cyclopropyl amine
aminocyclopropane
Identification
| Name | cyclopropyl amine |
| IUPAC | cyclopropanamine |
| CAS Number | 765-30-0 |
| EINECS | 212-142-2 |
| FDA UNII | 8PR8XTH1X1 |
| Molecular Formula | C3 H7 N |
| Molecular Weight | 57.09579000 |
| MDL Number | MFCD00001301 |
| Nikkaji Number | J79.937H |
| Beilstein | 741858 |
| XlogP3 | 0.10 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.81300 to 0.82000 @ 20.00 °C. |
| Pounds per Gallon - (est). | 6.773 to 6.831 |
| Refractive Index | 1.41900 to 1.42200 @ 20.00 °C. |
| Boiling Point | 50.50 °C. @ 760.00 mm Hg |
| Vapor Pressure | 299.800000 mmHg @ 25.00 °C. (est) |
| Flash Point | -14.00 °F. TCC ( -25.56 °C. ) |
| logP (o/w) | 0.070 |
| Soluble in | water, 1e+006 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | oral-rat LD50 445 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for cyclopropyl amine usage levels up to | not for fragrance use. |
| Recommendation for cyclopropyl amine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
aminocyclopropane
cyclopropanamine
cyclopropylamine
US Patents:
8,075,937 - Alkyldienamides exhibiting taste and sensory effect in flavor compositions
PubMed:
Further insights into the SAR of α-substituted cyclopropylamine derivatives as inhibitors of histone demethylase KDM1A.
PubMed:
Synthesis, biological activity and mechanistic insights of 1-substituted cyclopropylamine derivatives: a novel class of irreversible inhibitors of histone demethylase KDM1A.
PubMed:
Design and synthesis of a new series of cyclopropylamino-linking diarylpyrimidines as HIV non-nucleoside reverse transcriptase inhibitors.
PubMed:
Experimental and theoretical investigation on the outer valence electronic structure of cyclopropylamine by (e, 2e) electron momentum spectroscopy.
PubMed:
Synthesis, LSD1 Inhibitory Activity, and LSD1 Binding Model of Optically Pure Lysine-PCPA Conjugates.
PubMed:
Highly stereoselective synthesis of (borylmethyl)cyclopropylamines by copper-catalyzed aminoboration of methylenecyclopropanes.
PubMed:
Reprogramming fibroblasts to neural-precursor-like cells by structured overexpression of pallial patterning genes.
PubMed:
Cell-intrinsic regulation of murine dendritic cell function and survival by prereceptor amplification of glucocorticoid.
PubMed:
Formal substitution of bromocyclopropanes with nitrogen nucleophiles.
PubMed:
Nazarov reactions of vinyl cyclopropylamines: an approach to the imino-Nazarov problem.
PubMed:
Highly enantioselective synthesis of cyclopropylamine derivatives via Ru(II)-pheox-catalyzed direct asymmetric cyclopropanation of vinylcarbamates.
PubMed:
KDM1 is a novel therapeutic target for the treatment of gliomas.
PubMed:
trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT(2) receptor family.
PubMed:
The GPR88 receptor agonist 2-PCCA does not alter the behavioral effects of methamphetamine in rats.
PubMed:
Simple and sensitive stability-indicating ion chromatography method for the determination of cyclopropylamine in nevirapine and moxifloxacin hydrochloride drug substances.
PubMed:
Electrochemical cleavage of sulfonamides: an efficient and tunable strategy to prevent β-fragmentation and epimerization.
PubMed:
Predicting biological functions of compounds based on chemical-chemical interactions.
PubMed:
Synthesis and biological activities of vitamin D-like inhibitors of CYP24 hydroxylase.
PubMed:
Intermolecular [3+2] cycloaddition of cyclopropylamines with olefins by visible-light photocatalysis.
PubMed:
A generalized graph-theoretical matrix of heterosystems and its application to the VMV procedure.
PubMed:
Oligodeoxynucleotides inhibit Toll-like receptor 3 mediated cytotoxicity and CXCL8 release in keratinocytes.
PubMed:
Stereoselective preparation of β,γ-methano-GABA derivatives.
PubMed:
Scalable synthesis of (1-cyclopropyl)cyclopropylamine hydrochloride.
PubMed:
Administration route and carrier dependent effects on vaccine efficacy: implications for vaccine design.
PubMed:
Metal Complexes for DNA-Mediated Charge Transport.
PubMed:
Enantioselective syntheses of carbocyclic nuleosides 5'-homocarbovir, epi-4'-homocarbovir and their cyclopropylamine analogs using facially selective Pd-mediated allylations.
PubMed:
Adjuvant effect of cationic liposomes and CpG depends on administration route.
PubMed:
Synthesis and biological activity of optically active NCL-1, a lysine-specific demethylase 1 selective inhibitor.
PubMed:
Cyclopropylamines from N,N-dialkylcarboxamides and Grignard reagents in the presence of titanium tetraisopropoxide or methyltitanium triisopropoxide.
PubMed:
A new class of antitumor trans-amine-amidine-Pt(II) cationic complexes: influence of chemical structure and solvent on in vitro and in vivo tumor cell proliferation.
PubMed:
Scalable synthesis of a prostaglandin EP4 receptor antagonist.
PubMed:
Differences between amine- and phosphine-boranes: synthesis, photoelectron spectroscopy, and quantum chemical study of the cyclopropylic derivatives.
PubMed:
Neoadjuvant immunotherapy enhances radiosensitivity through natural killer cell activation.
PubMed:
Comparative analysis of small molecules and histone substrate analogues as LSD1 lysine demethylase inhibitors.
PubMed:
Diversity synthesis of N-substituted 2-amino-1,6-naphthyridine derivatives under microwave irradiation.
PubMed:
C-reactive protein impairs coronary arteriolar dilation to prostacyclin synthase activation: role of peroxynitrite.
PubMed:
Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide.
PubMed:
Novel trans-2-aryl-cyclopropylamine analogues as potent and selective dipeptidyl peptidase IV inhibitors.
PubMed:
Conformational preferences and basicities of monofluorinated cyclopropyl amines in comparison to cyclopropylamine and 2-fluoroethylamine.
PubMed:
Synthesis of highly functionalized pyrrolidines via a selective iodide-mediated ring expansion of methylenecyclopropyl amides.
PubMed:
Synthesis of a C-glucosylated cyclopropylamide and evaluation as a glycogen phosphorylase inhibitor.
PubMed:
Fluorinated phenylcyclopropylamines. Part 5: Effects of electron-withdrawing or -donating aryl substituents on the inhibition of monoamine oxidases A and B by 2-aryl-2-fluoro-cyclopropylamines.
PubMed:
Electrochemical mass spectrometric studies on 1-cyclopropyl-4-phenyl-1,2,3,6-tetrahydropyridine.
PubMed:
In vitro metabolism of a model cyclopropylamine to reactive intermediate: insights into trovafloxacin-induced hepatotoxicity.
PubMed:
Quantification and comparison of toll-like receptor expression and responsiveness in primary and immortalized human female lower genital tract epithelia.
PubMed:
Long-range electron and hole transport through DNA with tethered cyclometalated iridium(III) complexes.
PubMed:
Mechanisms of trovafloxacin hepatotoxicity: studies of a model cyclopropylamine-containing system.
PubMed:
Synthesis and characterization of iridium(III) cyclometalated complexes with oligonucleotides: insights into redox reactions with DNA.
PubMed:
Charge separation in a ruthenium-quencher conjugate bound to DNA.
PubMed:
Mechanistic analysis of a suicide inactivator of histone demethylase LSD1.
PubMed:
The Kulinkovich reaction in the synthesis of constrained n,n-dialkyl neurotransmitter analogues.
PubMed:
trans-2-Phenylcyclopropylamine is a mechanism-based inactivator of the histone demethylase LSD1.
PubMed:
CpG-induced IFNgamma expands TLR4-specific IL-18 responses in vivo.
PubMed:
Asymmetric synthesis of cyclopropylamines starting from N-sulfinyl alpha-chloro ketimines.
PubMed:
Microglial cells and peritoneal macrophages release activin A upon stimulation with Toll-like receptor agonists.
PubMed:
EPR studies of amine radical cations. Part 2. Thermal and photo-induced rearrangements of propargylamine and allylamine radical cations in low-temperature freon matrices.
PubMed:
Synthesis of beta-lactams by Ag+-induced ring expansion of 1-hydroxycyclopropylamines: a theoretical analysis.
PubMed:
Reassessment of the structural composition of the alkenone distributions in natural environments using an improved method for double bond location based on GC-MS analysis of cyclopropylimines.
PubMed:
Electron paramagnetic resonance study of the mononuclear Al species formed in the reaction of Al atoms and cyclopropylamine at 77 k in an adamantane matrix.
PubMed:
Cytochrome P450-catalyzed oxidation of N-benzyl-N-cyclopropylamine generates both cyclopropanone hydrate and 3-hydroxypropionaldehyde via hydrogen abstraction, not single electron transfer.
PubMed:
Diverse Toll-like receptors utilize Tpl2 to activate extracellular signal-regulated kinase (ERK) in hemopoietic cells.
PubMed:
First "hybrid" ligands of vanilloid TRPV1 and cannabinoid CB2 receptors and non-polyunsaturated fatty acid-derived CB2-selective ligands.
PubMed:
Sequence dependence of charge transport through DNA domains.
PubMed:
Pressure-induced polymorphism in cyclopropylamine.
PubMed:
Mutation of surface cysteine 374 to alanine in monoamine oxidase A alters substrate turnover and inactivation by cyclopropylamines.
PubMed:
Cyclopropylamine inactivation of cytochromes P450: role of metabolic intermediate complexes.
PubMed:
Fluorinated phenylcyclopropylamines. Part 4: effects of aryl substituents and stereochemistry on the inhibition of monoamine oxidases by 1-aryl-2-fluoro-cyclopropylamines.
PubMed:
Inhibition of nucleoside transport proteins by C8-alkylamine-substituted purines.
PubMed:
Synthesis and properties of gem-(difluorocyclopropyl)amine derivatives of bicyclo[n.1.0]alkanes.
PubMed:
Fluorinated phenylcyclopropylamines as inhibitors of monoamine oxidases.
PubMed:
Stereochemistry of cyclopropane formation involving group IV organometallic complexes.
PubMed:
Preliminary evidence of the role of hydrogen peroxide in the degradation of benzo[a]pyrene by a non-white rot fungus Fusarium solani.
PubMed:
Molecular orbital calculations of ring opening of the isoelectronic cyclopropylcarbinyl radical, cyclopropoxy radical, and cyclopropylaminium radical cation series of radical clocks.
PubMed:
Early upregulation of kinin B1 receptors in retinal microvessels of the streptozotocin-diabetic rat.
PubMed:
Theoretical study of the mechanism of the formation of 3-unsubstituted 4,4-disubstituted beta-lactams by silver-induced ring expansion of alkoxycyclopropylamines: a new synthetic route to 4-alkoxycarbonyl-4-alkyl-2-azetidinones.
PubMed:
Stereocontrolled synthesis of 3-(trans-2-aminocyclopropyl)alanine, a key component of belactosin A.
PubMed:
Cyclopropane structural units from homoaldol adducts.
PubMed:
Formation of cyclopropanone during cytochrome P450-catalyzed N-dealkylation of a cyclopropylamine.
PubMed:
Synthesis and pharmacological evaluation of some (pyridyl)cyclopropylmethyl amines and their methiodides as nicotinic receptor ligands.
PubMed:
Inter-subunit cross-linking of methylamine dehydrogenase by cyclopropylamine requires residue alphaPhe55.
PubMed:
Radical cation-mediated annulation. Stereoselective construction of bicyclo[5.3.0]decan-3-ones by aerobic oxidation of cyclopropylamines.
PubMed:
Detection of aminium ion intermediates: N-cyclopropyl versus N-carboxymethyl groups as reporters.
PubMed:
Effect of mobile phase amine additives on enantioselectivity for phenylalanine analogs.
PubMed:
N-dealkylation of an N-cyclopropylamine by horseradish peroxidase. Fate of the cyclopropyl group.
PubMed:
Enzymatic N-dealkylation of an N-cyclopropylamine: an unusual fate for the cyclopropyl group.
PubMed:
Cytotoxicity of two novel cisplatin analogues, (CPA)2Pt[DOLYM] and (DACH)Pt[DOLYM], to human cancer cells in vitro.
PubMed:
Characterization of the binding site of the histamine H3 receptor. 1. Various approaches to the synthesis of 2-(1H-imidazol-4-yl)cyclopropylamine and histaminergic activity of (1R,2R)- and (1S,2S)-2-(1H-imidazol-4-yl)-cyclopropylamine.
PubMed:
Synthesis and serotonin receptor affinities of a series of trans-2-(indol-3-yl)cyclopropylamine derivatives.
PubMed:
A major role for prostacyclin in nitric oxide-induced ocular vasorelaxation in the piglet.
PubMed:
High antagonist potency of GT-2227 and GT-2331, new histamine H3 receptor antagonists, in two functional models.
PubMed:
Enantiomeric Synthesis of L-(or 1'R,2'S)-Carbocyclic Cyclopropyl Nucleosides.
PubMed:
Model Studies of TTQ-Containing Amine Dehydrogenases.
PubMed:
Novel 19-(cyclopropylamino)-androst-4-en-3,17-dione: a mechanism-based inhibitor of aromatase.
PubMed:
Mechanisms of the biphasic effects of peroxides on the retinal vasculature of newborn and adult pigs.
PubMed:
Mechanistic studies on the monoamine oxidase B catalyzed oxidation of 1,4-disubstituted tetrahydropyridines.
PubMed:
In vitro anti-Mycobacterium avium activities of quinolones: predicted active structures and mechanistic considerations.
PubMed:
Synthesis, structure, and antitumor activity of 1,3-dithiol- and 1,3-dithiolan-2-ylidenemalonatoplatinum(II) complexes.
PubMed:
Reaction of lysyl oxidase with trans-2-phenylcyclopropylamine.
PubMed:
Inhibition and activation of porcine squalene epoxidase.
PubMed:
Inhibition of cholesterol synthesis by cyclopropylamine derivatives of squalene in human hepatoblastoma cells in culture.
PubMed:
Synthesis of [carbonyl-14C]sparfloxacin.
PubMed:
Inhibition by cyclopropylamine of the quinoprotein methylamine dehydrogenase is mechanism-based and causes covalent cross-linking of alpha and beta subunits.
PubMed:
Oxidation of cycloalkylamines by cytochrome P-450. Mechanism-based inactivation, adduct formation, ring expansion, and nitrone formation.
PubMed:
Deprenyl antagonizes acute lethality of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in mice.
PubMed:
Overview of the present state of MAO inhibitors.
PubMed:
Microscale syntheses of anti-tumour platinum compounds labelled with 191Pt.
PubMed:
In vivo distribution studies of radioactively labelled platinum complexes; cis-dichlorodiammine platinum(II), cis-trans-dichlorodihydroxy-bis-(isopropylamine) platinum(IV), cis-dichloro-bis-cyclopropylamine platinum(II), and cis-diammine 1,1-cyclobutanedicarboxylate platinum(II) in patients with malignant disease, using a gamma camera.
PubMed:
Effect of alpha-methylation on inactivation of monoamine oxidase by N-cyclopropylbenzylamine.
PubMed:
Bacterial degradation of N-cyclopropylmelamine. The steps to ring cleavage.
PubMed:
Synthesis and evaluation of substituted 2-phenylcyclobutylamines as analogues of hallucinogenic phenethylamines: lack of LSD-like biological activity.
PubMed:
Mutagenic properties of N-cyclopropyl and N-allyl-N-nitroso compounds. Studies on the nature of alkylating species.
PubMed:
N-[2-(o-iodophenoxy)ethyl]cyclopropylamine hydrochloride (LY121768), a potent and selective irreversible inhibitor of type A monoamine oxidase.
PubMed:
A comparative study of the distribution in the male rat of platinum-labelled cis-dichlorodiammine platinum (II), cis-trans-dichlorodihydroxy-bis-(isopropylamine) platinum (I), and cis-dichloro-bis-cyclopropylamine platinum (II).
PubMed:
Isomeric cyclopropyl ring-methylated homologues of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, an hallucinogen analogue.
PubMed:
Blood clearance of three radioactively labelled platinum complexes: cis-dichlorodiammine platinum II, cis, trans-dichlorodihydroxy-bis-(isopropylamine) platinum IV, and cis-dichloro-bis-cyclopropylamine platinum II, in patients with malignant disease.
PubMed:
Elevation of epinephrine concentration in rat brain by LY51641, a selective inhibitor of type A monoamine oxidase.
PubMed:
Effect of 2-(p-chlorophenyl)cyclopropylamine on 5-hydroxyindole concentration and monoamine oxidase activity in rat brain.
PubMed:
Pyridoxal 5'-phosphate levels in brain after treatments which impair cerebral glucose metabolism.
PubMed:
Analysis of the cardiac stimulant properties of (3,4-dihydroxyphenyl)-cyclopropylamine (ASL-7003) and 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene (A6,7DTN).
PubMed:
Conformational analogues of dopamine. Synthesis and pharmacological activity of (E)- and (Z)-2-(3,4-dihydroxyphenyl)cyclopropylamine hydrochlorides.
PubMed:
Resolution and absolute configuration of trans-2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine, a potent hallucinogen analogue.
PubMed:
Irritable aggression and open field behavior in rats given 2-phenylcyclopropylamines.
PubMed:
Selective in vivo inhibition of monoamine oxidase in rat tissues by N-[2-(O-chlorophenoxy)-ethyl]-cyclopropylamine.
PubMed:
(+/-)(E)-2-(3,4-Dihydroxyphenyl)cyclopropylamine hydrochloride (ASL-7003): a rigid analogue of dopamine.
PubMed:
Inhibition of monoamine oxidase by N-phenacyl-cyclopropylamine.
PubMed:
Effects of three monoamine oxidase inhibitors on ethanol preference in mice.
PubMed:
2-(4-imidazolyl)cyclopropylamine.
PubMed:
Kinetic studies and effects in vivo of a new monoamine oxidase inhibitor, N-[2-(o-chlorophenoxy)-ethyl]-cyclopropylamine.
PubMed:
A preliminary evaluation of trans-d1-2-phenyl-cyclopropylamine hydrochloride in the ambulatory treatment of depression.