Cyclopentamine

Identification

Generic Name
Cyclopentamine
DrugBank Accession Number
DB08999
Background

Cyclopentamine is a sympathomimetic alkylamine, classified as a vasoconstrictor. Cyclopentamine was an over the counter treatment for nasal congestion in Europe and Australia. It has been widely discontinued due to the safety, effectiveness, and availability of a similar drug, propylhexedrine.

Type
Small Molecule
Groups
Withdrawn
Structure
Weight
Average: 141.258
Monoisotopic: 141.151749616
Chemical Formula
C9H19N
Synonyms
  • Cyclopentamine

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Cyclopentamine.
Acetyl sulfisoxazoleThe risk or severity of adverse effects can be increased when Acetyl sulfisoxazole is combined with Cyclopentamine.
BendroflumethiazideThe risk or severity of adverse effects can be increased when Bendroflumethiazide is combined with Cyclopentamine.
BenzthiazideThe risk or severity of adverse effects can be increased when Benzthiazide is combined with Cyclopentamine.
BethanecholThe risk or severity of hypotension can be increased when Cyclopentamine is combined with Bethanechol.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cyclopentamine hydrochlorideF551446KF3538-02-3XGZPRABQSGUFBL-UHFFFAOYSA-N

Categories

ATC Codes
R01AA02 — Cyclopentamine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Dialkylamines
Alternative Parents
Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Aliphatic homomonocyclic compound / Hydrocarbon derivative / Organopnictogen compound / Secondary aliphatic amine
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
WB9Q6M8O60
CAS number
102-45-4
InChI Key
HFXKQSZZZPGLKQ-UHFFFAOYSA-N
InChI
InChI=1S/C9H19N/c1-8(10-2)7-9-5-3-4-6-9/h8-10H,3-7H2,1-2H3
IUPAC Name
(1-cyclopentylpropan-2-yl)(methyl)amine
SMILES
CNC(C)CC1CCCC1

References

Synthesis Reference

U.S. Patent 2,520,015.

General References
Not Available
KEGG Drug
D07370
PubChem Compound
7608
PubChem Substance
310264960
ChemSpider
7326
BindingDB
81456
RxNav
59094
ChEBI
134766
ChEMBL
CHEMBL329203
Wikipedia
Cyclopentamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)113-115U.S. Patent 2,520,015.
Predicted Properties
PropertyValueSource
Water Solubility0.476 mg/mLALOGPS
logP2.86ALOGPS
logP2.26Chemaxon
logS-2.5ALOGPS
pKa (Strongest Basic)10.61Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area12.03 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity44.93 m3·mol-1Chemaxon
Polarizability18.4 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0aor-9200000000-60876689abb067d5f0b9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-9800000000-a936f00330acc88e4893
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-646c482fb0db47bdb610
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-0900000000-1062346c667a8cc036a1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9100000000-21f977a86bb385f4f476
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-36bef58a78ee37c3b266
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9500000000-3db0d0d174f61ff6d79a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-136.22264
predicted
DeepCCS 1.0 (2019)
[M+H]+138.63011
predicted
DeepCCS 1.0 (2019)
[M+Na]+147.45888
predicted
DeepCCS 1.0 (2019)

Drug created at June 17, 2014 15:42 / Updated at February 21, 2021 18:52