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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014531
Secondary Accession Numbers
  • HMDB14531
Metabolite Identification
Common NameProcyclidine
DescriptionProcyclidine is only found in individuals that have used or taken this drug. It is a muscarinic antagonist that crosses the blood-brain barrier and is used in the treatment of drug-induced extrapyramidal disorders and in parkinsonism. [PubChem]The mechanism of action is unknown. It is thought that Procyclidine acts by blocking central cholinergic receptors, and thus balancing cholinergic and dopaminergic activity in the basal ganglia. Many of its effects are due to its pharmacologic similarities with atropine. Procyclidine exerts an antispasmodic effect on smooth muscle, and may produce mydriasis and reduction in salivation.
Structure
Data?1582753190
Synonyms
ValueSource
1-Cyclohexyl-1-phenyl-3-pyrrolidino-1-propanolChEBI
ProciclidinaChEBI
ProcyclidinumChEBI
TricyclamolChEBI
Glaxo wellcome brand OF procyclidine hydrochlorideHMDB
ICN brand OF procyclidine hydrochlorideHMDB
MucinilHMDB
Wellcome brand OF procyclidine hydrochlorideHMDB
ArpicolinHMDB
Hydrochloride, procyclidineHMDB
Monarch brand OF procyclidine hydrochlorideHMDB
OsnervanHMDB
ProcyclidHMDB
Procyclidine hydrochlorideHMDB
GlaxoSmithKline brand OF procyclidine hydrochlorideHMDB
Rosemont brand OF procyclidine hydrochlorideHMDB
KemadrenHMDB
KemadrinHMDB
Opus brand OF procyclidine hydrochlorideHMDB
Chemical FormulaC19H29NO
Average Molecular Weight287.4397
Monoisotopic Molecular Weight287.224914555
IUPAC Name1-cyclohexyl-1-phenyl-3-(pyrrolidin-1-yl)propan-1-ol
Traditional Nameprocyclidine
CAS Registry Number77-37-2
SMILES
OC(CCN1CCCC1)(C1CCCCC1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C19H29NO/c21-19(17-9-3-1-4-10-17,18-11-5-2-6-12-18)13-16-20-14-7-8-15-20/h1,3-4,9-10,18,21H,2,5-8,11-16H2
InChI KeyWYDUSKDSKCASEF-UHFFFAOYSA-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.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • N-alkylpyrrolidine
  • 1,3-aminoalcohol
  • Pyrrolidine
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organopnictogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point86 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0098 g/LNot Available
LogP4.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM172.630932474
[M+H]+Not Available171.533http://allccs.zhulab.cn/database/detail?ID=AllCCS00000704
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0098 g/LALOGPS
logP4.13ALOGPS
logP3.79ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)9.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.6 m³·mol⁻¹ChemAxon
Polarizability34.43 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.05431661259
DarkChem[M-H]-162.51131661259
DeepCCS[M+H]+170.24330932474
DeepCCS[M-H]-167.88530932474
DeepCCS[M-2H]-200.77130932474
DeepCCS[M+Na]+176.33630932474
AllCCS[M+H]+171.532859911
AllCCS[M+H-H2O]+168.232859911
AllCCS[M+NH4]+174.632859911
AllCCS[M+Na]+175.532859911
AllCCS[M-H]-176.832859911
AllCCS[M+Na-2H]-177.132859911
AllCCS[M+HCOO]-177.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ProcyclidineOC(CCN1CCCC1)(C1CCCCC1)C1=CC=CC=C12445.1Standard polar33892256
ProcyclidineOC(CCN1CCCC1)(C1CCCCC1)C1=CC=CC=C12206.5Standard non polar33892256
ProcyclidineOC(CCN1CCCC1)(C1CCCCC1)C1=CC=CC=C12137.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Procyclidine,1TMS,isomer #1C[Si](C)(C)OC(CCN1CCCC1)(C1=CC=CC=C1)C1CCCCC12348.6Semi standard non polar33892256
Procyclidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CCN1CCCC1)(C1=CC=CC=C1)C1CCCCC12601.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Procyclidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-9510000000-bb5c957fcb63641b16df2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Procyclidine GC-MS (1 TMS) - 70eV, Positivesplash10-00c3-9371000000-a8f31f6dd1ab688edc1c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Procyclidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-001i-9010000000-7d7f1b16f54aaca37f102014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 10V, Positive-QTOFsplash10-00dr-0090000000-346bcbb2ab2d7175b1bc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 20V, Positive-QTOFsplash10-001i-9240000000-b149734e30140564cb672016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 40V, Positive-QTOFsplash10-0a4l-9210000000-752d38a1eb305bdc9d052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 10V, Negative-QTOFsplash10-000i-0090000000-15b4d4f82fafa22bb2852016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 20V, Negative-QTOFsplash10-0079-9080000000-bcb7857676f4ed8009ed2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 40V, Negative-QTOFsplash10-00di-9010000000-1fd43c480f58b03227082016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 10V, Positive-QTOFsplash10-000i-0090000000-2c6fa3370147096c5f4a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 20V, Positive-QTOFsplash10-001i-9020000000-24b280b9f79606f082432021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 40V, Positive-QTOFsplash10-001r-9410000000-06aeaae65e74e5546cf42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 10V, Negative-QTOFsplash10-000i-0090000000-8ae387832bf542033b122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 20V, Negative-QTOFsplash10-000i-1490000000-6ae75c02122c9e6e0e042021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Procyclidine 40V, Negative-QTOFsplash10-001i-0490000000-f468d30ac48d7ded8da42021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00387 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00387 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00387
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4750
KEGG Compound IDC07378
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProcyclidine
METLIN IDNot Available
PubChem Compound4919
PDB IDNot Available
ChEBI ID8448
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Theodoridis GC, Stark L: Central role of solar information flow in pregenetic evolution. J Theor Biol. 1971 Jun;31(3):377-88. [PubMed:5556140 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular weight:
66127.4
References
  1. Myhrer T: Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment. Neurotoxicology. 2010 Dec;31(6):629-38. doi: 10.1016/j.neuro.2010.07.002. Epub 2010 Jul 17. [PubMed:20624420 ]
  2. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [PubMed:1426023 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular weight:
51420.4
References
  1. 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 ]
  2. 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 ]
  3. Larson EW, Pfenning MA, Richelson E: Selectivity of antimuscarinic compounds for muscarinic receptors of human brain and heart. Psychopharmacology (Berl). 1991;103(2):162-5. [PubMed:2027917 ]
  4. Waelbroeck M, Camus J, Tastenoy M, Lambrecht G, Mutschler E, Tacke R, Christophe J: Stereoselectivity of procyclidine binding to muscarinic receptor subtypes M1, M2 and M4. Eur J Pharmacol. 1990 Sep 18;189(2-3):135-42. [PubMed:2253700 ]
  5. Myhrer T: Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment. Neurotoxicology. 2010 Dec;31(6):629-38. doi: 10.1016/j.neuro.2010.07.002. Epub 2010 Jul 17. [PubMed:20624420 ]
  6. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [PubMed:1426023 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
References
  1. 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 ]
  2. 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 ]
  3. Larson EW, Pfenning MA, Richelson E: Selectivity of antimuscarinic compounds for muscarinic receptors of human brain and heart. Psychopharmacology (Berl). 1991;103(2):162-5. [PubMed:2027917 ]
  4. Waelbroeck M, Camus J, Tastenoy M, Lambrecht G, Mutschler E, Tacke R, Christophe J: Stereoselectivity of procyclidine binding to muscarinic receptor subtypes M1, M2 and M4. Eur J Pharmacol. 1990 Sep 18;189(2-3):135-42. [PubMed:2253700 ]
  5. Myhrer T: Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment. Neurotoxicology. 2010 Dec;31(6):629-38. doi: 10.1016/j.neuro.2010.07.002. Epub 2010 Jul 17. [PubMed:20624420 ]
  6. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [PubMed:1426023 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase
Gene Name:
CHRM4
Uniprot ID:
P08173
Molecular weight:
53048.7
References
  1. 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 ]
  2. 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 ]
  3. Waelbroeck M, Camus J, Tastenoy M, Lambrecht G, Mutschler E, Tacke R, Christophe J: Stereoselectivity of procyclidine binding to muscarinic receptor subtypes M1, M2 and M4. Eur J Pharmacol. 1990 Sep 18;189(2-3):135-42. [PubMed:2253700 ]
  4. Alberts P: Classification of the presynaptic muscarinic receptor subtype that regulates 3H-acetylcholine secretion in the guinea pig urinary bladder in vitro. J Pharmacol Exp Ther. 1995 Jul;274(1):458-68. [PubMed:7616431 ]
  5. Myhrer T: Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment. Neurotoxicology. 2010 Dec;31(6):629-38. doi: 10.1016/j.neuro.2010.07.002. Epub 2010 Jul 17. [PubMed:20624420 ]
  6. Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [PubMed:1426023 ]