetic effects and

mydriasis Mydriasis is the Pupillary dilation, dilation of the pupil, usually having a non-physiological cause, or sometimes a physiological pupillary response. Non-physiological causes of mydriasis include disease, Physical trauma, trauma, or the use of c ...

. The dose range is said to be 80 to 160mg orally and its duration is 6 to 8hours.

Pharmacology

2,5-DMA is a low- potency

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT_2A receptor

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...

, with an

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

(K_i) of 2,502nM, an of 160 to 3,548nM (depending on the signaling cascade and study), and an of 66 to 109%. It has also been assessed at several other

receptor Receptor may refer to: * Sensory receptor, in physiology, any neurite structure that, on receiving environmental stimuli, produces an informative nerve impulse *Receptor (biochemistry), in biochemistry, a protein molecule that receives and respond ...

s. In a much earlier study, its affinities (K_i) were 1,020nM at the serotonin 5-HT₁ receptor and 5,200nM at the serotonin 5-HT₂ receptor. The drug does not appear to bind to the

monoamine transporter Monoamine transporters (MATs) are proteins that function as integral Cell membrane, plasma-membrane Neurotransmitter transporter, transporters to regulate concentrations of extracellular monoamine neurotransmitters. The three major classes are se ...

s, at least at the assessed concentrations (up to 7,000nM). It was inactive at the human

trace amine-associated receptor 1 Trace amine-associated receptor 1 (TAAR1) is a trace amine-associated receptor (TAAR) protein that in humans is encoded by the ''TAAR1'' gene. TAAR1 is a primarily intracellular amine-activated and G protein-coupled receptor (GPCR) that is p ...

(TAAR1). 2,5-DMA shows dramatically reduced potency as a serotonin 5-HT_2A receptor agonist compared to the DOx drugs, such as

2,5-dimethoxy-4-methylamphetamine 2,5-Dimethoxy-4-methylamphetamine (DOM), also known as STP (standing for "Serenity, Tranquility, and Peace" and/or other phrases), is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is generally taken orally. DOM w ...

(DOM). 2,5-DMA substitutes for DOM in rodent drug discrimination tests, albeit with dramatically lower potency than other DOx drugs, suggesting that it may have psychedelic-like effects at very high doses. Conversely, 2,5-DMA shows no substitution for

dextroamphetamine Dextroamphetamine (international nonproprietary name, INN: dexamfetamine) is a potent central nervous system (CNS) stimulant and enantiomer of amphetamine that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narc ...

in such tests, suggesting that it lacks

psychostimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition ...

- or

-like effects, at least in rodents. Though 2,5-DMA appears to be inactive or of very low potency as a psychedelic in humans, it is a highly potent anti-inflammatory drug similarly to other DOx and 2C drugs. This was in spite of it being of very low potency as a serotonin 5-HT_2A receptor agonist in terms of

calcium Calcium is a chemical element; it has symbol Ca and atomic number 20. As an alkaline earth metal, calcium is a reactive metal that forms a dark oxide-nitride layer when exposed to air. Its physical and chemical properties are most similar to it ...

mobilization in the study ( = 3,548nM; = 109.0%). Based on the preceding findings, Charles D. Nichols has said that both fully anti-inflammatory non-psychedelic compounds like 2,5-DMA and fully psychedelic non-anti-inflammatory compounds like DOTFM are known.

Manufacturing

2,5-DMA is used by

Polaroid Corporation Polaroid Corporation was an American company that made instant film and cameras, which survives as a brand for consumer electronics. The company was founded in 1937 by Edwin H. Land, to exploit his Polaroid (polarizer), Polaroid polarizing polyme ...

in the

manufacturing Manufacturing is the creation or production of goods with the help of equipment, labor, machines, tools, and chemical or biological processing or formulation. It is the essence of the secondary sector of the economy. The term may refer ...

of Polaroid film.

References

External links

2,5-DMA - PiHKAL - Erowid

2,5-DMA - PiHKAL - Isomer Design
{{DEFAULTSORT:Dimethoxyamphetamine, 2,5- 5-HT2A agonists 5-HT2B agonists 5-HT2C agonists DOx (psychedelics) Serotonin receptor agonists

Use and effects

Pharmacology

Manufacturing

See also

References

External links