23150-35-8

Basic information

• Product Name: [R(R*,R*)]-2-amino-1-[p-(methylthio)phenyl]propane-1,3-diol
• Synonyms: [R(R*,R*)]-2-amino-1-[p-(methylthio)phenyl]propane-1,3-diol;[R-(RR]-2-Amino-1-[4-(Methylthio)Phenyl]-1,3-Propanediol;(1R,2R)-2-Amino-1-(4-methylthiophenyl)-1,3-propanediol;(1R,2R)-2-Amino-1-[4-(methylthio)phenyl]-1,3-propanediol;[1R,2R,(-)]-2-Amino-1-(4-methylthiophenyl)-1,3-propanediol;Einecs 245-460-5
• CAS NO: 23150-35-8
• Molecular Formula: C₁₀H₁₅NO₂S
• Molecular Weight: 213.2966
• EINECS: 245-460-5
• Mol File: 23150-35-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 428.2°Cat760mmHg
• Flash Point: 212.8°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 4.29E-08mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: [R(R*,R*)]-2-amino-1-[p-(methylthio)phenyl]propane-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: [R(R*,R*)]-2-amino-1-[p-(methylthio)phenyl]propane-1,3-diol(23150-35-8)
• EPA Substance Registry System: [R(R*,R*)]-2-amino-1-[p-(methylthio)phenyl]propane-1,3-diol(23150-35-8)

Safety Data

• Hazardous Substances Data: 23150-35-8(Hazardous Substances Data)

Usage

Description

[R(R,R)]-2-amino-1-[p-(methylthio)phenyl]propane-1,3-diol, commonly known as Mephedrone, is a synthetic stimulant drug that belongs to the cathinone class. It is structurally similar to drugs like ecstasy and cocaine, and is known for inducing feelings of euphoria, increased energy, and heightened sociability. However, it can also lead to hallucinations, paranoia, and agitation. Mephedrone is typically found in the form of a white powder, capsules, or crystals and is often snorted, ingested, or injected. Due to its potential for abuse and addiction, it is classified as a controlled substance in many countries.

Uses

Used in Pharmaceutical Research:
Mephedrone is used as a research chemical for studying the effects of stimulant drugs on the human body. Its structural similarity to other stimulants allows scientists to investigate the mechanisms of action and potential therapeutic applications.
Used in Forensic Analysis:
As a controlled substance, Mephedrone is often detected in forensic investigations related to drug abuse and addiction. Its identification in biological samples can help in understanding the extent of its use and the associated health risks.
Used in Drug Policy and Regulation:
Mephedrone serves as a case study for policymakers and regulatory authorities to develop and implement effective drug control measures. Its classification as a controlled substance helps in monitoring and preventing its abuse and addiction.
Please note that the use of Mephedrone for recreational purposes is illegal and dangerous due to its potential for abuse and addiction. The information provided here is for educational purposes and to understand its role in pharmaceutical research, forensic analysis, and drug policy and regulation.

InChI:InChI=1/C10H15NO2S/c1-14-8-4-2-7(3-5-8)10(13)9(11)6-12/h2-5,9-10,12-13H,6,11H2,1H3

Upstream product

• 14172-52-2 (1RS,2RS)-2-amino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol 
• 14052-59-6 D-threo-1-p-methylmercaptophenyl-2-dichloroacetamidopropane-1,3-diol 
• 135761-10-3 Acetic acid (R)-2-methyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-4-ylmethyl ester; compound with methanesulfonic acid 
• 139164-31-1 methyl D-threo-3-(4-methylthiophenyl)serinate hydrochloride 
• 160751-27-9 (2S,3S)-2-hydroxymethyl-3-(4-methylthiophenyl)-1H-aziridine 
• 160751-26-8 cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methylthiophenyl)aziridine 
• 160751-25-7 (S)-(-)-N-<(p-methylthio)benzylidene>-p-toluenesulfinamide 
• 119293-92-4 (+/-)-2-dichloroacetamido-β-hydroxy-4-methylmercaptopropiophenone 
• 17087-39-7 DL-threo-3-(4-methylthiophenyl)serine 
• 23150-29-0 (2S,3R)-2-amino-3-hydroxy-3-(4-mercaptomethylbenzene)propanoic acid 
• 100370-88-5 ethyl DL-threo-3-(4-methylthiophenyl)serinate hydrochloride 
• 16854-32-3 (1S,2S)-(+)-thiomicamine 
• 135204-38-5 (4S,5S)-5-(4-methylthiophenyl)-4-hydroxymethyl-2,2-dimethyl-1,3-oxazolidine 
• 135204-36-3 (4S,5S)-3-acetyl-2,2-dimethyl-4-formyl-5-<4-(methylthio)phenyl>-1,3-oxazolidine 

Downstream Products

• 4302-89-0 (1R,2R)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol 
• 4302-89-0 (1RS,2RS)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol 
• 16854-32-3 (1S,2S)-(+)-thiomicamine 
• 106886-53-7 (1R,2R)-1-<4-(methylthio)phenyl>-2-phthalimido-1,3-propanediol 
• 122934-50-3 (R)-(4-Methylsulfanyl-phenyl)-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-methanol 
• 96795-20-9 (1R,2R)-2-ethoxycarbonylamino-1-<4-(methylthio)phenyl>-1,3-propanediol 
• 96795-24-3 D-(-)-threo-2-phenyl-4-(4-(methylthio)phenyl)-2-oxazole-5-methanol 
• 96795-00-5 D-threo-4,5-dihydro-5-(4-methylsulphonylphenyl)-2-phenyl-4-oxazolemethanol 
• 129126-21-2 (R)-(4-Methanesulfonyl-phenyl)-((R)-2-phenyl-4,5-dihydro-oxazol-4-yl)-methanol 
• 15318-45-3 thiamphenicol 
• 76639-91-3 (1R,2R)-1-<4-(methylsulphonyl)phenyl>-2-phthalimido-1,3-propanediol 
• 96795-16-3 (1R,2R)-3-acetoxy-1-<4-(methylsulphonyl)phenyl>-2-phthalimido-1-propanol 
• 73231-34-2 Florfenicol 
• 96795-21-0 (4R,5R)-4-hydroxymethyl-5-<4-(methylthio)phenyl>-2-oxazolidinone 

Relevant articles and documents

Synthesis of 4-sulfur-substituted (2S,3R)-3-phenylserines by enzymatic resolution. Enantionure precursors for thiamphenicol and florfenicol

Enantiomerically pure 4-methylthio- and 4-methylsulfonylsubstitutcd (2S,3R)-3-phenylserines are prepared by enzymatic resolution of the corresponding racemic threo amides using the amidase from Ochrobactrum anthropi NCIMB 40321. The unwanted (2R,3S) enantiomers of the amides are separated from the enantiopure amino acids and easily racemized after Schiff base formation with the corresponding 4-(methylthio)- and 4-(methylsulfonyl)benzaldehyde. The racemization can be combined with the preparation of the racemic amides by aldol reaction under crystallization conditions to yield only the threo isomers. Enantiopure (25,3R)-3-[4-(methylthio)phenyl]serine and (2S,3R)-3-[4-(methylsulfonyl)phenyl]serine are thus obtained in 78% and 62% overall yields starting from the corresponding substituted benzaldehydes. (2S,3A)-3-[4-(Methylthio)phenyl]serine is reduced to (1R,2R)-2-amino-1-[4-(methylthio)phenyl]propane-1,3-diol with NaBH4/H2SO4 and can be used for the synthesis of thiamphenicol and florfenicol.

Asymmetric synthesis using sulfinimines (thiooxime S-oxides)

The addition of diethylaluminum cyanide and the lithium enolate of methyl α-bromoacetate to sulfinimines (thiooxime S-oxides) is highly diastereoselective affording α-amino nitriles and N-sulfinylaziridines, respectively. Hydrolysis of the α-amino nitriles gives α-amino acids in high ee, while hydrolysis of N-sulfinylaziridine carboxylic acids give β-hydroxy-α-amino acids. The latter compounds were transformed into (+)-thiamphenicol, a broad spectrum antibiotic and sphingosine, an important component of the sphingolipids.

Process for the stereochemical inversion of (2S,3S)-2-amino-3-phenyl-1,3-propanediols into their (2R,3R) enantiomers

A four step process for transforming (2S,3S)-2-amino-3-phenyl-1,3-propanediols into their (2R,3R)-enantiomers is described. The final compounds are useful intermediates for the synthesis of antibiotics like Chloramphenicol, Thiamphenicol and Florfenicol. The starting products generally are discard products in the synthesis of said antibiotics.