(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

• ChemBase ID: 125978
• Molecular Formular: C17H23NO3
• Molecular Mass: 289.36942
• Monoisotopic Mass: 289.1677936
• SMILES: CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)c1ccccc1
• Canonical SMILES: OCC(c1ccccc1)C(=O)O[C@@H]1C[C@@H]2CC[C@H](C1)N2C
• InChI: InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16?
• InChIKey: RKUNBYITZUJHSG-SPUOUPEWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate; (1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
• IUPAC Traditional name: (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate; l-atropine
• Brand Name: Atropen
• Synonyms: Atropine; Atropine; Hyoscyamine; Tropine tropate; endo-(±)-α-(Hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester; (8-甲基-8-氮杂双环[3.2.1]辛-3-基) endo-(+/-)-α-(羟甲基)苯乙酸酯; 莨菪碱; 龙葵碱; 阿托品

Database IDs

• CAS Number: 51-55-8
• EC Number: 200-104-8
• MDL Number: MFCD00022622
• Beilstein Number: 91260
• PubChem SID: 24890401; 162220321; 24890659
• PubChem CID: 174174
• CHEBI ID: 16684
• ATC CODE: S01FA01; A03BA01
• CHEMBL: 195
• Chemspider ID: 10194105
• DrugBank ID: DB00572
• IUPHAR ligand ID: 320
• KEGG ID: D00113
• Unique Ingredient Identifier: 7C0697DR9I
• Wikipedia Title: Atropine
• Medline Plus: a682487

CALCULATED PROPERTIES

• Acid pKa: 15.1457405
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.7801015
• LogD (pH = 7.4): -0.40574417
• Log P: 1.571241
• Molar Refractivity: 80.8164 cm^3
• Polarizability: 32.034832 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: dilute aqueous acid: soluble; ethanol: soluble; H2O: soluble2 mg/mL
• Apperance: white powder
• Melting Point: 115-118 °C

Safety Information

• RTECS: CK0700000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/28
• Safety Statements: 25-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300 + H330; H300-H330
• GHS Precautionary statements: P260-P264-P284-P301 + P310-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; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 2

Pharmacology Properties

• Admin Routes: Oral, IV, IM, rectal
• Bioavailability: 25%
• Excretion: 50% excreted unchanged in urine
• Half Life: 2 hours
• Metabolism: 50% hydrolysed to tropine and tropic acid
• Legal Status: Rx-only
• Pregnancy Category: C (US)
• Gene Information: human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133)mouse ... Chrm1(12669)rat ... Chrm1(25229), Chrm2(81645), Chrm3(24260), Drd2(24318), Htr1a(24473); human ... CHRM1(1128), CHRM2(1129), CHRM4(1132), CHRM5(1133), LOC730413(730413)mouse ... Chrm1(12669)rat ... Chrm1(25229), Chrm2(81645), Chrm3(24260), Drd2(24318), Htr1a(24473)

Product Information

• Purity: ≥95.0% (NT); ≥99% (TLC)
• Suitability: meets USP testing specifications
• Ignition Residue: ≤0.05%
• Empirical Formula (Hill Notation): C17H23NO3

DETAILS

Sigma Aldrich - A2468

Biochem/physiol Actions
位于中枢和外周毒蕈碱型乙酰胆碱受体处的竞争性非选择性拮抗剂。

Sigma Aldrich - A0132

Biochem/physiol Actions
位于中枢和外周毒蕈碱型乙酰胆碱受体处的竞争性非选择性拮抗剂。
Reconstitution
Solutions stable for several days at 4 °C.

Sigma Aldrich - 11320

Biochem/physiol Actions
Competitive nonselective antagonist at central and peripheral muscarinic acetylcholine receptors.