Levorphanol
Also known as Levorphan, Aromarone, 17-Methylmorphinan-3-ol
Key facts
What buyers check first
- CAS number
- 77-07-6
- Formula
- C17H23NO
- Appearance
- Crystals
- Melting point
- 198 to 199
- HS code
- 293341
- Category
- Analgesics and anti-inflammatories
What is Levorphanol?
Plain description, key identifiers and synonyms
Levorphanol is a morphinane alkaloid.
Identifiers
Registry numbers, names and line notations, tap to copy
- IUPAC name
- (1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
- CAS number
- 77-07-6 CAS number cross-checkedOther or deprecated CAS: 297-90-5
- EC numbers
- 201-002-6, 206-048-0
- Molecular formula
- C17H23NO
- UNII
- 27618J1N2X, V7R79HN3XD
- InChIKey
- JAQUASYNZVUNQP-USXIJHARSA-N
- InChI
- InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1
- Canonical SMILES
- CN1CCC23CCCCC2C1Cc1ccc(O)cc13
- Isomeric SMILES
- CN1CC[C@]23CCCC[C@H]2[C@H]1CC4=C3C=C(C=C4)O
Synonyms
- Levorphan
- Aromarone
- 17-Methylmorphinan-3-ol
- Levorfanol
- Levorphanolum
- Levorfanolo
- Ro 1-5431
- (-)-3-Hydroxy-N-methylmorphinan
- (-)-N-Methylmorphinan-3-ol
- DEA No. 9220
- Morphinan-3-ol, 17-methyl-
- Morphinan, 3-hydroxy-17-methyl-
- 3 Hydroxy N methylmorphinan
- 1,3,4,9,10,10a-Hexahydro-11-methyl-2H-10,4a-iminoethanophenanthren-6-ol, l-
- 2H-10,4a-Iminoethanophenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11-methyl-
- 2H-10,4a-Iminoethanophenanthren-6-ol, 1,3,4,9,10,10a-hexahydro-11-methyl-, l-
- Levodroman
- (1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
- LevoDromoran
- Levo Dromoran
- L Dromoran
- Levorphanol Dl-
- (1R,9R,10R)-17-methyl-17-azatetracyclo(7.5.3.0^(1,10).0^(2,7))heptadeca-2(7),3,5-trien-4-ol
- (1R,9R,10R)-17-methyl-17-azatetracyclo(7.5.3.01,10.02,7)heptadeca-2(7),3,5-trien-4-ol
- (1R,9R,10R)-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-trien-4-ol
Show all 33 synonymsShow fewer synonyms
- Methorfinan
- Racemorfano
- Levorphanol dl-form
- Levorphanal
- DEA No. 9733
- Levorphanol (INN)
- Racemorphan
- Racemorphane
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 | Crystalsexp.Measured value |
|---|---|
| Melting point | 198 to 199exp.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 | 257.38 g/molcalc.Computed value |
|---|---|
| Exact mass | 257.178 Dacalc.Computed value |
| LogP (octanol/water) | 3.08calc.Computed value |
| Topological polar surface area | 23.47 Ųcalc.Computed value |
| Hydrogen bond donors | 1calc.Computed value |
| Hydrogen bond acceptors | 2calc.Computed value |
| Rotatable bonds | 0calc.Computed value |
| Heavy atoms | 19calc.Computed value |
| Rings | 4calc.Computed value |
| Aromatic rings | 1calc.Computed value |
| Fraction sp3 carbons | 0.65calc.Computed value |
| Formal charge | 0calc.Computed value |
| Stereocentres | 3calc.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
- H301Toxic if swallowed.
- H312Harmful in contact with skin.
- H317May cause an allergic skin reaction.
- H331Toxic if inhaled.
- H334May cause allergy or asthma symptoms or breathing difficulties if inhaled.
- H336May cause drowsiness or dizziness.
Precautionary statements (24)
- P233Keep container tightly closed.
- P260Do not breathe dust, fume, gas, mist, vapours or spray.
- P261Avoid breathing dust, fume, gas, mist, vapours or spray.
- P264Wash skin thoroughly after handling.
- 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.
- P284In case of inadequate ventilation wear respiratory protection.
- P301 + P316If swallowed: Get emergency medical help immediately.
- P302 + P352If on skin: Wash with plenty of water.
- P304 + P340If inhaled: Remove person to fresh air and keep comfortable for breathing.
- P316Get emergency medical help immediately.
- P317Get medical help.
- 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.
- P342 + P316If experiencing respiratory symptoms: Get emergency medical help immediately.
- P362 + P364Take off contaminated clothing. And wash it before reuse.
- P403Store in a well-ventilated place.
- 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 aidLevorphanol suppliers
Trading restrictions apply to this substance
Levorphanol 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 2933.41 (levorphanol)
Our policy on controlled substancesLevorphanol 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
Levorphanol 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.
Analgesics, Opioid, Narcotics.
Therapeutic category: Analgesic.
Use classes: Pharmaceuticals.
Industries and functions
Pharmacological actions
- Analgesics, Opioid
- Narcotics
Pharmacology
Levorphanol is an Opioid Agonist. The mechanism of action of levorphanol is as a Full Opioid Agonist.
How it is made
5,6,7,8,-Tetrahydro-2-methylisoquinolinium bromide is metathesized with p-methoxybenzyl magnesium bromide, and the product rearranges at the expense of the 1,2-double bond to form 1-(p-methoxybenzyl)-2-methyl-1,2,5,6,7,8-hexahydroisoquinoline. ... A solution of the hydrochloride of 1-(p-methoxybenzyl)-2-methyl-1,2,5,6,7,8-hexahydroisoquinoline is then hydrogenated at the 3,4-positions with the aid of platinized charcoal, and subsequent treatment with ammonia liberates the dl-1,2,3,4,5,6,7,8-octahydro compound, which may be resolved into its (+)- and (-)-enantiomers by the usual procedures.
Read more
The final step in the preparation of the base involves heating the (-)-enantiomer with phosphoric acid at 150 °C whereby cyclization between the isoquinoline residue and the benzene ring occurs at the expense of the remaining double bond of the isoquinoline. During the treatment with phosphoric acid, the methoxy group simultaneously is converted to hydroxy, thus producing levorphanol. The tartrate may be produced by dissolution of the base in aqueous tartaric acid solution and recrystallizing.
Regulatory status
Inventories, regulations and trade controls that list this substance
Levorphanol 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 2933.41 (levorphanol)
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 Levorphanol is traded under.
Levorphanol (INN) and its salts
- India * partner reported99.6%
- Netherlands0.3%
- Canada<0.1%
- Egypt78.3%
- United States13.4%
- South Korea4.0%
* Partner reported figures, a lower bound.
The HS code shown for Levorphanol 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 Levorphanol, based on the data on this page
What is Levorphanol?
What is the CAS number of Levorphanol?
What is the molecular formula and weight of Levorphanol?
What is Levorphanol used for?
Is Levorphanol hazardous?
What is the HS code of Levorphanol?
Can I buy Levorphanol on CompoundList?
Guides for buyers
Practical guides that help when you source, ship or handle Levorphanol
- 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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