Identification

Name
Propylhexedrine
Accession Number
DB06714
Type
Small Molecule
Groups
Approved
Description

Propylhexedrine is an alpha-adrenergic agonist often used in nasal decongestant inhalers. It is used to give temporary relief for nasal congestion from colds, allergic rhinitis, or allergies.

Structure
Thumb
Synonyms
Not Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Benzedrex 09-19-2014Inhalant250 mg/1NasalBF ASCHER AND CO INC2014-09-19Not applicableUs
International/Other Brands
Benzedrex / Dristan inhaler / Obesin
Categories
UNII
LQU92IU8LL
CAS number
101-40-6
Weight
Average: 155.2804
Monoisotopic: 155.167399677
Chemical Formula
C10H21N
InChI Key
JCRIVQIOJSSCQD-UHFFFAOYSA-N
InChI
InChI=1S/C10H21N/c1-9(11-2)8-10-6-4-3-5-7-10/h9-11H,3-8H2,1-2H3
IUPAC Name
(1-cyclohexylpropan-2-yl)(methyl)amine
SMILES
CNC(C)CC1CCCCC1

Pharmacology

Indication

It is used to provide temporary symptomatic relief of nasal congestion due to colds, allergies and allergic rhinitis.

Associated Conditions
Pharmacodynamics

Like other monoamine releasing stimulants propylhexedrine is active as a norepinephrine and dopamine releaser in the central nervous system. The acute effects of the drug closely resemble the physiological and psychological effects of an epinephrine-provoked fight-or-flight response, including increased heart rate and blood pressure, vasoconstriction (constriction of the arterial walls), bronchodilation, and hyperglycemia (increased blood sugar).

Mechanism of action

Propylhexidrine causes the norepinephrine, dopamine, and serotonin (5HT) transporters to reverse their direction of flow. This inversion leads to a release of these transmitters from the vesicles to the cytoplasm and from the cytoplasm to the synapse. It also antagonizes the action of VMAT2, causing the release of more neurotransmitters.

TargetActionsOrganism
ASynaptic vesicular amine transporterNot AvailableHuman
UTrace amine-associated receptor 1
agonist
Human
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
Toxicity

The signs and symptoms that are produced after the acute overdosage of Propylhexidrine include Psychosis, Burning sensation.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
US2454746
General References
Not Available
External Links
Human Metabolome Database
HMDB0015659
KEGG Drug
D05637
PubChem Compound
7558
PubChem Substance
99443266
ChemSpider
7277
ChEBI
134783
ChEMBL
CHEMBL2105275
PharmGKB
PA165958387
Wikipedia
Propylhexedrine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
InhalantNasal250 mg/1
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0904 mg/mLALOGPS
logP3.37ALOGPS
logP2.7ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)10.61ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.54 m3·mol-1ChemAxon
Polarizability20.27 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9657
Blood Brain Barrier+0.9829
Caco-2 permeable+0.7226
P-glycoprotein substrateNon-substrate0.6278
P-glycoprotein inhibitor INon-inhibitor0.8635
P-glycoprotein inhibitor IINon-inhibitor0.9148
Renal organic cation transporterNon-inhibitor0.6
CYP450 2C9 substrateNon-substrate0.7991
CYP450 2D6 substrateSubstrate0.7284
CYP450 3A4 substrateNon-substrate0.6368
CYP450 1A2 substrateNon-inhibitor0.7982
CYP450 2C9 inhibitorNon-inhibitor0.9671
CYP450 2D6 inhibitorNon-inhibitor0.7367
CYP450 2C19 inhibitorNon-inhibitor0.8882
CYP450 3A4 inhibitorNon-inhibitor0.9827
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8718
Ames testNon AMES toxic0.9178
CarcinogenicityNon-carcinogens0.8877
BiodegradationNot ready biodegradable0.8187
Rat acute toxicity3.2412 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8496
hERG inhibition (predictor II)Non-inhibitor0.7482
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Secondary aliphatic amine / Organopnictogen compound / Hydrocarbon derivative / Aliphatic homomonocyclic compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
General Function
Monoamine transmembrane transporter activity
Specific Function
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
Molecular Weight
55712.075 Da
References
  1. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [PubMed:15955613]
  2. Docherty JR: Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA). Br J Pharmacol. 2008 Jun;154(3):606-22. doi: 10.1038/bjp.2008.124. [PubMed:18500382]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Trace-amine receptor activity
Specific Function
Receptor for trace amines, including beta-phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amin...
Gene Name
TAAR1
Uniprot ID
Q96RJ0
Uniprot Name
Trace amine-associated receptor 1
Molecular Weight
39091.34 Da
References
  1. Reese EA, Bunzow JR, Arttamangkul S, Sonders MS, Grandy DK: Trace amine-associated receptor 1 displays species-dependent stereoselectivity for isomers of methamphetamine, amphetamine, and para-hydroxyamphetamine. J Pharmacol Exp Ther. 2007 Apr;321(1):178-86. Epub 2007 Jan 11. [PubMed:17218486]
  2. Xie Z, Westmoreland SV, Bahn ME, Chen GL, Yang H, Vallender EJ, Yao WD, Madras BK, Miller GM: Rhesus monkey trace amine-associated receptor 1 signaling: enhancement by monoamine transporters and attenuation by the D2 autoreceptor in vitro. J Pharmacol Exp Ther. 2007 Apr;321(1):116-27. Epub 2007 Jan 18. [PubMed:17234900]
  3. Wolinsky TD, Swanson CJ, Smith KE, Zhong H, Borowsky B, Seeman P, Branchek T, Gerald CP: The Trace Amine 1 receptor knockout mouse: an animal model with relevance to schizophrenia. Genes Brain Behav. 2007 Oct;6(7):628-39. Epub 2006 Dec 21. [PubMed:17212650]
  4. Xie Z, Miller GM: Trace amine-associated receptor 1 is a modulator of the dopamine transporter. J Pharmacol Exp Ther. 2007 Apr;321(1):128-36. Epub 2007 Jan 18. [PubMed:17234899]
  5. Miller GM, Verrico CD, Jassen A, Konar M, Yang H, Panas H, Bahn M, Johnson R, Madras BK: Primate trace amine receptor 1 modulation by the dopamine transporter. J Pharmacol Exp Ther. 2005 Jun;313(3):983-94. Epub 2005 Mar 11. [PubMed:15764732]

Drug created on May 16, 2010 12:30 / Updated on November 02, 2018 06:19