un copié coller (un peu abrégé certes) sur les analogues non anesthesiques de la cocaine
des infos en PDF de rodhium archive
http://www.fichier-pdf.fr/2009/06/01/p7l73rc/
http://www.fichier-pdf.fr/2009/06/01/2fw9pdr/
IUPAC_name = (3-diethylamino-2,2-dimethylpropyl)-4-aminobenzoate
is a local anesthetic with stimulant properties nearly as cocaine
width= 220
CAS_number= 94-15-5
PubChem= 7177
DrugBank=C=16 | H=26 | N=2 | O=2
molecular_weight = 278.39
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3?-(4'-Chlorophenyl)-2?-(3'-phenylisoxazol-5'-yl)tropane
IUPAC_name = 3?-(4'-Chlorophenyl)-2?-(3'-phenylisoxazol-5'-yl)tropane
DrugBank=C=23 | H=23 | Cl=1 | N=2 | O=1
molecular_weight = 378.89
3?-(4'-Chlorophenyl)-2?-(3'-phenylisoxazol-5'-yl)tropane (?-CPPIT) is a cocaine analogue.
cite web :
http://e-collection.ethbib.ethz.ch/ecol ... h13287.pdf
Evaluation of Three Cocaine Analogues as PET tracers for the Dopamine Transporter and Synthetic Approaches to [F-18] -DFMO |accessdate=2008-01-11 |format= |work=]
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IUPAC_name = N-(2'-Fluoroethyl)-3?-(4'-chlorophenyl)-2?-(3'-phenylisoxazol-5'-yl)nortropane
width= 220
DrugBank=
C=24 | H=24 | Cl=1 | F=1 | N=2 | O=1
molecular_weight = 410.91
"N"-(2'-Fluoroethyl-)-3?-(4'-chlorophenyl)-2?-(3'-phenylisoxazol-5'-yl)nortropane (FE-?-CPPIT) is a cocaine analogue. cite web :
http://e-collection.ethbib.ethz.ch/ecol ... h13287.pdf
|title=Evaluation of Three Cocaine Analogues as PET tracers for the Dopamine Transporter and Synthetic Approaches to [F-18] -DFMO |accessdate=2008-01-11 |format= |work=]
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(-)-2?-Carbomethoxy-3?-phenyltropane (Troparil, ?-CPT, WIN-35065-2) is a stimulant drug used in scientific research. CPT is a phenyltropane based dopamine reuptake inhibitor and is derived from methylecgonidine. It is around the same potency as cocaine but lasts several times longer due to the lack of the metabolically labile ester link between the phenyl and tropane rings. The lack of an ester linkage removes the local anesthetic action from the drug, so CPT is a pure stimulant. This change in
activity also makes CPT slightly less cardiotoxic than cocaine. The most commonly used form of ?-CPT is the tartrate salt, but the hydrochloride and naphthalenedisulfonate salts are also available, as well as the free base.
CAS_number = 74163-84-1
PubChem = 170832
C=16 | H=21 | N=1 | O=2
molecular_weight = 259.343 g/mol
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(-)-2?-Carbomethoxy-3?-(4-fluorophenyl)tropane
Uses
CFT was discovered in 1979 during research into the mechanism of action of cocaine. A wide variety of similar tropane derivatives are also known, such as CPT and RTI-55, and various N-alkylated derivatives, many of which are even more potent than CFT; however the most widely used compound in scientific research has been CFT itself.
Radiolabelled forms of CFT have been used in humans and animals to map the distribution of dopamine transporters in the brain.
CFT was found to be particularly useful for this application as a normal fluorine atom can be substituted with the radioactive isotope 18F which is widely used in Positron emission tomography.
Another radioisotope-substituted analogue [11C] WIN-35,428 (where the carbon atom of either the N-methyl group, or the methyl from the 2-carbomethoxy group of CFT, has been replaced with 11C) is now more commonly used for this application, as it is quicker and easier in practice to make radiolabelled CFT by methylating nor-CFT or 2-desmethyl-CFT than by reacting methylecgonidine with parafluorophenylmagnesium bromide, and also avoids the requirement for a licence to work with the restricted precursor ecgonine.
CFT is about as addictive as cocaine in animal studies, but is taken less often due to its longer duration of action. Potentially this could make it a suitable drug to be used as a substitute for cocaine, in a similar manner to how methadone is used as a substitute for opiates in treating addiction.
Legal Status
CFT has no history of abuse in humans, but according to the chemical supplier Sigma-Aldrich it is illegal in the USA (Schedule II) and Germany (Kontrollierte Droge)
link :
http://www.sigmaaldrich.com/catalog/sea ... rand=SIGMA 1
presumably due to its similar effects to cocaine; however CFT is not specifically listed as a Schedule II drug on the DEA website :
http://www.usdoj.gov/dea/pubs/scheduling.html
or on the German controlled drug schedule :
http://bundesrecht.juris.de/btmg_1981/index.html
and so it is unclear on what basis Sigma-Aldrich has derived this legal information; Although previsions of the Federal Analog Act may be used by Sigma-Aldrich (and probably the DEA) to assume its illegality. While CFT might well be considered a controlled substance analogue in these countries there has never been any formal announcement by either the US or German government of CFT being added to the controlled substances list.
CFT might possibly also be considered a controlled substance analogue of cocaine in Canada, New Zealand and Australia, due to its related chemical structure to cocaine.
According to analog law one must consider structural similarity, and CFT might well not be considered substantially similar to cocaine, having been derived by the removal of an ester linkage rather than by simply substituting extra groups onto cocaine, although a para-fluoro group has also been added to CFT. Also the intent of the user must be considered as well, so CFT would probably not be considered illegal when it is being used solely for scientific research.
The relatively complex synthesis of CFT, as well as the fact that the main synthetic routes proceed via the restricted intermediate compound ecgonine, make it fairly unlikely that CFT will appear on the recreational market as a drug of abuse.
Toxicity
Sigma-Aldrich categorizes CFT as being a "very toxic" chemical and recommends the use of gloves, goggles, protective apron and respirator while handling it, and states it must only be used in a fume hood.
However this description is not supported by the known toxicology of CFT based on its widespread use in animals over a 30 year period and so this extreme caution is difficult to reconcile with the chemical and pharmacological properties of the drug; this may instead reflect concerns about its abuse potential rather than actual potential to cause poisoning.
The drug data sheet notes that serious side effects can occur following exposure to CFT, including CNS stimulation, dilation of eye pupils, euphoria, breathing difficulties, nervousness, restlessness, hypertension, fainting, paleness, arrhythmia, cardiac arrest, convulsions, and death. Prolonged or repeated exposure to CFT may result in habituation or addiction.
Chemical Properties
CAS number: 50370-56-4 or 77210-32-3
Molecular Formula: C16H20FNO2.C10H8S2O6
SMILES: CN1 [C@H] 2CC [C@@H] 1 [C@H] ( [C@H] (C2)C3=CC=C(C=C3)F)C(=O)OC
Molecular weight: 277.33 (free base) //////////// 565.55 (anhydrous naphthalenedisulfonate)
Melting Point: 202-204°C
Optical Rotation: [?] D = -62.5°
width= 180
CAS_number= 50370-56-4
PubChem= 105056
DrugBank= C=16 | H=20 | F=1 | N=1 | O=2
molecular_weight = 277.33 g/mol
(-)-2-?-Carbomethoxy-3-?-(4-fluorophenyl)tropane (?-CFT, WIN 35,428) is a stimulant drug used in scientific research.
CFT is a phenyltropane based dopamine reuptake inhibitor and is structurally derived from cocaine.
It is around 3-10x more potent than cocaine and lasts around 7 times longer based on animal studies. While the naphthalenedisulfonate salt is the most commonly used form in scientific research due to its high solubility in water, the free base and hydrochloride salts are known compounds and can also be produced.
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IUPAC name = Methyl (3S,4S)-1-methyl-4-naphthalen-2-ylpiperidine-3-carboxylate
width= 220
PubChem= 10684403
DrugBank= C=18 | H=21 | N=1 | O=2
molecular_weight = 283.364
smiles = COC(=O)C1CN(C)CCC1c3ccc2ccccc2c3
(-)-Methyl-1-methyl-4?-(2-naphthyl)piperidine-3?-carboxylate is a piperidine based stimulant drug which is synthesised from arecoline. It is similar to nocaine in chemical structure, and has two and a half times more activity than cocaine as a dopamine reuptake inhibitor. However it is also a potent serotonin reuptake inhibitor, with similar affinity to fluoxetine.
cite web :
http://pubs.acs.org/cgi-bin/abstract.cg ... 05561.html
title=Further SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors
accessdate=2008-01-11 |format= |work=] It is a structural isomer of another potent dopamine reuptake inhibitor, HDMP-28.
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IUPAC name = 2-Propanoyl-3-(4-isopropylphenyl)-tropane
C=20 | H=29 | N=1 | O=1
molecular_weight = 299.45
2-Propanoyl-3-(4-isopropylphenyl)-tropane or WF-31 (PIT) is a cocaine analogue.
Research shows WF-31 to be approximately ten times more potent than cocaine at binding to serotonin and at inhibiting serotonin uptake.
http://www3.interscience.wiley.com/cgi- ... 1&SRETRY=0
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IUPAC name = 2?-Propanoyl-3?-(4-tolyl)-tropane
C=18 | H=25 | N=1 | O=1
molecular_weight = 271.396
2?-Propanoyl-3?-(4-tolyl)-tropane also known as WF-11 or PTT is a cocaine analogue 20 times more potent than cocaine at binding to the dopamine transporter with increased selectivity for the norepinephrine transporters. It also shows marked increase in metabolic stability. In contrast to the findings of cocaine effects, WF-11 has been shown to produce a uniform downregulation of TH protein and activity gene expression with a regimen of use.
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IUPAC name = 2?-Propanoyl-3?-(2-naphthyl)-tropane
C=21 | H=25 | N=1 | O=1
molecular_weight = 307.43
2?-Propanoyl-3?-(2-naphthyl)-tropane or WF-23 is a cocaine analogue. It is 500-800 times more potent than cocaine at both dopamine and serotonin transporters.
cite web :
http://www.patentstorm.us/patents/60082 ... ption.html
title=Process for blocking 5-HT and dopamine uptake with biologically active tropane derivatives - US Patent 6008227 |accessdate=2008-01-11 |format= |work=]
