HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Tranylcypromine
2-Phenylcyclopropan-1-amine · 2-Phenylcyclopropylamine · Cyclopropanamine, 2-phenyl- · 2-Phenylcyclopropane-1-amine · 1-Amino-2-phenylcyclopropane
Identifikatoren & physikalische Daten
| CAS No. | 155-09-9 |
|---|---|
| Summenformel | C9H11N |
| Durchschnittliche Molmasse | 133,19 g/mol |
| Monoisotopische Masse | 133,08914935 g/mol |
| SMILES | NC1CC1c1ccccc1 |
| InChIKey | AELCINSCMGFISI-UHFFFAOYSA-N |
| PubChem CID | 5530 |
| ChEMBL | CHEMBL313833 |
| ChEBI | CHEBI:131512 |
| EC No. | 205-841-9 |
| DTXSID | DTXSID30859306 |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 26 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 116 |
| Arzneimittel | Pharmaceuticals |
| LogP (Verteilungskoeffizient) | log Kow= 1.58 @ 25 °C1.49 |
| Color/Form | Liquid |
| Löslichkeit | Sol in water /Sulfate/Very slightly sol in alcohol, ether /Sulfate/Practically insol in chloroform /Sulfate/ |
| Human Drugs | Breast FeedingLactationAntidepressive AgentsMonoamine Oxidase Inhibitors |
| Siedepunkt | 79-80 °C @ 1.5-1.6 mm Hg218.3±29.0 °C(Predicted) |
| Schmelzpunkt | 79-80 °C at 1.50E+00 mm HgMP: 164-166 °C /Hydrochloride/ |
| Stability/Shelf Life | STABLE IN LIGHT, HEAT & IN AIR /SULFATE/ |
| Collision Cross Section | 127.6 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)] |
| Other Experimental Properties | EITHER ODORLESS OR HAS FAINT, CINNAMALDEHYDE-LIKE ODOR & SLIGHTLY ACID TASTE /SULFATE/MELTS WITH DECOMP @ 218 °C /SULFATE/Crystals /Sulfate/Crystals from ethyl acetate & ether /Hydrochloride/WHITE CRYSTALLINE POWDER /SULFATE/ |
| Dichte | 1.065±0.06 g/cm3(Predicted) |
| Lagerbedingungen | 2-8°C(protect from light) |
| pKa (Säurekonstante) | 8.24±0.10(Predicted) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Tranylcypromine: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Cyclopropanamine, 2-phenyl-, trans-(.+-.)-: Human health tier I assessment |
| FDA-Anforderungen | Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392). |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Treatment | Treatment should normally consist of general supportive measures, close observation of vital signs and steps to counteract specific symptoms as they occur, since MAO inhibition may persist. External cooling is recommended if hyperpyrexia occurs. Barbiturates have been reported to help relieve myoclonic reactions, but frequency of administration should be controlled carefully because Tranylcypromine may prolong barbiturate activity. When hypotension requires treatment, the standard measures for managing circulatory shock should be initiated. If pressor agents are used, the rate of infusion should be regulated by careful observation of the patient because an exaggerated pressor response sometimes occurs in the presence of MAO inhibition. (L1712) |
| Wechselwirkungen | HEXOBARBITAL SLEEPING TIME IS PROLONGED BY PARNATE, INDICATING ITS ABILITY TO POTENTIATE OTHER DRUGS PRESUMABLY BY INTERFERING WITH THEIR DETOXIFICATION. /PARNATE/MAO INHIBITORS ALSO ENHANCE EFFECTS OF EXOGENOUSLY ADMIN AMINES, SUCH AS 5-HT & NOREPINEPHRINE, AS WELL AS PRECURSORS, SUCH AS 3,4-HYDROXYPHENYLALANINE (DOPA) & 5-HYDROXYTRYPTOPHAN. /MAO INHIBITORS/Meperidine should never be used for ... headaches /with the hypertensive episode/, and blood pressure should be evaluated immediately when a patient taking an MAO inhibitor reports a severe throbbing headache or a feeling of pressure in the head. /MAO INHIBITORS/MAO INHIBITORS ... INTERFERE WITH DETOXICATION MECHANISMS FOR CERTAIN OTHER DRUGS. THEY PROLONG & INTENSIFY EFFECTS OF CENTRAL DEPRESSANT AGENTS, SUCH AS GENERAL ANESTHETICS, SEDATIVES, ANTIHISTAMINES, ALCOHOL, & POTENT ANALGESICSOF ANTICHOLINERGIC AGENTS, PARTICULARLY THOSE USED IN THE TREATMENT OF PARKINSONISM& OF ANTIDEPRESSANT AGENTS, ESP IMIPRAMINE & AMITRIPTYLINE. /MAO INHIBITORS/For more Interactions (Complete) data for TRANYLCYPROMINE (37 total), please visit the HSDB record page. |
| Gesundheitliche Auswirkungen | Rare cases have been reported of hypertensive crisis, serotonin syndrome, myoclonus, hyperpyrexia, psychosis, and delirium, some of which progressed to coma. Additionally, in sensitive individuals or at extreme dosages, hypotension may lead to shock. [Wikipedia] |
| Hepatotoxicity | Tranylcypromine, like most monoamine oxidase inhibitors, can cause transient serum aminotransferase elevations in a proportion of patients. These elevations are usually mild, asymptomatic and self-limited and do not require dose modification. Tranylcypromine has also been associated with rare cases of acute, clinically apparent liver injury. The few cases described have resembled those caused by other MAO inhibitors. The time to clinical onset is typically 1 to 4 months and the usual pattern of serum enzyme elevations is hepatocellular (Case 1), although cholestatic injury has also been described. Immunoallergic features (rash, fever, eosinophilia) are uncommon as is autoantibody formation. |
| Unerwünschte Wirkungen | Common adverse effects of tranylcypromine include dry mouth, headaches, diarrhea, urinary hesitancy, insomnia, agitation, anxiety, nausea, and sexual dysfunction. Postural hypotension, sometimes leading to syncope, is another common adverse effect that warrants special attention for older patients on this medication. This adverse effect is dose-related and may require splitting the dose into 3 to 4 doses daily. More serious side effects include hepatotoxicity, seizures, and induction of mania. Additionally, in the United States, there is a black-box warning stating that this medication may lead to the activation of suicidal ideation and behavior in children, adolescents, and young adults aged 18 to 24 with major depressive disorder and other psychiatric disorders. |
| Expositionspfade | Interindividual variability in absorption. May be biphasic in some individuals. Peak plasma concentrations occur in one hour following oral administration with a secondary peak occurring within 2-3 hours. Biphasic absorption may represent different rates of absorption of the stereoisomers of the drug, though additional studies are required to confirm this. |
| Toxizitätsübersicht | Signs and Symptoms of OverdoseTranylcypromine irreversibly and nonselectively inhibits monoamine oxidase (MAO). Within neurons, MAO appears to regulate the levels of monoamines released upon synaptic firing. Since depression is associated with low levels of monoamines, the inhibition of MAO serves to ease depressive symptoms, as this results in an increase in the concentrations of these amines within the CNS. |
| Signs and Symptoms | In overdosage, some patients exhibit insomnia, restlessness and anxiety, progressing in severe cases to agitation, mental confusion and incoherence. Hypotension, dizziness, weakness and drowsiness may occur, progressing in severe cases to extreme dizziness and shock. A few patients have displayed hypertension with severe headache and other symptoms. Rare instances have been reported in which hypertension was accompanied by twitching or myoclonic fibrillation of skeletal muscles with hyperpyrexia, sometimes progressing to generalized rigidity and coma. |
| Human Toxicity Excerpts | EFFECTS OF OVERDOSAGE INCL AGITATION, HALLUCINATIONS, HYPERREFLEXIA, HYPERPYREXIA, & CONVULSIONS. BOTH HYPOTENSION & HYPERTENSION ALSO OCCUR. /MAO INHIBITORS/CHRONIC TOXICITY. ... MOST DANGEROUS ARE THOSE INVOLVING LIVER, BRAIN, & CARDIOVASCULAR SYSTEM. ... HYPERSENSITIVITY MAY BE RESPONSIBLE MECHANISM... /MAO INHIBITORS/...HAS EXHIBITED NO SPECIFIC OR SELECTIVE OCULAR TOXIC EFFECT IN USUAL DOSAGE OF 20 MG/DAY, BUT LARGE OVERDOSAGE TAKEN WITH SUICIDAL INTENT APPEARS TO HAVE RESULTED IN OCULAR & VISUAL DISTURBANCES IN 2 CASES.66-YR-OLD MAN TREATED FOR DEPRESSION (TRANYLCYPROMINE SULFATE 10 MG 3 TIMES/DAY FOR 6 DAYS) DEVELOPED INAPPROPRIATE ANTIDIURETIC HORMONE SECRETION WHICH DISAPPEARED AFTER DISCONTINUATION.For more Human Toxicity Excerpts (Complete) data for TRANYLCYPROMINE (8 total), please visit the HSDB record page. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)tranylcypromineDILI PositiveOralDOI:10.1016/j.drudis.2019.09.022 |
| Non-Human Toxicity Excerpts | IN ANIMALS IT PRODUCES IRRITABILITY, RESTLESSNESS, HYPERREFLEXIA, HYPERTONIA, SALIVATION, LACRIMATION, MYDRIASIS, & MILD ELEVATIONS IN BLOOD PRESSURE. IT SUPPRESSES APPETITE...TRANYLCYPROMINE 20 MG/KG PARENTERAL TO RATS INCR BRAIN SEROTONIN CONCN & DECR BRAIN GLYCOGENNO EFFECT ON BRAIN PHOSPHORYLASE A & B ACTIVITIES OR ON BRAIN ABILITY TO PRODUCE LACTATE ANAEROBICALLY FROM GLYCOGEN (THESE CONSIDERED INDICATORS OF GLYCOGENOLYSIS). |
| Zollcode | 2921309990 |
Anwendungen & Verwendung
Verwenden
2-Phenylcyclopropanamine is a useful reagent for the preparation of preparation of oxadiazole derivatives as fungicides.