3600-86-0

Basic information

• Product Name: 2,5-Dimethoxyphenethylamine
• Synonyms: 2-(2,5-Dimethoxyphenyl)ethanamine;RARECHEM AL BW 0357;2-(2,5-DIMETHOXY-PHENYL)-ETHYLAMINE;2,5-DIMETHOXYPHENETHYLAMINE;2,5-Dimethoxyphenylethylamine;2C-H;2,5-DIMETHOXYPHENETHYLAMIN 98.0%;2,5-Dimethoxyphenethylamine,97%
• CAS NO: 3600-86-0
• Molecular Formula: C₁₀H₁₅NO₂
• Molecular Weight: 181.23
• Product Categories: C9 to C10;Amines;Nitrogen Compounds;Aromatics;Miscellaneous Reagents
• Mol File: 3600-86-0.mol

Chemical Properties

• Boiling Point: 160 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: light yellow to colourless liquid
• Density: 1.089 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5424(lit.)
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• PKA: 9.72±0.10(Predicted)
• CAS DataBase Reference: 2,5-Dimethoxyphenethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethoxyphenethylamine(3600-86-0)
• EPA Substance Registry System: 2,5-Dimethoxyphenethylamine(3600-86-0)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38-34
• Safety Statements: 26-37/39-45-36/37/39
• RIDADR: 1760
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 3600-86-0(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

InChI:InChI=1/C10H15NO2/c1-12-9-3-4-10(13-2)8(7-9)5-6-11/h3-4,7H,5-6,11H2,1-2H3

Upstream product

• 40276-11-7 (E)-1,4-dimethoxy-2-(2-nitrovinyl) benzene 
• 72205-78-8 3-(2,5-dimethoxy-phenyl)-propionic acid amide 
• 436155-33-8 3-(2,5-dimethoxyphenyl)propanoylhydrazine 
• 108536-18-1 β-dimethoxy-2,5 phenyl nitro ethylene 
• 93-02-7 2,5-dimethoxybenzaldehyde 
• 14438-63-2 1-(2,5-dimethoxyphenyl)-2-nitroethanol 
• 72018-06-5 ethyl E-3-(2,5-dimethoxyphenyl)propanoate 
• 38489-74-6 trans-2,5-dimethoxycinnamic acid 
• 10538-49-5 3-(2,5-dimethoxyphenyl)propanoic acid 

Downstream Products

• 82802-87-7 (2,5-dimethoxy-phenethyl)-dimethyl-amine 
• 69226-57-9 (2,5-dimethoxy-phenethyl)-urea 
• 21581-41-9 2,5-dihydroxyphenylethylamine 
• 3489-95-0 (2,5-dimethoxy-phenethyl)-methyl-amine 
• 106274-40-2 N-<2-(2,5-dimethoxyphenyl)ethyl>acetamide 
• 50525-84-3 N-Chloroacetyl-2,5-dimethoxyphenethylamine 
• 106462-43-5 N-[2-(2,5-Dimethoxy-phenyl)-ethyl]-2-(4-methoxy-phenyl)-acetamide 
• 106462-40-2 2-(3,4-Dimethoxy-phenyl)-N-[2-(2,5-dimethoxy-phenyl)-ethyl]-acetamide 
• 97796-51-5 1-[2-(2,5-Dimethoxy-phenyl)-ethyl]-2-hydroxy-2,4-diphenyl-1,2-dihydro-pyrrol-3-one 
• 106462-42-4 N-[2-(2,5-Dimethoxy-phenyl)-ethyl]-2-(3-ethoxy-phenyl)-acetamide 
• 106462-44-6 N-[2-(2,5-Dimethoxy-phenyl)-ethyl]-2-(3-phenoxy-phenyl)-acetamide 
• 106462-45-7 N-[2-(2,5-Dimethoxy-phenyl)-ethyl]-2-(3-methoxy-4-phenoxy-phenyl)-acetamide 
• 88441-00-3 1-(2,5-dimethoxy-4-nitrophenyl)-2-(acetylamino)ethane 
• 194996-05-9 N-((tert-butoxy)carbonyl)-N'-(2-(phenyl)ethyl)-N''-(2-(2,5-dimethoxyphenyl)ethyl)iminodiacetic acid diamide 

Relevant articles and documents

Synthesis of 25X-BOMes and 25X-NBOHs (X = H, I, Br) for pharmacological studies and as reference standards for forensic purposes

An expeditious method is reported for the synthesis of three NBOHs (25H-, 25I- and 25B-NBOH; 9–38% overall yield) and three NBOMes (25H-, 25I- and 25B-NBOMe; 7–33% overall yield) from salicylaldehyde and 2-methoxyaldehyde, respectively. The X-ray structures of 25H-, 25I- and 25B-NBOH.HCl were also determined. Our approach should provide a general entry for preparing such a class of substances for pharmacological and forensic purposes.

Nanosensor for Sensitive Detection of the New Psychedelic Drug 25I-NBOMe

This work reports the synthesis, characterization, and sensing behavior of a hybrid nanodevice for the detection of the potent abuse drug 25I-NBOMe. The system is based on mesoporous silica nanoparticles, loaded with a fluorescent dye, functionalized with

Two immunoassays for the detection of 2C-B and related hallucinogenic phenethylamines

Introduction: The use of new psychoactive substances as drugs of abuse has dramatically increased over the last years. Hallucinogenic phenethylamines gained particular popularity as they have both stimulating and psychedelic effects. Although generally perceived as safe, these illicit drugs pose a serious health risk; they have been linked to cases of severe poisoning or even deaths. Therefore, simple, cost-effective and reliable methods are needed for rapid determination of abused hallucinogens. Methods: For this purpose, two haptens derived from 2C-H were designed, synthesized and subsequently attached to a carrier protein. Polyclonal antibodies obtained from a rabbit immunized with one of the prepared immunogens were used for the development of two immunoassays. Results: In this study, a lateral flow immunoassay (LFIA) and an enzyme linked immunosorbent assay (ELISA) for the detection of 2C-B and related hallucinogenic phenethylamines in urine were developed. The presented LFIA is primarily suitable for on-site monitoring as it is simple and can provide a visual evidence of 2C-B presence within a few minutes. Its reasonable sensitivity (LODLFIA = 15 ± 7 ng mL?1) allows detection of the drug presence in urine after acute exposure. For greater accuracy, highly sensitive ELISA (LODELISA = 6 ± 3 pg mL?1) is proposed for toxicological quantitative analyses of positive samples captured by the LFIA. Discussion: The comparison of the ELISA with the well-established UHPLC-MS-MS method shows excellent agreement of results, which confirms good potential of the ELISA to be used for routine analyses of 2C-B and related hallucinogenic phenethylamines of both main sub-families.

Design, synthesis and evaluation of thiourea derivatives as antimicrobial and antiviral agents

Background: The development of drug-resistant by bacteria appears rapidly and thus making the effectiveness of antibiotics severely limited. Methods: A series of thiourea derivatives was synthesized, characterized and evaluated for their in vitro antibacterial, antifungal and antiviral activities. Results: Structures of the newly synthesized compounds were confirmed by elemental and spectral analysis. The biological results showed that some of the target compounds displayed comparable antimicrobial and antiviral activities with reference drugs. Structure-activity relationship studies revealed that the ortho-chloro or fluoro substituted phenyl at Ar1 and substituted pyridinyl at Ar2 positions of the thiourea nucleus are essential for their in vitro antimicrobial and anti-HIV activity. In particular, compounds 8 and 10 showed better activity against the tested bacteria, fungi and viral strains than other synthesized PET derivatives reported in the present study. Conclusion: These results provide an encouraging lead that could be used for the development of new potent antiviral and antimicrobial agents.

Immunoassay for Phenethylamines of the 2C and DO Sub-Families

Immunoassay methods and their requisite components for the detection and determination of phenethylamines of the 2C and DO sub-families are described.

Immunoassay for Phenethylamines of the 2C and DO Sub-Families

Immunoassay methods and their requisite components for the detection and determination of phenethylamines of the 2C and DO sub-families are described.

IMMUNOASSAY FOR COMPOUNDS OF THE NBOME FAMILY

An immunoassay method for detecting and determining 'NBOMe' family designer drugs is described. Also described are components for use in implementing the method, namely, antibodies, detection agents, solid state devices and kits as well as immunogens used to raise the antibodies.

Comparative potencies of 3,4-methylenedioxymethamphetamine (MDMA) analogues as inhibitors of [3H]noradrenaline and [3H]5-HT transport in mammalian cell lines

Background and purpose: Illegal 'ecstasy' tablets frequently contain 3,4-methylenedioxymethamphetamine (MDMA)-like compounds of unknown pharmacological activity. Since monoamine transporters are one of the primary targets of MDMA action in the brain, a number of MDMA analogues have been tested for their ability to inhibit [3H]noradrenaline uptake into rat PC12 cells expressing the noradrenaline transporter (NET) and [3H]5-HT uptake into HEK293 cells stably transfected with the 5-HT transporter (SERT). Experimental approach: Concentration-response curves for the following compounds at both NET and SERT were determined under saturating substrate conditions: 4-hydroxy-3-methoxyamphetamine (HMA), 4-hydroxy-3-methoxymethamphetamine (HMMA), 3,4-methylenedioxy-N-hydroxyamphetamine (MDOH), 2,5-dimethoxy-4- bromophenylethylamine (2CB), 3,4-dimethoxymethamphetamine (DMMA), 3,4-methylenedioxyphenyl-2-butanamine (BDB), 3,4-methylenedioxyphenyl-N-methyl- 2-butanamine (MBDB) and 2,3-methylenedioxymethamphetamine (2,3-MDMA). Key results: 2,3-MDMA was significantly less potent than MDMA at SERT, but equipotent with MDMA at NET. 2CB and BDB were both significantly less potent than MDMA at NET, but equipotent with MDMA at SERT. MBDB, DMMA, MDOH and the MDMA metabolites HMA and HMMA, were all significantly less potent than MDMA at both NET and SERT. Conclusions and implications: This study provides an important insight into the structural requirements of MDMA analogue affinity at both NET and SERT. It is anticipated that these results will facilitate understanding of the likely pharmacological actions of structural analogues of MDMA.

Phenethylthiazolylthiourea (PETT) compounds as a new class of HIV-1 reverse transcriptase inhibitors. 2. Synthesis and further structure-activity relationship studies of PETT analogs

Phenylethylthiazolylthiourea (PETT) derivatives have been identified as a new series of nonnucleoside inhibitors of HIV-1 RT. Structure-activity relationship studies of this class of compounds resulted in the identification of N-[2-(2-pyridyl)ethyl]-N'-[2-(5-bromopyridyl)]-thiourea hydrochloride (trovirdine; LY300046.HCl) as a highly potent anti-HIV-1 agent. Trovirdine is currently in phase one clinical trials for potential use in the treatment of AIDS. Extension of these structure-activity relationship studies to identify additional compounds in this series with improved properties is ongoing. A part of this work is described here. Replacement of the two aromatic moleties of the PETT compounds by various substituted or unsubstituted heteroaromatic rings was investigated. In addition, the effects of multiple substitution in the phenyl ring were also studied. The antiviral activities were determined on wild-type and constructed mutants of HIV-1 RT and on wild-type HIV-1 and mutant viruses derived thereof, Ile100 and Cys181, in cell culture assays. Some selected compounds were determined on double- mutant viruses, HIV-1 (Ile100/Asn103) and HIV-1 (Ile100/Cys181). A number of highly potent analogs were synthesized. These compounds displayed IC50's against wild-type RT between 0.6 and 5 nM. In cell culture, these agents inhibited wild-type HIV-1 with ED50's between I and 5 nM in MT-4 cells. In addition, these derivatives inhibited mutant HIV-1 RT (Ile 100) with IC50's between 20 and 50 nM and mutant HIV-1 RT (Cys 181) with IC50's between 4 and 10 nM, and in cell culture they inhibited mutant HIV-1 (Ile100) with ED50's between 9 and 100 nM and mutant HIV-1 (Cys181) with ED50's between 3 and 20 nM.

Process for the preparation of (8As,12AS,13AS)-decahydroisoquino ((2,1-G) (1,6)-naphthyridin-8-one derivatives

The invention provides a process for preparing single enantiomers of compounds represented by the formula: STR1 and chiral acid addition salts thereof; wherein: X and Y are independently hydrogen; lower alkyl; lower alkoxy; or halo; or X and Y taken together is methylenedioxy or ethylene-1,2-dioxy; which includes reduction of a compound represented by the formula: STR2 to give a mixture of stereoisomers represented by the formula: STR3 wherein each wavy line independently represents a bond in either the α or β position; followed by dissolving the mixture of stereoisomers and a chiral resolving acid in a suitable solvent and allowing the solution to crystallize, giving a salt of the desired enantiomer.