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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 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 17:18:20 UTC

HMDB ID

HMDB0014935

Secondary Accession Numbers

HMDB14935

Metabolite Identification

Common Name

Tolazoline

Description

Tolazoline, also known as priscoline or divascol, 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. Tolazoline is a drug which is used for the treatment of pulmonary artery anomalies. Tolazoline is a very strong basic compound (based on its pKa). It is however most commonly used in veterinary medicine, to reverse xylazine-induced sedation. It is a vasodilator that is used to treat spasms of peripheral blood vessels (as in acrocyanosis). It has also been used (in conjunction with sodium nitroprusside) successfully as an antidote to reverse the severe peripheral vasoconstriction which can occur as a result of overdose with certain 5-HT2A agonist drugs such as 25I-NBOMe, DOB and Bromodragonfly (prolonged severe vasoconstriction can lead to gangrene if untreated). Tolazoline is a non-selective competitive α-adrenergic receptor antagonist.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 797                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       5.908   3.141   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0       7.154   0.983   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.747   1.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.414   3.461   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.413   0.840   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.184   2.128   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.413  -0.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -1.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -1.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -3.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -3.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.413  -3.780   0.000  0.00  0.00           C+0
CONECT    1    3    4                                                       
CONECT    2    3    6                                                       
CONECT    3    1    2    5                                                  
CONECT    4    1    6                                                       
CONECT    5    3    7                                                       
CONECT    6    2    4                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Benzyl-2-imidazoline	ChEBI
2-Benzyl-4,5-imidazoline	ChEBI
2-Benzylimidazoline	ChEBI
4,5-Dihydro-2-(phenylmethyl)-1H-imidazole	ChEBI
Tolazine	Kegg
Divascol	HMDB
Tolazoline hydrochloride	HMDB
Pridazole	HMDB
Tolazoline monohydrochloride	HMDB
Benzalolin	HMDB
Novartis brand OF tolazoline hydrochloride	HMDB
Priscoline	HMDB
Ciba vision brand OF tolazoline hydrochloride	HMDB
Priscol	HMDB

Chemical Formula

C₁₀H₁₂N₂

Average Molecular Weight

160.2157

Monoisotopic Molecular Weight

160.100048394

IUPAC Name

2-benzyl-4,5-dihydro-1H-imidazole

Traditional Name

tolazoline

CAS Registry Number

59-98-3

SMILES

C(C1=NCCN1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C10H12N2/c1-2-4-9(5-3-1)8-10-11-6-7-12-10/h1-5H,6-8H2,(H,11,12)

InChI Key

JIVZKJJQOZQXQB-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

Imidolactam
Monocyclic benzene moiety
2-imidazoline
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboxylic acid amidine
Amidine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:28502 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014935)

Source

Exogenous

Exogenous (HMDB: HMDB0014935)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.36 g/L	Not Available
LogP	1.5	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	135.083	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000830

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.36 g/L	ALOGPS
logP	2.05	ALOGPS
logP	1.2	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	10.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	24.39 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.07 m³·mol⁻¹	ChemAxon
Polarizability	17.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	134.584	31661259
DarkChem	[M-H]-	132.475	31661259
DeepCCS	[M+H]+	133.233	30932474
DeepCCS	[M-H]-	130.396	30932474
DeepCCS	[M-2H]-	166.682	30932474
DeepCCS	[M+Na]+	142.097	30932474
AllCCS	[M+H]+	134.5	32859911
AllCCS	[M+H-H2O]+	129.9	32859911
AllCCS	[M+NH4]+	138.9	32859911
AllCCS	[M+Na]+	140.1	32859911
AllCCS	[M-H]-	137.7	32859911
AllCCS	[M+Na-2H]-	138.4	32859911
AllCCS	[M+HCOO]-	139.3	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. Predicted by Afia on May 17, 2022.	2.26 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9169 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.79 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	57.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	983.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	317.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	124.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	105.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	300.9 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	291.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	291.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	786.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	317.6 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	975.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	223.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	260.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	379.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	254.9 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	26.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tolazoline	C(C1=NCCN1)C1=CC=CC=C1	2461.3	Standard polar	33892256
Tolazoline	C(C1=NCCN1)C1=CC=CC=C1	1516.8	Standard non polar	33892256
Tolazoline	C(C1=NCCN1)C1=CC=CC=C1	1575.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tolazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1CC1=CC=CC=C1	1731.1	Semi standard non polar	33892256
Tolazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1CC1=CC=CC=C1	1653.9	Standard non polar	33892256
Tolazoline,1TMS,isomer #1	C[Si](C)(C)N1CCN=C1CC1=CC=CC=C1	2343.5	Standard polar	33892256
Tolazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1CC1=CC=CC=C1	1952.6	Semi standard non polar	33892256
Tolazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1CC1=CC=CC=C1	1901.7	Standard non polar	33892256
Tolazoline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1CC1=CC=CC=C1	2492.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Tolazoline EI-B (Non-derivatized)	splash10-0006-9400000000-7b6f1c4b249d1fba8927	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tolazoline EI-B (Non-derivatized)	splash10-0006-9400000000-7b6f1c4b249d1fba8927	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolazoline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-2b6650aa08c5113fe295	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tolazoline 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 - Tolazoline LC-ESI-QQ , positive-QTOF	splash10-03di-0900000000-692cb3b89bff443fa65f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolazoline LC-ESI-QQ , positive-QTOF	splash10-03di-0900000000-03a59847388e2e741709	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolazoline LC-ESI-QQ , positive-QTOF	splash10-03di-4900000000-54d799a1c61663a2e513	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolazoline LC-ESI-QQ , positive-QTOF	splash10-0006-9100000000-c36b35a2866405756d0a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tolazoline LC-ESI-QQ , positive-QTOF	splash10-0006-9000000000-c543ee9f104cc9558d70	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 10V, Positive-QTOF	splash10-03di-0900000000-47a6c1a5a2d279ab4f92	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 20V, Positive-QTOF	splash10-03di-3900000000-aecd123663a1693e3524	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 40V, Positive-QTOF	splash10-0006-9300000000-ebfb2f09103e6beeeb32	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 10V, Negative-QTOF	splash10-0a4i-0900000000-6468e33c9df294b387c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 20V, Negative-QTOF	splash10-0a4i-2900000000-770e7f8c4b1e0ae79868	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 40V, Negative-QTOF	splash10-004l-9600000000-6bb3d6dbc9100efc4368	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 10V, Positive-QTOF	splash10-03di-0900000000-ec9dd3a4861a20c6f98c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 20V, Positive-QTOF	splash10-03xu-3900000000-01b9796933a01ad40ccf	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 40V, Positive-QTOF	splash10-00kf-9300000000-a6d07f8a048c587a6dd5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 10V, Negative-QTOF	splash10-0a4i-1900000000-1590a4c64e5f2e58a0d3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 20V, Negative-QTOF	splash10-0a4i-4900000000-1f5ee5c9b4a25f0e1faa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tolazoline 40V, Negative-QTOF	splash10-00mo-9300000000-bbec6eccba8e917e3e29	2021-10-11	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

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 DB00797	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00797	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00797

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5303

KEGG Compound ID

C07147

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tolazoline

METLIN ID

Not Available

PubChem Compound

5504

PDB ID

Not Available

ChEBI ID

28502

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

Not Available

Enzymes

Enzyme Details

1. 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

References

Song W, Zhang Y, Xia L, Liu G: [Effects of some mexiletine derivatives on alpha 1-adrenoceptors]. Yao Xue Xue Bao. 1998;33(2):102-5. [PubMed:11938943 ]

Enzyme Details

2. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

References

Roll C, Hanssler L: [Interaction of tolazoline and cimetidine in persistent fetal circulation of the newborn infant]. Monatsschr Kinderheilkd. 1993 Apr;141(4):297-9. [PubMed:8487790 ]

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

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Teskin O, Uydes-Dogan BS, Enc Y, Alp FI, Kaleli D, Keser S, Iyigun T, Bilgen F, Dagsali S, Ozdemir O: Comparative effects of tolazoline and nitroprusside on human isolated radial artery. Ann Thorac Surg. 2006 Jan;81(1):125-31. [PubMed:16368348 ]
Song W, Zhang Y, Xia L, Liu G: [Effects of some mexiletine derivatives on alpha 1-adrenoceptors]. Yao Xue Xue Bao. 1998;33(2):102-5. [PubMed:11938943 ]

Showing metabocard for Tolazoline (HMDB0014935)

MOL for HMDB0014935 (Tolazoline)

3D MOL for HMDB0014935 (Tolazoline)

3D SDF for HMDB0014935 (Tolazoline)

3D-SDF for HMDB0014935 (Tolazoline)

PDB for HMDB0014935 (Tolazoline)

3D PDB for HMDB0014935 (Tolazoline)

SMILES for HMDB0014935 (Tolazoline)

INCHI for HMDB0014935 (Tolazoline)

Structure for HMDB0014935 (Tolazoline)

3D Structure for HMDB0014935 (Tolazoline)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

References

References

References