(1R,2S)-2-Phenylcyclopropanaminium

Identification

Generic Name
(1R,2S)-2-Phenylcyclopropanaminium
DrugBank Accession Number
DB02665
Background

A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311)

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 134.1983
Monoisotopic: 134.096974389
Chemical Formula
C9H12N
Synonyms
  • (1R,2S)-tranylcypromine(1+)

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UTrypsin-1Not AvailableHumans
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Aralkylamines
Alternative Parents
Benzene and substituted derivatives / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives / Organic cations
Substituents
Aralkylamine / Aromatic homomonocyclic compound / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety / Organic cation / Organopnictogen compound / Primary aliphatic amine / Primary amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
7H4CZX4FYH
CAS number
1986-47-6
InChI Key
AELCINSCMGFISI-DTWKUNHWSA-O
InChI
InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/p+1/t8-,9+/m0/s1
IUPAC Name
(1R,2S)-2-phenylcyclopropan-1-aminium
SMILES
[NH3+][C@@H]1C[C@H]1C1=CC=CC=C1

References

Synthesis Reference

Vithal Jagannath Rajadhyaksha, "Method of synthesis of trans-2-phenylcyclopropylamine." U.S. Patent US4016204, issued October, 1964.

US4016204
General References
Not Available
PubChem Compound
11861988
PubChem Substance
46506494
ChemSpider
10036445
ChEBI
131517
PDBe Ligand
TPA

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0104 mg/mLALOGPS
logP-1.6ALOGPS
logP1.34Chemaxon
logS-4.2ALOGPS
pKa (Strongest Basic)9.62Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count0Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area27.64 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity52.99 m3·mol-1Chemaxon
Polarizability15.84 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9819
Blood Brain Barrier+0.9453
Caco-2 permeable+0.7871
P-glycoprotein substrateNon-substrate0.8338
P-glycoprotein inhibitor INon-inhibitor0.9558
P-glycoprotein inhibitor IINon-inhibitor0.9827
Renal organic cation transporterNon-inhibitor0.8684
CYP450 2C9 substrateNon-substrate0.7997
CYP450 2D6 substrateNon-substrate0.8768
CYP450 3A4 substrateNon-substrate0.7287
CYP450 1A2 substrateInhibitor0.8593
CYP450 2C9 inhibitorNon-inhibitor0.8734
CYP450 2D6 inhibitorNon-inhibitor0.6988
CYP450 2C19 inhibitorInhibitor0.8154
CYP450 3A4 inhibitorNon-inhibitor0.9587
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6521
Ames testNon AMES toxic0.9213
CarcinogenicityNon-carcinogens0.721
BiodegradationReady biodegradable0.8237
Rat acute toxicity2.4558 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9604
hERG inhibition (predictor II)Non-inhibitor0.9333
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-MSsplash10-0ftf-9600000000-5bccf892ddee08854f46
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]-128.99104
predicted
DeepCCS 1.0 (2019)
[M+H]+131.32666
predicted
DeepCCS 1.0 (2019)
[M+Na]+137.43236
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form aga...
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Trypsin-1
Molecular Weight
26557.88 Da
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. [Article]
  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. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:45