(-)-Tranylcypromine
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(-)-Tranylcypromine
structure -
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CAS No:
3721-26-4
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Formula:
C9H11N
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Chemical Name:
(-)-Tranylcypromine
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Synonyms:
Cyclopropanamine,2-phenyl-,(1R,2S)-;Cyclopropylamine,2-phenyl-,trans-(-)-;Cyclopropanamine,2-phenyl-,(1R-trans)-;(1R,2S)-2-Phenylcyclopropanamine;l-trans-2-Phenylcyclopropylamine;l-Tranylcypromine;(-)-trans-2-Phenylcyclopropylamine;(-)-Tranylcypromine;(1R,2S)-Tranylcypromine;(1R,2S)-2-Phenylcyclopropylamine;(1R,2S)-2-Phenylcyclopropan-1-amine
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CAS No:
Description
ChEBI: A 2-phenylcyclopropan-1-amine that is the (1S,2R)-enantiomer of tranylcypromine.
(1R,2S)-tranylcypromine is a 2-phenylcyclopropan-1-amine that is the (1R,2S)-enantiomer of tranylcypromine. It is a conjugate base of a (1R,2S)-tranylcypromine(1+). It is an enantiomer of a (1S,2R)-tranylcypromine.|Tranylcypromine is a nonhydrazine monoamine oxidase inhibitor (MAO inhibitor) used in therapy of severe depression. Tranylcypromine therapy is associated with rare instances of clinically apparent acute liver injury.|A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311)
(-)-Tranylcypromine Basic Attributes
133.19
133.19
205-841-9
DTXSID2023694
Liquid
N - Nervous system
Characteristics
26
1.5
1.1±0.1 g/cm3
79-80 °C at 1.50E+00 mm Hg
79-80 deg C @ 1.5-1.6 mm Hg
90.8±19.6 °C
1.584
Sol in water /Sulfate/|Very slightly sol in alcohol, ether /Sulfate/|Practically insol in chloroform /Sulfate/
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/
Safety Information
STABLE IN LIGHT, HEAT & IN AIR /SULFATE/
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.
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 amended; 21 U.S.C. 321-392).
Toxicity
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.
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 ANALGESICS; OF 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.
Drug Information
Tranylcypromine is a nonhydrazine monoamine oxidase inhibitor (MAO inhibitor) used in therapy of severe depression. Tranylcypromine therapy is associated with rare instances of clinically apparent acute liver injury.
Antidepressant Agents
Antidepressive Agents; Monoamine Oxidase Inhibitors; Anti-Anxiety Agents|DEG TO WHICH MAO IS INHIBITED IN PARTICULAR ORGAN OF BODY VARIES WITH PARTICULAR MAO INHIBITOR. SINCE MAO INHIBITION CANNOT BE EASILY MONITORED IN CLINICAL SITUATIONS (BECAUSE OF LONG LATENCY & DURATION OF ACTION), DRUGS ARE NEVER ADMIN PARENTERALLY. /MAO INHIBITORS/|MOST USEFUL EFFECT OF VARIOUS MAO INHIBITORS IS TO ELEVATE MOOD OF DEPRESSED PT. /MAO INHIBITORS/|MAO INHIBITORS ARE AMONG MOST EFFECTIVE REM SUPPRESSORS KNOWN. THIS EFFECT HAS BEEN USED THERAPEUTICALLY IN TREATMENT OF NARCOLEPSY. ... MAO INHIBITORS LOWER BLOOD PRESSURE & PROVIDE SYMPTOMATIC RELIEF IN ANGINA PECTORIS. /MAO INHIBITORS/|For more Therapeutic Uses (Complete) data for TRANYLCYPROMINE (11 total), please visit the HSDB record page.
MAJORITY OF SMALL NUMBER OF DEATHS...OCCURRED AFTER DOSES OF OVER 350 MG; PT HAVE SURVIVED AFTER INGESTION OF THIS AMT, HOWEVER. DEPENDENCE ON TRANYLCYPROMINE HAS BEEN REPORTED OCCASIONALLY. /SULFATE/|...CONTRAINDICATED IN PT WITH CEREBROVASCULAR DEFECTS, CARDIOVASCULAR DISORDERS OR PHEOCHROMOCYTOMA... /SULFATE/|SWITCHING PT FROM ONE MAO INHIBITOR TO ANOTHER OR TO TRICYCLIC ANTIDEPRESSANT REQUIRES REST PERIOD OF 10-14 DAYS. /MAO INHIBITORS/|...TRANYLCYPROMINE CAN CAUSE REACTION IF ADMIN WHEN EFFECT OF PHENELZINE IS STILL PRESENT.|For more Drug Warnings (Complete) data for TRANYLCYPROMINE (20 total), please visit the HSDB record page.
Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)|Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)|A chemically heterogeneous group of drugs that have in common the ability to block oxidative deamination of naturally occurring monoamines. (From Gilman, et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p414) (See all compounds classified as Monoamine Oxidase Inhibitors.)
THE MAO INHIBITORS ARE ABSORBED READILY WHEN GIVEN BY MOUTH. THESE DRUGS PRODUCE MAXIMAL INHIBITION OF MAO WITHIN 5-10 DAYS. ... ALTHOUGH THEIR BIOLOGICAL ACTIVITY IS PROLONGED BECAUSE OF THE CHARACTERISTICS OF THEIR INTERACTION WITH THE ENZYME, THEIR CLINICAL EFFICACY APPEARS TO BE REDUCED WHEN THE DRUG IS GIVEN LESS FREQUENTLY THAN ONCE DAILY. /MAO INHIBITORS/
RESULTS SUGGEST THAT D- & DL-TRANYLCYPROMINE HAVE DIRECT & INDIRECT ACTIONS ON TRYPTAMINERGIC NEUROTRANSMISSION.|TRANYLCYPROMINE-HCL ADMIN IP (20 MG/KG) TO RATS: INCR IN HIPPOCAMPUS & DIENCEPHALON CONCN OF 2-PHENYLETHYLAMINE & TRYPTAMINE WERE MUCH HIGHER THAN THOSE OF M- & P-TYRAMINE. THESE MAY BE INVOLVED IN CNS NEURONAL FUNCTIONING, THEREFORE COMPONENT OF TRANYLCYPROMINE ACTIVITY.|PLATELET MAO ACTIVITY MARKEDLY DECR (DL-TRANYLCYPROMINE SULFATE 10 & 20 MG ORAL): UPTAKE OF 5-HYDROXYTRYPTAMINE, DOPAMINE & METARAMINOL ONLY SLIGHTLY DECR. MAO INHIBITOR ANTIDEPRESSANT ACTIVITY PROBABLY LESS RELATED TO CATECHOLAMINE UPTAKE INHIBITION THAN OXIDASE INHIBITION|...PRODUCE IRREVERSIBLE INACTIVATION OF MAO BY FORMING STABLE COMPLEXES WITH ENZYME. ... THERE IS EVIDENCE THAT SOME MAO INHIBITORS PREVENT RELEASE OF NOREPINEPHRINE FROM NERVE ENDINGS BY NERVE IMPULSES. /MAO INHIBITORS/|... TRANYLCYPROMINE IS A POTENT BUT NOT SPECIFIC INHIBITOR OF CYP2C19.
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.
Jatrosom
(-)-Tranylcypromine Use and Manufacturing
Burger, Yost, J Amer Chem Soc 70, 2198 (1948); Tedeschi, US patent 2,997,422 (1961 to SK & F).
MEDICATION
Parnate, Tylciprine /Sulfate/|DOSAGE FORMS--TABLETS NF: 10 MG. /SULFATE/
TRANYLCYPROMINE WAS WITHDRAWN FROM MARKET FOR SOME MONTHS DURING 1964, BUT AGAIN BECAME AVAIL FOR USE IN PT UNDER CLOSE MEDICAL OBSERVATION.
DETERMINATION OF TRANYLCYPROMINE IN URINE AND SERUM BY ELECTRON CAPTURE GLC.
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals
Computed Properties
Molecular Weight:133.19
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:133.089149355
Monoisotopic Mass:133.089149355
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:116
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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