MW 169.65 Da, Purity >97%. Irreversible monoamine oxidase (MAO) inhibitor. Increases serotonergic, noradrenergic activity and augments dopamine transmission. Additionally inhibits LSD1 (BHC110), inhibiting histone demethylation (IC50 = >50 μM). Anticonvulsant and antidepressant.
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Key facts
- CAS number
- 1986-47-6
- Purity
- > 97%
- Form
- Solid
- Molecular weight
- 169.65 Da
- Molecular formula
- C9H12ClN
- PubChem identifier
- 2723716
- Nature
- Synthetic
Alternative names
AOF1, AOF2, Amine oxidase (flavin containing), Amine oxidase (flavin containing) A, Amine oxidase (flavin containing) B, Amine oxidase (flavin containing) domain 2, Amine oxidase, flavin containing, 2, BHC110, BRAF35-HDAC complex protein BHC110, BRAF35/HDAC complex, 110-kD subunit, C6orf193, CPRF, EC1, FAD-binding protein BRAF35-HDAC complex, 110 kDa subunit, FLJ33898, FLJ34109, FLJ43328, Flavin-containing amine oxidase domain-containing protein 1, Flavin-containing amine oxidase domain-containing protein 2, KDM 1, KDM1A_HUMAN, KDM1B_HUMAN, KIAA0601, LSD 1, LSD2, Lysine (K) specific demethylase 1, Lysine (K) specific demethylase 1A, Lysine demethylase 1A, Lysine-specific demethylase 1, Lysine-specific demethylase 1A, Lysine-specific demethylase 2, Lysine-specific histone demethylase 1, Lysine-specific histone demethylase 1A, Lysine-specific histone demethylase 1B, Lysine-specific histone demethylase 2, MAO, MAO-A, MAO-B, Monoamine oxidase, Monoamine oxidase A, Monoamine oxidase B, Monoamine oxidase type A, Monoamine oxidase type B, TA1, TAAR1_HUMAN, TaR-1, Trace amine receptor 1, Trace amine-associated receptor 1, Trar1, amine oxidase (flavin containing) domain 1, amine oxidase, flavin containing 1, bA204B7.3, dJ298J15.2, lysine (K)-specific demethylase 1B
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MW 169.65 Da, Purity >97%. Irreversible monoamine oxidase (MAO) inhibitor. Increases serotonergic, noradrenergic activity and augments dopamine transmission. Additionally inhibits LSD1 (BHC110), inhibiting histone demethylation (IC50 = >50 μM). Anticonvulsant and antidepressant.
Key facts
- CAS number
- 1986-47-6
- Purity
- > 97%
- Form
- Solid
- Molecular weight
- 169.65 Da
- Molecular formula
- C9H12ClN
- PubChem identifier
- 2723716
- Nature
- Synthetic
- Solubility
Soluble in water to 100 mM.
- Biochemical name
- Tranylcypromine hydrochloride
- Biological description
Irreversible monoamine oxidase (MAO) inhibitor. Increases serotonergic, noradrenergic activity and augments dopamine transmission. Additionally inhibits LSD1 (BHC110), inhibiting histone demethylation (IC50 = >50 μM). Anticonvulsant and antidepressant.
- Canonical SMILES
- C1C(C1N)C2=CC=CC=C2.Cl
- Isomeric SMILES
- C1[C@H]([C@@H]1N)C2=CC=CC=C2.Cl
- InChI
- InChI=1S/C9H11N.ClH/c10-9-6-8(9)7-4-2-1-3-5-7;/h1-5,8-9H,6,10H2;1H/t8-,9+;/m0./s1
- InChIKey
- ZPEFMSTTZXJOTM-OULXEKPRSA-N
- IUPAC name
- (1R,2S)-2-phenylcyclopropan-1-amine;hydrochloride
Storage
- Shipped at conditions
- Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
- +4°C
- Appropriate long-term storage conditions
- +4°C
- Storage information
- Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary info
- This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
Monoamine oxidase A and B (MAO-A and MAO-B) are enzymes that play a role in the oxidative deamination of monoamines with alternate names such as MAO-A and MAO-B. They have a mass of approximately 60 kDa and are found in various tissues including the brain liver and intestines. These enzymes contribute to the metabolic breakdown of neurotransmitters such as serotonin dopamine and norepinephrine. TAAR1 also known as Trace amine-associated receptor 1 is a receptor expressed in the central nervous system and peripheral tissues responding to endogenous trace amines. KDM1 also called LSD1 (Lysine-specific demethylase 1) and LSD2 or AOF1 are enzymes involved in histone demethylation important for chromatin remodeling and gene expression regulation. Both LSD1 and LSD2 are expressed in multiple tissues including the brain and reproductive organs.
- Biological function summary
Monoamine oxidases and TAAR1 are important for the modulation of neurotransmitter systems and maintain amine homeostasis. These proteins lack complex formation impacting neurotransmitter levels differently. KDM1/LSD1 and LSD2/AOF1 function to remove methyl groups from lysine residues on histones affecting gene expression patterns thereby modifying transcriptional programs. In their role in chromatin demethylation they contribute to the regulation of several essential genes across various tissues.
- Pathways
Monoamine oxidases play a critical part in the catabolic pathways related to neurotransmitter degradation such as the serotonin and dopamine pathways. In these pathways they have intersections with other proteins like the catechol-O-methyltransferase (COMT). TAAR1 links to the signal transduction pathways that modulate intracellular cAMP levels. KDM1/LSD1 and LSD2 take part in the histone modification pathway which holds importance in transcription regulation and has connections to proteins like histone deacetylases (HDACs).
- Associated diseases and disorders
Monoamine oxidases link to conditions like depression and Parkinson's disease with their inhibition leading to increased availability of neurotransmitters. MAO inhibitors (MAOIs) are therapeutic agents for these disorders showing the importance of these enzymes. TAAR1 has associations with schizophrenia and mood disorders interacting with dopamine receptor signaling. KDM1/LSD1 and LSD2 hold connections to oncogenesis in certain cancers by affecting gene expression implicating interactions with other epigenetic regulators in these disease states.
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2 product images
Chemical Structure - Tranylcypromine hydrochloride (2-PCPA), Irreversible monoamine oxidase (MAO) inhibitor (ab120606)
2D chemical structure image of ab120606, Tranylcypromine hydrochloride (2-PCPA), Irreversible monoamine oxidase (MAO) inhibitor
Functional Studies - Tranylcypromine hydrochloride (2-PCPA), Irreversible monoamine oxidase (MAO) inhibitor (ab120606)
MCF7 cells were incubated at 37°C for 24h with vehicle control (0 μM) and different concentrations of tranylcypromine hydrochloride (ab120606). Increased expression of Histone 3 K4 di-methyl (Anti-Histone H3 (di methyl K4) antibody - ChIP Grade ab7766) in MCF7 cells correlates with an increase in tranylcypromine hydrochloride concentration, as described in literature.
Nuclear extracts were prepared with RIPA buffer (containing protease inhibitors and sodium orthovanadate), 10 μg of each were loaded on the gel and the WB was run under reducing conditions. After transfer the membrane was blocked for an hour using 5% BSA before being incubated with Anti-Histone H3 (di methyl K4) antibody - ChIP Grade ab7766 at 1 μg/ml and Anti-Histone H3 antibody - Nuclear Marker and ChIP Grade ab1791 at 1 μg/ml overnight at 4°C. Antibody binding was detected using an anti-rabbit antibody conjugated to HRP (Goat Anti-Rabbit IgG H&L (HRP) ab97051) at 1/10000 dilution and visualised using ECL development solution.
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