2,5-Dimethoxyamphetamine

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2,5-Dimethoxyamphetamine (2,5-DMA), also known as DMA-4 or as DOH, is a drug of the phenethylamine and amphetamine families.[1][2] It is one of the dimethoxyamphetamine (DMA) series of positional isomers.[1][2] The drug is notable in being the parent compound of the DOx (4-substituted-2,5-dimethoxyamphetamine) series of drugs.[1][2]

Use and effects

2,5-DMA is said to be inactive as a psychedelic, at least at the doses that have been assessed.[1][2] However, it has been reported to produce some stimulant-like effects, as well as sympathomimetic effects and mydriasis.[1][2] The dose range is said to be 80 to 160Script error: No such module "String".mg orally and its duration is 6 to 8Script error: No such module "String".hours.[1][2]

Pharmacology

2,5-DMA activities
Target Affinity (Ki, nM)
5-HT1A 2,583
5-HT1B 8,435 (rat)
5-HT1D ND
5-HT1E ND
5-HT1F ND
5-HT2A 211–5,200 (Ki)
160–3,548 (EC50Tooltip half-maximal effective concentration)
58–109% (EmaxTooltip maximal efficacy)
5-HT2B 1,039 (Ki)
3,390–>10,000 (EC50)
93% (Emax)
5-HT2C 104–>10,000 (Ki)
3,144 (EC50)
76% (Emax)
5-HT3 ND
5-HT4 ND
5-HT5A ND
5-HT6 ND
5-HT7 ND
α1A–α1D ND
α2A–α2C ND
β1, β2 ND
D1 ND
D2 >7,000
D3–D5 ND
H1–H4 ND
M1–M5 ND
TAAR1 >10,000 (EC50) (human)
I1 ND
σ1, σ2 ND
SERTTooltip Serotonin transporter >7,000 (Ki)
ND (IC50Tooltip half-maximal inhibitory concentration)
ND (EC50)
NETTooltip Norepinephrine transporter >7,000 (Ki)
ND (IC50)
ND (EC50)
DATTooltip Dopamine transporter >7,000 (Ki)
ND (IC50)
ND (EC50)
MAO-ATooltip Monoamine oxidase A >100,000 (IC50)
MAO-BTooltip Monoamine oxidase B >100,000 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [3][4][5][6][7][8]
[9][10][11][12][13][14]

2,5-DMA is a low-potency serotonin 5-HT2A receptor partial agonist, with an affinity (Ki) of 2,502Script error: No such module "String".nM, an EC50Tooltip half-maximal effective concentration of 160 to 3,548Script error: No such module "String".nM (depending on the signaling cascade and study), and an EmaxTooltip maximal efficacy of 66 to 109%.[6][7][10][11] It has also been assessed at several other receptors.[6][7] In a much earlier study, its affinities (Ki) were 1,020Script error: No such module "String".nM at the serotonin 5-HT1 receptor and 5,200Script error: No such module "String".nM at the serotonin 5-HT2 receptor.[15][16] The drug does not appear to bind to the monoamine transporters, at least at the assessed concentrations (up to 7,000Script error: No such module "String".nM).[6][7] It was inactive at the human trace amine-associated receptor 1 (TAAR1).[6][7] 2,5-DMA shows dramatically reduced potency as a serotonin 5-HT2A receptor agonist compared to the DOx drugs, such as 2,5-dimethoxy-4-methylamphetamine (DOM).[6][7]

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.[17] It also substitutes for 5-MeO-DMT in rodent drug discrimination tests.[18] Conversely, 2,5-DMA shows no substitution for dextroamphetamine in such tests, suggesting that it lacks psychostimulant- or amphetamine-like effects, at least in rodents.[17]

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.[11][19] This was in spite of it being of very low potency as a serotonin 5-HT2A receptor agonist in terms of calcium mobilization in the study (EC50 = 3,548Script error: No such module "String".nM; Emax = 109.0%).[11] 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.[19]

Manufacturing

2,5-DMA is used by Polaroid Corporation in the manufacturing of Polaroid film.[20][21]

See also

References

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  1. ↑ a b c d e f Script error: No such module "citation/CS1".
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  6. ↑ a b c d e f Script error: No such module "Citation/CS1".
  7. ↑ a b c d e f Script error: No such module "Citation/CS1".
  8. ↑ Script error: No such module "Citation/CS1".
  9. ↑ Script error: No such module "Citation/CS1".
  10. ↑ a b Script error: No such module "Citation/CS1".
  11. ↑ a b c d Script error: No such module "Citation/CS1".
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  13. ↑ Script error: No such module "Citation/CS1".
  14. ↑ Script error: No such module "Citation/CS1".
  15. ↑ Script error: No such module "Citation/CS1".
  16. ↑ Script error: No such module "Citation/CS1".
  17. ↑ a b Script error: No such module "Citation/CS1".
  18. ↑ Script error: No such module "Citation/CS1".
  19. ↑ a b Script error: No such module "citation/CS1".
  20. ↑ Script error: No such module "citation/CS1".
  21. ↑ Script error: No such module "citation/CS1".

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External links

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