(1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydro-1H-2-benzopyran-5,6-diol hydrate hydrochloride

• ChemBase ID: 155379
• Molecular Formular: C20H30ClNO4
• Molecular Mass: 383.9095
• Monoisotopic Mass: 383.18633613
• SMILES: c1cc(c(c2c1[C@@H](O[C@@H](C2)C12CC3CC(C1)CC(C3)C2)CN)O)O.O.Cl
• Canonical SMILES: NC[C@@H]1O[C@@H](Cc2c1ccc(c2O)O)C12CC3CC(C2)CC(C1)C3.O.Cl
• InChI: InChI=1S/C20H27NO3.ClH.H2O/c21-10-17-14-1-2-16(22)19(23)15(14)6-18(24-17)20-7-11-3-12(8-20)5-13(4-11)9-20;;/h1-2,11-13,17-18,22-23H,3-10,21H2;1H;1H2/t11?,12?,13?,17-,18-,20?;;/m0../s1
• InChIKey: KNACNUUSUYTFDY-LIWDBWMRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydro-1H-2-benzopyran-5,6-diol hydrate hydrochloride
• IUPAC Traditional name: (1R,3S)-3-(adamantan-1-yl)-1-(aminomethyl)-3,4-dihydro-1H-2-benzopyran-5,6-diol hydrate hydrochloride
• Synonyms: (-)-(1R,3S)-3-Adamantyl-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran hydrochloride hydrate; A-77636 hydrochloride hydrate

Database IDs

• CAS Number: 145307-34-2(anhydrous)
• PubChem SID: 24277883; 162249517
• PubChem CID: 68671454

CALCULATED PROPERTIES

• Acid pKa: 9.540895
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.122662
• LogD (pH = 7.4): 1.4239244
• Log P: 2.5734036
• Molar Refractivity: 92.3712 cm^3
• Polarizability: 36.538227 Å^3
• Polar Surface Area: 75.71 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: white to off-white solid

Safety Information

• Storage Condition: desiccated; protect from light
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... DRD1(1812)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H27NO3 · HCl · xH2O

DETAILS

Sigma Aldrich - A255

Biochem/physiol Actions
Potent, orally active D1 dopamine receptor agonist.
Caution
Hygroscopic, photosensitive, and oxygen-sensitive. Solutions should be freshly prepared.
Legal Information
Manufactured and sold under exclusive license from Abbott Laboratories.