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2,5-Dimethoxyamphetamine
Pharmaceutical compound From Wikipedia, the free encyclopedia
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2,5-Dimethoxyamphetamine (2,5-DMA), also known as DMA-4 or as DOH, is a psychoactive 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 psychedelic drugs.[1][2] It is taken orally.[1][2][3]
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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][3] The dose range is said to be 80 to 160 mg orally and its duration is 6 to 8 hours.[1][2] However, it has also been said to be active with stimulant-like effects at a dose of 50 mg.[3]
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Pharmacology
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Pharmacodynamics
2,5-DMA is a low-potency serotonin 5-HT2A receptor partial agonist, with an affinity (Ki) of 2,502 nM, an EC50 of 160 to 3,548 nM (depending on the signaling cascade and study), and an Emax of 66 to 109%.[8][9][12][13] It has also been assessed at several other receptors.[8][9] In a much earlier study, its affinities (Ki) were 1,020 nM at the serotonin 5-HT1 receptor and 5,200 nM at the serotonin 5-HT2 receptor.[17][18] The drug does not appear to bind to the monoamine transporters, at least at the assessed concentrations (up to 7,000 nM).[8][9] It was inactive at the human trace amine-associated receptor 1 (TAAR1).[8][9] 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).[8][9]
2,5-DMA produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[7] However, it produces a very weak head-twitch response compared to other structurally related psychedelics like DOM, DOET, DOPR, and even DOBU.[7] In addition, it is less potent in comparison.[7] 2,5-DMA substitutes for DOM in rodent drug discrimination tests, albeit with dramatically lower potency than other DOx drugs.[19] It also substitutes for 5-MeO-DMT in rodent drug discrimination tests.[20] These findings suggesting that 2,5-DMA might produce weak hallucinogenic effects at sufficiently high doses.[7][19][20] 2,5-DMA shows no substitution for dextroamphetamine in drug discrimination tests, suggesting that it lacks psychostimulant- or amphetamine-like effects, at least in rodents.[19] Unlike other DOx drugs like DOM, DOPR, DOBU, and DOAM, 2,5-DMA does not produce hyperlocomotion in rodents and instead dose-dependently produces only hypolocomotion.[7] On the other hand, it does similarly produce hypothermia at higher doses.[7]
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.[13][21] 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 = 3,548 nM; Emax = 109.0%).[13] 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.[21]
Pharmacokinetics
2,5-DMA crosses the blood–brain barrier in rodents.[7] It showed the lowest brain/plasma ratio among DOM and its higher homologues.[7]
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Chemistry
Synthesis
The chemical synthesis of 2,5-DMA has been described.[1][2][22]
Analogues and derivatives
Analogues and derivatives of 2,5-DMA include the DOx series like DOM, DOB, and DOI, FLY compounds like DOB-FLY, Bromo-DragonFLY (DOB-DFLY), DOH-5-hemiFLY, 25-NB compounds like DOM-NBOMe, DOB-NBOMe, and DOI-NBOMe, and other compounds like trimethoxyamphetamines (TMAs) and pentamethoxyamphetamine (PeMA).[1][2]
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History
2,5-DMA was first described in the scientific literature by F. Benington and colleagues by at least 1968.[23][24] Subsequently, it was described in greater detail by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1]
Society and culture
Manufacturing
2,5-DMA is used by Polaroid Corporation in the manufacturing of Polaroid film.[3][25][26]
See also
- Dimethoxyamphetamine
- Substituted methoxyphenethylamine
- DOx (psychedelics)
- Stimulant § Serotonin 5-HT2A receptor agonists
- Motivation-enhancing drug § Serotonin 5-HT2A receptor agonists
- 2,5-Dimethoxyphenethylamine (2C-H)
- 2,4,5-Trimethoxyamphetamine (2,4,5-TMA, TMA-2, or DOMeO)
- 5-HT2A receptor § Anti-inflammatory effects
References
External links
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