Tranylcypromine

Tranylcypromine (CAS 13492-01-8)

Tranylcypromine | CAS 13492-01-8 is rated 5.0 out of 5 by 1.
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Synonym: trans-2-Phenylcyclopropylamine hemisulfate salt
Application: An irreversible inhibitor of MAO and inhibitor of histone demethylation
CAS Number: 13492-01-8
Purity: ≥98%
Molecular Weight: 182.23
Molecular Formula: C9H11N•1/2H2SO4
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
Submit a review for this product and receive 15 CruzCredits

Tranylcypromine is an irreversible inhibitor of monoamine oxidase (MAO), and an inhibitor of CYP2A6 (Ki= 0.08 μM) and histone demethylase BHC110/LSD1. The inhibitor targets MAO-A and MAO-B and has been used as a chemical scaffold to design new demethylase inhibitors. Studies suggest that tranylcypromine can increase both brain trace amines and GABA(B)-receptors, and regulate phospholipid metabolism. Tranylcypromine has been shown to increase Histone H3 lysine 4 (H3K4) methylation and transcriptional derepression of Egr1 and Oct4 in P19 embryonal carcinoma cells (sc-24760). Studies indicate that it is an effective inhibitor of histone demethylation and can antagonize the effects of phenylephrine.


References

1. Hayashi, M., et al., 1983. Different mode of action between norepinephrine and phenylephrine on prostaglandin synthesis by dog renal inner medullary slices. Japanese journal of pharmacology. 33(3): 563-71. PMID: 6312148
2. Zhang, W., et al., 2001. Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro. Drug metabolism and disposition: the biological fate of chemicals. 29(6): 897-902. PMID: 11353760
3. Lee, Min Gyu., et al., 2006. Histone H3 lysine 4 demethylation is a target of nonselective antidepressive medications. Chemistry & biology. 13(6): 563-7. PMID: 16793513
4. Frieling, Helge., et al., 2006. Tranylcypromine: new perspectives on an "old" drug. European archives of psychiatry and clinical neuroscience. 256(5): 268-73. PMID: 16927039
5. Lundquist, Pinelopi., et al., 2007. Effect on [11C]DASB binding after tranylcypromine-induced increase in serotonin concentration: positron emission tomography studies in monkeys and rats. Synapse (New York, N.Y.). 61(6): 440-9. PMID: 17372973
6. Binda, Claudia., et al., 2010. Biochemical, structural, and biological evaluation of tranylcypromine derivatives as inhibitors of histone demethylases LSD1 and LSD2. Journal of the American Chemical Society. 132(19): 6827-33. PMID: 20415477

Physical State :
Solid
Solubility :
Soluble in water (25 mg/ml).
Storage :
Store at -20° C
Melting Point :
164-166° C
Boiling Point :
218.3° C at 760 mmHg
IC50 :
demethylase BHC110/LSD1: IC50 = <2 µM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
GZ2625000
Transport :
UN 2811, Class 6.1, Packing group II
PubChem CID :
26069
MDL Number :
MFCD00079222
EC Number :
236-807-1
SMILES :
C1[C@H]([C@@H]1[NH3+])C2=CC=CC=C2.C1[C@@H]([C@H]1[NH3+])C2=CC=CC=C2.[O-]S(=O)(=O)[O-]

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Certificate of Analysis

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Tranylcypromine  Product Citations

See how others have used Tranylcypromine. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 25103574  Liu, D. et al. 2014. Genes Nutr. 9: 422.

PMID: # 22534778  Piao, JY. et al. 2012. Analyst. 137: 2669-73.

Citations 1 to 2 of 2 total

I am trying to use the TCP inhibitor in my in vitro LSD1 demethylase assay. It has not been working even at 10 uM of TCP (LSD1 = 100 nM). Do you any suggestions?

Asked by: sak1
Thank you for your question. Please contact our Technical Service Department for assistance in troubleshooting this chemical.
Answered by: Technical Support
Date published: 2019-01-26
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Rated 5 out of 5 by from Blazevic Blazevic, S. et al. (PubMed 26348077) used Tranylcypromine (SKF trans-355), an irreversible inhibitor of MAO and inhibitor of histone demethylation, to induce peripheral serotonin imbalance in rats and study its possible consequences on bone remodeling and hematopoiesis. -SCBT Publication Review
Date published: 2015-07-15
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