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Chemical Compound Review

AC1L9GQ0     (2R,3R,4S,5S,6R)-2- [(2R,3S,4R,6R)-4,6...

Synonyms: 2'-Deoxymaltose
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Disease relevance of DOM


Psychiatry related information on DOM

  • In tests of stimulus generalization, using rats trained to discriminate DOM from saline, the 2-demethyl and N-propyl derivatives were found to produce stimulus effects similar to those of DOB [6].
  • However, most doses of DOM tended to decrease unacclimated motor activity, while amphetamine increased this behavior [7].
  • Alcohol-drinking colonies failed to establish a dominance hierarchy and displayed little aggression, with an average of 14.6 +/- 6.1 offensive attacks compared with 58.5 +/- 12.3 attacks carried out by DOM sucrose/quinine rats [8].

High impact information on DOM

  • We also find that zebra mussels absorb some dissolved metals that have been complexed by the DOM; although absorption of dissolved selenium was unaffected by DOC, absorption of dissolved cadmium, silver and mercury by the mussels increased 32-, 8.7- and 3.6-fold, respectively, in the presence of high-molecular-weight DOC [9].
  • DOM is the unique SRCAP homolog in Drosophila melanogaster [10].
  • In DOM males, c-fos expression was elevated within the supraoptic nucleus of the hypothalamus [11].
  • Metergoline pretreatment shifted the LSD and DMT dose-response curves for pausing to the right by a factor of 2--3, but shifted the DOM and mescaline dose-response patterns to a much greater extent [12].
  • Injection of 5,7-DHT into the medial forebrain bundle at the hypothalamic level slightly potentiated LSD, attenuated DOM, and did not affect the pausing produced by mescaline [12].

Chemical compound and disease context of DOM

  • To assess the relation between urinary endogenous sex steroid levels and the risk of postmenopausal breast cancer, a nested case-cohort study was conducted within a large cohort (the DOM cohort) in the Netherlands (n=9,349) [13].
  • Chronic spinal dogs treated chronically with LSD became tolerant to its ability to produce mydriasis, tachycardia, tachypnea and hyperreflexia, and were cross tolerant to the ability of tryptamine, psilocin, mescaline, DMT, DOM and DOB to produce these same effects [14].
  • For example, in tests of stimulus generalization, neither a (+)amphetamine stimulus nor a DOM stimulus generalized to PMMA [15].

Biological context of DOM

  • Taken together, these data implicate SRCAP and DOM in developmental gene activation [10].
  • The associations of body fat and body fat distribution with breast cancer risk were examined in a prospective study in 9,746 post-menopausal women with a natural menopause, aged 49-66 at intake, participating in a breast cancer screening project (the DOM project in Utrecht) [4].
  • These results were compared and contrasted to the behavioral profiles previously established for hallucinogenic compounds such as LSD and DOM, the psychoactive properties of which have been suggested to be mediated by 5HT-2 binding sites [16].
  • From these data, IC50 values were determined for the inhibition of the LSD-appropriate responding elicited by either 0.1 mg/kg LSD (15-min pretreatment time) or 0.4 mg/kg (-)DOM (75-min pretreatment) [17].
  • Although the XML can be read and manipulated using DOM or SAX parsers, one loses the convenience and usability of an object oriented programming paradigm. caBIONet is a set of .NET wrapper classes (managers, genes, chromosomes, sequences, etc.) capable of serializing the XML data stream into local .NET objects [18].

Anatomical context of DOM

  • Breast-cancer incidence in relation to height, weight and body-fat distribution in the Dutch "DOM" cohort [19].
  • It has been reported that hallucinogens such as LSD, DOM, and DOI can block the neurotoxic effects of NMDA antagonists, possibly by activating inhibitory 5-HT2A receptors on GABAergic interneurons that normally inhibit glutamatergic projections to the retrosplenial and cingulate cortexes [20].
  • In choroid plexus, DOM and LSD stimulated phosphoinositide hydrolysis and both responses were blocked by mianserin and less effectively by spiperone [21].
  • The cohort consisted of 5577 women aged 55-70 years from the DOM project, a population based breast cancer screening program in the Netherlands. Instrumental Neutron Activation Analysis was used to measure the selenium content of toenail clippings [22].
  • The rank order of potency for the physiological effects of three phenethylamine hallucinogens in the locus coeruleus (LC) was identical to that previously shown for their 5-HT2 binding affinity [-) DOB greater than DOM greater than ( + )DOB) [23].

Associations of DOM with other chemical compounds

  • As such, (a) it would appear that the DOM stimulus is primarily a 5-HT2-mediated, and not 5-HT1C-mediated, phenomenon, and (b) compound 26 may find application in other pharmacologic investigations where spiperone may not be a suitable antagonist [24].
  • These results suggest that quipazine and lisuride substitute for the stimulus properties of the phenylalkglamine hallucinogen (-)DOM via agonist activity at 5-HT2A receptors [25].
  • 2. Intrathecal injection of 5-MeODMT or DOM produced dose-related back muscle contractions (a previously undocumented behaviour) and wet-dog shakes which were both markedly attenuated by ritanserin pretreatment (1 mg kg-1, i.p.) indicating the involvement of 5-HT2 receptors [26].
  • Tryptamine produces pharmacologic effects in man and the chronic spinal dog which are similar to those produced by LSD, mescaline, psilocin, DMT, DOM and DOB [14].
  • By use of dialysis we showed that DOM did not interfere with the HPLC analysis of free TNT [27].

Gene context of DOM

  • Concentrations of IGF-I and IGFBP-3 (determined by ligand blot analysis) in FFL from both DOM and SUB were lower (p < 0.05) in GRFi than in HSAi cows [28].
  • Certain 4-substituted 1-(2,5-dimethoxyphenyl)-2-aminopropanes such as DOM (4-methyl), DOB (4-bromo), and DOI (4-iodo) appear to be 5-HT2-selective agonists and serve as effective training drugs in rats [29].
  • Consistent with these results, stimulus generalization occurs with 5 both in rats trained to discriminate 8-OH-DPAT from saline and in rats trained to discriminate the 5-HT2 agonist DOM from saline [30].
  • In contrast, IGFBP-2 in FFL was elevated in SUB, but not DOM, in GRFi compared to HSAi cows.(ABSTRACT TRUNCATED AT 400 WORDS)[28]
  • The selected L. acidophilus DOM La strain carries a mutated thyA gene and has an obligate requirement for thymidine [31].

Analytical, diagnostic and therapeutic context of DOM


  1. Evaluation of screening for breast cancer in a non-randomised study (the DOM project) by means of a case-control study. Collette, H.J., Day, N.E., Rombach, J.J., de Waard, F. Lancet (1984) [Pubmed]
  2. Interaction among SOX10, PAX3 and MITF, three genes altered in Waardenburg syndrome. Bondurand, N., Pingault, V., Goerich, D.E., Lemort, N., Sock, E., Caignec, C.L., Wegner, M., Goossens, M. Hum. Mol. Genet. (2000) [Pubmed]
  3. DNA fusion vaccines induce epitope-specific cytotoxic CD8(+) T cells against human leukemia-associated minor histocompatibility antigens. Rice, J., Dunn, S., Piper, K., Buchan, S.L., Moss, P.A., Stevenson, F.K. Cancer Res. (2006) [Pubmed]
  4. A prospective study on obesity and subcutaneous fat patterning in relation to breast cancer in post-menopausal women participating in the DOM project. den Tonkelaar, I., Seidell, J.C., Collette, H.J., de Waard, F. Br. J. Cancer (1994) [Pubmed]
  5. Rapid N-acetyltransferase 2 imputed phenotype and smoking may increase risk of colorectal cancer in women (Netherlands). van der Hel, O.L., Bueno de Mesquita, H.B., Sandkuijl, L., van Noord, P.A., Pearson, P.L., Grobbee, D.E., Peeters, P.H. Cancer Causes Control (2003) [Pubmed]
  6. 5-HT1 and 5-HT2 binding characteristics of 1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane analogues. Glennon, R.A., McKenney, J.D., Lyon, R.A., Titeler, M. J. Med. Chem. (1986) [Pubmed]
  7. Behavioral and neuropharmacological analysis of amphetamine and 2,5-dimethoxy-4-methylamphetamine in rats. Tilson, H.A., Baker, T.G., Chamberlain, J.H. Psychopharmacologia. (1975) [Pubmed]
  8. The impact of moderate daily alcohol consumption on aggression and the formation of dominance hierarchies in rats. Duncan, E.A., Tamashiro, K.L., Nguyen, M.M., Gardner, S.R., Woods, S.C., Sakai, R.R. Psychopharmacology (Berl.) (2006) [Pubmed]
  9. Uptake of dissolved organic carbon and trace elements by zebra mussels. Roditi, H.A., Fisher, N.S., Sañudo-Wilhelmy, S.A. Nature (2000) [Pubmed]
  10. Human SRCAP and Drosophila melanogaster DOM are homologs that function in the notch signaling pathway. Eissenberg, J.C., Wong, M., Chrivia, J.C. Mol. Cell. Biol. (2005) [Pubmed]
  11. Social stress in hamsters: defeat activates specific neurocircuits within the brain. Kollack-Walker, S., Watson, S.J., Akil, H. J. Neurosci. (1997) [Pubmed]
  12. Neurotransmitter basis of the behavioral effects of hallucinogens. Rech, R.H., Commissaris, R.L. Neuroscience and biobehavioral reviews. (1982) [Pubmed]
  13. Urinary endogenous sex hormone levels and the risk of postmenopausal breast cancer. Onland-Moret, N.C., Kaaks, R., van Noord, P.A., Rinaldi, S., Key, T., Grobbee, D.E., Peeters, P.H. Br. J. Cancer (2003) [Pubmed]
  14. Relationship of CNS tryptaminergic processes and the action of LSD-like hallucinogens. Martin, W.R., Sloan, J.W. Pharmacol. Biochem. Behav. (1986) [Pubmed]
  15. Initial characterization of PMMA as a discriminative stimulus. Glennon, R.A., Young, R., Dukat, M., Cheng, Y. Pharmacol. Biochem. Behav. (1997) [Pubmed]
  16. Effects of 5HT-1A agonists on locomotor and investigatory behaviors in rats differ from those of hallucinogens. Mittman, S.M., Geyer, M.A. Psychopharmacology (Berl.) (1989) [Pubmed]
  17. The role of the 5-HT2A and 5-HT2C receptors in the stimulus effects of hallucinogenic drugs. I: Antagonist correlation analysis. Fiorella, D., Rabin, R.A., Winter, J.C. Psychopharmacology (Berl.) (1995) [Pubmed]
  18. caBIONet--A .NET wrapper to access and process genomic data stored at the National Cancer Institute's Center for Bioinformatics databases. Kraj, P., McIndoe, R.A. Bioinformatics (2005) [Pubmed]
  19. Breast-cancer incidence in relation to height, weight and body-fat distribution in the Dutch "DOM" cohort. Kaaks, R., Van Noord, P.A., Den Tonkelaar, I., Peeters, P.H., Riboli, E., Grobbee, D.E. Int. J. Cancer (1998) [Pubmed]
  20. Antagonism of a PCP drug discrimination by hallucinogens and related drugs. West, W.B., Lou, A., Pechersky, K., Chachich, M.E., Appel, J.B. Neuropsychopharmacology (2000) [Pubmed]
  21. Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis. Sanders-Bush, E., Burris, K.D., Knoth, K. J. Pharmacol. Exp. Ther. (1988) [Pubmed]
  22. Selenium and the risk of postmenopausal breast cancer in the DOM cohort. van Noord, P.A., Maas, M.J., van der Tweel, I., Collette, C. Breast Cancer Res. Treat. (1993) [Pubmed]
  23. Phenethylamine hallucinogens in the locus coeruleus: potency of action correlates with rank order of 5-HT2 binding affinity. Rasmussen, K., Glennon, R.A., Aghajanian, G.K. Eur. J. Pharmacol. (1986) [Pubmed]
  24. Antagonism of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane stimulus with a newly identified 5-HT2- versus 5-HT1C-selective antagonist. Ismaiel, A.M., De Los Angeles, J., Teitler, M., Ingher, S., Glennon, R.A. J. Med. Chem. (1993) [Pubmed]
  25. Role of 5-HT2A and 5-HT2C receptors in the stimulus effects of hallucinogenic drugs. II: Reassessment of LSD false positives. Fiorella, D., Rabin, R.A., Winter, J.C. Psychopharmacology (Berl.) (1995) [Pubmed]
  26. Involvement of 5-HT2 receptors in the behaviours produced by intrathecal administration of selected 5-HT agonists and the TRH analogue (CG 3509) to rats. Fone, K.C., Johnson, J.V., Bennett, G.W., Marsden, C.A. Br. J. Pharmacol. (1989) [Pubmed]
  27. Binding of 2,4,6-trinitrotoluene and its degradation products in a soil organic matter two-phase system. Eriksson, J., Skyllberg, U. J. Environ. Qual. (2001) [Pubmed]
  28. Effect of somatotropin and/or equine chorionic gonadotropin on serum and follicular insulin-like growth factor I and insulin-like growth factor binding proteins in cattle. Stanko, R.L., Cohick, W.S., Shaw, D.W., Harvey, R.W., Clemmons, D.R., Whitacre, M.D., Armstrong, J.D. Biol. Reprod. (1994) [Pubmed]
  29. Site-selective serotonin agonists as discriminative stimuli. Glennon, R.A. Psychopharmacology series. (1988) [Pubmed]
  30. N,N-di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin. Glennon, R.A., Titeler, M., Lyon, R.A., Slusher, R.M. J. Med. Chem. (1988) [Pubmed]
  31. Development of a chromosome-plasmid balanced lethal system for Lactobacillus acidophilus with thyA gene as selective marker. Fu, X., Xu, J.G. Microbiol. Immunol. (2000) [Pubmed]
  32. Cumulative genetic defects in carcinogen metabolism may increase breast cancer risk (The Netherlands). van der Hel, O.L., Bueno-de-Mesquita, H.B., van Gils, C.H., Roest, M., Slothouber, B., Grobbee, D.E., Peeters, P.H. Cancer Causes Control (2005) [Pubmed]
  33. Fat distribution in relation to age, degree of obesity, smoking habits, parity and estrogen use: a cross-sectional study in 11,825 Dutch women participating in the DOM-project. den Tonkelaar, I., Seidell, J.C., van Noord, P.A., Baanders-van Halewijn, E.A., Ouwehand, I.J. International journal of obesity. (1990) [Pubmed]
  34. Dissolved organic matter in pore water of freshwater sediments: effects of separation procedure on quantity, quality and functionality. Akkanen, J., Lyytikäinen, M., Tuikka, A., Kukkonen, J.V. Chemosphere (2005) [Pubmed]
  35. The relationship between fat distribution and some chronic diseases in 11,825 women participating in the DOM-project. van Noord, P.A., Seidell, J.C., den Tonkelaar, I., Baanders-van Halewijn, E.A., Ouwehand, I.J. International journal of epidemiology. (1990) [Pubmed]
  36. Metal distribution and binding in balneological peats and their aqueous extracts. Burba, P., Beer, A.M., Lukanov, J. Fresenius' journal of analytical chemistry. (2001) [Pubmed]
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