An official website of the United States government

Tranylcypromine

PubChem CID
19493
Structure
Tranylcypromine_small.png
Tranylcypromine_3D_Structure.png
Molecular Formula
Synonyms
  • tranylcypromine
  • (1R,2S)-2-phenylcyclopropan-1-amine
  • 3721-26-4
  • (1R,2S)-2-phenylcyclopropanamine
  • Parnate
Molecular Weight
133.19 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-18
Description
(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.
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 is a racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine with the chiral centers both located on the cylopropane ring. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).
Tranylcypromine is a Monoamine Oxidase Inhibitor. The mechanism of action of tranylcypromine is as a Monoamine Oxidase Inhibitor.
See also: Tranylcypromine Sulfate (has salt form); Tranylcypromine hydrochloride (is active moiety of).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Tranylcypromine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,2S)-2-phenylcyclopropan-1-amine
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

AELCINSCMGFISI-DTWKUNHWSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1[C@H]([C@@H]1N)C2=CC=CC=C2
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C9H11N
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

155-09-9
3721-28-6

2.3.2 Deprecated CAS

95-62-5

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 Metabolomics Workbench ID

2.3.10 NCI Thesaurus Code

2.3.11 Nikkaji Number

2.3.12 Pharos Ligand ID

2.3.13 RXCUI

2.3.14 Wikidata

2.3.15 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Jatrosom
  • Parnate
  • Sulfate, Tranylcypromine
  • trans 2 Phenylcyclopropylamine
  • trans-2-Phenylcyclopropylamine
  • Transamine
  • Tranylcypromine
  • Tranylcypromine Sulfate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
133.19 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.5
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
133.089149355 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
133.089149355 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
26 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
10
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
116
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Color / Form

Liquid
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1633

3.2.2 Boiling Point

79-80 °C @ 1.5-1.6 mm Hg
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1633

3.2.3 Melting Point

79-80 °C at 1.50E+00 mm Hg
MP: 164-166 °C /Hydrochloride/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1633

3.2.4 Solubility

48600 mg/L
Sol in water /Sulfate/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1633
Very slightly sol in alcohol, ether /Sulfate/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1633
Practically insol in chloroform /Sulfate/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1633

3.2.5 LogP

1.58
HANSCH,C ET AL. (1995)
log Kow= 1.58 @ 25 °C
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 58

3.2.6 Stability / Shelf Life

STABLE IN LIGHT, HEAT & IN AIR /SULFATE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1033

3.2.7 Dissociation Constants

3.2.8 Collision Cross Section

127.27 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

126.96 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

3.2.9 Kovats Retention Index

Standard non-polar
1198 , 1198 , 1210 , 1195 , 1206 , 1210 , 1185.9 , 1198.5 , 1223
Semi-standard non-polar
1225 , 1225 , 1217.4 , 1235 , 1248 , 1259 , 1259 , 1271 , 1240.3
Standard polar
1834 , 1834 , 1850 , 1852 , 1860 , 1904

3.2.10 Other Experimental Properties

EITHER ODORLESS OR HAS FAINT, CINNAMALDEHYDE-LIKE ODOR & SLIGHTLY ACID TASTE /SULFATE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1033
MELTS WITH DECOMP @ 218 °C /SULFATE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1033
Crystals /Sulfate/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1633
Crystals from ethyl acetate & ether /Hydrochloride/
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1633
WHITE CRYSTALLINE POWDER /SULFATE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1033

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
3.3.1.1 Human Drugs
Breast Feeding; Lactation; Antidepressive Agents; Monoamine Oxidase Inhibitors
Human drug -> Prescription
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

Source of Spectrum
QC-7-3510-1
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Other Spectra

Intense mass spectral peaks: 56 m/z, 115 m/z, 132 m/z, 133 m/z
Pfleger, K., H. Maurer and A. Weber. Mass Spectral and GC Data of Drugs, Poisons and their Metabolites. Parts I and II. Mass Spectra Indexes. Weinheim, Federal Republic of Germany. 1985., p. 171

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

For the treatment of major depressive episode without melancholia.

7.2 LiverTox Summary

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.

7.3 Drug Classes

Breast Feeding; Lactation; Antidepressive Agents; Monoamine Oxidase Inhibitors
Antidepressant Agents

7.4 FDA National Drug Code Directory

7.5 Drug Labels

Drug and label

7.6 Clinical Trials

7.6.1 ClinicalTrials.gov

7.6.2 EU Clinical Trials Register

7.7 Therapeutic Uses

Antidepressive Agents; Monoamine Oxidase Inhibitors; Anti-Anxiety Agents
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
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/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 181
MOST USEFUL EFFECT OF VARIOUS MAO INHIBITORS IS TO ELEVATE MOOD OF DEPRESSED PT. /MAO INHIBITORS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 181
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/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 181
For more Therapeutic Uses (Complete) data for TRANYLCYPROMINE (11 total), please visit the HSDB record page.

7.8 Drug Warnings

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/
American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 484
...CONTRAINDICATED IN PT WITH CEREBROVASCULAR DEFECTS, CARDIOVASCULAR DISORDERS OR PHEOCHROMOCYTOMA... /SULFATE/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1033
SWITCHING PT FROM ONE MAO INHIBITOR TO ANOTHER OR TO TRICYCLIC ANTIDEPRESSANT REQUIRES REST PERIOD OF 10-14 DAYS. /MAO INHIBITORS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 183
...TRANYLCYPROMINE CAN CAUSE REACTION IF ADMIN WHEN EFFECT OF PHENELZINE IS STILL PRESENT.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 183
For more Drug Warnings (Complete) data for TRANYLCYPROMINE (20 total), please visit the HSDB record page.

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Tranylcypromine belongs to a class of antidepressants called monoamine oxidase inhibitors (MAOIs). Tranylcypromine is a non-hydrazine monoamine oxidase inhibitor with a rapid onset of activity. MAO is an enzyme that catalyzes the oxidative deamination of a number of amines, including serotonin, norepinephrine, epinephrine, and dopamine. Two isoforms of MAO, A and B, are found in the body. MAO-A is mainly found within cells located in the periphery and catalyzes the breakdown of serotonin, norepinephrine, epinephrine, dopamine and tyramine. MAO-B acts on phenylethylamine, norepinephrine, epinephrine, dopamine and tyramine, is localized extracellularly and is found predominantly in the brain. While the mechanism of MAOIs is still unclear, it is thought that they act by increasing free serotonin and norepinephrine concentrations and/or by altering the concentrations of other amines in the CNS. It has been postulated that depression is caused by low levels of serotonin and/or norepinephrine and that increasing serotonergic and norepinephrinergic neurotransmission results in relief of depressive symptoms. MAO A inhibition is thought to be more relevant to antidepressant activity than MAO B inhibition. Selective MAO B inhibitors, such as selegiline, have no antidepressant effects.

8.2 MeSH Pharmacological Classification

Antidepressive 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.)
Monoamine Oxidase Inhibitors
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.)
Anti-Anxiety Agents
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.)

8.3 FDA Pharmacological Classification

1 of 2
FDA UNII
3E3V44J4Z9
Active Moiety
TRANYLCYPROMINE
Pharmacological Classes
Established Pharmacologic Class [EPC] - Monoamine Oxidase Inhibitor
Pharmacological Classes
Mechanisms of Action [MoA] - Monoamine Oxidase Inhibitors
FDA Pharmacology Summary
Tranylcypromine is a Monoamine Oxidase Inhibitor. The mechanism of action of tranylcypromine is as a Monoamine Oxidase Inhibitor.
2 of 2
Non-Proprietary Name
TRANYLCYPROMINE
Pharmacological Classes
Monoamine Oxidase Inhibitor [EPC]; Monoamine Oxidase Inhibitors [MoA]

8.4 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AF - Monoamine oxidase inhibitors, non-selective

N06AF04 - Tranylcypromine

8.5 Absorption, Distribution and Excretion

Absorption
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.
Volume of Distribution
1.1-5.7 L/kg
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/
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 441

8.6 Metabolism / Metabolites

Hepatic.

8.7 Biological Half-Life

1.5-3.2 hours in patients with normal renal and hepatic function

8.8 Mechanism of Action

Tranylcypromine 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.
RESULTS SUGGEST THAT D- & DL-TRANYLCYPROMINE HAVE DIRECT & INDIRECT ACTIONS ON TRYPTAMINERGIC NEUROTRANSMISSION.
SMITH DF; HINDLIMB EXTENSOR REFLEX OF SPINAL RATS GIVEN TRANYLCYPROMINE STEREOISOMERS; J NEURAL TRANSM 44 (4): 303 (1979)
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.
PHILIPS ET AL; EXPERIENTIA 36 (2): 241 (1980)
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
GENTIL ET AL; BIOCHEM PHARMACOL 27 (8): 1197 (1978)
...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/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 181
... TRANYLCYPROMINE IS A POTENT BUT NOT SPECIFIC INHIBITOR OF CYP2C19.
Klaassen, C.D., M.O. Amdur, Doull J. (eds.). Casarett and Doull's Toxicology. The Basic Science of Poisons. 5th ed. New York, NY: McGraw-Hill, 1995., p. 155

9 Use and Manufacturing

9.1 Uses

MEDICATION

Use (kg; approx.) in Germany (2009): >25

Consumption (g per capita; approx.) in Germany (2009): 0.000305

Calculated removal (%): 75.3

9.1.1 Use Classification

Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

9.2 Methods of Manufacturing

Burger, Yost, J Amer Chem Soc 70, 2198 (1948); Tedeschi, US patent 2,997,422 (1961 to SK & F).
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1633

9.3 Formulations / Preparations

Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1633
DOSAGE FORMS--TABLETS NF: 10 MG. /SULFATE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1033

9.4 General Manufacturing Information

TRANYLCYPROMINE WAS WITHDRAWN FROM MARKET FOR SOME MONTHS DURING 1964, BUT AGAIN BECAME AVAIL FOR USE IN PT UNDER CLOSE MEDICAL OBSERVATION.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 180

10 Identification

10.1 Clinical Laboratory Methods

DETERMINATION OF TRANYLCYPROMINE IN URINE AND SERUM BY ELECTRON CAPTURE GLC.
BASELT ET AL; DETERMINATION OF SERUM & URINE CONCN OF TRANYLCYPROMINE BY ELECTRON CAPTURE GLC; J ANAL TOX 1 (5): 215 (1977)

11 Safety and Hazards

11.1 Accidental Release Measures

11.1.1 Disposal Methods

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.

11.2 Regulatory Information

New Zealand EPA Inventory of Chemical Status
Tranylcypromine: Does not have an individual approval but may be used under an appropriate group standard

11.2.1 FDA Requirements

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).
21 CFR 200-299, 300-499, 820, and 860 (4/1/97)

11.3 Other Safety Information

Chemical Assessment

IMAP assessments - Cyclopropanamine, 2-phenyl-, trans-(.+-.)-: Human health tier I assessment

IMAP assessments - Cyclopropanamine, 2-phenyl-, trans-(.+-.)-: Environment tier I assessment

12 Toxicity

12.1 Toxicological Information

12.1.1 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.

Likelihood score: D (possible rare cause of clinically apparent liver injury).

12.1.2 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Because little information is available on the use of tranylcypromine during breastfeeding, an alternate drug may be preferred, especially while nursing a newborn or preterm infant.

◉ Effects in Breastfed Infants

A woman with severe depression took tranylcypromine 100 to 120 mg daily, as well as pimozide, diazepam and alprazolam during pregnancy and postpartum. She breastfed her infant until about 2 weeks postpartum when the infant developed abdominal distension and feeding intolerance. The symptoms resolved on discontinuation of breastfeeding.

◉ Effects on Lactation and Breastmilk

Nine subjects were treated with an average dose of 29 mg daily (range 10 to 40 mg daily) of oral tranylcypromine for an average of 16 days. Serum prolactin levels increased by 3 mcg/L.The clinical relevance of these findings in nursing mothers is not known. The prolactin level in a mother with established lactation may not affect her ability to breastfeed.

12.1.3 Acute Effects

12.1.4 Interactions

HEXOBARBITAL SLEEPING TIME IS PROLONGED BY PARNATE, INDICATING ITS ABILITY TO POTENTIATE OTHER DRUGS PRESUMABLY BY INTERFERING WITH THEIR DETOXIFICATION. /PARNATE/
Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-230
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/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 181
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/
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 445
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/
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 445
For more Interactions (Complete) data for TRANYLCYPROMINE (37 total), please visit the HSDB record page.

12.1.5 Human Toxicity Excerpts

EFFECTS OF OVERDOSAGE INCL AGITATION, HALLUCINATIONS, HYPERREFLEXIA, HYPERPYREXIA, & CONVULSIONS. BOTH HYPOTENSION & HYPERTENSION ALSO OCCUR. /MAO INHIBITORS/
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 443
CHRONIC TOXICITY. ... MOST DANGEROUS ARE THOSE INVOLVING LIVER, BRAIN, & CARDIOVASCULAR SYSTEM. ... HYPERSENSITIVITY MAY BE RESPONSIBLE MECHANISM... /MAO INHIBITORS/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 182
...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.
Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 930
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.
PETERSON ET AL; J AM MED ASSOC 239: 1422 (1978)
For more Human Toxicity Excerpts (Complete) data for TRANYLCYPROMINE (8 total), please visit the HSDB record page.

12.1.6 Non-Human Toxicity Excerpts

IN ANIMALS IT PRODUCES IRRITABILITY, RESTLESSNESS, HYPERREFLEXIA, HYPERTONIA, SALIVATION, LACRIMATION, MYDRIASIS, & MILD ELEVATIONS IN BLOOD PRESSURE. IT SUPPRESSES APPETITE...
Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-230
TRANYLCYPROMINE 20 MG/KG PARENTERAL TO RATS INCR BRAIN SEROTONIN CONCN & DECR BRAIN GLYCOGEN; NO EFFECT ON BRAIN PHOSPHORYLASE A & B ACTIVITIES OR ON BRAIN ABILITY TO PRODUCE LACTATE ANAEROBICALLY FROM GLYCOGEN (THESE CONSIDERED INDICATORS OF GLYCOGENOLYSIS).
RINAUDO ET AL; BOLL- SOC ITAL BIOL SPER 55 (2): 148 (1979)

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Wiley References

14.6 Chemical Co-Occurrences in Literature

14.7 Chemical-Gene Co-Occurrences in Literature

14.8 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 Chemical Co-Occurrences in Patents

15.4 Chemical-Disease Co-Occurrences in Patents

15.5 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Protein Bound 3D Structures

16.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

16.2 Chemical-Target Interactions

16.3 Drug-Drug Interactions

16.4 Drug-Food Interactions

  • Avoid alcohol. Ingesting alcohol may increase the CNS depressant effects of tranylcypromine.
  • Avoid St. John's Wort. Administering tranylcypromine with St. John's Wort may increase the risk of serotonin syndrome.
  • Avoid tyramine-containing foods and supplements. Tyramine-containing foods and beverages can cause a sudden elevation in blood pressure or a hypertensive crisis. Foods that contain tyramine include aged cheese, ripe bananas, red wine, some alcoholic beverages (beer), cured food, pickled food, and fava beans.

17 Biological Test Results

17.1 BioAssay Results

18 Classification

18.1 MeSH Tree

18.2 NCI Thesaurus Tree

18.3 ChEBI Ontology

18.4 WHO ATC Classification System

18.5 FDA Pharm Classes

18.6 ChemIDplus

18.7 ChEMBL Target Tree

18.8 NORMAN Suspect List Exchange Classification

18.9 CCSBase Classification

18.10 EPA DSSTox Classification

18.11 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Cyclopropanamine, 2-phenyl-, trans-(.+-.)-
    https://services.industrialchemicals.gov.au/search-assessments/
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  7. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  8. Hazardous Substances Data Bank (HSDB)
  9. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  10. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  11. ChEBI
  12. FDA Pharm Classes
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  13. LiverTox
  14. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  15. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  16. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  17. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  18. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  19. Therapeutic Target Database (TTD)
  20. DailyMed
  21. Drugs and Lactation Database (LactMed)
  22. Drugs@FDA
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  23. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    (+)-tranylcypromine | Parnate
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  24. EU Clinical Trials Register
  25. National Drug Code (NDC) Directory
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  26. IUPAC Digitized pKa Dataset
    cyclopropane, trans-1-amino-2-phenyl-
    https://github.com/IUPAC/Dissociation-Constants
  27. Japan Chemical Substance Dictionary (Nikkaji)
  28. Metabolomics Workbench
  29. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  30. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  31. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  32. Protein Data Bank in Europe (PDBe)
  33. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  34. SpectraBase
    (1R,2S)-2-phenyl-1-cyclopropanamine
    https://spectrabase.com/spectrum/ElD2k2JwsfR
  35. Springer Nature
  36. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  37. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  38. Wikidata
  39. Wikipedia
  40. Wiley
  41. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Monoamine Oxidase Inhibitors
    https://www.ncbi.nlm.nih.gov/mesh/68008996
  42. PubChem
  43. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  44. PATENTSCOPE (WIPO)
  45. NCBI
CONTENTS