125-29-1 Usage
Description
Hydrocodone is a semi-synthetic opioid derived from codeine, chemically classified as a morphinane-like compound. It is a beige solid with potent agonist activity that does not require 3-O-demethylation, although it can occur via CYP2D6. The 3-position protection and the 7,8-dihydro-6-keto C ring contribute to its increased binding to the μ-receptor, making it a powerful analgesic and antitussive agent. Hydrocodone is approximately 4 to 5 times less potent than hydromorphone, which is about equal to morphine. It is a controlled substance and falls under the category of narcotics.
Uses
1. Used in Pharmaceutical Industry:
Hydrocodone is used as an analgesic (narcotic) for the treatment of moderate to severe pain. It is combined with other medications such as acetaminophen (Vicodin, Lortab) or aspirin (Lortab ASA) to enhance its pain-relieving effects.
2. Used in Cough Suppressants:
Hydrocodone is used as an antitussive to suppress the cough reflex. It is widely used in commercial anticough drugs in combination with various agents such as guaifenesin (entuss), homatropine (hycodan), phenylpropanolamine (hycomine), phenyltoloxamine (tussionex), and pseudoephedrine and guaiphenesin (tussened).
3. Used in Antitussive Agents:
Hydrocodone is marketed as an antitussive agent, available in combination with the anticholinergic agent homatropine as a syrup and a tablet. The addition of the anticholinergic agent aims to discourage abuse.
4. Used in Delayed Release Suspension Form:
Hydrocodone is available in a delayed-release suspension form (Tussionex), which uses a sulfonated styrene divinylbenzene copolymer complexed with hydromorphone and chlorpheniramine that acts as a cation-exchange resin, slowly releasing the drugs over a 12-hour period.
Originator
Dicodid,Knoll,Belgium
Manufacturing Process
60 g of codeine about 94.5% (anhydrous codeine alkaloid basis) was dissolved
in a solution made from 10 ml concentrated sulfuric acid and 390 ml water
The mixture was refluxed for one hour with 25.0 g of 5% Pd on charcoal. The
hot solution was immediately filtered and the catalyst was washed with 400
ml of dilute sulfuric acid of the same strength as was used in the
rearrangement described above. To the combined cooled filtrate and wash,
750 ml if benzene was added, after which the mixture was cooled to 15°C,
stirred, and made alkaline to pH 10 by addition of 80 ml of 40% NaOH. After
shaking and separating the aqueous layer was extracted twice with 500 ml
benzene. The combined benzene extracts are then extracted three times with
500 ml and twice with 400 ml portions of fresh 10% sodium bisulfite solution.
Crude dihydrocodeinone was precipitated from bisulfite solution by eddition of
180 ml 40% NaOH at 15°C (to pH 10). The product was filtered, washed well
and air-dried at room temperature. The melting point was about 184°C and
yield about 35-38 g or 58-59%. The product was darken and the rest of Pd on
charcoal and the original alkaloid were removed with column of Al2O3 (eluent
- dry ethylene chloride) to give the dihyrocodeinone.
Therapeutic Function
Narcotic analgesic, Antitussive
Safety Profile
Poison by intravenous and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 125-29-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 5 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 125-29:
(5*1)+(4*2)+(3*5)+(2*2)+(1*9)=41
41 % 10 = 1
So 125-29-1 is a valid CAS Registry Number.
InChI:InChI=1/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-12,17H,4-5,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1
125-29-1Relevant articles and documents
Studies on regioselective hydrogenation of thebaine and its conversion to hydrocodone
Leisch, Hannes,Carroll, Robert J.,Hudlicky, Tomas,Cox, D. Phillip
, p. 3979 - 3981 (2007)
Thebaine was subjected to catalytic hydrogenation under a variety of conditions in order to determine the regioselectivity for C-6/C-7 versus C-8/C-14 olefin saturation.
-
Carroll,F.I. et al.
, p. 996 - 1001 (1976)
-
14,17-Cyclonorcodeinone dimethylacetal: A New Codeinon Derivative, II
Fleischhacker, W.,Richter, B.,Voellenkle, H.
, p. 399 - 411 (1991)
In addition to a short communication describing the synthesis of 14,17-cyclonorcodeinone dimethylacetal 1a we wish to present a simple alternative route together with a selection of some reactions depending on the great reactivity of this highly strained small ring system.The structure of 1a is established by X-ray analysis.
Transition metal-catalyzed redox isomerization of codeine and morphine in water
Gomez, Antonio Bermejo,Holmberg, Paer,Baeckvall, Jan-E.,Martin-Matute, Belen
, p. 39519 - 39522 (2014)
A water-soluble rhodium complex formed from commercially available [Rh(COD)(CH3CN)2]BF4 and 1,3,5-triaza-7- phosphaadamantane (PTA) catalyzes the isomerization of both codeine and morphine into hydrocodone and hydromorphone with very high efficiency. The reaction is performed in water, allowing isolation of the final products by simple filtration, which results in very high isolated yields. The reactions can be easily scaled up to 100 g.
PROCESS FOR THE PREPARATION OF BENZHYDROCODONE HYDROCHLORIDE
-
Paragraph 0190-0191, (2018/03/25)
The invention is directed to processes for the preparation of benzhydrocodone hydrochloride. More particularly, the invention is directed to processes for a one-pot synthesis of benzhydrocodone hydrochloride of improved yield and/or purity.
General, Simple, and Chemoselective Catalysts for the Isomerization of Allylic Alcohols: The Importance of the Halide Ligand
Erbing, Elis,Vázquez-Romero, Ana,Bermejo Gómez, Antonio,Platero-Prats, Ana E.,Carson, Fabian,Zou, Xiaodong,Tolstoy, P?ivi,Martín-Matute, Belén
supporting information, p. 15659 - 15663 (2016/10/25)
Remarkably simple IrIIIcatalysts enable the isomerization of primary and sec-allylic alcohols under very mild reaction conditions. X-ray absorption spectroscopy (XAS) and mass spectrometry (MS) studies indicate that the catalysts, with the general formula [Cp*IrIII], require a halide ligand for catalytic activity, but no additives or additional ligands are needed.
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