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

• ChemBase ID: 126658
• Molecular Formular: C17H21NO4
• Molecular Mass: 303.35294
• Monoisotopic Mass: 303.14705816
• SMILES: CN1[C@H]2CC[C@@H]1[C@@H]([C@H](C2)OC(=O)c1ccccc1)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1[C@H](C[C@H]2N([C@@H]1CC2)C)OC(=O)c1ccccc1
• InChI: InChI=1S/C17H21NO4/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/t12-,13+,14-,15+/m0/s1
• InChIKey: ZPUCINDJVBIVPJ-LJISPDSOSA-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
• IUPAC Traditional name: cocaine
• Synonyms: Cocaine free base; methylbenzoylecgonine; benzoylmethylecgonine; ecgonine methyl ester benzoate; 2b-Carbomethoxy -3b-benzoyloxy tropane; Cocaine; Ecgonine methyl ester benzoate solution; Cocaine solution; 苯甲酰甲基芽子碱; 可卡因 游离碱; 苯甲酰甲基芽子碱 溶液; 可卡因 溶液

Database IDs

• CAS Number: 50-36-2
• EC Number: 200-032-7
• MDL Number: MFCD00056906
• PubChem SID: 24893116; 24882022; 162220988
• PubChem CID: 5760; 446220
• CHEBI ID: 27958
• ATC CODE: S01HA01; R02AD03; N01BC01; S02DA02
• CHEMBL: 120901
• Chemspider ID: 10194104
• DrugBank ID: DB00907
• IUPHAR ligand ID: 2286
• KEGG ID: D00110
• Unique Ingredient Identifier: I5Y540LHVR
• Wikipedia Title: Cocaine

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: HCl: 1800-2500 mg/mL (20°C)
• Melting Point: 98°C (208.4°F)
• Boiling Point: 187°C (368.6°F)
• Flash Point: 2 °C; 35.6 °F

Safety Information

• RTECS: YM2800000
• European Hazard Symbols: Flammable (F); Toxic (T); Harmful (Xn)
• UN Number: 1544; 1648
• German water hazard class: 2; 3
• Hazard Class: 3; 6.1
• Packing Group: 2
• Risk Statements: 11-20/21/22-36; 23/24/25-43
• Safety Statements: 16-26-36/37; 22-36/37/39-45
• GHS Pictograms: GHS02; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H312-H319-H332; H301-H311-H317-H331
• GHS Precautionary statements: P210-P280-P305 + P351 + P338; P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 2; UN 1648 3/PG 2
• Drug Control: kontrollierte Droge in Deutschlandregulated 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: -20°C

Pharmacology Properties

• Admin Routes: Topical, Oral, Insufflation, IV, PO
• Bioavailability: Oral: 33%; Insufflated: 60–80%; Nasal Spray: 25–43%
• Dependency Liability: High
• Excretion: Renal (benzoylecgonine and ecgonine methyl ester)
• Half Life: 1 hour
• Metabolism: Hepatic CYP3A4
• Legal Status: A (UK); Schedule 8 (Australia); Schedule I (Canada); Schedule II (US)
• Pregnancy Category: C
• Gene Information: human ... DRD3(1814), KCNH1(3756), KCNH2(3757), SCN10A(6336), SCN11A(11280), SCN5A(6331), SLC6A2(6530), SLC6A3(6531), SLC6A4(6532)mouse ... Slc6a2(20538)rat ... Chrm1(25229), Slc6a3(24898), Slc6a4(25553); human ... KCNH1(3756), KCNH2(3757), SLC6A2(6530), SLC6A3(6531), SLC6A4(6532)mouse ... Slc6a2(20538)rat ... Chrm1(25229), Slc6a3(24898), Slc6a4(25553)

Product Information

• Concentration: 1 mg/mL in acetonitrile
• Grade: analytical standard, for drug analysis
• Empirical Formula (Hill Notation): C17H21NO4

DETAILS

Sigma Aldrich - C8912

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.