Blood pressure is raised with rel-Tranylcypromine (SKF 385; intravenous injection, 0.1 to 3.0 mg/kg; mongrel dogs, 5-10 kg). The dosage that is given determines how much and how long the medicine raises blood pressure. It is typically possible to obtain the animal's depressor response to rel-Tranylcypromine by repeatedly administering the drug[1].

Absorption, Distribution and Excretion
Individual differences exist in absorption. Some individuals may experience biphasic absorption. Peak plasma drug concentrations are reached within 1 hour after oral administration, with a secondary peak occurring within 2-3 hours. Biphasic absorption may indicate different absorption rates of the drug's stereoisomers, but further research is needed to confirm this. Dosage: 1.1-5.7 L/kg Monoamine oxidase inhibitors are readily absorbed after oral administration. These drugs achieve maximum inhibition of monoamine oxidase within 5-10 days. Although their biological activity is prolonged due to their enzyme-interacting properties, their clinical efficacy appears to decrease when the dosing frequency is less than once daily. /Monoamine Oxidase Inhibitors/

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Metabolism/Metabolites
Hepatic metabolism.

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Biological Half-Life
1.5-3.2 hours in patients with normal renal and hepatic function.

Hepatotoxicity
Like most monoamine oxidase inhibitors, tranylcypromine can cause transient elevations in serum transaminases in some patients. These elevations are usually mild, asymptomatic, and resolve spontaneously without dose adjustment. Tranylcypromine is also associated with rare cases of acute, clinically significant liver injury. A few reported cases are similar to liver injury caused by other monoamine oxidase inhibitors. Clinical symptoms usually appear within 1 to 4 months, with the most common pattern of serum enzyme elevation being hepatocellular (Case 1), but cholestatic liver injury has also been reported. Immune allergic reactions (rash, fever, eosinophilia) and autoantibody formation are uncommon. Probability score: D (likely a rare cause of clinically significant liver injury). Pregnancy and Lactation Effects ◉ Overview of Use During Lactation Due to limited information on the use of tranylcypromine during lactation, alternative medications may be preferred, especially in breastfed newborns or preterm infants.
◉ Effects on Breastfed Infants
A woman with severe depression took 100 to 120 mg of tranylcypromine daily during pregnancy and postpartum, along with pimozide, diazepam, and alprazolam. She continued breastfeeding until about 2 weeks postpartum, when the infant developed bloating and feeding intolerance. Symptoms disappeared after breastfeeding was discontinued.
◉ Effects on Lactation and Breast Milk
Nine subjects received an average of 29 mg (range 10 to 40 mg) of tranylcypromine orally daily for an average duration of 16 days. Serum prolactin levels increased by 3 μg/L. The clinical significance of these findings in breastfeeding women is unclear. Prolactin levels in established lactating mothers may not affect their ability to breastfeed.

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Interactions
Parnalet prolongs the sleep time of hexobarbital, suggesting that it may enhance the effects of other drugs by interfering with their detoxification effects. /Panat/
Monoamine oxidase inhibitors (MAOIs) can also enhance the effects of exogenous amines (such as serotonin and norepinephrine) and their prodrugs (such as 3,4-hydroxyphenylalanine (DOPA) and serotonin). /Monoamine oxidase inhibitors/
Pethidine should never be used to treat headaches accompanied by hypertension. Patients taking MAOIs should have their blood pressure immediately assessed if they experience severe throbbing headaches or pressure in the head. /Monoamine oxidase inhibitors/
MAOIs can interfere with the detoxification mechanisms of certain other drugs. They can prolong and enhance the effects of central nervous system depressants (such as general anesthetics, sedatives, antihistamines, alcohol, and potent analgesics); enhance the effects of anticholinergic drugs (especially those used to treat Parkinson's disease); and enhance the effects of antidepressants (especially imipramine and amitriptyline). /Monoamine oxidase inhibitors/
For more complete data on interactions of tranicopropylamine (37 in total), please visit the HSDB record page.

[1]. TODA N, et al. The sympathomimetic effects of SKF-385 on blood pressure in dog. Jpn J Pharmacol. 1962;12:166-179.

(1R,2S)-transphenylcyclopropane is a 2-phenylcyclopropane-1-amine, the (1R,2S)-enantiomer of transphenylcyclopropane. It is the conjugate base of (1R,2S)-transphenylcyclopropane(1+). It is the enantiomer of (1S,2R)-transphenylcyclopropane. It is a propylamine formed by the cyclization of the amphetamine side chain. This monoamine oxidase inhibitor is effective in treating major depressive disorder, dysthymia, and atypical depression. It is also used to treat panic disorder and phobias (from JAMA Drug Evaluation Yearbook, 1994, p. 311). Transphenylcyclopropane is a racemic mixture composed of equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropane-1-amine, both with chiral centers located on the cyclopropane ring. An irreversible monoamine oxidase inhibitor used as an antidepressant (International Nonproprietary Name: tranphenylcyclopropane). Tranphenylcyclopropane is a monoamine oxidase inhibitor. Its mechanism of action is as a monoamine oxidase inhibitor. Tranphenylcyclopropane is a non-hydrazine monoamine oxidase inhibitor (MAO inhibitor) used to treat major depressive disorder. Tranphenylcyclopropane treatment has been associated with rare cases of clinically significant acute liver injury. Tranphenylcyclopropane is an orally bioavailable, non-selective, irreversible, non-hydrazine monoamine oxidase (MAO) and lysine-specific demethylase 1 (LSD1/BHC110) inhibitor with antidepressant and anxiolytic activities, as well as potential antitumor activity. After oral administration, the antidepressant and anxiolytic effects of tranphenylcyclopropane are achieved by inhibiting monoamine oxidase (MAO). MAO is an enzyme that catalyzes the breakdown of monoamine neurotransmitters, including serotonin, norepinephrine, epinephrine, and dopamine. This can increase the concentration and activity of these neurotransmitters. The antitumor effect of transphenylcyclopropane is achieved by inhibiting LSD1. Inhibition of LSD1 prevents the transcription of LSD1 target genes. LSD1 is a flavin-dependent monoamine oxidoreductase and histone demethylase, upregulated in various cancers, and plays a key role in tumor cell proliferation, migration, and invasion. Amphetamines are propylamine compounds formed by the cyclization of the amphetamine side chain. This monoamine oxidase inhibitor is effective in treating major depressive disorder, dysthymia, and atypical depression. It is also used to treat panic disorder and phobias. (From JAMA Drug Evaluation Yearbook, 1994, p. 311) See also: transphenylcyclopropane sulfate (salt form). Drug Indications For the treatment of major depressive episodes without melancholy. Mechanism of Action Transphenylcyclopropane irreversibly and nonselectively inhibits monoamine oxidase (MAO). Within neurons, MAO appears to regulate the levels of monoamines released during synaptic firing. Since depression is associated with low levels of monoamine neurotransmitters, inhibition of monoamine oxidase (MAO) can alleviate depressive symptoms because it leads to increased concentrations of these neurotransmitters in the central nervous system. Results showed that D- and DL-trans-cyclopropylamine have both direct and indirect effects on tryptaminergic neurotransmission. Intraperitoneal injection of trans-cyclopropylamine hydrochloride (20 mg/kg) into rats resulted in significantly higher increases in the concentrations of 2-phenylethylamine and tryptamine in the hippocampus and diencephalon than in M- and P-tyramine. These may be involved in neuronal function in the central nervous system and are therefore components of trans-cyclopropylamine activity. Platelet monoamine oxidase (MAO) activity was significantly reduced (oral administration of DL-trans-cyclopropylamine sulfate 10 and 20 mg): serotonin, dopamine, and metaraminol uptake were only slightly reduced. The antidepressant activity of MAO inhibitors may be less related to the inhibition of catecholamine uptake and more related to the inhibition of the oxidase. …This leads to irreversible inactivation of MAO by forming a stable complex with the enzyme. Evidence suggests that some monoamine oxidase inhibitors (MAO inhibitors) can block nerve impulse transmission to nerve endings, thereby inhibiting the release of norepinephrine. /Monoamine Oxidase Inhibitors/
...trans-cyclopropane is a potent but non-specific CYP2C19 inhibitor.

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Therapeutic Uses
Antidepressants; Monoamine oxidase inhibitors; Anti-anxiety drugs
Specific MAO inhibitors inhibit monoamine oxidase to varying degrees in specific organs. Due to their slow onset and long duration of action, MAO inhibitors are difficult to monitor in clinical settings, therefore, they are never administered parenterally. Monoamine Oxidase Inhibitors (MAO Inhibitors)
The most effective effect of various MAO inhibitors is to improve mood in patients with depression. MAO inhibitors are among the most effective known rapid eye movement (REM) sleep depressants. This effect has been used to treat narcolepsy. ...MAO inhibitors can lower blood pressure and relieve angina symptoms. /Monamine Oxidase Inhibitors/
For more complete data on the therapeutic uses of tranicyclopropamide (11 in total), please visit the HSDB record page.

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Drug Warnings
In rare cases of death, most occurred after taking doses exceeding 350 mg; however, some patients have survived after taking this drug. Tranicyclopropamide dependence has been reported occasionally. /Sulfate/
…Contraindicated in patients with cerebrovascular defects, cardiovascular disease, or pheochromocytoma… /Sulfate/
Patients should have a 10-14 day rest period before switching from one monoamine oxidase inhibitor to another or switching to a tricyclic antidepressant. /Monamine Oxidase Inhibitors/
…Taking transcyclopropamide may cause adverse reactions if the effects of phenelzine have not yet worn off.
For more complete data on the drug warnings of transcyclopropamide (20 in total), please visit the HSDB record page.

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Pharmacodynamics
Trans-cyclopropylamine belongs to a class of antidepressants called monoamine oxidase inhibitors (MAOIs). Trans-cyclopropylamine is a non-hydrazine monoamine oxidase inhibitor with a rapid onset of action. Monoamine oxidase (MAO) is an enzyme that catalyzes the oxidative deamination of various amines, including serotonin, norepinephrine, epinephrine, and dopamine. Two MAO isoenzymes exist in the body: MAO-A and MAO-B. MAO-A is mainly found in peripheral cells and catalyzes the breakdown of serotonin, norepinephrine, epinephrine, dopamine, and tyramine. MAO-B acts on phenylethylamine, norepinephrine, epinephrine, dopamine, and tyramine, and is located extracellularly, mainly in brain tissue.
Although the mechanism of action of monoamine oxidase inhibitors (MAOIs) is not fully understood, they are generally believed to exert their effects by increasing the concentrations of free serotonin and norepinephrine in the central nervous system (CNS) and/or altering the concentrations of other amines. Some studies hypothesize that depression is caused by excessively low levels of serotonin and/or norepinephrine, and that increasing serotonergic and noradrenergic neurotransmission could alleviate depressive symptoms. Compared to MAOB inhibition, MAOA inhibition is considered to be more associated with antidepressant activity. Selective MAOB inhibitors, such as selegiline, do not have antidepressant effects.

C9H11N

133.19

133.089

155-09-9

Tranylcypromine hemisulfate;13492-01-8;Tranylcypromine-d5 hydrochloride;107077-98-5

19493

Liquid

1.1±0.1 g/cm3

218.3±29.0 °C at 760 mmHg

79-80 °C at 1.50E+00 mm Hg
MP: 164-166 °C /Hydrochloride/

90.8±19.6 °C

0.1±0.4 mmHg at 25°C

1.584

1.25

1

1

1

10

116

2

C1C=CC(C2C[C@H]2N)=CC=1

AELCINSCMGFISI-DTWKUNHWSA-N

InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8-,9+/m0/s1

(1R,2S)-2-phenylcyclopropan-1-amine

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)