76-99-3 Usage
Description
(+/-)-METHADONE, also known as Methadone, is a synthetic opioid with the chemical formula C21H27NO. It is a ketone that is heptan-3-one substituted by a dimethylamino group at position 6 and two phenyl groups at position 4. Methadone is used medically as an analgesic for chronic pains and also as a substitute for heroin in the treatment of addiction. It is marketed as a racemate, with the R-enantiomer being 7-50 times more potent than the S-enantiomer in terms of opioid activity. Methadone is a μ-receptor agonist with complex and highly variable pharmacokinetic parameters, and its major metabolic pathway is via N-demethylation to form the inactive 2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine (EDDP).
Uses
Used in Pain Management:
(+/-)-METHADONE is used as an analgesic for the treatment of chronic pain. It is particularly effective in managing severe pain due to its potent opioid activity, which is primarily attributed to the R-enantiomer.
Used in Opioid Addiction Treatment:
(+/-)-METHADONE is used as a substitute for heroin in the treatment of opioid addiction. It helps to reduce withdrawal symptoms and cravings, allowing patients to recover from their addiction more effectively. Methadone may only be dispensed for the treatment of opioid addiction by a program certified by the Federal Substance Abuse and Mental Health Services Administration.
Used in Research and Development:
(+/-)-METHADONE is also used in research and development for the study of its pharmacological properties, potential applications, and the development of new drugs with improved efficacy and safety profiles.
Therapeutic Function
Narcotic analgesic
Biological Functions
Methadone (Dolophine) has an analgesic profile and
potency similar to that of morphine but a longer duration
of action and better oral bioavailability.The kinetic
properties of methadone and its derivative, LAAM,
have been shown to be useful in the treatment of opioid
addiction.
Methadone is a useful analgesic drug for the treatment
of moderate to severe pain. Unlike morphine, it is
generally not used epidurally because of its long duration
of action. It is also rarely or never used in PCA systems
or in pregnant women during labor. The side effects
and signs of overdose following methadone
administration are similar to those observed with morphine.
Overdose is treated with naloxone. Clearance of
methadone is via the urine and bile as the cyclic Ndemethylated
drug. The ability to N-demethylate the
drug decreases in elderly patients, prolonging the action of methadone. In such patients, dosing intervals should
be longer than in younger patients. In addition, the pH
of the urine has a major effect on clearance of the drug.
Alkalinization of the urine or renal insufficiency decreases
excretion of the drug.
Drug interactions and precautions for the use of
methadone are similar to those of morphine. In addition,
rifampicin and hydantoins markedly increase the
metabolism of methadone and can precipitate withdrawal
from methadone. Conversely, the tricyclic antidepressants
and certain benzodiazepines can inhibit
metabolism of methadone, thereby increasing accumulation
of the drug, prolonging its half-life, and intensifying
its side effects. Continuous dosing with methadone
may lead to drug accumulation and to an increased incidence
of side effects; methadone is generally not used
for PCA. In pregnant heroin-addicted women, substitution
of methadone for heroin has been shown to be associated
with fewer low-birth-weight newborns and
fewer learning and cognition problems later in the life
of the child.
Pharmacology
Methadone is a diphenylpropylamine. It has very good oral bioavailability
(~85%) with an oral to parenteral ratio of 1:2. Its plasma half-life can be
highly variable (3–50h, average 24h) but its duration of action is relatively
short. With repeated dosing, problems with accumulation can occur because
of this discrepancy between half-life and analgesic effect. Careful monitoring
is therefore required when converting patients to long-term methadone.
A lso, there is incomplete cross-tolerance with morphine. The racemic
mixture in common use has agonist actions at the MOP receptor (mainly the
laevo isomer) as well as antagonist activity at the NMDA receptor dextro
isomer). Given the importance of this receptor in central sensitisation in a
variety of pain states, there may be cases where methadone offers particular
advantages over and above other opioids (e.g. neuropathic pain).
Plasma concentrations of methadone can be reduced by carbamazepine,
and its metabolism is accelerated by phenytoin.
Safety Profile
Poison by ingestion,
intraperitoneal, intravenous, subcutaneous,
and intraduodenal routes. Human systemic
effects: coma, nausea or vomiting,
respiratory changes, respiratory depression,
somnolence. An experimental teratogen.
Experimental reproductive effects. Caution:
Abuse leads to habituation or addiction.
When heated to decomposition it emits
toxic fumes of NOx. See also
METHADONE HYDROCHLORIDE.
Check Digit Verification of cas no
The CAS Registry Mumber 76-99-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 6 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 76-99:
(4*7)+(3*6)+(2*9)+(1*9)=73
73 % 10 = 3
So 76-99-3 is a valid CAS Registry Number.
InChI:InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3
76-99-3Relevant articles and documents
Non-Racemic Mixtures of Various Ratios of D- and L-methadone and Methods of Treating Pain Using the Same
-
Paragraph 0096; 0097; 0098, (2016/09/12)
Non-racemic mixtures of D- and L-methadone containing a ratio ranging from about 2.5:1 to about 3.5:1 by weight of D-methadone to L-methadone, such as for example about 2.9:1 to about 3.1:1 by weight of D-methadone to L-methadone, or about 3:1 by weight of D-methadone to L-methadone, have been found to exhibit surprising and unexpected beneficial results in the treatment of neuropathic pain. Additionally, non-racemic mixtures of D- and L-methadone containing a ratio ranging from about 2.5:1 to about 3.5:1 by weight of D-methadone to L-methadone, about 2.9:1 to about 3.1:1 by weight of D-methadone to L-methadone, or for example about 3:1 by weight of D-methadone to L-methadone, in combination with other non-methadone opioids have been found to exhibit surprising and unexpected beneficial results in the treatment of mixed pain.
(R)-6-(DIMETHYLAMINO)-4,4-DIPHENYLHEPTAN-3-ONE
-
, (2014/12/09)
(R)-6-(dimethylamino)-4,4-diphenylheptan-3-one and a process to produce thereof.
Quaternary ammonium immunogenic conjugates and immunoassay reagents
-
, (2008/06/13)
This invention relates to novel quaternary ammonium immunogenic conjugates and reporter reagents useful for eliciting antibodies and in immunoassays. Processes for preparing such quaternary ammonium immunogenic conjugates and their use in immunoassays and in eliciting antibodies are also disclosed.
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