An irreversible, mechanism-based inhibitor of LSD1
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Tranylcypromine (hydrochloride)

Item No. 10010494

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,2S)-rel-2-phenyl-cyclopropanamine, monohydrochloride
CAS Number
1986-47-6
Synonyms
  • 2-PCPA
  • trans-2-Phenylcyclopropylamine
Molecular Formula
C9H11N • HCl
Formula Weight
169.7
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 2.5 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 2 mg/ml
SMILES
N[C@@H]1CC1c1ccccc1
InChi Code
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
InChi Key
ZPEFMSTTZXJOTM-OULXEKPRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $28

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    250 mg

    $50

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    500 mg

    $93

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    1 g

    $129

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    Product Description

    Tranylcypromine is an irreversible, mechanism-based inhibitor of lysine-specific demethylase 1 (LSD1; IC50 = 20.7 µM in a cell-free assay).1 It also irreversibly inhibits monoamine oxidase A (MAO-A) and MAO-B with IC50 values of 2.3 and 0.95 µM, respectively. Tranylcypromine inhibits nucleosomal demethylation of histone H3 lysine 4 (H3K4; IC50 = <2 µM) and increases global H3K4 methylation in pluripotent embryonal carcinoma cells.2 It induces mouse epiblast stem cells (EpiSCs) to form small, compact, domed colonies expressing the pluripotency marker ALP, indicating a conversion to more undifferentiated state; however, full conversion to pluripotent murine embryonic stem cells (mESCs) requires tranylcypromine in combination with inhibitors of ALK5, MEK, FGFR, and GSK3.3 Tranylcypromine enables the GSK3 inhibitor CHIR99021 (Item No. 13122) to promote the differentiation of keratinocytes into induced pluripotent stem cells (iPSCs) when transduced with the transcription factors Oct4 and Klf4.3 It also decreases proliferation of neural progenitors in the hippocampal dentate gyrus in adult mice when administered at a dose of 10 mg/kg for ten days.4 Tranylcypromine (0.5-10 mg/kg) decreases the time juvenile rats spend immobile in the forced swim test, indicating antidepressant-liked activity.5 Formulations containing tranylcypromine have been used in the treatment of treatment-resistant major depressive disorder.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schmidt, D.M.Z., and McCafferty, D.G. trans-2-Phenylcyclopropylamine is a mechanism-based inactivator of the histone demethylase LSD1. Biochemistry 46, 4408-4416 (2007).

    2. Lee, M.G., Wynder, C., Schidt, D.M., et al. Histone H3 lysine 4 demethylation is a target of nonselective antidepressive medications. Chem. Biol. 13(6), 563-567 (2006).

    3. Zhou, H., Li, W., Zhu, S., et al. Conversion of mouse epiblast stem cells to an earlier pluripotency state by small molecules. The Journal of Biological Chemisty 285(39), 29676-29680 (2010).

    4. Sun, G., Alzayady, K., Stewart, R., et al. Histone demethylase LSD1 regulates neural stem cell proliferation. Mol. Cell. Biol. 30(8), 1997-2005 (2010).

    5. Reed, A.L., Happe, H.K., Petty, F., et al. Juvenile rats in the forced-swim test model the human response to antidepressant treatment for pediatric depression. Psychopharmacology (Berl.) 197(3), 433-441 (2008).