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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (14) Show 14 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2023-02-21 17:18:19 UTC

HMDB ID

HMDB0014918

Secondary Accession Numbers

HMDB14918

Metabolite Identification

Common Name

Phenelzine

Description

Phenelzine is only found in individuals that have used or taken this drug. It is an irreversible non-selective inhibitor of monoamine oxidase. May be used to treat major depressive disorder.Although the exact mechanism of action has not been determined, it appears that the irreversible, nonselective inhibition of MAO by phenelzine relieves depressive symptoms by causing an increase in the levels of serotonin, norepinephrine, and dopamine in the neuron.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Nardil	HMDB
2 Phenethylhydrazine	HMDB
2-Phenethylhydrazine	HMDB
Nardelzine	HMDB
beta Phenylethylhydrazine	HMDB
Phenelzine sulfate	HMDB
Parke davis brand OF phenelzine sulfate	HMDB
Phenethylhydrazine	HMDB
beta-Phenylethylhydrazine	HMDB
Fenelzin	HMDB
Pfizer brand OF phenelzine sulfate	HMDB
Sulfate, phenelzine	HMDB
United drug brand OF phenelzine sulfate	HMDB
Warner chilcott brand OF phenelzine sulfate	HMDB

Chemical Formula

C₈H₁₂N₂

Average Molecular Weight

136.1943

Monoisotopic Molecular Weight

136.100048394

IUPAC Name

(2-phenylethyl)hydrazine

Traditional Name

phenelzine

CAS Registry Number

51-71-8

SMILES

NNCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C8H12N2/c9-10-7-6-8-4-2-1-3-5-8/h1-5,10H,6-7,9H2

InChI Key

RMUCZJUITONUFY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Alkylhydrazine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Hydrazine derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

primary amine (CHEBI:8060 )
a small molecule (CPD-13895 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11.1 g/L	Not Available
LogP	1.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.1 g/L	ALOGPS
logP	1.2	ALOGPS
logP	1.2	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Basic)	5.55	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	38.05 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.26 m³·mol⁻¹	ChemAxon
Polarizability	15.8 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	127.813	31661259
DarkChem	[M-H]-	124.754	31661259
DeepCCS	[M+H]+	127.788	30932474
DeepCCS	[M-H]-	124.776	30932474
DeepCCS	[M-2H]-	161.643	30932474
DeepCCS	[M+Na]+	136.515	30932474
AllCCS	[M+H]+	130.1	32859911
AllCCS	[M+H-H2O]+	125.4	32859911
AllCCS	[M+NH4]+	134.4	32859911
AllCCS	[M+Na]+	135.6	32859911
AllCCS	[M-H]-	130.9	32859911
AllCCS	[M+Na-2H]-	132.6	32859911
AllCCS	[M+HCOO]-	134.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenelzine	NNCCC1=CC=CC=C1	1918.7	Standard polar	33892256
Phenelzine	NNCCC1=CC=CC=C1	1333.8	Standard non polar	33892256
Phenelzine	NNCCC1=CC=CC=C1	1286.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenelzine,1TMS,isomer #1	C[Si](C)(C)NNCCC1=CC=CC=C1	1441.1	Semi standard non polar	33892256
Phenelzine,1TMS,isomer #1	C[Si](C)(C)NNCCC1=CC=CC=C1	1431.2	Standard non polar	33892256
Phenelzine,1TMS,isomer #1	C[Si](C)(C)NNCCC1=CC=CC=C1	1848.9	Standard polar	33892256
Phenelzine,1TMS,isomer #2	C[Si](C)(C)N(N)CCC1=CC=CC=C1	1458.0	Semi standard non polar	33892256
Phenelzine,1TMS,isomer #2	C[Si](C)(C)N(N)CCC1=CC=CC=C1	1522.3	Standard non polar	33892256
Phenelzine,1TMS,isomer #2	C[Si](C)(C)N(N)CCC1=CC=CC=C1	2176.8	Standard polar	33892256
Phenelzine,2TMS,isomer #1	C[Si](C)(C)N(NCCC1=CC=CC=C1)[Si](C)(C)C	1673.6	Semi standard non polar	33892256
Phenelzine,2TMS,isomer #1	C[Si](C)(C)N(NCCC1=CC=CC=C1)[Si](C)(C)C	1642.7	Standard non polar	33892256
Phenelzine,2TMS,isomer #1	C[Si](C)(C)N(NCCC1=CC=CC=C1)[Si](C)(C)C	1845.9	Standard polar	33892256
Phenelzine,2TMS,isomer #2	C[Si](C)(C)NN(CCC1=CC=CC=C1)[Si](C)(C)C	1628.3	Semi standard non polar	33892256
Phenelzine,2TMS,isomer #2	C[Si](C)(C)NN(CCC1=CC=CC=C1)[Si](C)(C)C	1594.3	Standard non polar	33892256
Phenelzine,2TMS,isomer #2	C[Si](C)(C)NN(CCC1=CC=CC=C1)[Si](C)(C)C	1796.1	Standard polar	33892256
Phenelzine,3TMS,isomer #1	C[Si](C)(C)N(CCC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1827.2	Semi standard non polar	33892256
Phenelzine,3TMS,isomer #1	C[Si](C)(C)N(CCC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1761.2	Standard non polar	33892256
Phenelzine,3TMS,isomer #1	C[Si](C)(C)N(CCC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1778.3	Standard polar	33892256
Phenelzine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNCCC1=CC=CC=C1	1676.3	Semi standard non polar	33892256
Phenelzine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNCCC1=CC=CC=C1	1681.8	Standard non polar	33892256
Phenelzine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NNCCC1=CC=CC=C1	1958.6	Standard polar	33892256
Phenelzine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)CCC1=CC=CC=C1	1679.3	Semi standard non polar	33892256
Phenelzine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)CCC1=CC=CC=C1	1789.3	Standard non polar	33892256
Phenelzine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(N)CCC1=CC=CC=C1	2271.8	Standard polar	33892256
Phenelzine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NCCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2050.5	Semi standard non polar	33892256
Phenelzine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NCCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2063.9	Standard non polar	33892256
Phenelzine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(NCCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2052.1	Standard polar	33892256
Phenelzine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(CCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2036.6	Semi standard non polar	33892256
Phenelzine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(CCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2047.9	Standard non polar	33892256
Phenelzine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NN(CCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2058.2	Standard polar	33892256
Phenelzine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2445.8	Semi standard non polar	33892256
Phenelzine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2358.3	Standard non polar	33892256
Phenelzine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2124.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phenelzine EI-B (Non-derivatized)	splash10-0a4l-9800000000-fec970db2245559d8531	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenelzine EI-B (Non-derivatized)	splash10-0a4l-9800000000-fec970db2245559d8531	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenelzine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9200000000-b2c57d1368223a96c523	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenelzine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9000000000-833e467e14c48ae4f6b3	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenelzine LC-ESI-qTof , Positive-QTOF	splash10-01t9-0592000000-92a48c620c961fdb430f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenelzine , positive-QTOF	splash10-0a4i-0900000000-cf09dbe619ab21f16ce0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenelzine 35V, Positive-QTOF	splash10-0a4i-2900000000-fcb3587623714354e760	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 10V, Positive-QTOF	splash10-000i-0900000000-6c9dda205486ea199582	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 20V, Positive-QTOF	splash10-0a4i-1900000000-d6caecbd05b28ce80778	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 40V, Positive-QTOF	splash10-052f-9200000000-e6be767f746d7eec77ba	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 10V, Negative-QTOF	splash10-000i-1900000000-97c518b056fc3f0c5992	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 20V, Negative-QTOF	splash10-000i-4900000000-6d2d5af23910f83be107	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 40V, Negative-QTOF	splash10-0kx3-9600000000-9577503e15a41993941b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 10V, Positive-QTOF	splash10-0a4i-0900000000-5ca1a374df7ceed01896	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 20V, Positive-QTOF	splash10-0a4i-3900000000-9f4b820ee530441e453f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 40V, Positive-QTOF	splash10-004l-9100000000-40882216bbd046d0ab4e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 10V, Negative-QTOF	splash10-000i-0900000000-e9776c924504e8fd7ea8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 20V, Negative-QTOF	splash10-052f-6900000000-27086fbc61d9efcf4d5a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenelzine 40V, Negative-QTOF	splash10-004i-9100000000-f3ed866d0f02ae18d439	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00780	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00780	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00780

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3547

KEGG Compound ID

C07430

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenelzine

METLIN ID

Not Available

PubChem Compound

3675

PDB ID

Not Available

ChEBI ID

248018

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Nolen WA: [Classical monoamine oxidase inhibitor: not registered for, but still a place in the treatment of depression]. Ned Tijdschr Geneeskd. 2003 Oct 4;147(40):1940-3. [PubMed:14574774 ]
Sowa BN, Holt A, Todd KG, Baker GB: Monoamine oxidase inhibitors, their structural analogues, and neuroprotection. Indian J Exp Biol. 2004 Sep;42(9):851-7. [PubMed:15462176 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Chiche F, Le Guillou M, Chetrite G, Lasnier F, Dugail I, Carpene C, Moldes M, Feve B: Antidepressant phenelzine alters differentiation of cultured human and mouse preadipocytes. Mol Pharmacol. 2009 May;75(5):1052-61. doi: 10.1124/mol.108.052563. Epub 2009 Feb 6. [PubMed:19201819 ]
Chenu F, El Mansari M, Blier P: Long-term administration of monoamine oxidase inhibitors alters the firing rate and pattern of dopamine neurons in the ventral tegmental area. Int J Neuropsychopharmacol. 2009 May;12(4):475-85. doi: 10.1017/S1461145708009218. Epub 2008 Aug 13. [PubMed:18700056 ]
Wooters TE, Bardo MT: The monoamine oxidase inhibitor phenelzine enhances the discriminative stimulus effect of nicotine in rats. Behav Pharmacol. 2007 Nov;18(7):601-8. [PubMed:17912044 ]
Volz HP, Gleiter CH: Monoamine oxidase inhibitors. A perspective on their use in the elderly. Drugs Aging. 1998 Nov;13(5):341-55. [PubMed:9829163 ]
Nolen WA: [Classical monoamine oxidase inhibitor: not registered for, but still a place in the treatment of depression]. Ned Tijdschr Geneeskd. 2003 Oct 4;147(40):1940-3. [PubMed:14574774 ]
Pickar D, Murphy DL, Cohen RM, Campbell IC, Lipper S: Selective and nonselective monoamine oxidase inhibitors: behavioral disturbances during their administration to depressed patients. Arch Gen Psychiatry. 1982 May;39(5):535-40. [PubMed:7092487 ]
McIntyre RS, Soczynska JK, Konarski JZ, Kennedy SH: The effect of antidepressants on glucose homeostasis and insulin sensitivity: synthesis and mechanisms. Expert Opin Drug Saf. 2006 Jan;5(1):157-68. [PubMed:16370964 ]
MacKenzie EM, Grant SL, Baker GB, Wood PL: Phenelzine causes an increase in brain ornithine that is prevented by prior monoamine oxidase inhibition. Neurochem Res. 2008 Mar;33(3):430-6. Epub 2007 Aug 31. [PubMed:17768678 ]

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Chiche F, Le Guillou M, Chetrite G, Lasnier F, Dugail I, Carpene C, Moldes M, Feve B: Antidepressant phenelzine alters differentiation of cultured human and mouse preadipocytes. Mol Pharmacol. 2009 May;75(5):1052-61. doi: 10.1124/mol.108.052563. Epub 2009 Feb 6. [PubMed:19201819 ]
Chenu F, El Mansari M, Blier P: Long-term administration of monoamine oxidase inhibitors alters the firing rate and pattern of dopamine neurons in the ventral tegmental area. Int J Neuropsychopharmacol. 2009 May;12(4):475-85. doi: 10.1017/S1461145708009218. Epub 2008 Aug 13. [PubMed:18700056 ]
Wooters TE, Bardo MT: The monoamine oxidase inhibitor phenelzine enhances the discriminative stimulus effect of nicotine in rats. Behav Pharmacol. 2007 Nov;18(7):601-8. [PubMed:17912044 ]
Volz HP, Gleiter CH: Monoamine oxidase inhibitors. A perspective on their use in the elderly. Drugs Aging. 1998 Nov;13(5):341-55. [PubMed:9829163 ]
Nolen WA: [Classical monoamine oxidase inhibitor: not registered for, but still a place in the treatment of depression]. Ned Tijdschr Geneeskd. 2003 Oct 4;147(40):1940-3. [PubMed:14574774 ]
Pickar D, Murphy DL, Cohen RM, Campbell IC, Lipper S: Selective and nonselective monoamine oxidase inhibitors: behavioral disturbances during their administration to depressed patients. Arch Gen Psychiatry. 1982 May;39(5):535-40. [PubMed:7092487 ]
MacKenzie EM, Grant SL, Baker GB, Wood PL: Phenelzine causes an increase in brain ornithine that is prevented by prior monoamine oxidase inhibition. Neurochem Res. 2008 Mar;33(3):430-6. Epub 2007 Aug 31. [PubMed:17768678 ]
McIntyre RS, Soczynska JK, Konarski JZ, Kennedy SH: The effect of antidepressants on glucose homeostasis and insulin sensitivity: synthesis and mechanisms. Expert Opin Drug Saf. 2006 Jan;5(1):157-68. [PubMed:16370964 ]

Enzyme Details

3. 4-aminobutyrate aminotransferase, mitochondrial

General function:: Involved in 4-aminobutyrate transaminase activity
Specific function:: Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:: ABAT
Uniprot ID:: P80404
Molecular weight:: 56438.405

References

MacKenzie EM, Grant SL, Baker GB, Wood PL: Phenelzine causes an increase in brain ornithine that is prevented by prior monoamine oxidase inhibition. Neurochem Res. 2008 Mar;33(3):430-6. Epub 2007 Aug 31. [PubMed:17768678 ]
Tanay VA, Parent MB, Wong JT, Paslawski T, Martin IL, Baker GB: Effects of the antidepressant/antipanic drug phenelzine on alanine and alanine transaminase in rat brain. Cell Mol Neurobiol. 2001 Aug;21(4):325-39. [PubMed:11775064 ]
McKenna KF, McManus DJ, Baker GB, Coutts RT: Chronic administration of the antidepressant phenelzine and its N-acetyl analogue: effects on GABAergic function. J Neural Transm Suppl. 1994;41:115-22. [PubMed:7931216 ]
McManus DJ, Baker GB, Martin IL, Greenshaw AJ, McKenna KF: Effects of the antidepressant/antipanic drug phenelzine on GABA concentrations and GABA-transaminase activity in rat brain. Biochem Pharmacol. 1992 Jun 9;43(11):2486-9. [PubMed:1610412 ]
Todd KG, Baker GB: GABA-elevating effects of the antidepressant/antipanic drug phenelzine in brain: effects of pretreatment with tranylcypromine, (-)-deprenyl and clorgyline. J Affect Disord. 1995 Dec 13;35(3):125-9. [PubMed:8749840 ]
Todd KG, Baker GB: Neurochemical effects of the monoamine oxidase inhibitor phenelzine on brain GABA and alanine: A comparison with vigabatrin. J Pharm Pharm Sci. 2008 May 16;11(2):14s-21s. [PubMed:19203467 ]
McKenna KF, Baker GB, Coutts RT: N2-acetylphenelzine: effects on rat brain GABA, alanine and biogenic amines. Naunyn Schmiedebergs Arch Pharmacol. 1991 May;343(5):478-82. [PubMed:1881457 ]

Enzyme Details

4. Membrane primary amine oxidase

General function:: Involved in copper ion binding
Specific function:: Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:: AOC3
Uniprot ID:: Q16853
Molecular weight:: 84621.27

References

Tipnis UR, Tao M, Boor PJ: Purification and characterization of semicarbazide-sensitive amine oxidase from porcine aorta. Cell Mol Biol (Noisy-le-grand). 1992 Aug-Sep;38(5-6):575-84. [PubMed:1483111 ]
Kumar D, Trent MB, Boor PJ: Allylamine and beta-aminopropionitrile induced aortic medial necrosis: mechanisms of synergism. Toxicology. 1998 Feb 6;125(2-3):107-15. [PubMed:9570326 ]
Chiche F, Le Guillou M, Chetrite G, Lasnier F, Dugail I, Carpene C, Moldes M, Feve B: Antidepressant phenelzine alters differentiation of cultured human and mouse preadipocytes. Mol Pharmacol. 2009 May;75(5):1052-61. doi: 10.1124/mol.108.052563. Epub 2009 Feb 6. [PubMed:19201819 ]
Biasi D, Caramaschi P, Pacor ML, Carletto A, Melchiori S, Manzo T, Bambara LM: [Multiple osseous avascular necrosis in a patient with systemic lupus erythematosus with antiphospholipid antibody positivity]. Recenti Prog Med. 1995 Nov;86(11):449-50. [PubMed:8539478 ]
MacKenzie EM, Grant SL, Baker GB, Wood PL: Phenelzine causes an increase in brain ornithine that is prevented by prior monoamine oxidase inhibition. Neurochem Res. 2008 Mar;33(3):430-6. Epub 2007 Aug 31. [PubMed:17768678 ]
Lizcano JM, Fernandez de Arriba A, Tipton KF, Unzeta M: Inhibition of bovine lung semicarbazide-sensitive amine oxidase (SSAO) by some hydrazine derivatives. Biochem Pharmacol. 1996 Jul 26;52(2):187-95. [PubMed:8694842 ]

Enzyme Details

5. Alanine aminotransferase 1

General function:: Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:: Catalyzes the reversible transamination between alanine and 2-oxoglutarate to form pyruvate and glutamate. Participates in cellular nitrogen metabolism and also in liver gluconeogenesis starting with precursors transported from skeletal muscles (By similarity).
Gene Name:: GPT
Uniprot ID:: P24298
Molecular weight:: 54636.415

References

Todd KG, Baker GB: Neurochemical effects of the monoamine oxidase inhibitor phenelzine on brain GABA and alanine: A comparison with vigabatrin. J Pharm Pharm Sci. 2008 May 16;11(2):14s-21s. [PubMed:19203467 ]
Tanay VA, Parent MB, Wong JT, Paslawski T, Martin IL, Baker GB: Effects of the antidepressant/antipanic drug phenelzine on alanine and alanine transaminase in rat brain. Cell Mol Neurobiol. 2001 Aug;21(4):325-39. [PubMed:11775064 ]
McKenna KF, Baker GB, Coutts RT: N2-acetylphenelzine: effects on rat brain GABA, alanine and biogenic amines. Naunyn Schmiedebergs Arch Pharmacol. 1991 May;343(5):478-82. [PubMed:1881457 ]

Enzyme Details

6. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

8. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Runge-Morris M, Feng Y, Zangar RC, Novak RF: Effects of hydrazine, phenelzine, and hydralazine treatment on rat hepatic and renal drug-metabolizing enzyme expression. Drug Metab Dispos. 1996 Jul;24(7):734-7. [PubMed:8818569 ]

Enzyme Details

9. Cytochrome P450 3A43

General function:: Involved in monooxygenase activity
Specific function:: Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:: CYP3A43
Uniprot ID:: Q9HB55
Molecular weight:: 57756.285

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

10. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters

Showing metabocard for Phenelzine (HMDB0014918)

MOL for HMDB0014918 (Phenelzine)

3D MOL for HMDB0014918 (Phenelzine)

3D SDF for HMDB0014918 (Phenelzine)

3D-SDF for HMDB0014918 (Phenelzine)

PDB for HMDB0014918 (Phenelzine)

3D PDB for HMDB0014918 (Phenelzine)

SMILES for HMDB0014918 (Phenelzine)

INCHI for HMDB0014918 (Phenelzine)

Structure for HMDB0014918 (Phenelzine)

3D Structure for HMDB0014918 (Phenelzine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

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