Dimethoxymethamphetamine

Base Information

• Chemical Name: Dimethoxymethamphetamine
• CAS No.: 33236-61-2
• Molecular Formula: C₁₂H₁₉NO₂
• Molecular Weight: 209.288
• ChEMBL ID: CHEMBL3303399
• DSSTox Substance ID: DTXSID20903160
• Nikkaji Number: J510.152B
• Wikidata: Q5277309
• Wikipedia: Dimethoxymethamphetamine
• Mol file: 33236-61-2.mol

Synonyms:Dimethoxymethamphetamine;3,4-dimethoxymethamphetamine;33236-61-2;SCHEMBL8828295;CHEMBL3303399;DTXSID20903160;N-methyl-3,4-dimethoxyamphetamine;AKOS006025917;PD048062;1-(3,4-Dimethoxyphenyl)-N-methyl-2-propanamine;Q5277309;[2-(3,4-dimethoxy-phenyl)-1-methyl-ethyl]-methyl-amine

Chemical Property of Dimethoxymethamphetamine

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 209.141578849
• Heavy Atom Count: 15
• Complexity: 175

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC(=C(C=C1)OC)OC)NC

Technology Process of Dimethoxymethamphetamine

There total 8 articles about Dimethoxymethamphetamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

3,4-dimethoxyphenylacetone (776-99-8) + methylamine (74-89-5) → 1-(3,4-dimethoxyphenyl)-N-methylpropan-2-amine (33236-61-2)

Guidance literature:

3,4-dimethoxyphenylacetone; methylamine; With sodium tetrahydroborate; In methanol; water; at 4 ℃; for 0.5h;

With hydrogenchloride; In methanol; water; pH=1;

With sodium hydroxide; In methanol; water; pH=13;

Reference yield: 64.0%

3,4-dimethoxyphenylacetone (776-99-8) + methylamine hydrochloride (593-51-1) → 1-(3,4-dimethoxyphenyl)-N-methylpropan-2-amine (33236-61-2)

Guidance literature:

3,4-dimethoxyphenylacetone; methylamine hydrochloride; With titanium(IV) isopropylate; triethylamine; In ethanol; at 20 ℃; for 16h; Inert atmosphere;

With sodium tetrahydroborate; In ethanol; at 20 ℃; for 16h;

DOI:10.1016/j.tetasy.2013.05.003

Reference yield:

(E)-1,2-dimethoxy-4-(2-nitroprop-1-enyl)benzene (37629-53-1) → 1-(3,4-dimethoxyphenyl)-N-methylpropan-2-amine (33236-61-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Fe, FeCl₃, aq. HCl

2: aq. HCl, NaBH₃CN / methanol

With hydrogenchloride; iron(III) chloride; iron; sodium cyanoborohydride; In methanol;

DOI:10.1016/0040-4020(75)80276-6

upstream raw materials:

N-Methylformamide

3,4-dimethoxyphenylacetone

2-(3,4-dimethoxyphenyl)-1-methylethylamine

methylamine

Downstream raw materials:

(+/-)-DHMA

N-(1-methyl-2-(3,4-dimethoxy-phenyl)-ethyl)-N-methyl-hydroxylamine

3,4-dihydroxymethamphetamine hydrobromide

2-(3-(benzyloxy)phenyl)-N-(1-(3,4-dimethoxyphenyl)propan-2-yl)-N-methylacetamide

Refernces

• 1、 Felim, Anne,Herrera, Guadalupe,Neudoerffer, Anne,Blanco, Manuel,O'Connor, Jose-Enrique,Largeron, Martine. "Synthesis and in vitro cytotoxicity profile of the R-enantiomer of 3,4-dihydroxymethamphetamine (R-(-)-HHMA): Comparison with related catecholamines". experimental part. p. 211 - 219. Retrieved 2011/02/22.