1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine

Base Information

• Chemical Name: 1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine
• CAS No.: 64584-34-5
• Deprecated CAS: 82830-53-3
• Molecular Formula: C₁₁H₁₆INO₂
• Molecular Weight: 321.158
• UNII: OOM10GW9UE
• DSSTox Substance ID: DTXSID7040520
• Nikkaji Number: J246.190K
• Wikipedia: 2,5-Dimethoxy-4-iodoamphetamine
• Wikidata: Q209251
• Pharos Ligand ID: C4TLUCU591R9
• Metabolomics Workbench ID: 63441
• ChEMBL ID: CHEMBL6616
• Mol file: 64584-34-5.mol

Synonyms:1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane;1-(4-iodo-2,5-dimethoxyphenyl)-2-aminopropane;2,5-dimethoxy-4-iodoamphetamine;2,5-dimethoxy-4-iodoamphetamine hydrochloride;2,5-dimethoxy-4-iodophenylisopropylamine;4-DOI;4-iodo-2,5-dimethoxyphenylisopropylamine;4-iodo-2,5-dimethoxyphenylisopropylamine hydrochloride, (+-)-isomer;4-iodo-2,5-dimethoxyphenylisopropylamine hydrochloride, (R)-isomer;4-iodo-2,5-dimethoxyphenylisopropylamine, (+-)-isomer;4-iodo-2,5-dimethoxyphenylisopropylamine, (R)-isomer;4-iodo-2,5-dimethoxyphenylisopropylamine, 123I-labeled;4-iodo-2,5-dimethoxyphenylisopropylamine, 131I-labeled;DOI cpd;DOI-P

Chemical Property of 1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine

Chemical Property:

• Vapor Pressure: 2.06E-05mmHg at 25°C
• Refractive Index: 1.573
• Boiling Point: 361.545 °C at 760 mmHg
• Flash Point: 172.456 °C
• PSA: 44.48000
• Density: 1.509 g/cm³
• LogP: 2.89840
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 321.02258
• Heavy Atom Count: 15
• Complexity: 191

Purity/Quality:

99%, ^*data from raw suppliers

1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC1=CC(=C(C=C1OC)I)OC)N
• Uses: 2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine of the phenethylamine family. It is also a powerful anti-inflammatory that is effective at doses on the order of 100 micrograms in humans, far below its effective dose as a psychedelic. Despite being a substituted amphetamine, it is not a stimulant. DOI has a stereocenter and R-(-)-DOI is the more active stereoisomer. DOI is a 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonist. Its psychedelic effects are mediated by its agonistic properties at the 5-HT2A receptor. This is a controlled substance.

Technology Process of 1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine

There total 4 articles about 1-(4-Iodo-2,5-dimethoxyphenyl)propan-2-amine 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: 78.0%

2,5-dimethoxyphenylisopropylamine (2801-68-5) → 4-iodo-2,5-dimethoxyphenylisopropylamine (64584-34-5,82830-53-3,82864-06-0,99665-04-0)

Guidance literature:

With iodine; silver sulfate; In ethanol; for 17h; Ambient temperature;

DOI:10.1016/S0040-4039(00)73715-4

Reference yield:

(+/-)-N-acetyl-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (82830-50-0) → 4-iodo-2,5-dimethoxyphenylisopropylamine (64584-34-5,82830-53-3,82864-06-0,99665-04-0)

Guidance literature:

With sodium hydroxide; In ethylene glycol; Heating;

DOI:10.1139/v73-210

Reference yield:

N-Acetyl-1-(4-amino-2,5-dimethoxyphenyl)-2-aminopropan-hydrochlorid (42203-73-6) → 4-iodo-2,5-dimethoxyphenylisopropylamine (64584-34-5,82830-53-3,82864-06-0,99665-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) NaNO₂, aq. HCl, (ii) aq. KI

2: aq. NaOH / ethane-1,2-diol / Heating

With sodium hydroxide; In ethylene glycol;

DOI:10.1139/v73-210

upstream raw materials:

2,5-dimethoxyphenylisopropylamine

(+/-)-N-acetyl-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane

N-Acetyl-1-(4-amino-2,5-dimethoxyphenyl)-2-aminopropan-hydrochlorid

Downstream raw materials:

(+)-DOI

Refernces

• 1、 Coutts,Malicky. "The synthesis of some analogs of the hallucinogen 1 (2,5 dimethoxy 4 methylphenyl) 2 aminopropane (DOM)". . p. 1402 - 1409. Retrieved 2007/10/05.