(1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide hydrochloride

• ChemBase ID: 154258
• Molecular Formular: C15H23ClN2O
• Molecular Mass: 282.80892
• Monoisotopic Mass: 282.14989105
• SMILES: CCN(CC)C(=O)[C@@]1(C[C@@H]1CN)c1ccccc1.Cl
• Canonical SMILES: NC[C@H]1C[C@@]1(c1ccccc1)C(=O)N(CC)CC.Cl
• InChI: InChI=1S/C15H22N2O.ClH/c1-3-17(4-2)14(18)15(10-13(15)11-16)12-8-6-5-7-9-12;/h5-9,13H,3-4,10-11,16H2,1-2H3;1H/t13-,15+;/m1./s1
• InChIKey: XNCDYJFPRPDERF-PBCQUBLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide hydrochloride
• IUPAC Traditional name: milnacipran hydrochloride
• Synonyms: (1R,2S)-rel-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide monohydrochloride; F 2207; Midalcipran; Toledomin; Milnacipran hydrochloride; (1R,2S)-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide Hydrochloride; Levomilnacipran; Savella; cis-(-)-Milnacipran Hydrochloride; (1R-cis)-Milnacipran Hydrochloride

Database IDs

• CAS Number: 101152-94-7; 175131-61-0
• MDL Number: MFCD00901293
• PubChem SID: 162248397
• PubChem CID: 163701

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.5899252
• LogD (pH = 7.4): -0.91125065
• Log P: 1.4217067
• Molar Refractivity: 73.8095 cm^3
• Polarizability: 28.916954 Å^3
• Polar Surface Area: 46.33 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble19 mg/mL
• Apperance: white solid

Safety Information

• RTECS: GZ1014010
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Description: Store with desiccants
• Empirical Formula (Hill Notation): C15H22N2O · HCl

DETAILS

Sigma Aldrich - M1318

Biochem/physiol Actions
Serotonin and norepinephrine reuptake inhibitor (SNRI)

Toronto Research Chemicals - M344590

The (1R-cis)-enatiomer of Milnacipran (M344600). A selective norepinephrine and serotonin reuptake inhibitor approved for the management of fibromyalgia.

REFERENCES

• Moret, C. et al.: Neuropharmacology, 24, 1211 (1985)
• Palmier, C. et al.: Eur. J. Clin. Pharmacol., 37, 235 (1985)
• Spencer, C.M. et al.: Drugs, 56, 405 (1985)