Codeine
Also known as Methylmorphine, Codicept, Codeine anhydrous
Key facts
What buyers check first
- Appearance
- Orthorhombic crystals from water, dilute alcohol, ether
- Melting point
- 157.5 °C
- Boiling point
- 250 °C
- Density
- 1.32 at 68 °F - Denser than water, will sink
- Flash point
- 75 °C
- HS code
- 293911
- Category
- Analgesics and anti-inflammatories
What is Codeine?
Plain description, key identifiers and synonyms
Codeine is a morphinane alkaloid found in the opium poppy, Papaver somniferum var. album, has analgesic, anti-tussive and anti-diarrhoeal properties. It has a role as an opioid analgesic, a xenobiotic, a prodrug, an antitussive, an opioid receptor agonist, an environmental contaminant and a drug allergen. It is a morphinane alkaloid and an organic heteropentacyclic compound. It is functionally related to a morphine. It is a conjugate base of a codeine(1+).
Codeine is an opiate used to treat pain.
Identifiers
Registry numbers, names and line notations, tap to copy
- IUPAC name
- (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
- CAS number
- 76-57-3 CAS number cross-checked
- EC number
- 200-969-1
- Molecular formula
- C18H21NO3
- UNII
- UX6OWY2V7J
- InChIKey
- OROGSEYTTFOCAN-DNJOTXNNSA-N
- InChI
- InChI=1S/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/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
- Canonical SMILES
- COc1ccc2c3c1OC1C(O)C=CC4C(C2)N(C)CCC341
- Isomeric SMILES
- CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O
Synonyms
- Methylmorphine
- Codicept
- Codeine anhydrous
- Coducept
- l-Codeine
- Morphine monomethyl ether
- (-)-Codeine
- O3-Methylmorphine
- codeinum
- Codeine base
- Morphine 3-methyl ether
- Norcodine, N-methyl
- Norcodeine, N-methyl
- Codeine polistirex
- Morphine-3-methyl ether
- codeina
- Codeinum monohydricum
- O(3)-methylmorphine
- IDS-NC-005(SECT.-2)
- 7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
- 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-ol
- Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-
- Morphinan-6alpha-ol, 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methyl-
- DEA No. 9050
- (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
Show all 38 synonymsShow fewer synonyms
- Morphinan-6-alpha-ol, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-
- Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5-alpha,6-alpha)-
- (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
- N Methylmorphine
- (1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7(18),8,10,15-tetraen-14-ol
- (1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7,9,11(18),15-tetraen-14-ol
- (1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol
- (1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),15-tetraen-14-ol
- (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolin-7-ol
- (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7-ol
- Codein
- Codeine Anhydrate
- Codeine (1.0 mg/mL in Methanol)
Physical and chemical properties
Measured values and descriptors computed from the structure
Physical and chemical properties
Measured values, check the supplier specification for your grade
| Appearance | Orthorhombic crystals from water, dilute alcohol, etherexp.Measured value |
|---|---|
| Melting point | 157.5 °Cexp.Measured value |
| Boiling point | 250 °Cexp.Measured value |
| Density | 1.32 at 68 °F - Denser than water, will sinkexp.Measured value |
| Flash point | 75 °Cexp.Measured value |
| Solubility | Soluble in waterexp.Measured value |
Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.
Computed descriptors
Calculated from the structure, useful for screening and formulation
| Molecular weight | 299.37 g/molcalc.Computed value |
|---|---|
| Exact mass | 299.1521 Dacalc.Computed value |
| LogP (octanol/water) | 1.5calc.Computed value |
| Topological polar surface area | 41.93 Ųcalc.Computed value |
| Hydrogen bond donors | 1calc.Computed value |
| Hydrogen bond acceptors | 4calc.Computed value |
| Rotatable bonds | 1calc.Computed value |
| Heavy atoms | 22calc.Computed value |
| Rings | 5calc.Computed value |
| Aromatic rings | 1calc.Computed value |
| Fraction sp3 carbons | 0.56calc.Computed value |
| Formal charge | 0calc.Computed value |
| Stereocentres | 5calc.Computed value |
| Lipinski rule of five | Passes (0 violations)calc.Computed value |
Calculated for screening. Confirm critical figures with the supplier.
Murcko scaffold
The ring system that remains when every side chain is removed
Safety and hazards
GHS classification summary, not a safety data sheet
Hazard statements
- H302Harmful if swallowed.
- H317May cause an allergic skin reaction.
- H318Causes serious eye damage.
- H336May cause drowsiness or dizziness.
- H361dSuspected of damaging the unborn child.
- H362May cause harm to breast-fed children.
Precautionary statements (24)
- P203Obtain, read and follow all safety instructions before use.
- P260Do not breathe dust, fume, gas, mist, vapours or spray.
- P261Avoid breathing dust, fume, gas, mist, vapours or spray.
- P263Avoid contact during pregnancy and while nursing.
- P264Wash skin thoroughly after handling.
- P264 + P265Wash skin thoroughly after handling. Do not touch eyes.
- P270Do not eat, drink or smoke when using this product.
- P271Use only outdoors or in a well-ventilated area.
- P272Contaminated work clothing should not be allowed out of the workplace.
- P280Wear protective gloves, protective clothing, eye protection and face protection.
- P301 + P317If swallowed: Get medical help.
- P302 + P352If on skin: Wash with plenty of water.
- P304 + P340If inhaled: Remove person to fresh air and keep comfortable for breathing.
- P305 + P354 + P338If in eyes: Immediately rinse with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
- P317Get medical help.
- P318If exposed or concerned, get medical advice.
- P319Get medical help if you feel unwell.
- P321Specific treatment (see supplemental first aid instructions on the label).
- P330Rinse mouth.
- P333 + P317If skin irritation or rash occurs: Get medical help.
- P362 + P364Take off contaminated clothing. And wash it before reuse.
- P403 + P233Store in a well-ventilated place. Keep container tightly closed.
- P405Store locked up.
- P501Dispose of contents and container in accordance with local regulations.
GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.
Full safety data and first aidCodeine suppliers
Trading restrictions apply to this substance
Codeine is prohibited on CompoundList. Listings, quotes and messages are disabled. This page is kept for information only.
Listing and enquiries are not allowed for this substance.
Reference: UN Single Convention on Narcotic Drugs 1961, HS 2022 subheading 2939.11 (opium alkaloids and their derivatives)
Our policy on controlled substancesCodeine price
Indicative price range per kg from live supplier offers
Prices are not shown for prohibited substances.
Uses and applications
What the substance is used for, by industry and function
Analgesics, Opioid, Antitussive Agents, Narcotics.
Codeine (DEA Code Number: 9050) is a Schedule II controlled substance.
Schedule II Controlled Substance: (A) The drug or other substance has a high potential for abuse, (B) The drug or other substance has a currently accepted medical use in treatment in the United States or a currently accepted medical use with severe restrictions, and (C) Abuse of the drug or other substances may lead to severe psychological or physical dependence.
Codeine is an opiate, a component of opium, and an opioid agonist used as an analgesic, antitussive, and antidiarrheal agent. In Europe, codeine has been used in an illicit synthetic opioid mixture including hydrocodone and dihydrocodeine, called Brown.
Use classes: Pharmaceuticals, Anaesthetics.
Industries and functions
Pharmacological actions
- Analgesics, Opioid
- Antitussive Agents
- Narcotics
Roles
- aetiopathogenetic role
- agonist
- allergen
- analgesic
- antitussive
- drug allergen
- environmental contaminant
- neurotransmitter agent
- opioid agent
- opioid analgesic
- opioid receptor agonist
- pharmaceutical
- pro-agent
- prodrug
- xenobiotic
Functional uses
- Pharmaceutical
Pharmacology
Codeine anhydrous is an Opioid Agonist. The mechanism of action of codeine anhydrous is as a Full Opioid Agonist.
How it is made
Codeine is extracted from opium (concentration in opium 0.7 to 2.5%, depending on the source), but mostly prepared by methylation of morphine in a phase transfer reaction.
Although some codeine is obtained from opium directly, the quantity is not sufficient to meet the extensive use of this alkaloid as a valuable medicinal agent. Much more codeine is used than morphine. This need is met by making it by partial synthesis from morphine. The process involves methylating the phenolic OH of the latter with phenyltrimethylammonium hydroxide.
Read more
Dry morphine is dissolved in a solution of potassium hydroxide in absolute alcohol, the methylating agent added, and the solution heated. After cooling, water is added, the solution is acidified with sulfuric acid, the dimethylaniline product separated, and the alcohol removed by distillation. Treatment with caustic soda solution precipitates the codeine, while any unreacted morphine is held in solution by the sodium hydroxide. The crude codeine is purified by crystallization as the sulfate.
Regulatory status
Inventories, regulations and trade controls that list this substance
Codeine is prohibited on CompoundList. Listings, quotes and messages are disabled. This page is kept for information only.
Listing and enquiries are not allowed for this substance.
Reference: UN Single Convention on Narcotic Drugs 1961, HS 2022 subheading 2939.11 (opium alkaloids and their derivatives)
Our policy on controlled substancesControls
- US DEA controlled substance or listed chemical
- Controlled narcotic drug
Health and food
- Active ingredient in FDA approved drug labels
HS code and trade data
Customs classification and reported world trade statistics
Global trade
World import and export statistics for the HS code Codeine is traded under.
Concentrates of poppy straw, buprenorphine (INN), codeine, dihydrocodeine (INN)…
- United Kingdom33.3%
- Spain21.3%
- Czech Republic8.6%
- United States30.8%
- United Kingdom13.2%
- Germany6.3%
The HS code shown for Codeine is indicative (it was matched by name in the HS nomenclature). Confirm the classification with your customs broker before shipping.
Frequently asked questions
Quick answers about Codeine, based on the data on this page
What is Codeine?
What is the CAS number of Codeine?
What is the molecular formula and weight of Codeine?
What is Codeine used for?
Is Codeine hazardous?
What is the HS code of Codeine?
Can I buy Codeine on CompoundList?
Guides for buyers
Practical guides that help when you source, ship or handle Codeine
- Article, QualityPharma grades explained: IP vs BP vs USP vs EPWhat the Indian, British, US and European pharmacopoeias are, how their monographs differ, what multi grade claims mean and why a grade alone does not make a product fit for medicines.Read
- Guide, SafetyHow to read a safety data sheet in 10 minutesA section by section method to pull the essentials out of any 16 section SDS: identity, hazards, composition, storage, PPE, properties, transport and emergency measures.Read
- Guide, SafetyGHS pictograms, signal words and hazard statements explainedA practical guide to the nine GHS pictograms, the signal words Danger and Warning, H and P statements, and how to read a chemical label in seconds.Read
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