123134-25-8

Basic information

• Product Name: (-)-(S,S)-trans-Tramadol
• Synonyms: 1-(3-Methoxyphenyl)-2α-(dimethylaminomethyl)cyclohexane-1α-ol;(-)-(S,S)-trans-Tramadol;(1S)-1-(3-Methoxyphenyl)-2α-[(dimethylamino)methyl]cyclohexane-1α-ol;(S)-Tramadol;(S,S)-tramadol
• CAS NO: 123134-25-8
• Molecular Formula: C₁₆H₂₅NO₂
• Molecular Weight: 263.38
• Product Categories: Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 123134-25-8.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 388.1°Cat760mmHg
• Flash Point: 188.5°C
• Appearance: /
• Density: 1.047g/cm³
• Storage Temp.: Refrigerator
• CAS DataBase Reference: (-)-(S,S)-trans-Tramadol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(S,S)-trans-Tramadol(123134-25-8)
• EPA Substance Registry System: (-)-(S,S)-trans-Tramadol(123134-25-8)

Safety Data

• Hazardous Substances Data: 123134-25-8(Hazardous Substances Data)

Usage

Description

(-)-(S,S)-trans-Tramadol, also known as the (S,S)-enantiomer of tramadol, is a chiral compound with both stereocenters having an S-configuration. It is a 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol derivative and is recognized for its analgesic properties. (-)-(S,S)-trans-Tramadol exhibits a significantly lower analgesic potency compared to its (R,R)-enantiomer counterpart. As a clear, colorless, viscous liquid, (-)-(S,S)-trans-Tramadol is a valuable pharmaceutical compound with potential applications in pain management.

Uses

Used in Pharmaceutical Industry:
(-)-(S,S)-trans-Tramadol is used as an analgesic for the management of moderate to severe pain. Its application in this industry is due to its ability to provide pain relief through its interaction with the opioid receptors in the central nervous system, offering an alternative to other opioid analgesics with potentially fewer side effects.
Used in Research and Development:
In the field of pharmaceutical research and development, (-)-(S,S)-trans-Tramadol serves as a valuable compound for studying the effects of stereochemistry on the potency and efficacy of drugs. Its lower analgesic potency compared to the (R,R)-enantiomer makes it an interesting subject for exploring the role of stereoisomerism in drug design and optimization.
Used in Drug Formulation:
(-)-(S,S)-trans-Tramadol is also utilized in the formulation of various pharmaceutical products, such as tablets, capsules, and liquid formulations, for the treatment of pain. Its inclusion in these formulations is due to its analgesic properties, which can help alleviate pain and improve the quality of life for patients suffering from various conditions.

Upstream product

• 108-94-1 cyclohexanone 
• 42036-65-7 2-dimethylaminomethylcyclohexanone hydrochloride 
• 124-40-3 dimethyl amine 
• 75209-54-0 (E)-1-(3-methoxyphenyl)cyclohept-1-en 
• 2082-28-2 1-(m-methoxyphenyl)cycloheptanol 
• 502-42-1 cycloheptanone 
• 2398-37-0 3-methoxyphenyl bromide 
• 769092-24-2 2-[(dimethylamino)methyl]cyclohexanone 
• 31600-88-1 m-methoxyphenyllithium 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 333-27-7 methyl trifluoromethanesulfonate 
• 3188-13-4 ethyl chloromethyl ether 
• 74-88-4 methyl iodide 

Downstream Products

• 73986-53-5 (±)-cis-2-[(dimethylamino)methyl]-1-(3-hydroxyphenyl)cyclohexanol 
• 152538-36-8 (-)-tramadol 
• 22204-88-2 (-)-tramadol hydrochloride 
• 280565-80-2 (-)-cis-tramadol (R)-(-)-mandelate 
• 280565-80-2 (+)-cis-tramadol R-(-)-mandelate 
• 280565-80-2 C₁₆H₂₅NO₂*C₈H₈O₃ 
• 2914-77-4 (R,R)-tramadol 
• 1112063-73-6 (1S,2S)-2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol (S)-naproxen salt 
• 1112045-11-0 (1R,2R)-2-((dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol (S)-naproxen salt 
• 1206889-11-3 (+)-tramadol-(S)-ibuprofen salt 
• 2914-78-5 DL-Tramadolhydrochlorid 
• 36282-47-0 tramadol hydrochloride 

Relevant articles and documents

Catalytic Intramolecular Coupling of Ketoalkenes by Allylic C(sp3)?H Bond Cleavage: Synthesis of Five- and Six-Membered Carbocyclic Compounds

In the presence of a catalytic amount of cobalt(II) acetylacetonate/Xantphos in combination with trimethylaluminum, various ketoalkenes underwent an intramolecular cyclization reaction triggered by cleavage of the allylic C(sp3)?H bond, affording carbocyclic compounds with high regio- and diastereoselectivity. Mono-, bi-, and tricarbocyclic compounds were produced in good yields. One of the products thus obtained was derivatized into tramadol in four simple steps. Notably, these intramolecular cyclizations took place in the absence of a gem-disubstituent on the tethered carbon chain (without the Thorpe-Ingold effect). (Figure presented.).

Development of highly efficient resolutions of racemic tramadol using mandelic acid

Two methods for the resolution of tramadol are described. One uses the active pharmaceutical ingredient (API), tramadol hydrochloride as input material. The other utilises the crude free base obtained from the Grignard reaction on tramadol Mannich base. B

Application of microreactor technology in process development

The microreactor technology is an efficient tool for kilogram-scale syntheses in continuous mode and is particularly effective for hazardous reactions that do not allow scale-up in conventional reactors. Applications to several classes of reactions including highly exothermic reactions, high-temperature reactions, reactions with unstable intermediates, and reactions involving hazardous reagents are described herein.

Across-the-World Automated Optimization and Continuous-Flow Synthesis of Pharmaceutical Agents Operating Through a Cloud-Based Server

The power of the Cloud has been harnessed for pharmaceutical compound production with remote servers based in Tokyo, Japan being left to autonomously find optimal synthesis conditions for three active pharmaceutical ingredients (APIs) in laboratories in Cambridge, UK. A researcher located in Los Angeles, USA controlled the entire process via an internet connection. The constituent synthetic steps for Tramadol, Lidocaine, and Bupropion were thus optimized with minimal intervention from operators within hours, yielding conditions satisfying customizable evaluation functions for all examples.