File:Methadone_enantiomers_labelled.svg · Wikimedia Commons · See Wikimedia Commons
(RS)-methadone
Sign in to saveAlso known as (+-)-methadone, (±)-methadone, DL-methadone, 6-dimethylamino-4,4-diphenyl-3-heptanone, methadone
Methadone, sold under the brand names Dolophine and Methadose among others, is a potent synthetic opioid used medically to treat chronic pain and opioid use disorder. Prescribed for daily use, the medicine relieves cravings and opioid withdrawal symptoms. Withdrawal management using methadone can be accomplished in less than a month, or it may be done gradually over a longer period of time, or simply maintained for the rest of the patient's life. While a single dose has a rapid effect, maximum effect can take up to five days of use. After long-term use, in people with normal liver function, ef
OverviewAI-generated
(RS)-methadone is a chemical compound with the formula C₂₁H₂₇NO. Its IUPAC name is 6-(dimethylamino)-4,4-diphenylheptan-3-one. The substance has a mass of 309.209264 and a weight of 309.4. It possesses a charge of 0, an xlogp value of 3.9, and a topological polar surface area of 20.3. The molecule contains zero hydrogen bond donors and two hydrogen bond acceptors.
The defined daily dose for this compound is 25. It is associated with the Commons category "Methadone" and has been referenced by 2,352 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 420419989
- Drug.image
- Methadone enantiomers labelled.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 350
- Drug.caption
- Skeletal formula of methadone's enantiomers. (S) corresponds to the D-enantiomer, and (R) corresponds to the L-enantiomer.
- Drug.imageL
- Dextromethadone ball-and-stick model from xtal 1958.png
- Drug.image_classL
- bg-transparent
- Drug.widthL
- 175
- Drug.altL
- Ball-and-stick model of the less active dextromethadone.
- Drug.imageR
- Levomethadone-xtal-1974-ball-and-stick.png
- Drug.image_classR
- bg-transparent
- Drug.widthR
- 175
- Drug.altR
- Ball-and-stick model of the more active levomethadone.
- Drug.tradename
- Dolophine, Methadose, Methatabs, others
- Drug.MedlinePlus
- a682134
- Drug.DailyMedID
- Methadone
via Wikipedia infobox
Chemical data
- Formula
- C21H27NO
- Molecular weight
- 309.4 g/mol
- IUPAC name
- 6-(dimethylamino)-4,4-diphenylheptan-3-one
- SMILES
- CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2
- InChIKey
- USSIQXCVUWKGNF-UHFFFAOYSA-N
- XLogP
- 3.9
- Polar surface area
- 20.3 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
3 papers- Pharmacokinetic-pharmacodynamic modeling of mood and withdrawal symptoms in relation to plasma concentrations of methadone in patients undergoing methadone maintenance treatment.Journal of clinical psychopharmacology · 2012Shiran MR, Lennard MS, Iqbal MZ et al.DOI: 10.1097/JCP.0b013e3182664ecd
- Effect of omeprazole on oral and intravenous RS-methadone pharmacokinetics and pharmacodynamics in the rat.Journal of pharmaceutical sciences · 2002Carlos MA, Du Souich P, Carlos R et al.DOI: 10.1002/jps.10031
- Contribution of the activities of CYP3A, CYP2D6, CYP1A2 and other potential covariates to the disposition of methadone in patients undergoing methadone maintenance treatment.British journal of clinical pharmacology · 2009Shiran MR, Lennard MS, Iqbal MZ et al.DOI: 10.1111/j.1365-2125.2008.03312.x
via PubMed
~34 min read
Encyclopedic overview
30 sectionsContents
- Medical uses
- Opioid addiction
- Pain
- Adverse effects
- Withdrawal symptoms
- Physical symptoms
- Cognitive symptoms
- Black box warning
- Overdose
- Tolerance and dependence
- Driving
- Mortality
- Pharmacology
- Mechanism of action
- Metabolism
- Route of administration
- Chemistry
- Detection in biological fluids
- Conformation
- History
- Society and culture
- Brand names
- Economics
- Regulation
- United States and Canada
- Methadone clinics
- Other countries
- Veterinary use
- References
- External links
Methadone, sold under the brand names Dolophine and Methadose among others, is a potent synthetic opioid used medically to treat chronic pain and opioid use disorder. Prescribed for daily use, the medicine relieves cravings and opioid withdrawal symptoms. Withdrawal management using methadone can be accomplished in less than a month, or it may be done gradually over a longer period of time, or simply maintained for the rest of the patient's life. While a single dose has a rapid effect, maximum effect can take up to five days of use. After long-term use, in people with normal liver function, effects last 8 to 36 hours. Methadone is usually taken by mouth and rarely by injection into a muscle or vein.
Side effects are similar to those of other opioids. These frequently include dizziness, sleepiness, nausea, vomiting, and sweating. Serious risks include opioid abuse and respiratory depression. Abnormal heart rhythms may also occur due to a prolonged QT interval. The number of deaths in the United States involving methadone poisoning declined from 4,418 in 2011 to 3,300 in 2015. Risks are greater with higher doses. Methadone is made by chemical synthesis and acts on opioid receptors.
Excerpted from Wikipedia’s “(RS)-methadone” article, available under the CC BY-SA 4.0 licence.