Tranylcypromine (CED0004725)

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:35 UTC

Update Date

2026-05-14 16:47:55 UTC

Accession Number

CHEM002265

Identification

Common Name

Tranylcypromine

Class

Small Molecule

Description

Tranylcypromine is an exogenous organic compound with the formula C9H11N and an average molecular weight of 133.19 g/mol. It exists as a solid at room temperature. Tranylcypromine belongs to the amines, a subclass of organonitrogen compounds within the organic compounds. This compound is found in antidepressants, as well as in other smoking requisites and pipe accessories within household cleaning and consumer products. The recorded route of exposure is oral. Tranylcypromine irreversibly inhibits monoamine oxidase (MAO), specifically targeting amine oxidase [flavin-containing] A (MAOA) and amine oxidase [flavin-containing] B (MAOB). Other protein targets include the D(2) dopamine receptor (DRD2) and the 5-hydroxytryptamine receptor 2A (HTR2A). Within neurons, MAO appears to regulate the levels of monoamines released upon synaptic firing. Because depression is associated with low levels of monoamines, the inhibition of MAO serves to ease depressive symptoms. Consequently, tranylcypromine is effective in the treatment of major depression, atypical depression, and dysthymic disorder. Additionally, it is useful in the treatment of phobic and panic disorders.

Contaminant Type

Amine
Anti-Anxiety Agent
Antidepressant
Antidepressive Agent
Drug
Human Neurotoxin
Metabolite
Monoamine Oxidase Inhibitor
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Parnate	Kegg
Parnic acid	Generator
Allphar brand OF tranylcypromine sulfate	HMDB
GlaxoSmithKline brand OF tranylcypromine sulfate	HMDB
Goldshield brand OF tranylcypromine sulfate	HMDB
Jatrosom	HMDB
Link brand OF tranylcypromine sulfate	HMDB
SmithKline brand OF tranylcypromine sulfate	HMDB
Sulfate, tranylcypromine	HMDB
Transamine	HMDB
Tranylcypromine sulfate	HMDB
Esparma brand OF tranylcypromine sulfate	HMDB
trans 2 Phenylcyclopropylamine	HMDB
trans-2-Phenylcyclopropylamine	HMDB

Chemical Formula

C₉H₁₁N

Average Molecular Mass

133.190 g/mol

Monoisotopic Mass

133.089 g/mol

CAS Registry Number

155-09-9

IUPAC Name

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

Traditional Name

tranylcypromine sulfate

SMILES

N[C@@H]1CC1C1=CC=CC=C1

InChI Identifier

InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8?,9-/m1/s1

InChI Key

AELCINSCMGFISI-YGPZHTELSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Substituents

Aralkylamine
Benzenoid
Monocyclic benzene moiety
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Primary aliphatic amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	79-80°C at 1.50E+00 mm Hg
Boiling Point	Not Available
Solubility	4.86E+004 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	1.49 g/L	ALOGPS
logP	1.5	ALOGPS
logP	1.34	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	9.62	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	26.02 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	41.7 m³·mol⁻¹	ChemAxon
Polarizability	15.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0f6x-9800000000-230ec64c0c4e335281c3	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00lr-0900000000-747bd6c24d23e0dc3b30	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00lr-3900000000-07e0a486860af42efca8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zi3-9700000000-7ce3af5a04eec9a5a1d2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-387ae3c4508041ed7f03	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0900000000-ff5149796df2404afa22	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00ou-9300000000-a90e0e8ff4d27cddf576	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0900000000-f88420912e5970f9665b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014l-6900000000-612bebf2afd4a2d06608	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002f-9100000000-5ab488145ab6cf0850b9	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0159-0900000000-f25847cc17ac78de452a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0900000000-d180e1330ea80a51da49	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00or-9700000000-372b2fa84e615277aebf	Not Available	View Spectrum
MS	MS Spectrum	splash10-00lr-4900000000-a7221eab5a5f5d286c2a	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

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.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

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.

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. (4)

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
257.0	Log mg/kg	[140:460]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
377	Antidepressants	Healthcare, pharmaceuticals & veterinary products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
562	Pipe Accessories	Household cleaning & consumer products	Not Available

Pathways

5 pathways

Tranylcypromine Amine Oxidase Norepinephrine Antidepressant Action Pathway

Safinamide Action Pathway

Tranylcypromine Amine Oxidase Serotonin Antidepressant Action Pathway

Tranylcypromine Drug Metabolism

Tranylcypromine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Amine oxidase [flavin-containing] B	P27338	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21397	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Lysine-specific histone demethylase 1A	O60341	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	0.700643
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Trace amine-associated receptor 1	Q96RJ0	Humans	Predicted (SEA)	0.544945
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	26.4687
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	17.5161
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q60492	Cavia porcellus	Predicted (SEA)	54.8059
Click to view 3D structure	Cytochrome P450 2A6	P11509	Humans	Predicted (SEA)	1.32344
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21396	Rattus norvegicus	Predicted (SEA)	10.1982
Click to view 3D structure	Sigma intracellular receptor 2	Q5U3Y7	Rattus norvegicus	Predicted (SEA)	40.5594
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	209.882
Click to view 3D structure	Replicase polyprotein 1ab	P0DTD1	SARS-CoV-2	Predicted (SEA)	49.9792
Click to view 3D structure	Amine oxidase [flavin-containing] B	P19643	Rattus norvegicus	Predicted (SEA)	16.5819
Click to view 3D structure	Cytochrome P450 2A13	Q16696	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Sodium-dependent dopamine transporter	P23977	Rattus norvegicus	Predicted (SEA)	133.901
Click to view 3D structure	Protein deacetylase HDAC6	Q9UBN7	Humans	Predicted (SEA)	452.615
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	397.887
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	411.433
Click to view 3D structure	Norepinephrine transporter	Q9WTR4	Rattus norvegicus	Predicted (SEA)	95.9102
Click to view 3D structure	Histone deacetylase 1	Q13547	Humans	Predicted (SEA)	862.647
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	651.754
Click to view 3D structure	Histone deacetylase 2	Q92769	Humans	Predicted (SEA)	561.838
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	399.055
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Known	Tranylcypromine irreversibly 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.
Click to view 3D structure	Amine oxidase [flavin-containing] A	P21397	Humans	Known	Tranylcypromine irreversibly 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.
Click to view 3D structure	Amine oxidase [flavin-containing] B	P27338	Humans	Known	Tranylcypromine irreversibly 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.
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Known	Tranylcypromine irreversibly 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.