2-amino-3-hydroxy-N'-[(2,3,4-trihydroxyphenyl)methyl]propanehydrazide hydrochloride

• ChemBase ID: 73027
• Molecular Formular: C10H16ClN3O5
• Molecular Mass: 293.70414
• Monoisotopic Mass: 293.07784831
• SMILES: c1(c(c(c(cc1)CNNC(=O)C(N)CO)O)O)O.Cl
• Canonical SMILES: OCC(C(=O)NNCc1ccc(c(c1O)O)O)N.Cl
• InChI: InChI=1S/C10H15N3O5.ClH/c11-6(4-14)10(18)13-12-3-5-1-2-7(15)9(17)8(5)16;/h1-2,6,12,14-17H,3-4,11H2,(H,13,18);1H
• InChIKey: ULFCBIUXQQYDEI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-hydroxy-N'-[(2,3,4-trihydroxyphenyl)methyl]propanehydrazide hydrochloride
• IUPAC Traditional name: benserazide hydrochloride
• Synonyms: Serazide; Ro 4-4602; Benserazide hydrochloride; DL-Serine 2-(2,3,4-trihydroxybenzyl)hydrazide hydrochloride; Benserazide hydrochloride; DL-Serine 2-[(2,3,4-Trihydroxyphenyl)methyl]hydrazide Hydrochloride; DL-Serine N2-(2,3,4-trihydroxybenzyl)hydrazide Hydrochloride; N-(DL-Seryl)-N'-(2,3,4-trihydroxybenzyl)hydrazine Hydrochloride; Ro-4-4602; DL-SERINE 2; BENSERAZIDE

Database IDs

• CAS Number: 14919-77-8
• EC Number: 238-991-9
• MDL Number: MFCD00078571
• PubChem SID: 24277886; 162037947
• PubChem CID: 26964

CALCULATED PROPERTIES

• Acid pKa: 8.688219
• H Acceptors: 7
• H Donor: 7
• LogD (pH = 5.5): -3.9209604
• LogD (pH = 7.4): -2.2601278
• Log P: -1.9928483
• Molar Refractivity: 73.2301 cm^3
• Polarizability: 24.415533 Å^3
• Polar Surface Area: 148.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble10 mg/mL; Methanol; Water
• Apperance: solid; White to Off-White Solid
• Melting Point: 146-148°C

Safety Information

• Storage Condition: 0°C; -20°C; -20°C Freezer
• RTECS: VT9632300
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... DDC(1644)

Product Information

• Purity: ≥98% (TLC)
• Salt Data: hydrochloride

DETAILS

MP Biomedicals - 02154261

Hydrochloride Tan solid

Selleck Chemicals - S2453

Research Area: Neurological Disease
Biological Activity:
Benserazide is a peripherally-acting aromatic L-amino acid decarboxylase (AAAD) or DOPA decarboxylase inhibitor. It inhibits this decarboxylation, and since it itself cannot cross the blood-brain barrier, this allows dopamine to build up solely in the brain instead. Adverse effects caused by peripheral dopamine, such as nausea and arrhythmia, are minimized. However, benserazide cannot reduce the centrally-mediated side effects of levodopa, particularly dyskinesia. [1][2]

Sigma Aldrich - B7283

Biochem/physiol Actions
Inhibitor of L-aromatic amino acid decarboxylase.

Toronto Research Chemicals - B120500

Used as antiparkinsonian. A peripheral decarboxylase inhibitor.

REFERENCES

• http://en.wikipedia.org/wiki/Benserazide
• Burkard, W.P., et al.: Experientia, 18, 411 (1962)
• Marion, M.-H., et al.: Adv. Neurol., 45, 493 (1962)
• Pinder, R.M., et al.: Drugs, 11, 329 (1976)