3,4-Dimethoxyamphetamine

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3,4-Dimethoxyamphetamine
3,4-Dimethoxyamphetamine.svg
Clinical data
Other names3,4-DMA; Dimethoxyamphetamine; DMA; 3,4-Dimethoxy-α-methylphenethylamine; α-Methylhomoveratrylamine; EA-1316; NSC-144717
Drug class Serotonergic psychedelic; Hallucinogen
Identifiers
  • 1-(3,4-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.003.985 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H17NO2
Molar mass 195.262 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=C(C=C1)OC)OC)N
  • InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)11(7-9)14-3/h4-5,7-8H,6,12H2,1-3H3
  • Key:KAZPHAGSWZTKDW-UHFFFAOYSA-N

3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families. [1] [2] It is one of the dimethoxyamphetamine (DMA) series of positional isomers. [1] [2]

The drug has been assessed in various biochemical and preclinical studies. [2] It has been tried in humans at doses of up to 700 mg intravenously, with mescaline-like effects reported. [2] [1] 3,4-DMA is also orally active and has produced sympathomimetic effects at a dose of 160 mg. [2] [1] Its duration of action is unknown. [2] [1]

Its affinity (Ki) for the rat serotonin 5-HT2A receptor has been assessed [2] and was found to be 43,300 nM. [3] For comparison, the affinity of para-methoxyamphetamine (PMA) was 33,600 nM, of 2,5-dimethoxyamphetamine (2,5-DMA) was 5,200 nM, and of 2,5-dimethoxy-4-methylamphetamine (DOM) was 100 nM in the same study. [3] 3,4-DMA has been found to be a monoamine oxidase inhibitor (MAOI), with an IC50 Tooltip half-maximal inhibitory concentration of 20,000 nM for monoamine oxidase A (MAO-A), whereas it was inactive at monoamine oxidase B (MAO-B) (IC50 > 100,000 nM). [4] [5]

3,4-DMA produces 3-methoxy-4-hydroxyamphetamine (MHA) as its major metabolite in dogs and monkeys. [2]

See also

Related Research Articles

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<span class="mw-page-title-main">5-MeO-AMT</span> Chemical compound

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<i>para</i>-Methoxyamphetamine Chemical compound

para-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogen effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties.

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<span class="mw-page-title-main">2,4,5-Trimethoxyamphetamine</span> Pharmaceutical compound

2,4,5-Trimethoxyamphetamine (2,4,5-TMA), also known as TMA-2 or as 2,5-dimethoxy-4-methoxyamphetamine (DOMeO), is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the trimethoxyamphetamine (TMA) series of positional isomers. The drug is also notable in being the 4-methoxylated member of the DOx series of drugs.

<span class="mw-page-title-main">3,4,5-Trimethoxyamphetamine</span> Pharmaceutical compound

Trimethoxyamphetamine, also known as 3,4,5-trimethoxyamphetamine (3,4,5-TMA), α-methylmescaline, or mescalamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the trimethoxyamphetamine (TMA) series of positional isomers. The drug is notable in being the amphetamine analogue of mescaline (3,4,5-trimethoxyphenethylamine).

Trimethoxyamphetamines (TMAs) are a family of positionally isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the positions of the three methoxy groups: TMA (TMA-1), TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are substituted amphetamines and are analogues of the phenethylamine cactus alkaloid mescaline and the DOx drugs.

<span class="mw-page-title-main">2,5-Dimethoxy-4-ethylamphetamine</span> Psychedelic drug

2,5-Dimethoxy-4-ethylamphetamine (DOET) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is closely related to DOM and is a synthetic analogue of the naturally occurring phenethylamine psychedelic mescaline. The drug acts as a selective agonist of the serotonin 5-HT2 receptors, including of the serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptors.

<span class="mw-page-title-main">2C (psychedelics)</span> Family of phenethylamine psychedelics

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<span class="mw-page-title-main">Aleph (psychedelic)</span> Chemical compound

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<span class="mw-page-title-main">3,4-Dimethoxyphenethylamine</span> Chemical compound

3,4-Dimethoxyphenethylamine (DMPEA) is a chemical compound of the phenethylamine class. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine and to 3,4-dimethoxyamphetamine (3,4-DMA).

Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and 3,5-DMA. Three of the isomers were characterized by Alexander Shulgin in his book PiHKAL. Little is known about their dangers or toxicity.

<i>para</i>-Methoxymethamphetamine Stimulant and psychedelic designer drug

para-Methoxymethamphetamine (PMMA), also known as 4-methoxy-N-methylamphetamine (4-MMA), is a serotonergic drug of the amphetamine family related to para-methoxyamphetamine (PMA). It is the 4-methoxy analogue of methamphetamine. Little is known about the pharmacological properties, metabolism, and toxicity of PMMA; because of its structural similarity to PMA, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose. In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA.

<span class="mw-page-title-main">5-Fluoro-AMT</span> Chemical compound

5-Fluoro-α-methyltryptamine, also known as PAL-212 or PAL-544, is a putative stimulant, entactogen, and psychedelic tryptamine derivative related to α-methyltryptamine (αMT).

<span class="mw-page-title-main">3-Methoxyamphetamine</span> Stimulant drug of the amphetamine class

3-Methoxyamphetamine (3-MA), also known as meta-methoxyamphetamine (MMA), is a monoamine releasing agent (MRA) of the amphetamine family. It is a positional isomer of para-methoxyamphetamine.

<span class="mw-page-title-main">2,5-Dimethoxyamphetamine</span> Pharmaceutical compound

2,5-Dimethoxyamphetamine (2,5-DMA), also known as DMA-4 or as DOH, is a drug of the phenethylamine and amphetamine 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.

DO<i>x</i> Class of chemical compounds

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. They are 4-substituted derivatives of 2,5-dimethoxyamphetamine and are structurally related to the naturally occurring phenethylamine psychedelic mescaline.

<span class="mw-page-title-main">5-Chloro-αMT</span> Chemical compound

5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known serotonin–dopamine releasing agents (SDRAs). It is also a potent serotonin 5-HT2A receptor agonist and hence may be a serotonergic psychedelic. The drug has been investigated in animals as a potential treatment for cocaine dependence.

<span class="mw-page-title-main">4-Methylthiomethamphetamine</span> Pharmaceutical compound

4-Methylthiomethamphetamine, also known as N-methyl-4-methylthioamphetamine (NMMTA), is a monoamine releasing agent (MRA) of the amphetamine family related to 4-methylthioamphetamine (4-MTA) and N,N-dimethyl-4-methylthioamphetamine. Much less is known about 4-MTMA compared to 4-MTA.

<i>N</i>,<i>N</i>-Dimethyl-4-methylthioamphetamine Pharmaceutical compound

N,N-Dimethyl-4-methylthioamphetamine, also known as 4-methylthio-N,N-dimethylamphetamine (4-MTDMA), is a monoamine releasing agent (MRA) of the amphetamine family related to 4-methylthioamphetamine (4-MTA) and 4-methylthiomethamphetamine.

References

  1. 1 2 3 4 5 Shulgin AT, Shulgin A (1991). "#55 3,4-DMA; 3,4-DIMETHOXYAMPHETAMINE". PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN   9780963009609. OCLC   25627628.
  2. 1 2 3 4 5 6 7 8 Shulgin A, Manning T, Daley PF (2011). "#38. DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley: Transform Press. ISBN   978-0-9630096-3-0.
  3. 1 2 Shannon M, Battaglia G, Glennon RA, Titeler M (June 1984). "5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA)". Eur J Pharmacol. 102 (1): 23–29. doi:10.1016/0014-2999(84)90333-9. PMID   6479216.
  4. ↑ Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10: 1590. doi: 10.3389/fphar.2019.01590 . PMC   6989591 . PMID   32038257.
  5. ↑ Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE (April 2005). "Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling". J Med Chem. 48 (7): 2407–2419. doi:10.1021/jm0493109. PMID   15801832.


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