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

• ChemBase编号: 783
• 分子式: C17H21NO4
• 平均质量: 303.35294
• 单一同位素质量: 303.14705816
• SMILES: O([C@@H]1[C@@H](C2N(C(CC2)C1)C)C(=O)OC)C(=O)c1ccccc1
• Canonical SMILES: COC(=O)[C@H]1[C@H](CC2N(C1CC2)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-PFSRBDOWSA-N

名称和登记号

名称

• IUPAC标准名: methyl (2R,3S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC传统名: cocaine
• 商标名: Cocaine
• 别名: D-pseudococaine; Corine; Cola; Coke; Cocktail; Zip; Yeyo; Trails; Toot; Toke; Sweet Stuff; Sugar; Star-Spangled Powder; Star Dust; Snort; Sleighride; Rock; Prime Time; Pimp's Drug; Neurocaine; Moonrocks; Methyl Benzoylecgonine; Line; Leaf; Lady; L-Cocaine; L-Cocain; Kokayeen; Kokan; Kokain; Kibbles N' Bits; Jam; Isococaine; Isococain; Isocaine; Hell; Heaven; Happy Trails; Happy Powder; Happy Dust; Green Gold; Goofball; Gold Dust; Girl; G-Rock; Freeze; Foo Foo; Florida Snow; Flex; Flake; Erytroxylin; Eritroxilina; Dust; Cocaine; Benzoylethylecgonine; Bazooka; Badrock; Benzoylmethylecgonine; Bernice; Bernies; Beta-Cocain; Blast; Blizzard; Blow; Bouncing Powder; Bump; Burese; C" Carrie; Cocaine Free Base; Cocaina; Cocaine-M; Cocain; Coca; COC; Cholly; Chicken Scratch; Charlie; Cecil; Caviar; Carrie; Candy; Cabello; Dextrocaine; Depsococaine; Delcaine; Dama Blanca

登记号

• CAS号: 50-36-2
• PubChem SID: 160964246
• PubChem CID: 5760

理论计算性质

JChem

• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): -0.8337083
• LogD (pH = 7.4): 0.82485026
• Log P: 2.282108
• 摩尔折射率: 81.1604 cm^3
• 极化性: 32.167484 Å^3
• 极化表面积: 55.84 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.97
• LOG S: -1.78
• 溶解度: 5.03e+00 g/l

分子性质

理化性质

• 溶解度: 1800 mg/L
• 疏水性(logP): 2.3

详细说明

DrugBank - DB00907

• Drug Groups: illicit; approved
• Description: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake. [PubChem]
• Indication: For the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities.
• Pharmacology: Cocaine is a local anesthetic indicated for the introduction of local (topical) anesthesia of accessible mucous membranes of the oral, laryngeal and nasal cavities.
• Toxicity: Intense agitation, convulsions, hypertension, rhythm disturbance, coronary insufficiency, hyperthermia, rhabdomyolysis, and renal impairment. Oral mouse LD₅₀ = 96 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Cocaine is metabolized to benzoylecgonine and ecgonine methyl ester, which are both excreted in the urine. In the presence of alcohol, a further active metabolite, cocaethylene is formed, and is more toxic then cocaine itself.
• Absorption: Cocaine is absorbed from all sites of application, including mucous membranes and gastrointestinal mucosa. By oral or intra-nasal route, 60 to 80% of cocaine is absorbed.
• Half Life: 1 hour
• References: Siegel RK, Elsohly MA, Plowman T, Rury PM, Jones RT: Cocaine in herbal tea. JAMA. 1986 Jan 3;255(1):40. [Pubmed] ; Volkow ND, Wang GJ, Fischman MW, Foltin R, Fowler JS, Franceschi D, Franceschi M, Logan J, Gatley SJ, Wong C, Ding YS, Hitzemann R, Pappas N: Effects of route of administration on cocaine induced dopamine transporter blockade in the human brain. Life Sci. 2000 Aug 11;67(12):1507-15. [Pubmed] ; Dimitrijevic N, Dzitoyeva S, Manev H: An automated assay of the behavioral effects of cocaine injections in adult Drosophila. J Neurosci Methods. 2004 Aug 30;137(2):181-4. [Pubmed] ; Uz T, Akhisaroglu M, Ahmed R, Manev H: The pineal gland is critical for circadian Period1 expression in the striatum and for circadian cocaine sensitization in mice. Neuropsychopharmacology. 2003 Dec;28(12):2117-23. [Pubmed] ; McClung CA, Sidiropoulou K, Vitaterna M, Takahashi JS, White FJ, Cooper DC, Nestler EJ: Regulation of dopaminergic transmission and cocaine reward by the Clock gene. Proc Natl Acad Sci U S A. 2005 Jun 28;102(26):9377-81. Epub 2005 Jun 20. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Siegel RK, Elsohly MA, Plowman T, Rury PM, Jones RT: Cocaine in herbal tea. JAMA. 1986 Jan 3;255(1):40. Pubmed
• Volkow ND, Wang GJ, Fischman MW, Foltin R, Fowler JS, Franceschi D, Franceschi M, Logan J, Gatley SJ, Wong C, Ding YS, Hitzemann R, Pappas N: Effects of route of administration on cocaine induced dopamine transporter blockade in the human brain. Life Sci. 2000 Aug 11;67(12):1507-15. Pubmed
• Dimitrijevic N, Dzitoyeva S, Manev H: An automated assay of the behavioral effects of cocaine injections in adult Drosophila. J Neurosci Methods. 2004 Aug 30;137(2):181-4. Pubmed
• Uz T, Akhisaroglu M, Ahmed R, Manev H: The pineal gland is critical for circadian Period1 expression in the striatum and for circadian cocaine sensitization in mice. Neuropsychopharmacology. 2003 Dec;28(12):2117-23. Pubmed
• McClung CA, Sidiropoulou K, Vitaterna M, Takahashi JS, White FJ, Cooper DC, Nestler EJ: Regulation of dopaminergic transmission and cocaine reward by the Clock gene. Proc Natl Acad Sci U S A. 2005 Jun 28;102(26):9377-81. Epub 2005 Jun 20. Pubmed