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approved demethylating agents for the treatment of solid tumors which can be a focus of research in the future. Treatment utilizing demethylating agents can
Demethylating_agent
Drug type for epigenetic therapy
A hypomethylating agent (or demethylating agent) is a drug that inhibits DNA methylation: the modification of DNA nucleotides by addition of a methyl
Hypomethylating_agent
Local anesthetic drug
qualities that put it at risk for abuse. Procaine is also a DNA-demethylating agent with growth-inhibitory effects in human cancer cells. A 1% procaine
Procaine
Biological process
contributes to the atherosclerotic lesion. An ex vivo experiment using the demethylating agent Decitabine (5-aza-2 -deoxycytidine) was shown to induce MCT3 expression
DNA_methylation
American physician
Fraga, MF; Espada, J; Esteller, M (Aug 15, 2003). "Procaine is a DNA-demethylating agent with growth-inhibitory effects in human cancer cells". Cancer Research
Peter_DeMarco
Human gene
by promoter DNA methylation in gastric cancer. Treatment with a demethylating agent restored its expression in cancer cells, and methylation of ZNF559
ZNF559
Substance that blocks the removal of methyl groups
by preventing DNA methylation. DNA methylation DNA demethylation Demethylating agent Vanden Bossche, H. (1992). "Inhibitors of P450-dependent steroid
Demethylation_inhibitor
Negative regulation (or limiting) of body weight and cell proliferation
neighboring gene on chromosome 11, increases. Cells treated with Azad, a demethylating agent, grow much slower than cells cultured in the absence of Azad. At
H19_(gene)
Field of study in cancer research
levels from cancer cell lines before and after treatment with a demethylating agent Since bisulfite sequencing is considered the gold standard for measuring
Cancer_epigenetics
Chemical compound
shown that halomon and a related halogenated monoterpene may act as demethylating agents, suggesting a possible mechanism of action for the pharmacological
Halomon
Protein-coding gene in the species Homo sapiens
in Human Placenta and Fetal Membranes by lipopolysaccharide and demethylating agent 5-aza-2'-deoxycytidine". Reproductive Biology and Endocrinology.
TIMP1
Chemical compound
Lübbert M, Silverman LR (January 2014). "Clinical development of demethylating agents in hematology". The Journal of Clinical Investigation. 124 (1): 40–6
Azacitidine
Protein-coding gene in humans
The effect of DNA demethylation is evident by the capability of demethylating agents, such as 5-aza-2-deoxycytidine, to induce CTAs re-expression in tumour
CTAG1B
Protein-coding gene in humans
Imazeki F, et al. (2007). "Methylation status of genes upregulated by demethylating agent 5-aza-2'-deoxycytidine in hepatocellular carcinoma". Oncology. 71
CSRP1
Protein-coding gene in the species Homo sapiens
lines (SCC8, SCC11B, SCC17AS, SCC22B, and SCC25) with the CpG site-demethylating agent, 5-aza-2′-deoxycytidine, increased the levels of SMCT1 mRNA in all
Sodium-coupled monocarboxylate transporter 1
Sodium-coupled_monocarboxylate_transporter_1
Protein-coding gene in the species Homo sapiens
efficiency of epigenetic regulating molecules. For example, Zebularine, a demethylating agent, could be used to remove the methyl groups from the CpGs of the dlc1
DLC1
Chemical compound
be used to make Norethisterone & Allylestrenol. With a suitable demethylating agent can be used to make estrone. Clomestrone Prenortestosterone [1089-78-7]
Estrone_methyl_ether
1994. " Expression of the MAGE1 tumor antigen is upregulated by the demethylating agent 5-aza-2'-deoxycytidine ". Cancer Research. 54(7): 1766-1771. De Smet
Tumor antigens recognized by T lymphocytes
Tumor_antigens_recognized_by_T_lymphocytes
Protein-coding gene
could be restored by treating HPV-positive cervical cell lines with demethylating agents like 5-aza-2'-deoxycytidine. IFN-κ reactivation may be a useful therapeutic
IFNK
Class of drugs used to treat malignant tumors
Antineoplastic agents, also known as anticancer drugs or antineoplastic drugs, are medications used to treat malignant tumors. These drugs work through
Antineoplastic
Form of dynamic modification
silencing with synergistic combination of HDAC inhibitors or HDI and DNA-demethylating agents. HDIs are primarily used as adjunct therapy in several cancer types
Chromatin_remodeling
Hallucinogenic class of psychoactive drug
O-demethylation of the methyl phenyl ether groups. All three possible O-demethylated metabolites, compounds 118-120, have been characterized in rabbit liver
Psychedelic_drug
Chemical compound
as demethylating reagent. For example, treatment with 7-methylguanosine gives guanosine. Other N-methylated nucleosides in tRNA are not demethylated by
Tert-Butylthiol
Chemical compound
available and is a strong Lewis acid. It is an excellent demethylating or dealkylating agent for the cleavage of ethers, also with subsequent cyclization
Boron_tribromide
Movement of an organism or entity in response to a chemical stimulus
methylation of the MCPs will increase (because CheB-P is not present to demethylate). The MCPs no longer respond to the attractant when they are fully methylated;
Chemotaxis
Pharmaceutical compound
properties. Like tyramine, hordenine acts as a norepinephrine releasing agent. As of September 2012[update], hordenine is widely sold as an ingredient
Hordenine
Chemical compound
hydroxylase activity. THA was studied clinically as an antihypertensive agent but was never marketed. The drug did not produce hallucinogenic effects
2,4,5-Trihydroxyamphetamine
Chemical compound
psychedelic drug of the methylenedioxyphenethylamine family. It is the α-demethylated homologue of MMDA, and is also closely related to mescaline (3,4
Lophophine
Chemical compound
duration than indatraline because norindatraline is inactive, whereas demethylating N-methylindatraline does not terminate the actions of the parent compound
Indatraline
Quaternary ammonium cation
some protoberberine alkaloids in plants. Heating at 190 °C, berberine demethylates, giving berberrubine. Alkylation of the resulting zwitterion gives access
Berberine
Use of epigenome-influencing techniques to treat medical conditions
complement exposure therapy by targeting BDNF-related pathways, such as demethylating the BDNF gene promoter or altering histone acetylation patterns to facilitate
Epigenetic_therapy
Organic dye
C6H5CH(C6H4N(CH3)2)2 + HCl + ½ O2 → [C6H5C(C6H4N(CH3)2)2]Cl + H2O A typical oxidizing agent is manganese dioxide. Hydrolysis of MG gives an alcohol: [C6H5C(C6H4N(CH3)2)2]Cl
Malachite_green
Class of drugs
aromatized. AAS that are 17α-alkylated (and not also 4,5α-reduced or 19-demethylated) are also aromatized but to a lesser extent than is testosterone. However
Anabolic_steroid
Therapeutic use of norepinephrine
is a substituted phenethylamine and catecholamine. It is the N-demethylated analogue of epinephrine (adrenaline; 3,4,β-trihydroxy-N-methylphenethylamine)
Norepinephrine_(medication)
Pharmaceutical compound
compared to MDMA and (R)-MDMA. It is possible that MDDMA could be partially demethylated into MDMA. However, based on (R)-MDDMA and (R)-MDMA having very different
MDDMA
Central nervous system stimulant
classes and as a drug acts as a serotonin–norepinephrine–dopamine releasing agent. It is related to the other dimethylphenethylamines as a positional isomer
Methamphetamine
Opioid analgesic
phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Eisleb, its analgesic properties were first recognized
Pethidine
Compounds that damage or destroy monoaminergic neurons
5-DDM-DOM 5-Hydroxyindoleacetaldehyde (5-HIAL) RHPP+ RHPTP Monoamine-depleting agent Kostrzewa RM (2022). "Survey of Selective Monoaminergic Neurotoxins Targeting
Monoamine_neurotoxin
Chemical compound
7-methylxanthine by demethylation of the N1 position, which is subsequently demethylated into xanthine or oxidized by CYP2A6 and CYP1A2 into 1,7-dimethyluric
Paraxanthine
Psychoactive drug, often called ecstasy
low purity due to bulking agents that are added to dilute the drug and increase profits (notably lactose) and binding agents. Tablets sold as ecstasy sometimes
MDMA
Antibiotic medication
about 50%. It is primarily metabolized into 9-hydroxyminocycline. Two N-demethylated metabolites are also formed. The rest is predominantly excreted into
Minocycline
Synthetic decongestant
effects than others. Pseudoephedrine acts as a norepinephrine releasing agent, indirectly activating adrenergic receptors. As such, it is an indirectly
Pseudoephedrine
Chemical compound
in plants. Syringic acid can be prepared by selectively hydrolyzing (demethylating) eudesmic acid with 20% sulfuric acid. Syringic acid can be found in
Syringic_acid
Chemical compound
formaldehyde, hydrogen peroxide, and the product N-H terminus. LSD1 cannot demethylate H3K4 trimethyl (N-tri-methyl-lysine) because the initial iminium species
Bomedemstat
Pharmaceutical compound
O-demethylation of the methyl phenyl ether groups. All three possible O-demethylated metabolites, compounds 118-120, have been characterized in rabbit liver
2,5-Dimethoxy-4-methylamphetamine
2,5-Dimethoxy-4-methylamphetamine
Pharmacology of the antiparkinsonian and antidepressant selegiline
levoamphetamine, selegiline acts as a weak norepinephrine and/or dopamine releasing agent. The clinical significance of this action is unclear, but it may be relevant
Pharmacology_of_selegiline
Chemical compound
extent, CYP1A2, CYP2D6, CYP2C9, and CYP2C19. The main metabolite, N-demethylated piperazine derivative, is also active. The major route of elimination
Imatinib
Pharmaceutical compound
TAAR1. In terms of metabolism, TMA-2 is known to be at least partially O-demethylated in animals in vivo. It might produce 2,4,5-trihydroxyamphetamine (THA)
2,4,5-Trimethoxyamphetamine
Study of how diet changes gene expression
tea and genistein from soybeans can inhibit DNA methyltransferases, demethylating DNA and activating previously silenced genes. These compounds are being
Nutritional_epigenetics
Appetite suppressant
monohydrate salt.[citation needed] Sibutramine and its two active N-demethylated metabolites may be measured in biofluids by liquid chromatography-mass
Sibutramine
Chemical compound
norbaeocystin (4-PO-T), and aeruginascin (4-PO-TMT). The compound is the N-demethylated derivative of psilocybin and the 4-phosphorylated derivative of norpsilocin
Baeocystin
Tricyclic antidepressant medication
Asendin among others, is a tricyclic antidepressant (TCA). It is the N-demethylated metabolite of loxapine. Amoxapine first received marketing approval in
Amoxapine
Chemical compound
leonurine-10-O-β-D-glucuronide (the glucuronide metabolite of leonurine) and an O-demethylated leonurine analog that has not yet had its structure definitively confirmed
Leonurine
Pharmaceutical compound
active metabolite of DOM in animals. The drug is one of two possible O-demethylated analogues and metabolites of DOM, the other being 5-DM-DOM (5-O-desmethyl-DOM;
2-DM-DOM
Chemical compound of RNA
In DNA, the uracil nucleobase is replaced by thymine (T). Uracil is a demethylated form of thymine. Uracil is a common and naturally occurring pyrimidine
Uracil
Irreversible non-selective MAO inhibitor and antidepressant drug
pressure monitoring are advised. Other stimulants or wakefulness-promoting agents, such as methylphenidate, modafinil, and bupropion, are not automatically
Tranylcypromine
Semi-synthetic opioid
strong as morphine. Dihydrocodeine (DHC) is O-demethylated into dihydromorphine (DHM) by CYP2D6 and N-demethylated into nordihydrocodeine (NDHC) by CYP3A4,
Dihydrocodeine
Cellular mechanism
recruits TET1 to the 8-OHdG lesion (see Figure). This allows TET1 to demethylate an adjacent methylated cytosine. Demethylation of cytosine is an epigenetic
DNA_repair
Synthetic opioid pain medication
the cytochrome P450 isozyme CYP2B6, CYP2D6, and CYP3A4, being O- and N-demethylated to five different metabolites. Of these, desmetramadol (O-desmethyltramadol)
Tramadol
Chemical compound
make all 8 stereoisomers of the phenyltropane paroxetine homolog. N-demethylating the S-α,β (1S,2S,3R) isomer resulted in a 54-fold increase in DAT IC50
RTI-274
Psychedelic drug
creation of a quaternary ammonium salt, which is then dequaternized (demethylated) in ethanolamine to yield DMT. The same two-step procedure is used to
Dimethyltryptamine
Protein in E. coli
alkylation damage to single stranded (SS) DNA caused by SN2 type of chemical agents. It efficiently removes methyl groups from 1-methyl adenines, 3-methyl cytosines
AlkB
Medication, stimulant and decongestant
Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent low blood pressure during anesthesia. It has
Ephedrine
Group of stereoisomers
eye examinations. Hydroxyamfetamine acts as a norepinephrine releasing agent and hence is an indirectly acting sympathomimetic. It is a substituted phenethylamine
4-Hydroxyamphetamine
White blood cells of the immune system
certain region within the FOXP3 gene (TSDR, Treg-specific-demethylated region) is found demethylated, which allows to monitor Treg cells through a PCR reaction
Regulatory_T_cell
Protein-coding gene in the species Homo sapiens
KDM1A gene. LSD1 is a flavin-dependent monoamine oxidase, which can demethylate mono- and di-methylated lysines, specifically histone 3, lysine 4 (H3K4)
KDM1A
Pharmaceutical compound
cyclizes to the iminoquinone. 2,5-DDM-DOM has been found to be an alkylating agent and a potent neurotoxin similarly to 6-hydroxydopamine. 2,5-DDM-DOM and
2,5-DDM-DOM
Study of DNA modifications that do not change its sequence
recruits the demethylating enzyme TET1 to an association, and brings TET1 to about 600 locations on the genome where TET1 can then demethylate and activate
Epigenetics
Chemical compound found in some species of mushrooms
(ALP) and non-specific esterases in tissues and fluids. Psilocin is demethylated and oxidatively deaminated by monoamine oxidase (MAO), specifically monoamine
Psilocybin
Pharmaceutical compound
psychedelic 2C-B (2,5-dimethoxy-4-bromophenethylamine). It is the 2-O-demethylated analogue of 2C-B. The drug is a potent agonist of the serotonin 5-HT2A
2-OH-2C-B
Monoamine oxidase inhibitor; racemic form of rasagiline
racemic N-methyl analogue of rasagiline) Desmethylselegiline (DMS; the N-demethylated analogue of selegiline) Finberg JP (February 2020). "The discovery and
AGN-1135
Chemical compound
is undergoing clinical trials. Norketotifen is a biologically active demethylated metabolite of ketotifen and has a similar potency as ketotifen as an
Norketotifen
Blue dye also used as a medication
in the thesis of Dr. D. L. Romanowsky in the 1890s), it gets serially demethylated and forms all the tri-, di-, mono- and non-methyl intermediates, which
Methylene_blue
Opioid analgesic
opioid analgesic and the main active metabolite of tramadol. Tramadol is demethylated by the liver enzyme CYP2D6 to desmetramadol in the same way as codeine
Desmetramadol
Chemical compound
Pseudophenmetrazine is a psychostimulant of the phenylmorpholine group. It is the N-demethylated and cis-configured analogue of phendimetrazine as well as the cis-configured
Pseudophenmetrazine
Mammalian protein found in humans
in the formal +3 valence state (Cob(III)-Me). The cobalamin is then demethylated by zinc-activated thiolate homocysteine, generating methionine and reducing
Methionine_synthase
Principal psychoactive metabolite of the oneirogen ibogaine
serotonin releasing agent, although findings are conflicting and other studies have found that it is inactive as a serotonin releasing agent. As with ibogaine
Noribogaine
Gene regulation in autoimmune diseases
proteins, more specifically the TET1-TET3 enzymes and TET2 in T cells can demethylate DNA which helps to set and clarify the early stages of RA. The RA development
Epigenetics of autoimmune disorders
Epigenetics_of_autoimmune_disorders
of the threo diastereoisomer. Also of note is that methylphenidate in demethylated form is acidic; a metabolite (and precursor) known as ritalinic acid
List of methylphenidate analogues
List_of_methylphenidate_analogues
Pharmaceutical compound
hypolocomotion. Earlier reports had stated that 5-MeO-NMT and its N-demethylated analogue 5-methoxytryptamine were inactive, but this proved not to be
5-MeO-NMT
Chemical compound
derived from ferulic acid are called ferulates. Ferulic acid is a reducing agent. The double bond in the side chain is subjected to cis–trans isomerization
Ferulic_acid
Chemical compound
discontinued worldwide by 2007. Pargyline is used as an antihypertensive agent in the treatment of hypertension (high blood pressure). The dosage was 12
Pargyline
Chemical compound
8-oxo-dG is an important first step. TET1 is a key enzyme involved in demethylating 5mCpG. However, TET1 is only able to act on 5mCpG if an ROS has first
8-Oxo-2'-deoxyguanosine
Anabolic steroid
phenylpropionate ester of nandrolone (19-nortestosterone), which itself is the 19-demethylated analogue of testosterone. NPP was first described in 1957 and was introduced
Nandrolone_phenylpropionate
Pharmaceutical compound
California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "The demethylated homologue of BOH is BOHH, and is the methylenedioxy analogue of norepinephrine
BOHH
Toxic mercury cation
blood. Methylmercury salts along with dimethylmercury are the causative agents of the infamous Minamata disease. Methylmercury is designated as a "priority
Methylmercury
Chemical compound
triazoles inhibits the enzyme cytochrome P-450, so it can no longer demethylate lanosterol, an intermediate needed in ergosterol synthesis. In fish,
Cyproconazole
Antidepressant
been marketed. The drug is a tertiary amine TCA, with its side chain-demethylated metabolite northiaden (desmethyldosulepin) being a secondary amine. Other
Dosulepin
Hypnotic medication
if any advantages in efficacy or tolerability in elderly persons. Newer agents such as the melatonin receptor agonists may be more suitable and effective
Zopiclone
Recreational drug
mephedrone is thought to be metabolised by three phase 1 pathways. It can be demethylated to the primary amine (producing compounds 2, 3 and 5), the ketone group
Mephedrone
Chemical compound and essential nutrient
transporters that occur within the kidneys (see transport). Trimethylglycine is demethylated in the liver and kidneys to dimethylglycine (tetrahydrofolate receives
Choline
Sedating antidepressant
measures to prevent respiratory aspiration is also advisable. Antiarrhythmic agents may be an appropriate measure to treat cardiac arrhythmias resulting from
Doxepin
Process of copying a segment of DNA into RNA
TET1 enzymes to EGR1 binding sites in promoters, the TET enzymes can demethylate the methylated CpG islands at those promoters. Upon demethylation, these
Transcription_(biology)
Chemical compound
SoRI-20041 See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators
NS-2359
Chemical compound
potassium hydroxide, giving 2-acetyl-7-methoxybenzofuran (3), which was demethylated using hydrobromic acid. Reichl S, Müller-Goymann CC (January 2003). "The
Befunolol
Medication used in treatment of migraines
doi:10.1208/s12248-008-9028-5. PMC 2751378. PMID 18454322. [...] the N-demethylated metabolites from zolmitriptan and eletriptan are both active at the 5-HT1B/1D
Zolmitriptan
Pharmaceutical compound
active metabolite of DOM in animals. The drug is one of two possible O-demethylated analogues and metabolites of DOM, the other being 2-DM-DOM (2-O-desmethyl-DOM;
5-DM-DOM
Chemical compound
SoRI-20041 See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators
Tesofensine
Chemical compound
serotonin 5-HT2A receptor. Norbaeocystin is an N-demethylated derivative of baeocystin (itself an N-demethylated derivative of psilocybin), and a phosphorylated
Norbaeocystin
Class of drugs
non-selective adenosine receptor antagonist. It is also an anti-asthmatic agent and a demethylated metabolite of caffeine. Small open-label trials suggest that theophylline
Adenosine A2A receptor antagonist
Adenosine_A2A_receptor_antagonist
DEMETHYLATING AGENT
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