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trans-2-Phenylcyclopropylamine hemisulfate salt

Names

[ CAS No. ]:
13492-01-8

[ Name ]:
trans-2-Phenylcyclopropylamine hemisulfate salt

[Synonym ]:
TRANS-2-PHENYLCYCLOPROPYLAMINE HEMISULFATE SALT
Tranylcypromine sulfate
Tranylcypromine
Tranylcypromine (hemisulfate)

Biological Activity

[Description]:

Tranylcypromine hemisulfate is an irreversible, nonselective MAO inhibitor used in the treatment of depression.

[Related Catalog]:

Signaling Pathways >> Epigenetics >> Histone Demethylase
Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase
Research Areas >> Neurological Disease

[In Vitro]

Tranylcypromine (10 nM to 10 µM) exerts neuroprotective effects against toxicity induced by human Aβ(1-42) oligomers independently from the presence of glial cells[1]. Tranylcypromine (100 μM) significantly protects RGCs from glutamate neurotoxicity-induced apoptosis as well as apoptosis induced by oxidative stress. Tranylcypromine promotes mitogen-activated protein kinase 12 (p38 MAPKγ) expression under conditions of glutamate (Glu)-induced stress. Besides, tranylcypromine contributes to RGC survival via alterations of p38 MAPKγ activity[3].

[In Vivo]

Tranylcypromine treatment significantly and substantially reduces the lesion size and improves generalized hyperalgesia in a dose-dependent fashion in mice with induced endometriosis. In addition, tranylcypromine treatment results in reduced immunoreactivity to biomarkers of proliferation, angiogenesis, and H3K4 methylation, leading to arrested EMT and lesion growth[2]. Tranylcypromine (500 mM) injection exerts neuroprotective effects within intracellular apoptotic signaling pathways and suppresses morphologic changes in the retina of the rat, suppresses caspase 3 activity and recovers p38 MAPKγ expression in the retina after NMDA-induced injury, and enhances RGC survival after retinal injury via the attenuation of NMDA neurotoxicity[3]. Tranylcypromine (10 µg/g) causes an approximate and significant doubling of labeled cells in the combined brain regions examined, as detected by BrdU immunohistochemistry. Tranylcypromine causes the greatest increase in cell proliferation in the cerebellum[4].

[Animal admin]

Briefly, the rats are anesthetized with an intraperitoneal injection of a 1:1 mixture of xylazine hydrochloride (4 mg/kg) and ketamine hydrochloride (10 mg/kg). Then, the pupil is dilated with phenylephrine hydrochloride and tropicamide eye drops, and 20 nmol NMDA with or without tranylcypromine is injected into the vitreous cavity. To assess the inhibitory effect of mitogen-activated protein kinase (MAPK), 100 nmol BIRB796 is intravitreally injected at the same time of NMDA injection. The injections are performed under a microscope using a 33-gauge needle connected to a microsyringe; the needle is inserted approximately 1.0 mm behind the corneal limbus. Next, either PBS (vehicle control) or 500 mM tranylcypromine (1000 nmol) mixed with 10 mM NMDA (20 nmol) in a total volume of 2.0 μL is injected into the vitreous cavity.

[References]

[1]. Caraci F, et al. Neuroprotective effects of the monoamine oxidase inhibitor tranylcypromine and its amide derivatives against Aβ(1-42)-induced toxicity. Eur J Pharmacol. 2015 Oct 5;764:256-263.

[2]. Sun Q, et al. Tranylcypromine, a lysine-specific demethylase 1 (LSD1) inhibitor, suppresses lesion growth and improves generalized hyperalgesia in mouse with induced endometriosis. Reprod Biol Endocrinol. 2016 Apr 9;14:17.

[3]. Tsutsumi T, et al. Potential Neuroprotective Effects of an LSD1 Inhibitor in Retinal Ganglion Cells via p38 MAPK Activity. Invest Ophthalmol Vis Sci. 2016 Nov 1;57(14):6461-6473.

[4]. Romanczyk TB, et al. The antidepressant tranylcypromine alters cellular proliferation and migration in the adult goldfish brain. Anat Rec (Hoboken). 2014 Oct;297(10):1919-26.


[Related Small Molecules]

GSK-J4 | QC6352 | GSK2879552 | SP-2509 | CPI-455 | Phenelzine (sulfate) | 5-Carboxy-8-hydroxyquinoline | Clorgyline hydrochloride | ML324 | Rosmarinic acid | pargyline hydrochloride | GSK-LSD1 Dihydrochloride | NCGC00244536 | Daminozide | ORY-1001(trans)

Chemical & Physical Properties

[ Density]:
1.065g/cm3

[ Boiling Point ]:
218.3ºC at 760mmHg

[ Molecular Formula ]:
C9H12NO2S0.5

[ Molecular Weight ]:
182.23

[ Flash Point ]:
90.8ºC

[ PSA ]:
135.02000

[ LogP ]:
4.83100

[ Vapour Pressure ]:
0.127mmHg at 25°C

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
Soluble in water; very slightly soluble in ethanol (96%) and in ether .

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GZ2625000
CAS REGISTRY NUMBER :
13492-01-8
LAST UPDATED :
199610
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C9-H11-N.1/2H2-O4-S
MOLECULAR WEIGHT :
360.46
WISWESSER LINE NOTATION :
L3TJ AZ BR 2 &..H2.S-O4

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
34 mg/kg/60D-I
TOXIC EFFECTS :
Peripheral Nerve and Sensation - paresthesis Musculoskeletal - joints
REFERENCE :
AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 140,1229,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1200 ug/kg/3D-I
TOXIC EFFECTS :
Vascular - BP lowering not characterized in autonomic section
REFERENCE :
AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 144,119,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
45 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ABMGAJ Acta Biologica et Medica Germanica. (Berlin, Ger. Dem. Rep.) V.1-41, 1958-82. For publisher information, see BBIADT. Volume(issue)/page/year: 18,617,1967
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
38 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,359,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
41 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EJPHAZ European Journal of Pharmacology. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1967- Volume(issue)/page/year: 6,115,1969
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
37 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,359,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BJPCAL British Journal of Pharmacology and Chemotherapy. (London, UK) V.1-33, 1946-68. For publisher information, see BJPCBM. Volume(issue)/page/year: 25,158,1965 *** REVIEWS *** TOXICOLOGY REVIEW IDPYAK Industrial Pharmacology. (Mount Kisco, NY) V.1-3, 1974-79. Discontinued. Volume(issue)/page/year: 2,209,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5685 No. of Facilities: 8 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 239 (estimated) No. of Female Employees: 157 (estimated)

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H311-H331

[ Precautionary Statements ]:
P261-P264-P280-P301 + P310-P311

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
36/37/39-45

[ RIDADR ]:
UN 2811 6

[ WGK Germany ]:
3

[ RTECS ]:
GZ2625000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)


Related Compounds