Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-18 09:09:22 UTC

Update Date

2023-02-21 17:15:58 UTC

HMDB ID

HMDB0001942

Secondary Accession Numbers

HMDB0005002
HMDB01942
HMDB05002

Metabolite Identification

Common Name

Phenylpropanolamine

Description

Phenylpropanolamine, also known as D-norephedrine, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Phenylpropanolamine is a drug which is used for the treatment of nasal congestion, control of urinary incontinence, priapism and obesity. Based on a literature review a significant number of articles have been published on Phenylpropanolamine.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
D-Norephedrine	Kegg
Norephedrine	Kegg
DL-Norephedrine	HMDB
DL-Phenylpropanolamine	HMDB
Hydriatine	HMDB
L-NOREPHEDRINE	HMDB
L-Phenyl propanolamine	HMDB
Mucorama	HMDB
Nobese	HMDB
Obestat	HMDB
Prestwick_388	HMDB
Propadrine	HMDB
Phenylpropanolamine hydrochloride	MeSH, HMDB
Propagest	MeSH, HMDB
Dexatrim	MeSH, HMDB
Hydrochloride, phenylpropanolamine	MeSH, HMDB
Prolamine	MeSH, HMDB
Phenylpropanolamine	MeSH
Triaminic DM	MeSH, HMDB

Chemical Formula

C₉H₁₃NO

Average Molecular Weight

151.2056

Monoisotopic Molecular Weight

151.099714043

IUPAC Name

(1S,2R)-2-amino-1-phenylpropan-1-ol

Traditional Name

phenylpropanolamine

CAS Registry Number

14838-15-4

SMILES

C[C@@H](N)[C@@H](O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m1/s1

InChI Key

DLNKOYKMWOXYQA-VXNVDRBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Aralkylamine
1,2-aminoalcohol
Secondary alcohol
Organic nitrogen compound
Hydrocarbon derivative
Aromatic alcohol
Organopnictogen compound
Primary amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

amphetamines (CHEBI:36 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 15127820)

Cellular substructure

Membrane (HMDB: HMDB0001942)
Cell membrane (HMDB: HMDB0001942)

Organ

Liver (HMDB: HMDB0001942)
Kidney (HMDB: HMDB0001942)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001942)

Source

Exogenous

Exogenous (HMDB: HMDB0001942)

Endogenous

Endogenous (HMDB: HMDB0001942)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001942)

Biological role

Drug metabolite (HMDB: HMDB0001942)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	194 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	733 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	20.6 g/L	ALOGPS
logP	0.57	ALOGPS
logP	0.89	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	9.37	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.91 m³·mol⁻¹	ChemAxon
Polarizability	16.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	134.526	31661259
DarkChem	[M-H]-	132.632	31661259
AllCCS	[M+H]+	134.781	32859911
AllCCS	[M-H]-	133.681	32859911
DeepCCS	[M+H]+	140.824	30932474
DeepCCS	[M-H]-	138.428	30932474
DeepCCS	[M-2H]-	171.914	30932474
DeepCCS	[M+Na]+	146.736	30932474
AllCCS	[M+H]+	134.8	32859911
AllCCS	[M+H-H2O]+	130.3	32859911
AllCCS	[M+NH4]+	138.9	32859911
AllCCS	[M+Na]+	140.1	32859911
AllCCS	[M-H]-	133.7	32859911
AllCCS	[M+Na-2H]-	135.1	32859911
AllCCS	[M+HCOO]-	136.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	2.13 minutes	32390414
Predicted by Siyang on May 30, 2022	9.4123 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.07 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	157.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	728.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	294.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	97.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	65.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	253.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	289.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	494.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	672.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	124.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	695.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	175.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	406.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	391.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	87.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylpropanolamine	C[C@@H](N)[C@@H](O)C1=CC=CC=C1	2288.6	Standard polar	33892256
Phenylpropanolamine	C[C@@H](N)[C@@H](O)C1=CC=CC=C1	1284.5	Standard non polar	33892256
Phenylpropanolamine	C[C@@H](N)[C@@H](O)C1=CC=CC=C1	1356.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylpropanolamine,1TMS,isomer #1	C[C@@H](N)[C@@H](O[Si](C)(C)C)C1=CC=CC=C1	1402.6	Semi standard non polar	33892256
Phenylpropanolamine,1TMS,isomer #2	C[C@@H](N[Si](C)(C)C)[C@@H](O)C1=CC=CC=C1	1454.6	Semi standard non polar	33892256
Phenylpropanolamine,2TMS,isomer #1	C[C@@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=CC=C1	1504.5	Semi standard non polar	33892256
Phenylpropanolamine,2TMS,isomer #1	C[C@@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=CC=C1	1532.3	Standard non polar	33892256
Phenylpropanolamine,2TMS,isomer #1	C[C@@H](N[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C1=CC=CC=C1	1698.4	Standard polar	33892256
Phenylpropanolamine,2TMS,isomer #2	C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1640.6	Semi standard non polar	33892256
Phenylpropanolamine,2TMS,isomer #2	C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1637.0	Standard non polar	33892256
Phenylpropanolamine,2TMS,isomer #2	C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1901.4	Standard polar	33892256
Phenylpropanolamine,3TMS,isomer #1	C[C@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1726.6	Semi standard non polar	33892256
Phenylpropanolamine,3TMS,isomer #1	C[C@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1667.0	Standard non polar	33892256
Phenylpropanolamine,3TMS,isomer #1	C[C@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1721.4	Standard polar	33892256
Phenylpropanolamine,1TBDMS,isomer #1	C[C@@H](N)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	1651.7	Semi standard non polar	33892256
Phenylpropanolamine,1TBDMS,isomer #2	C[C@@H](N[Si](C)(C)C(C)(C)C)[C@@H](O)C1=CC=CC=C1	1708.4	Semi standard non polar	33892256
Phenylpropanolamine,2TBDMS,isomer #1	C[C@@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	1939.3	Semi standard non polar	33892256
Phenylpropanolamine,2TBDMS,isomer #1	C[C@@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	1933.4	Standard non polar	33892256
Phenylpropanolamine,2TBDMS,isomer #1	C[C@@H](N[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2006.4	Standard polar	33892256
Phenylpropanolamine,2TBDMS,isomer #2	C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2081.2	Semi standard non polar	33892256
Phenylpropanolamine,2TBDMS,isomer #2	C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2049.8	Standard non polar	33892256
Phenylpropanolamine,2TBDMS,isomer #2	C[C@H]([C@@H](O)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2115.2	Standard polar	33892256
Phenylpropanolamine,3TBDMS,isomer #1	C[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2362.2	Semi standard non polar	33892256
Phenylpropanolamine,3TBDMS,isomer #1	C[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2263.2	Standard non polar	33892256
Phenylpropanolamine,3TBDMS,isomer #1	C[C@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2092.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpropanolamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9600000000-b39c5f4d78772cae806e	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpropanolamine GC-MS (1 TMS) - 70eV, Positive	splash10-004i-6910000000-5f584053def735d7e242	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpropanolamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpropanolamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpropanolamine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000j-0900000000-1599181977614a0d00dd	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpropanolamine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-05ox-4900000000-3ee623f48a8306bcaf2c	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpropanolamine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0ugi-9600000000-afe25efb2c27bc61ad3a	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpropanolamine LC-ESI-QTOF , positive-QTOF	splash10-00lr-1900000000-033f74cd4a3197c7510b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpropanolamine Linear Ion Trap , positive-QTOF	splash10-001i-0900000000-6f806bd0a58cb073b571	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpropanolamine -1V, Positive-QTOF	splash10-00lr-1900000000-67f5a63c6c4d589d1b96	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 10V, Positive-QTOF	splash10-0f89-0900000000-e5a6de9f258209c42ea3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 20V, Positive-QTOF	splash10-0159-0900000000-983fa1b112e4d0fc78e1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 40V, Positive-QTOF	splash10-014i-5900000000-94c2913c48414f6f2f68	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 10V, Negative-QTOF	splash10-0udi-0900000000-9a4b3eaff66d145e5863	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 20V, Negative-QTOF	splash10-0zgi-2900000000-3c0efa3ebff61c0c1a7d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 40V, Negative-QTOF	splash10-057i-9800000000-430f9914117dd6db13e1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 10V, Positive-QTOF	splash10-001i-0900000000-bd416c91052a9169cf44	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 20V, Positive-QTOF	splash10-014i-1900000000-72a0c1340e1e43018391	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 40V, Positive-QTOF	splash10-0006-9200000000-92f5cd8bb5a23727da79	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 10V, Negative-QTOF	splash10-000x-9600000000-9d8b01ad2c9953ab2939	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 20V, Negative-QTOF	splash10-00nf-7900000000-85ff14d88d237302bc5d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropanolamine 40V, Negative-QTOF	splash10-004i-9000000000-7f166534dabf6f41827e	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
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
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.0 (0.005-5.0) uM	Adult (>18 years old)	Both	Normal	15127820	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00397

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022757

KNApSAcK ID

Not Available

Chemspider ID

25082

KEGG Compound ID

C02343

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenylpropanolamine

METLIN ID

1846

PubChem Compound

26934

PDB ID

Not Available

ChEBI ID

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)

Download (PDF)

General References

Ho TS, Pedersen-Bjergaard S, Rasmussen KE: Experiences with carrier-mediated transport in liquid-phase microextraction. J Chromatogr Sci. 2006 Jul;44(6):308-16. [PubMed:16884585 ]
Stockley CS, Wing LM, Miners JO: Stereospecific high-performance liquid chromatographic assay for the enantiomers of phenylpropanolamine in human plasma. Ther Drug Monit. 1991 Jul;13(4):332-8. [PubMed:1780966 ]
Dowse R, Haigh JM, Kanfer I: Determination of phenylpropanolamine in serum and urine by high-performance liquid chromatography. J Pharm Sci. 1983 Sep;72(9):1018-20. [PubMed:6631684 ]
Fallis RJ, Fisher M: Cerebral vasculitis and hemorrhage associated with phenylpropanolamine. Neurology. 1985 Mar;35(3):405-7. [PubMed:3974900 ]
Swain RA, Harsha DM, Baenziger J, Saywell RM Jr: Do pseudoephedrine or phenylpropanolamine improve maximum oxygen uptake and time to exhaustion? Clin J Sport Med. 1997 Jul;7(3):168-73. [PubMed:9262882 ]
Sullivan J, Abrams P: Pharmacological management of incontinence. Eur Urol. 1999;36 Suppl 1:89-95. [PubMed:10393480 ]

Enzymes

Enzyme Details

1. 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

Enzyme Details

2. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

Enzyme Details

3. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

Showing metabocard for Phenylpropanolamine (HMDB0001942)

MOL for HMDB0001942 (Phenylpropanolamine)

3D MOL for HMDB0001942 (Phenylpropanolamine)

3D SDF for HMDB0001942 (Phenylpropanolamine)

3D-SDF for HMDB0001942 (Phenylpropanolamine)

PDB for HMDB0001942 (Phenylpropanolamine)

3D PDB for HMDB0001942 (Phenylpropanolamine)

SMILES for HMDB0001942 (Phenylpropanolamine)

INCHI for HMDB0001942 (Phenylpropanolamine)

Structure for HMDB0001942 (Phenylpropanolamine)

3D Structure for HMDB0001942 (Phenylpropanolamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes