methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride

• ChemBase ID: 130672
• Molecular Formular: C17H22ClNO4
• Molecular Mass: 339.81388
• Monoisotopic Mass: 339.12373587
• SMILES: CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)OC.Cl
• Canonical SMILES: COC(=O)[C@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1.Cl
• InChI: InChI=1S/C17H21NO4.ClH/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11;/h3-7,12-15H,8-10H2,1-2H3;1H/t12-,13+,14-,15+;/m0./s1
• InChIKey: PIQVDUKEQYOJNR-VZXSFKIWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride
• IUPAC Traditional name: cocaine hydrochloride
• Synonyms: Cocaine hydrochloride solution; Cocaine hydrochloride; Ecgonine methyl ester benzoate hydrochloride; (1R,2R,3S,5S)-3-(Benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic Acid Methyl Ester Hydrochloride; (-)-Cocaine Hydrochloride; Cocaine Muriate; NSC 25263; Sal de Merck; Cocaine Hydrochloride; 可卡因 盐酸盐 溶液; 苯甲酰甲基芽子碱 盐酸盐; 可卡因 盐酸盐

Database IDs

• CAS Number: 53-21-4
• EC Number: 200-167-1
• MDL Number: MFCD00058119
• PubChem SID: 162224950
• PubChem CID: 656832

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.8337083
• LogD (pH = 7.4): 0.82485026
• Log P: 2.282108
• Molar Refractivity: 81.1604 cm^3
• Polarizability: 32.167484 Å^3
• Polar Surface Area: 55.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Water
• Apperance: White Solid
• Melting Point: 187-1890C
• Flash Point: 11 °C; 51.8 °F

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: YM3050000
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1230; 1544
• German water hazard class: 1; 2; 3
• Hazard Class: 3; 6.1
• Packing Group: 2; 3
• Risk Statements: 11-23/24/25-39/23/24/25; 60-25-43
• Safety Statements: 16-36/37-45; 53-22-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301-H311-H331-H370; H301-H317-H360
• GHS Precautionary statements: P201-P280-P301 + P310-P308 + P313; P210-P260-P280-P301 + P310-P311
• 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, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1230 3/PG 2; UN 1544 6.1/PG 3
• Drug Control: Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; USDEA Schedule II; Home Office Schedule 2; regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.5% (HPLC)
• Concentration: ~1 mg/mL in methanol; 1.0 mg/mL±5% in methanol
• Grade: analytical standard, for drug analysis
• Impurities: ~1.2 mL solution
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C17H21NO4 · HCl

DETAILS

Sigma Aldrich - C5776

Biochem/physiol Actions
分别以大约 300nM、900nM 和 400nM 的 Kis 抑制多巴胺、去甲肾上腺素和 5-羟色胺转运蛋白。不同于苯异丙胺，它不会影响儿茶酚胺的释放。

Sigma Aldrich - 19330

Packaging
ampoule contains 1.2mL solution

Sigma Aldrich - 51621

Biochem/physiol Actions
Inhibits the dopamine, norepinephrine, and serotonin transporters with Kis of about 300 nM, 900 nM, and 400 nM, respectively. Unlike amphetamines, it has no effect on catecholamine release.

Toronto Research Chemicals - C633500

Inhibits the dopamine, norepinephrine, and serotonin transporters. Unlike amphetamines, it has no effect on catecholamine release. Controlled substance. Anesthetic (local).

REFERENCES

• Blakely, R.D., et al.: Curr. Opin. Neurobiol., 10, 328 (2000)
• Cowell, R. M., et al.: Eur. J. Pharmacol., 389, 59 (2000)
• Fleckenstein, A.E., Eur. J. Pharmacol., 406, 1 (2000)
• Torres, G.E., et al.: Nat. Rev. Neurosci., 4, 13 (2000)