ChemicalBook > CAS DataBase List > Tranylcypromine

Tranylcypromine

Product Name
Tranylcypromine
CAS No.
1986-47-6
Chemical Name
Tranylcypromine
Synonyms
TRANS-2-PHENYLCYCLOPROPYLAMINE HYDROCHLORIDE;TRANYLCYPROMINE HYDROCHLORIDE;trans-2-PhenylcyclopropanaMine hydrochloride;trans-2-Phenylcyclopropylamine hydrochloride,97%;SKF-385 HCl;TRANYLCYPROMINE;TIMTEC-BB SBB003859;Tranylcypromine hydr;SKF-385 hydrochloride;Tranylcypromine HCl (2-PCPA)
CBNumber
CB9141768
Molecular Formula
C9H12ClN
Formula Weight
169.65
MOL File
1986-47-6.mol
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Tranylcypromine Property

Melting point:
162-169 °C(lit.)
storage temp. 
2-8°C
solubility 
Methanol (Slightly), Water (Slightly)
form 
Powder or Chunks
color 
White to light beige
optical activity
[α]/D 1 to +1.0°, c = 1 in H2O
Stability:
Hygroscopic
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Safety

Hazard Codes 
T,Xn
Risk Statements 
36/37/38-25-20/21-52-22
Safety Statements 
45-36/37/39-26
RIDADR 
3249
WGK Germany 
3
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29214990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P22370
Product name
trans-2-Phenylcyclopropylamine hydrochloride
Purity
97%
Packaging
1g
Price
$131
Updated
2024/03/01
Sigma-Aldrich
Product number
P22370
Product name
trans-2-Phenylcyclopropylamine hydrochloride
Purity
97%
Packaging
2.5g
Price
$310
Updated
2024/03/01
Cayman Chemical
Product number
10010494
Product name
Tranylcypromine (hydrochloride)
Purity
≥98%
Packaging
500mg
Price
$84
Updated
2024/03/01
Cayman Chemical
Product number
10010494
Product name
Tranylcypromine (hydrochloride)
Purity
≥98%
Packaging
1g
Price
$117
Updated
2024/03/01
Cayman Chemical
Product number
10010494
Product name
2-PCPA (hydrochloride)
Purity
≥98%
Packaging
10mg
Price
$10
Updated
2021/12/16
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Tranylcypromine Chemical Properties,Usage,Production

Chemical Properties

white to light beige powder or chunks

Uses

Antidepressant;MAO inhibitor

Uses

As with the MAO inhibitor drugs described above, tranylcypromine is also used for depressions that do not respond to other drugs.

Uses

Non-selective MAO-A/B inhibitor

Definition

ChEBI: (1R,2S)-tranylcypromine hydrochloride is a hydrochloride obtained by combining (1R,2S)-tranylcypromine with one equivalent of hydrochloric acid. It contains a (1R,2S)-tranylcypromine(1+). It is an enantiomer of a (1S,2R)-tranylcypromine hydrochloride.

General Description

A cell-permeable phenylcyclopropylamine that inhibits the monoamine oxidase and histone demethylase activities, respectively, of MAO A/B (Ki = 101.9 and 16.0 M, respectively) and LSD1/2 (Ki = 242.7 and 180.0 M, respectively), four members of a flavin-dependent amine oxidase family enzymes, by a covalent adduct formation with the enzyme-bound FAD. In addition to preventing LSD1-CoREST (Corepressor of RE1-Silencing Transcription factor) complex-mediated H3K4 demethylation (IC50<2 M), TCP also inhibits LSD1-HCF-1 (Host Cell Factor-1) complex-mediated H3K9 demethylase activity, which is demonstrated to be an essential mechanism for the replication and latent infection of the α-herpesviruses HSV and VZV. The combined treatment of 2 M TCP and 10 M CHIR99061 is reported to enable the reprogramming of Oct4/Klf4-transduced primary HNEKs (Human Neonatal Epidermal Keratinocytes) into iPS (induced Pluripotent Stem) cells, albeit at a 100-time lower efficiency as seen in cultures transduced with 4-TFs (Oct44, Klf4, Sox2, and c-Myc).

Biological Activity

Irreversible inhibitor of lysine-specific demethylase 1 (LSD1/BHC110) and monoamine oxidase (MAO) (K i values are 242, 102 and 16 μ M for LSD1, MAO-A and MAO-B respectively). Inhibits histone demethylation.

Clinical Use

MAOI antidepressant

Synthesis

Tranylcypromine, (?à)-trans-2-phenylcyclopropylamine (7.2.10), differs from the drugs described above in that it is not a derivative of hydrazine. It is synthesized from the ethyl ester of 2-phenylcyclopropan carboxylic acid (7.2.7), which is synthesized by the reaction of styrene with ethyl diazoacetate. 2-phenylcyclopropancarboxylic acid ethyl ester (7.2.7) is hydrolyzed by alkali to 2-phenylcyclopropancarboxylic acid (7.2.8) and the trans-isomer is separated for further reactions. The reaction of the trans-isomer with thionyl chloride gives trans-2-phenylcyclopropancarboxylic acid chloride (7.2.9), which upon reaction with sodium azide gives the respective acid azide, which undergoes Curtius rearrangement to the transcyclopropylamine (7.2.10) [48,49].

Drug interactions

Potentially hazardous interactions with other drugs
Alcohol: some alcoholic and dealcoholised drinks contain tyramine which can cause hypertensive crisis.
Alpha-blockers: enhanced hypotensive effect; avoid with indoramin.
Analgesics: CNS excitation or depression with pethidine, other opioids and nefopam - avoid; increased risk of serotonergic effects and convulsions with tramadol - avoid.
Antibacterials: increased risk of hypertension and CNS excitation with linezolid and tedizolid - avoid for at least 2 weeks after stopping MAOIs.
Antidepressants: enhancement of CNS effects and toxicity. Care with all antidepressants including drug free periods when changing therapies.
Antidiabetics: possibly enhanced hypoglycaemic effect.
Antiepileptics: antagonism of anticonvulsant effect; avoid carbamazepine with or within 2 weeks of MAOIs.
Antihypertensives: enhanced hypotensive effect.
Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol.
Antipsychotics: effects enhanced by clozapine.
Anxiolytics: avoid buspirone with or within 2 weeks of MAOIs.
Atomoxetine: avoid concomitant use and for 2 weeks after use; increased risk of convulsions.
Bupropion: avoid with or for 2 weeks after MAOIs.
Dapoxetine: risk of hypertensive crisis - avoid.
Diuretics: enhanced hypotensive effect; avoid with indoramin.
Dopaminergics: avoid with entacapone, safinamide and tolcapone; hypertensive crisis with levodopa and rasagiline - avoid for at least 2 weeks after stopping MAOI; hypotension with selegiline.
5HT1 agonist: risk of CNS toxicity with sumatriptan, rizatriptan and zolmitriptan - avoid sumatriptan and rizatriptan for 2 weeks after MAOI.
Metaraminol: risk of hypertensive crisis - avoid for at least 2 weeks after stopping MAOIs.
Methyldopa: avoid concomitant use.
Opicapone: avoid concomitant use.
Sympathomimetics: hypertensive crisis with sympathomimetics - avoid.
Tetrabenazine: risk of CNS excitation and hypertension avoid.

Metabolism

Tranylcypromine undergoes considerable hepatic metabolism, including breakdown of the side chain and probably conjugation. Excretion is renal mainly as metabolites.

storage

room temperature (desiccate)

Tranylcypromine Preparation Products And Raw materials

Raw materials

Preparation Products

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Tranylcypromine Suppliers

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View Lastest Price from Tranylcypromine manufacturers

Career Henan Chemical Co
Product
TRANS-2-PHENYLCYCLOPROPYLAMINE HYDROCHLORIDE 1986-47-6
Price
US $9.80/KG
Min. Order
1g
Purity
≥99%
Supply Ability
100kg
Release date
2020-01-08

1986-47-6, TranylcypromineRelated Search:

Yohimbine hydrochloride TRANS-3-BENZYLOXYMETHYLCYCLOBUTANOL TRANS-3-(TRIMETHYLSILYL)ALLYL ALCOHOL TRANS-2-PHENYL-1-CYCLOPROPANECARBOXYLIC ACID TRANS-2-PHENYLCYCLOPROPYLAMINE HYDROCHLO RIDE (TRANYLCYPROMINE HCL),TRANYLCYPROMINE Tranylcypromine Hemisulfate CYCLOPROPYLBENZENE Tranylcypromine dl-Tranylcypromine,Tranylcypromine (base and/or unspecified salts) Cyclopropylamine Dextroamphetamine hydrochloride cis-Tranylcypromine hydrochloride S-Tranylcypromine Tranylcypromine-d5 TRANYLCYPROMINE-D5 HCL R-Tranylcypromine N-acetyl-tranylcypromine dichlorobis(tranylcypromine)platinum(II)

  • trans-2-Phenylcyclopropylamine hydrochloride,97%
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  • trans-2-PhenylcyclopropanaMine hydrochloride
  • SKF-385 HCl
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  • (DL)-Trans-2-phenylcyclopropylamine
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  • TRANS-2-PHENYLCYCLOPROPYLAMINE HYDROCHLORIDE
  • TRANYLCYPROMINE HYDROCHLORIDE
  • TIMTEC-BB SBB003859
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  • trans 2-Amino-1-phenyl-cyclopropane Hydrochloride
  • Tranylcypromine, HCl - CAS 1986-47-6 - Calbiochem
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  • DL-TRANYLCYPROMINE HEMISULFATE; TRANS-2-PHENYLCYCLOPROPYLAMINE HEMISULFATE SALT
  • Trans-Racemic 2-phenylcyclopropan-1-amine Hydrochloride
  • TRANYLCYPROMINE
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  • Tranylcypromine hydrochlorideQ: What is Tranylcypromine hydrochloride Q: What is the CAS Number of Tranylcypromine hydrochloride Q: What is the storage condition of Tranylcypromine hydrochloride Q: What are the applications of Tranylcypromine hydrochloride
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  • 1986-47-6
  • C6H5C3H4NH2HCl
  • C9H11NHCl
  • Building Blocks
  • Biochemicals and Reagents
  • Amine Salts
  • BioChemical
  • Organic Building Blocks
  • L to O
  • Nitrogen Compounds
  • Monoamine oxidase inhibitor
  • Enzymes, Inhibitors, and Substrates
  • Enzyme Inhibitors by Enzyme
  • Enzyme Inhibitors
  • Chemical Amines
  • Amines
  • Aromatics
  • Inhibitors
  • Amine Salts