Tranylcypromine hydrochloride

Names

[ CAS No. ]:
1986-47-6

[ Name ]:
Tranylcypromine hydrochloride

[Synonym ]:
(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

Biological Activity

[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 Oxidase

Research 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

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%

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