dimethoxyphenylethylamine

Summary

Summary: A derivative of phenethylamine containing two substituent methoxy groups in the phenyl ring.

Top Publications

  1. Drees J, Stone J, Wu A. Morbidity involving the hallucinogenic designer amines MDA and 2C-I. J Forensic Sci. 2009;54:1485-7 pubmed publisher
    ..This report demonstrates the utility of testing for a wider menu of compounds using LC-MS/MS in order to better characterize the prevalence and toxicities of novel amines such as 2C-I...
  2. Morikawa N, Nakagawa Hattori Y, Mizuno Y. Effect of dopamine, dimethoxyphenylethylamine, papaverine, and related compounds on mitochondrial respiration and complex I activity. J Neurochem. 1996;66:1174-81 pubmed
    We report the effect of papaverine, tetrahydro-papaverine, laudanosine, dimethoxyphenylethylamine, dopamine, and its metabolites on mitochondrial respiration and activities of the enzymes in the electron transfer complexes, as ..
  3. Suzuki J, Dekker M, Valenti E, Arbelo Cruz F, Correa A, Poklis J, et al. Toxicities associated with NBOMe ingestion-a novel class of potent hallucinogens: a review of the literature. Psychosomatics. 2015;56:129-39 pubmed publisher
    ..0%), leukocytosis (25.0%), and hyperglycemia (20.0%). NBOMe ingestion is associated with severe adverse effects. Clinicians need to have a high index of suspicion for NBOMe ingestion in patients reporting the recent use of hallucinogens. ..
  4. Lobos M, Borges Y, Gonzalez E, Cassels B. The action of the psychoactive drug 2C-B on isolated rat thoracic aorta. Gen Pharmacol. 1992;23:1139-42 pubmed
    ..5. These results suggest that 2C-B behaves as a partial agonist toward both alpha 1-adrenergic and 5-HT2 serotonergic receptors. The endothelium only seems to act as a diffusional barrier to the drug...
  5. Goto K, Mochizuki H, Hattori T, Nakamura N, Mizuno Y. Neurotoxic effects of papaverine, tetrahydropapaverine and dimethoxyphenylethylamine on dopaminergic neurons in ventral mesencephalic-striatal co-culture. Brain Res. 1997;754:260-8 pubmed
    We report neurotoxic effects of papaverine, tetrahydropapaverine, dimethoxyphenylethylamine (DMPEA), and 1-methyl-4-phenylpyridinium ion (MPP+) on dopaminergic neurons in ventral mesencephalic-striatal co-culture...
  6. Koshimura I, Imai H, Hidano T, Endo K, Mochizuki H, Kondo T, et al. Dimethoxyphenylethylamine and tetrahydropapaverine are toxic to the nigrostriatal system. Brain Res. 1997;773:108-16 pubmed
    We report the toxic effects of 3,4-dimethoxyphenylethylamine (DMPEA), and tetrahydropapaverine (THP) on the rat nigrostriatal system; THP is a tetrahydroisoquinoline compound which may be derived from DMPEA by conjugation of DMPEA and ..
  7. Rohanova M, Palenicek T, Balikova M. Disposition of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) and its metabolite 4-bromo-2-hydroxy-5-methoxyphenethylamine in rats after subcutaneous administration. Toxicol Lett. 2008;178:29-36 pubmed publisher
    ..The kinetics of the drug partitioning between blood to brain may be important for the subsequent assessment of its psychotropic or toxic effects...
  8. Huang H, Bai Y. Persistent psychosis after ingestion of a single tablet of '2C-B'. Prog Neuropsychopharmacol Biol Psychiatry. 2011;35:293-4 pubmed publisher
  9. Kanamori T, Kuwayama K, Tsujikawa K, Miyaguchi H, Iwata Y, Inoue H. Synthesis and identification of urinary metabolites of 4-iodo-2,5-dimethoxyphenethylamine. J Forensic Sci. 2011;56:1319-23 pubmed publisher
    ..The data presented in this study will be very useful for the analysis of 2C-I and its metabolites in forensic samples...

More Information

Publications27

  1. Theobald D, Fritschi G, Maurer H. Studies on the toxicological detection of the designer drug 4-bromo-2,5-dimethoxy-beta-phenethylamine (2C-B) in rat urine using gas chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2007;846:374-7 pubmed
    ..Assuming similar metabolism, the described STA procedure should be suitable for proof of an intake of 2C-B in human urine...
  2. Cole M, Lea C, Oxley N. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B): a review of the public domain literature. Sci Justice. 2002;42:223-4 pubmed
  3. Adamowicz P, Tokarczyk B, Stanaszek R, Slopianka M. Fatal mephedrone intoxication--a case report. J Anal Toxicol. 2013;37:37-42 pubmed publisher
    ..Mephedrone was found in blood and vitreous humor at the concentrations of 5.5 and 7.1 µg/mL, respectively, revealing that this was a fatal mephedrone intoxication...
  4. Panoutsopoulos G. Contribution of aldehyde oxidizing enzymes on the metabolism of 3,4-dimethoxy-2-phenylethylamine to 3,4-dimethoxyphenylacetic acid by guinea pig liver slices. Cell Physiol Biochem. 2006;17:47-56 pubmed
    ..Oxidation of aromatic aldehydes is catalyzed mainly by aldehyde dehydrogenase and aldehyde oxidase...
  5. Caudevilla Gálligo F, Riba J, Ventura M, González D, Farre M, Barbanoj M, et al. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B): presence in the recreational drug market in Spain, pattern of use and subjective effects. J Psychopharmacol. 2012;26:1026-35 pubmed publisher
    ..While it elicits perceptual modifications that are analogous to other psychedelics, the lower impairment and higher pleasurable effects make it comparable with entactogens...
  6. Bosak A, LoVecchio F, Levine M. Recurrent seizures and serotonin syndrome following "2C-I" ingestion. J Med Toxicol. 2013;9:196-8 pubmed publisher
    ..Comprehensive drug testing revealed the presence of 2C-I. The pharmacologic properties of 2C-I are also discussed...
  7. Morita M, Hosokami T, Konno T, Kinuno K, Mafune E, Takasugi N. Preliminary preformulation studies of a 2-(3,4-dimethoxyphenyl)ethylamine derivative for oral administration at an exploratory stage of new drug development. Chem Pharm Bull (Tokyo). 1995;43:476-82 pubmed
    ..After oral administration of the improved formulation, the serum level of alpha-anhydrate in beagle dogs was almost triple that after the oral administration of the capsule of the hydrochloride form...
  8. Ambrose J, Bennett H, Lee H, Josephson S. Cerebral vasculopathy after 4-bromo-2,5-dimethoxyphenethylamine ingestion. Neurologist. 2010;16:199-202 pubmed publisher
    ..Neurologic consequences of 2C-B usage are currently unknown...
  9. Kanamori T, Nagasawa K, Kuwayama K, Tsujikawa K, Iwata Y, Inoue H. Analysis of 4-bromo-2,5-dimethoxyphenethylamine abuser's urine: identification and quantitation of urinary metabolites. J Forensic Sci. 2013;58:279-87 pubmed publisher
    ..Our results suggest that MAO plays a crucial role in the metabolism of 2C-B in humans...
  10. Hermanns Clausen M, Angerer V, Kithinji J, Grumann C, Auwärter V. Bad trip due to 25I-NBOMe: a case report from the EU project SPICE II plus. Clin Toxicol (Phila). 2017;55:922-924 pubmed publisher
    ..The finding of 2C-I in the serum sample 50?minutes after intake indicates a fast metabolic breakdown of 25I-NBOMe due to first-pass metabolism. ..
  11. Theobald D, Pütz M, Schneider E, Maurer H. New designer drug 4-iodo-2,5-dimethoxy-beta-phenethylamine (2C-I): studies on its metabolism and toxicological detection in rat urine using gas chromatographic/mass spectrometric and capillary electrophoretic/mass spectrometric techniques. J Mass Spectrom. 2006;41:872-86 pubmed
    ..Assuming similar metabolism, the described STA procedure should be suitable for proof of an intake of 2C-I in human urine...
  12. Carmo H, de Boer D, Remião F, Carvalho F, dos Reys L, de Lourdes Bastos M. Metabolism of the designer drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in mice, after acute administration. J Chromatogr B Analyt Technol Biomed Life Sci. 2004;811:143-52 pubmed
    ..The identification of 2C-B metabolites may give important clues for the biological and toxicological effects of this drug of abuse and provides new important data for forensic analysis on samples taken from 2C-B abusers...
  13. Villalobos C, Bull P, Sáez P, Cassels B, Huidobro Toro J. 4-Bromo-2,5-dimethoxyphenethylamine (2C-B) and structurally related phenylethylamines are potent 5-HT2A receptor antagonists in Xenopus laevis oocytes. Br J Pharmacol. 2004;141:1167-74 pubmed
    ..As an alternative hypothesis, we suggest that the psychostimulant activity of the PEAs may not be exclusively associated with partial or full 5-HT(2A) receptor agonism...
  14. Charlton C, Crowell B. Effects of dopamine metabolites on locomotor activities and on the binding of dopamine: relevance to the side effects of L-dopa. Life Sci. 2000;66:2159-71 pubmed
    ..L-dopa, and DA is extensively methylated, the methyl metabolites of DA, 3-methoxytyramine (3-MT) and 3,4-dimethoxyphenylethylamine (DIMPEA), may be also involved...
  15. Giroud C, Augsburger M, Rivier L, Mangin P, Sadeghipour F, Varesio E, et al. 2C-B: a new psychoactive phenylethylamine recently discovered in Ecstasy tablets sold on the Swiss black market. J Anal Toxicol. 1998;22:345-54 pubmed
    ..Quantitation of 2C-B was performed by HPLC-DAD and CE-DAD. The amounts of 2C-B found in the tablets (3-8 mg) were in the range of the minimum quantity required to induce the effects characteristic of this drug...
  16. Tominaga T, Inoue O, Suzuki K, Yamasaki T, Hirobe M. Evaluation of 13N-amines as tracers. Int J Rad Appl Instrum B. 1987;14:485-90 pubmed
    ..13N-ammonia formed thereby was converted into amino acids (mainly glutamine by glutamine synthetase) and trapped. 13N-amines were found to be potential metabolic trapping tracers for the study of disposition and metabolism of amines...
  17. Maher H, Awad T, Deruiter J, Clark C. GC-MS and GC-IRD studies on dimethoxyphenethylamines (DMPEA): regioisomers related to 2,5-DMPEA. J Chromatogr Sci. 2012;50:1-9 pubmed publisher
    ..Perfluoroacylated derivatives of the six regioisomeric dimethoxyphenethylamines were successfully resolved via capillary GC on a non-polar stationary phase consisting of 50% phenyl and 50% methyl polysiloxane (Rxi-50)...
  18. Palenicek T, Fujáková M, Brunovsky M, Horacek J, Gorman I, Balikova M, et al. Behavioral, neurochemical and pharmaco-EEG profiles of the psychedelic drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in rats. Psychopharmacology (Berl). 2013;225:75-93 pubmed publisher
    ..Behavioral, neurochemical and pharmaco-EEG profiles of a new synthetic drug 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in rats were examined...