(1R,2S)-2-Phenylcyclopropanaminium

Identification

Name
(1R,2S)-2-Phenylcyclopropanaminium
Accession Number
DB02665  (EXPT03088)
Type
Small Molecule
Groups
Experimental
Description

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)

Structure
Thumb
Synonyms
  • (1R,2S)-tranylcypromine(1+)
Categories
Not Available
UNII
Not Available
CAS number
1986-47-6
Weight
Average: 134.1983
Monoisotopic: 134.096974389
Chemical Formula
C9H12N
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTrypsin-1Not AvailableHuman
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
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
External Links
PubChem Compound
11861988
PubChem Substance
46506494
ChemSpider
10036445
ChEBI
131517
HET
TPA

Clinical Trials

Clinical Trials
Not Available

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-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 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 / Benzenoid / Monocyclic benzene moiety / Organopnictogen compound / Hydrocarbon derivative / Primary amine / Primary aliphatic amine / Organic cation / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. [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. 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 07:05