CAS 1986-47-6|Tranylcypromine hydrochloride
| Common Name | Tranylcypromine hydrochloride | ||
|---|---|---|---|
| CAS Number | 1986-47-6 | Molecular Weight | 169.651 |
| Density | / | Boiling Point | 218.3ºC at 760mmHg |
| Molecular Formula | C9H12ClN | Melting Point | 162-169ºC(lit.) |
| MSDS | ChineseUSA | Flash Point | 90.8ºC |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | Tranylcypromine hydrochloride,(±)-trans-2-Phenylcyclopropylaminehydrochloride |
|---|---|
| Synonym | More Synonyms |
Tranylcypromine hydrochloride BiologicalActivity
| Description | Tranylcypromine hydrochloride (SKF 385 hydrochloride) is an irreversible inhibitor of lysine-specific demethylase 1 (LSD1/BHC110) and monoamine oxidase (MAO). Tranylcypromine hydrochloride inhibits LSD1, MAO A and MAO B with IC50s of 20.7, 2.3 and 0.95 μM, respectively. Tranylcypromine hydrochloride can be used for the research of depression[1][2][3]. |
|---|---|
| Related Catalog | Signaling Pathways >>Neuronal Signaling >>Monoamine OxidaseResearch Areas >>Neurological Disease |
| Target | MAO-A:2.3 μM (IC50) MAO-B:0.95 μM (IC50) |
| In Vitro | Tranylcypromine hydrochlorid (50 μM-5 mM; 1 h or 12-14 h) inhibits histone and nucleosomal demethylation[1]. Tranylcypromine hydrochlorid (2 μM; 3 h) shows a specific derepression of OCT4 transcription[1]. Tranylcypromine hydrochlorid (0-100 μM; 15 min) shows IC50 values of 20.7, 2.3 and 0.95 μM for LSD1, MAO A and MAO B, respectively[2]. Tranylcypromine hydrochlorid (0-800 μM) shows Ki values of 242.7, 101.9 and 16 μM for LSD1, MAO A and MAO B, respectively[2]. Western Blot Analysis[1] Cell Line: Sf21 insect cell line Concentration: 50 μM, 200 μM, 1 mM and 5 mM Incubation Time: 12-14 hours or 1 hour Result: Showed inhibitory activities of histone H3K4 demethylation and nucleosomal demethylation. RT-PCR[1] Cell Line: P19 EC cell line Concentration: 2 μM Incubation Time: 3 hours Result: Decreased Oct4 mRNA levels. |
| In Vivo | Tranylcypromine hydrochlorid (3 mg/kg; i.p. once daily for 3 days) decreases LPS-mediated microglial activation and proinflammatory cytokine COX-2 and IL-6 levels in wild-type mice[3]. Tranylcypromine hydrochlorid (3 mg/kg; i.p. once daily for 7 days) down-regulates Aβ-mediate microglial activation in 5xFAD mice[3]. Animal Model: Wild-type mice[3] Dosage: 3 mg/kg Administration: Intraperitoneal injection; 3 mg/kg once daily for 3 days Result: Significantly down-regulated LPS-stimulated microglial activation in the cortex and Hippocampus, and LPS-induced astrocyte activation only in the cortex. Reduced LPS-induced COX-2 levels in hippocampus CA1, decreased LPS-evoked IL-6 levels in the cortex and hippocampus CA1 and suppressed LPS-mediated IL-1β levels in the cortex. Animal Model: 5xFAD mice[3] Dosage: 3 mg/kg Administration: Intraperitoneal injection; 3 mg/kg once daily for 7 days Result: Differentially regulated microglial and astrocyte activation in this mouse model of AD. |
| References | [1]. Lee MG, et al. Histone H3 lysine 4 demethylation is a target of nonselective antidepressive medications. Chem Biol. 2006 Jun;13(6):563-7. [2]. Schmidt DM, McCafferty DG. trans-2-Phenylcyclopropylamine is a mechanism-based inactivator of the histone demethylase LSD1. Biochemistry. 2007 Apr 10;46(14):4408-16. [3]. Park H, et al. The MAO Inhibitor Tranylcypromine Alters LPS- and Aβ-Mediated Neuroinflammatory Responses in Wild-type Mice and a Mouse Model of AD. Cells. 2020 Aug 28;9(9):1982. |
Chemical & Physical Properties
| Boiling Point | 218.3ºC at 760mmHg |
|---|---|
| Melting Point | 162-169ºC(lit.) |
| Molecular Formula | C9H12ClN |
| Molecular Weight | 169.651 |
| Flash Point | 90.8ºC |
| Exact Mass | 169.065826 |
| PSA | 26.02000 |
| LogP | 3.00350 |
| Appearance of Characters | Powder or Chunks | White to light beige |
| Vapour Pressure | 0.127mmHg at 25°C |
| InChIKey | ZPEFMSTTZXJOTM-OULXEKPRSA-N |
| SMILES | Cl.NC1CC1c1ccccc1 |
| Storage condition | 2-8°C |
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302-H315-H319-H335 |
| Precautionary Statements | P261-P305 + P351 + P338 |
| Hazard Codes | T: Toxic; |
| Risk Phrases | R36/37/38 |
| Safety Phrases | 45-36/37/39-26 |
| RIDADR | UN 3249 |
| WGK Germany | 3 |
| Packaging Group | III |
| Hazard Class | 6.1(b) |
| HS Code | 2921499090 |
Customs
| HS Code | 2921499090 |
|---|---|
| Summary | 2921499090 other aromatic monoamines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0% |
Articles18
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Synonyms
| (1R,2S)-2-Phenylcyclopropanamine hydrochloride (1:1) |
| (1R,2S)-tranylcypromine hydrochloride |
| Cyclopropanamine, 2-phenyl-, (1R,2S)-, hydrochloride (1:1) |
| trans-2-Phenylcyclopropylamine hydrochloride |
| Tranylcypromine hydrochloride |
| trans-2-Phenylcyclopropanamine hydrochloride |
| MFCD00063602 |
