(R)-3,4-Dimethoxyamphetamine
[CAS# 64778-78-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: (R)-3,4-Dimethoxyamphetamine
• Synonyms: (R)-1-(3,4-Dimethoxyphenyl)-2-aminopropane; (R)-1-Methyl-2-(3,4-dimethoxyphenyl)ethylamine; (R)-2-Amino-1-(3,4-dimethoxyphenyl)propane
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 195.26
• CAS Registry Number: 64778-78-5
• SMILES: C[C@H](CC1=CC(=C(C=C1)OC)OC)N

Properties

• Solubility: Slightly soluble (5.7 g/L) (25 ºC), Calc.^*
• Density: 1.023±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.512, Calc.^*
• Boiling Point: 289.0±25.0 ºC (760 mmHg), Calc.^*
• Flash Point: 139.8±30.4 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

(R)-3,4-Dimethoxyamphetamine, also known as (R)-3,4-dimethoxy-α-methylphenethylamine, is a chemical compound that belongs to the class of substituted amphetamines. It has the molecular formula C10H15NO2 and is characterized by two methoxy groups (-OCH3) attached to the aromatic ring at positions 3 and 4. This compound is a structural isomer of other methoxy-phenethylamines, and its chemical properties are largely influenced by the presence of these methoxy substitutions.

The discovery and synthesis of (R)-3,4-dimethoxyamphetamine stem from the broader interest in the synthesis of phenethylamine derivatives, which are compounds that exhibit a wide range of pharmacological activities. Many of these compounds, including (R)-3,4-dimethoxyamphetamine, have been explored for their effects on the central nervous system due to their structural similarity to known psychoactive substances.

(R)-3,4-Dimethoxyamphetamine has been studied primarily in the context of its pharmacological effects, as the presence of the methoxy groups on the aromatic ring is thought to influence its activity. This compound, like other amphetamines, is believed to interact with neurotransmitter systems in the brain, particularly with those involving dopamine, norepinephrine, and serotonin. It may have stimulant effects due to these interactions, although its specific pharmacological profile is less well-documented in the literature compared to more widely studied compounds like methamphetamine or MDMA.

In terms of application, (R)-3,4-dimethoxyamphetamine does not appear to have widespread use in commercial or medicinal contexts. However, it has been used in scientific research for its role as a synthetic intermediate in the study of substituted amphetamines and related compounds. Its structure and properties make it a subject of interest for researchers exploring the structure-activity relationships within the class of phenethylamines, as well as for those investigating the development of new psychoactive substances.

The compound is also of interest in the study of chemical analogs and derivatives that could have potential therapeutic or recreational effects, though (R)-3,4-dimethoxyamphetamine itself has not found significant use in clinical practice or as a therapeutic agent. The structure of (R)-3,4-dimethoxyamphetamine and its related compounds have been explored for their potential to influence the brain's neurotransmitter systems, with a focus on understanding how modifications to the aromatic ring and side chains affect their activity.

Overall, (R)-3,4-dimethoxyamphetamine is a chemical compound that has been studied primarily within the context of synthetic organic chemistry and pharmacology. It has been synthesized for use in research focused on understanding the behavior of substituted amphetamines, but it does not have significant commercial or medical applications. Its primary role in the literature is as a model compound for exploring the effects of methoxy substitutions on the activity of phenethylamine derivatives.

References

Iwasaki, A. et al. (2006). Microbial synthesis of chiral amines by (R)-specific transamination with Arthrobacter sp. KNK168. Applied Microbiology and Biotechnology, 69(5), 499-505.
DOI: https://doi.org/10.1007/s00253-005-0002-1

Iwasaki, A., Yamada, Y., Ikenaka, Y. et al. (2003). Microbial synthesis of (R)- and (S)-3,4-dimethoxyamphetamines through stereoselective transamination. Biotechnology Letters, 25(21), 1843-1846.
DOI: https://doi.org/10.1023/a:1026229610628

Rangisetty, J. B., Bondarev, M. L., Chang-Fong, J. et al. (2001). PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA. Pharmacology Biochemistry and Behavior, 69(1-2), 261-267.
DOI: https://doi.org/10.1016/s0091-3057(01)00530-5