2,5-DMA: Difference between revisions

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'''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 [[chemical class::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-Dimethoxyamphetamine''' (also known as '''2,5-DMA''', unformally as simply '''DMA''', and unofficially as '''DOH''') is a lesser-known psychoactive substance of the [[chemical class::amphetamine]] class. 2,5-DMA belongs to the [[DOx]] family of substituted amphetamines.

2,~~5-DMA was first synthesized in Tuckahoe, New York by Richard Baltzly~~ and ~~Johannes S. Buck in 1939.<ref>https://doi.org/10.1021%2Fja01858a046</ref> Its effects in humans were explored~~ in the by [[~~Alexander Shulgin~~]], ~~who published his findings in the book~~ [[~~PiHKAL|PiHKAL (Phenethylamines I Have Known~~ and ~~Loved)~~]].

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]].

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 ~~majpr~~ gross physiological effects. High dosages were reported to be considerably stimulating albeit with no sensory effects.

2,5-DMA was first synthesized in Tuckahoe, New York by Richard Baltzly and Johannes S. Buck in 1939.<ref>{{cite journal | vauthors=((Baltzly, R.)), ((Buck, J. S.)) | journal=Journal of the American Chemical Society | title=Amines Related to 2,5-Dimethoxyphenethylamine. 1 I | volume=62 | issue=1 | pages=161–164 | date= January 1940 | url=https://pubs.acs.org/doi/abs/10.1021/ja01858a046 | issn=0002-7863 | doi=10.1021/ja01858a046}}</ref> Its effects in humans were explored in the by [[Alexander Shulgin]], who published his findings in the book [[PiHKAL|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]].

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==Chemistry==

2,5-DMA, or 2,5-dimethoxyamphetamine, is a substituted [[phenethylamines|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|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]].

2,5-DMA, or 2,5-dimethoxyamphetamine, is a substituted [[phenethylamines|phenethylamine]] and [[amphetamines|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|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==

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*'''[[Effect::Cognitive euphoria]]'''

*'''[[Effect::Increased sense of humor]]'''

*'''[[Effect::~~Increased motivation~~]]'''

*'''[[Effect::Motivation enhancement]]'''

*'''[[Effect::Novelty enhancement]]'''

*'''[[Effect::Paranoia]]'''

*'''[[Effect::Increased music appreciation]]'''

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 {{SubstanceBox/2,5-DMA}}
-'''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 [[chemical class::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-Dimethoxyamphetamine''' (also known as '''2,5-DMA''', unformally as simply '''DMA''', and unofficially as '''DOH''') is a lesser-known psychoactive substance of the [[chemical class::amphetamine]] class. 2,5-DMA belongs to the [[DOx]] family of substituted amphetamines.
-,5-DMA was first synthesized in Tuckahoe, New York by Richard Baltzly and Johannes S. Buck in 1939.<ref>https://doi.org/10.1021%2Fja01858a046</ref> Its effects in humans were explored in the by [[Alexander Shulgin]], who published his findings in the book [[PiHKAL|PiHKAL (Phenethylamines I Have Known and Loved)]].
+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]].
-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 majpr gross physiological effects. High dosages were reported to be considerably stimulating albeit with no sensory effects.
+,5-DMA was first synthesized in Tuckahoe, New York by Richard Baltzly and Johannes S. Buck in 1939.<ref>{{cite journal | vauthors=((Baltzly, R.)), ((Buck, J. S.)) | journal=Journal of the American Chemical Society | title=Amines Related to 2,5-Dimethoxyphenethylamine. 1 I | volume=62 | issue=1 | pages=161–164 | date= January 1940 | url=https://pubs.acs.org/doi/abs/10.1021/ja01858a046 | issn=0002-7863 | doi=10.1021/ja01858a046}}</ref> Its effects in humans were explored in the by [[Alexander Shulgin]], who published his findings in the book [[PiHKAL|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]].
@@ Line 13: / Line 15: @@
 ==Chemistry==
-,5-DMA, or 2,5-dimethoxyamphetamine, is a substituted [[phenethylamines|phenethylamine]] and [[amphetamine]] featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain along with a methyl group at the alpha carbon. 2,5-DMA contains methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as a hydrogen atom attached to carbon R<sub>4</sub> of the phenyl ring. 2,5-DMA belongs to the [[DOx|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]].
+,5-DMA, or 2,5-dimethoxyamphetamine, is a substituted [[phenethylamines|phenethylamine]] and [[amphetamines|amphetamine]] featuring a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain along with a methyl group at the alpha carbon. 2,5-DMA contains methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as a hydrogen atom attached to carbon R<sub>4</sub> of the phenyl ring.
+,5-DMA belongs to the [[DOx|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==
@@ Line 40: / Line 44: @@
 *'''[[Effect::Cognitive euphoria]]'''
 *'''[[Effect::Increased sense of humor]]'''
-*'''[[Effect::Increased motivation]]'''
+*'''[[Effect::Motivation enhancement]]'''
+*'''[[Effect::Novelty enhancement]]'''
 *'''[[Effect::Paranoia]]'''
 *'''[[Effect::Increased music appreciation]]'''