22204-88-2 Usage
Chemical Properties
White Cyrstalline Solid
Originator
Tramadol,Gruenenthal,W. Germany,1977
Uses
An Analgesic
Manufacturing Process
5 g of magnesium turnings are treated while stirring with a mixture of 37.4 g
of m-bromoanisole and 160 ml of absolute tetrahydrofuran at such a rate that
the reaction mixture boils gently because of the heat produced by the
immediately starting reaction. Thereafter, the reaction mixture is boiled under
reflux while stirring until all the magnesium dissolves. The reaction mixture is
cooled to 0°C to -10°C and then a mixture of 23.25 g of 2-
dimethylaminomethylcyclohexanone and 45 ml of absolute tetrahydrofuran is
added dropwise.
The resulting mixture is stirred for 4 hours at room temperature and then
poured, while stirring slowly, into a mixture of 25 g of ammonium chloride, 50
ml of water and 50 g of ice. The layers are separated and the aqueous layer is
extracted twice with 50 ml portions of ether. The organic layers are combined,
dried with sodium sulfate and evaporated. The residue is distilled, and 1-(m_x0002_methoxyphenyl)-2-dimethylaminomethyl-cyclohexanol-(1), boiling point at 0.6
mm Hg 138°C to 140°C, is obtained in a yield of 78.6% of theoretical. The hydrochloride obtained from the product, e.g., by dissolving in ether and
treating with dry hydrogen chloride, melts at 168°C to 175°C. By
recrystallization from moist dioxan this hydrochloride is separated into isomers
melting at 162°C to 163°C and 175°C to 177°C, respectively.
Therapeutic Function
Analgesic
Clinical Use
Analgesic
Drug interactions
Potentially hazardous interactions with other drugs
Analgesics: possible opioid withdrawal with
buprenorphine and pentazocine.
Anticoagulants: enhances effect of coumarins.
Antidepressants: possibly increased serotonergic
effects with duloxetine, mirtazapine or venlafaxine;
possible CNS excitation or depression with MAOIs
and moclobemide - avoid with MAOIs as increased
risk of serotonergic effects and convulsions; increased
risk of CNS toxicity with SSRIs or tricyclics.
Antiepileptics: effect reduced by carbamazepine.
Antihistamines: increased sedative effects with
sedating antihistamines.
Antipsychotics: enhanced hypotensive and sedative
effects; increased risk of convulsions.
Atomoxetine: increased risk of convulsions.
Dapoxetine: possible increased risk of serotonergic
effects - avoid.
Dopaminergics: avoid with selegiline.
Nalmefene: avoid concomitant use.
Sodium oxybate: enhanced effect of sodium oxybate
- avoid concomitant use.
Metabolism
Tramadol is metabolised by N- and O-demethylation
via the cytochrome P450 isoenzymes CYP3A4 and
CYP2D6 and glucuronidation or sulfation in the liver.
Only O-desmethyl-tramadol is pharmacologically active.
Tramadol and its metabolites are almost completely
excreted renally.
Check Digit Verification of cas no
The CAS Registry Mumber 22204-88-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,2,0 and 4 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 22204-88:
(7*2)+(6*2)+(5*2)+(4*0)+(3*4)+(2*8)+(1*8)=72
72 % 10 = 2
So 22204-88-2 is a valid CAS Registry Number.
InChI:InChI=1/C16H25NO2/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3
22204-88-2Relevant articles and documents
SUBSTITUTED CYCLOHEXANOLS
-
Page/Page column 35, (2009/02/11)
Disclosed herein are substituted cyclohexanol opioid receptor modulators and/or neurotransmitter reuptake modulators of Formula I or Formula II, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.
Tramadol analogs and uses thereof
-
, (2008/06/13)
Compounds of formula I are effective in treating disorders modulated by opiate receptor activity and/or monoamine activity. In formula I, R1 is selected from alkyl, aryl, alkylaryl, substituted alkyl, substituted aryl, and substituted alkylaryl; R2 is selected from hydrogen, hydroxy, cyano, haloalkyl, glycosyl, SO2R5, and OR5; R3 and R4 are independently selected from hydrogen and lower alkyl, or R3 and R4 taken together with nitrogen form a five- or six-membered heterocyclic or substituted heterocyclic ring; and R5 is selected from alkyl, aryl, alkylaryl, substituted alkyl, substituted aryl, and substituted alkylaryl.
Process
-
, (2008/06/13)
A process for preparing a substantially single enantiomer of tramadol, or a pharmaceutically-acceptable salt thereof, proceeds by means of a classical salt resolution using a substantially single enantiomer of O,O-di-p-toluoyltartaric acid as a resolving agent.
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