5-phenyl-4,5-dihydro-1,3-oxazol-2-amine

• ChemBase ID: 1286
• Molecular Formular: C9H10N2O
• Molecular Mass: 162.1885
• Monoisotopic Mass: 162.07931295
• SMILES: O1C(CN=C1N)c1ccccc1
• Canonical SMILES: NC1=NCC(O1)c1ccccc1
• InChI: InChI=1S/C9H10N2O/c10-9-11-6-8(12-9)7-4-2-1-3-5-7/h1-5,8H,6H2,(H2,10,11)
• InChIKey: SYAKTDIEAPMBAL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-phenyl-4,5-dihydro-1,3-oxazol-2-amine
• IUPAC Traditional name: aminorex fumarate; aminorex
• Brand Name: Apiquel; Monocil
• Synonyms: 2-Amino-5-phenyl-2-oxazoline; Aminoxafen; Apiquel; CPDD 0039; McN 742; NSC 66592; NSC 66952; Aminorex; 4,5-Dihydro-5-phenyl-2-oxazolamine; Aminoxaphen; Aminorex

Database IDs

• CAS Number: 2207-50-3
• MDL Number: MFCD00214070
• PubChem SID: 46507089; 160964746
• PubChem CID: 16630

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.475702
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.39614096
• LogD (pH = 7.4): 1.1140741
• Log P: 1.4621556
• Molar Refractivity: 45.7481 cm^3
• Polarizability: 17.671291 Å^3
• Polar Surface Area: 47.61 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.16
• LOG S: -2.31
• Solubility (Water): 7.92e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble; ethanol: soluble; H2O: insoluble
• Apperance: white solid

Safety Information

• RTECS: RQ4500000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Drug Control: USDEA Schedule I; Home Office Schedule 4.1; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Product Information

• Empirical Formula (Hill Notation): C9H10N2O

DETAILS

DrugBank - DB01490

• Drug Groups: illicit; experimental
• Description: An amphetamine-like anorectic agent. It may cause pulmonary hypertension. [PubChem]
• External Links: Wikipedia

Sigma Aldrich - A170

Substrates
Anorexic; a substrate of the serotonin transporter that also releases serotonin from platelets.

Toronto Research Chemicals - A629200

Aminorex is a metabolite of Levamisole (L331100). Aminorex is an anorectic stimulant drug of the 2-amino-5-aryl oxazoline class. Aminorex has been shown to have locomotor stimulant effects similar to Methamphetamine (M258795).

REFERENCES

• Poos, G., et al.: J. Med. Chem., 6, 266 (1963)
• Watson, A., et al.: Res. Vet. Sci., 45, 411 (1963)
• Russell, B., et al.: Pharmacol. Biochem. Behav., 51, 375 (1963)