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

• ChemBase ID: 783
• Molecular Formular: C17H21NO4
• Molecular Mass: 303.35294
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• IUPAC Traditional name: cocaine
• Brand Name: Cocaine
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 1.97
• LOG S: -1.78
• Solubility (Water): 5.03e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1800 mg/L
• Hydrophobicity(logP): 2.3

DETAILS

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

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