152-02-3

Basic information

• Product Name: levallorphan
• Synonyms: levallorphan;(-)-3-Hydroxy-N-allylmorphinan;17-Allylmorphinan-3-ol;2H-10,4a-Iminoethanophenanthren-6-ol, 11-allyl-1,3,4,9,10,10a-hexahydro- (6CI);l-N-Allyl-3-hydroxymorphinan;MCL 113;Morphinan-3-ol, 17-(2-propenyl)- (9CI);Morphinan-3-ol, 17-allyl- (8CI)
• CAS NO: 152-02-3
• Molecular Formula: C₁₉H₂₅NO
• Molecular Weight: 283.45
• EINECS: 205-799-1
• Mol File: 152-02-3.mol

Chemical Properties

• Melting Point: 180-182°
• Boiling Point: 425.96°C (rough estimate)
• Flash Point: 214.2°C
• Appearance: /
• Density: 1.0260 (rough estimate)
• Vapor Pressure: 4.02E-08mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• CAS DataBase Reference: levallorphan(CAS DataBase Reference)
• NIST Chemistry Reference: levallorphan(152-02-3)
• EPA Substance Registry System: levallorphan(152-02-3)

Safety Data

• Hazardous Substances Data: 152-02-3(Hazardous Substances Data)

Usage

Brand name

Lorfan (Roche).

Purification Methods

It crystallises from aqueous EtOH. It is a narcotic antagonist. [Schneider & Grüssner Helv Chim Acta 34 2211 1951, Hellerbach Helv Chim Acta 39 429 1956.]

InChI:InChI=1/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18-,19-/m0/s1

Upstream product

• 106-95-6 allyl bromide 
• 1531-12-0 norlevorphanol 
• 51072-36-7 (+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 74570-02-8 4-((S)-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 
• 104-01-8 4-Methoxyphenylacetic acid 
• 3399-73-3 2-(1-cyclohexenyl)ethylamine 
• 51072-34-5 N-(2-cyclohex-1-enylethyl)-2-(4-methoxyphenyl)-acetamide 
• 51072-35-6 1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydro-isoquinoline 
• 63867-85-6 3-acetoxy-17-methyl-morphinane 
• 77-07-6 racemorphan 
• 74570-02-8 (+)-1-(p-hydroxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 74570-02-8 4-((R)-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 
• 93477-35-1 (+/-)-1-(4-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline hydrobromide 
• 125-70-2 levomethorphan 

Downstream Products

• 1531-12-0 norlevorphanol 
• 71-82-9 levallorphan tartarate 
• 1210893-67-6 C₁₆H₁₉NO₂ 
• 1210893-65-4 C₁₉H₂₅NO₂ 
• 1210893-66-5 C₁₉H₂₅NO₃ 

Related news

Safety and efficacy of a combination of pethidine and levallorphan (cas 152-02-3) for pain relief during labor: An observational study09/28/2019

Aim To evaluate the safety, effect on breastfeeding and efficacy of a combination of pethidine and levallorphan (Pethilorfan) for pain relief during labor.Methods We compared maternal or neonatal morbidities, suckling difficulties in newborns and breastfeeding rates between 177 women who receive...detailed

Relevant articles and documents

Method for preparing levallorphan tartrate

The invention provides a method for preparing levallorphan tartrate and belongs to the technical field of drug and chemical synthesis. The method takes methoxyphenylacetic acid and 2-(cyclohexenyl)ethylamine as initial raw materials, and comprises nine reaction steps such as acylation condensation, Bischler-Napieralski ring formation reaction, imine reduction, ether bond hydrolysis, resolution, N-alkylation, Grewe cyclization reaction, and salifying. According to the method, the levallorphan tartrate and each intermediate can be obtained at high yield and high purity, and the method can serve as an industrial method for performing large-scale production.

Mixed κ agonists and μ agonists/antagonists as potential pharmacotherapeutics for cocaine abuse: Synthesis and opioid receptor binding affinity of N-substituted derivatives of morphinan

A series of new N-substituted derivatives of morphinan was synthesized and their binding affinity for the three opioid receptors (μ, δ, and κ) was determined. A paradoxical effect of N-propargyl (MCL-117) and N-(3-iodoprop-(2E)-enyl) (MCL-118) substituents on the binding affinities for the μ and κ opioid receptors was observed. All of these novel derivatives showed a preference for the μ and κ versus δ binding.

Anticonvulsant effects of new morphinan derivatives

We synthesized a series of compounds that are modified in positions 3 and 17 of the morphinan ring system, with the intention of developing ideal anticonvulsant agents. We examined the effects of these compounds on kainic acid (KA)-induced seizures, and on locomotor patterns in rats. We found that compounds 5, 6, and 8 exhibit novel anticonvulsant effects, with negligible psychotropic effects.